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  • 1990-1994  (879)
  • 1970-1974
  • 1860-1869
  • 1991  (879)
  • Organic Chemistry  (822)
  • Ultrastructure
  • 1
    Electronic Resource
    Electronic Resource
    Diethylene glycol (DEG)-associated myocardial changes: A pilot investigation of chronic intoxication in guinea-pigs (1991)
    Springer
    International journal of legal medicine 104 (1991), S. 93-97 
    Details
    ISSN: 1437-1596
    Keywords: Diethylene glycol ; Intoxication ; Myocardium ; Myocytolysis ; Ultrastructure ; Mitochondria ; Guinea pig ; Diethylenglycol ; Intoxikation ; Myokard ; Myozytolyse ; Ultrastruktur ; Mitochondrien ; Meerschweinchen
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine , Law
    Description / Table of Contents: Zusammenfassung Das Myokard von Meerschweinchen, welche mit subletalen Mengen von Diethylenglycol über eine Zeitdauer von 2–11 Tagen gefüttert worden waren, wurde mikroskopisch und elektronenmikroskopisch untersucht. Eine Koagulationsmyozytolyse und Verlust von Myofibrillen war fleckförmig verstreut über das Myokard. Diese Veränderungen waren in den Kontrollen nicht zu beobachten. Die begleitenden ultrastrukturellen Veränderungen bestanden in Schwellung, Pleomorphie, Hyperplasie von Mitochondrien, begleitet von einer Erweiterung der interfibrillären Räume und Verlagerung, Verzerrung und Ruptur angrenzender Fibrillen.
    Notes: Summary The myocardium of guinea pigs fed on sublethal doses of diethylene glycol (DEG) over a period of 2–11 days was examined for microscopical and ultrastructural changes. Coagulative myocytolysis and loss of myofibrils, not observed in the controls, was patchily distributed throughout the myocardium. The accompanying ultrastructural features included swelling, pleomorphism and hyperplasia of mitochondria with an associated distension of the interfibrillary spaces and a displacement, distortion and rupture of adjacent myofibrils.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01626038
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  • 2
    Electronic Resource
    Electronic Resource
    Effect of dopamine agonist medication on prolactin producing pituitary adenomas (1991)
    Springer
    Virchows Archiv 418 (1991), S. 439-446 
    Details
    ISSN: 1432-2307
    Keywords: Bromocriptine ; Pituitary neoplasm ; Prolactin ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Conventional light microscopy, immunocyto-chemistry, electron microscopy and in situ hybridization were used to evaluate the effect of dopamine agonists (bromocriptine-LAR and bromocriptine) on the morphology of surgically removed prolactin (PRL)-producing pituitary adenomas. Dopamine agonist therapy resulted in decrease of serum PRL, clinical improvement and tumour shrinkage. Using light and electron microscopy cellular atrophy, interstitial and perivascular fibrosis were noted; in several tumours connective tissue accumulation was pronounced. The cellular response was not uniform. In some adenomas populations of large cells and small cells were distinguished. The large cells contained immunoreactive PRL and expressed the PRL gene indicating resistance to dopamine agonists. It appears that these cells retained the potential to secrete PRL and proliferate despite exposure to dopamine agonists. In the small cells, PRL immunoreactivity and PRL gene expression decreased providing evidence that both PRL release and synthesis were blocked. Small cells can persist in tumours after discontinuation of dopamine agonist medication suggesting these small cells are irreversibly suppressed and are not capable of regaining their endocrine function and proliferative capability. The formation of irreversibly suppressed PRL cells may explain why some PRL-producing adenomas do not recur after withdrawal of dopamine agonists.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01605931
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  • 3
    Electronic Resource
    Electronic Resource
    Immunohistochemical characterization of HLA-DR-antigen positive dendritic cells in phaeochromocytomas and paragangliomas as a prognostic marker (1991)
    Springer
    Virchows Archiv 418 (1991), S. 33-39 
    Details
    ISSN: 1432-2307
    Keywords: HLA-DR ; Phaeochromocytomas ; Paragangliomas ; Immunohistochemistry ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Twelve cases of phaeochromocytoma (PCC) and four cases of paraganglioma (PGG) were studied by immunohistochemistry and immunoelectron microscopy in order to demonstrate HLA-DR (Ia)-antigen-positive dendritic cells (IaDCs). Dense infiltration of IaDCs was detected in the majority of PCCs revealing high urinary or serum catecholamine levels, but in aggressively growing PCCs, a familial PCC and all PGGs, few IaDCs were demonstrated. Interestingly, these IaDCs were negative for S-100 protein. Although S-100-protein-positive sustentacular-like cells (SCs), morphologically similar to IaDCs, were also present, these were clearly distinguished from IaDCs by our double immunostaining method. Ultrastructurally, IaDCs had smooth or slightly indented nuclei and contained a moderate amount of endoplasmic reticulum, small mitochondria and vacuoles, extending elongated cytoplasmic processes. These results suggest that determination of the quantity of IaDCs is a highly effective method of assessing the character of PCCs, in particular, their prognosis.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01600242
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  • 4
    Electronic Resource
    Electronic Resource
    Cell-mediated cytotoxicity in acute rat cardiac allograft rejection: An immunological and ultrastructural study (1991)
    Springer
    Virchows Archiv 418 (1991), S. 41-50 
    Details
    ISSN: 1432-2307
    Keywords: Cell-mediated cardiocyte injury ; Acute cardiac allograft rejection ; Mononuclear cellular infiltration ; Immunohistochemistry ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary To clarify the immune mechanism of cytotoxicity in acute cardiac allograft rejection, we observed interactions between cardiocytes and mononuclear cells using immunohistochemistry and light and electron microscopy. All allografted WKA rat hearts transplanted to F344 recipients stopped beating by the 7th day after the transplantation. The population of helper/inducer T cells (Th) and IL2R+ cells was large for the first 3 days, whereas that of cytotoxic/suppressor T cells (Tc-s) and macrophages increased from the 4th day. TheTh/Tc-s ratios were more than 2.0 until the 3rd day, then decreased to less than 1.0. In circulating T lymphocytes; theTh/Tc-s ratios were under 1.0 on the 1st, 6th and 7th days. Electron microscopically IL2R+ cells, Tc-s and macrophages were often seen in close contact with the plasma membrane of the cardiocytes. The majority of IL2R+ cells are NK cells, Tc-s andTh. Of these, the population of Tc-s was small until the 3rd day. Thus, NK cells play a pivotal role in the early stage of the rejection, and Tc-s and macrophages then aggravate cell-mediated cardiocyte injury.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01600243
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  • 5
    Electronic Resource
    Electronic Resource
    Ultrastructure of oesophageal melanocytosis (1991)
    Springer
    Virchows Archiv 418 (1991), S. 515-522 
    Details
    ISSN: 1432-2307
    Keywords: Oesophagus ; Melanocyte ; Melanoma ; Ultrastructure ; Endoscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Four examples of an endoscopically detected oesophageal melanotic lesion were examined by light microscopy, light microscope histochemistry and transmission electron microscopy, and were compared with 13 control samples of normal oesophageal epithelium. By light microscopy, pigmented melanocytes lacking atypia and mitoses were observed amongst the keratinocytes in the basal layer of the oesophageal mucosa. Junctional activity was absent. The mechanism of pigmentation was studied and found to consist of: an increase in the number of melanocytes in the basal layer of the mucosa, an increase in the quantity of melanin in these melanocytes, transfer of melanin from melanocytes to keratinocytes and to macrophages and fibroblasts in the tunica propria. Since all the lesions demonstrated increased numbers of both melanocytes and melanosomes, the term oesophagealmelanocytosis rather thanmelanosis is suggested, to emphasise the essential character of the lesion as a cellular proliferation. The value of sampling these pigmented lesions during endoscopy is emphasised as a means of obtaining well-preserved material for the evaluation of a lesion which some authorities have viewed as a possible precursor for oesophageal malignant melanoma.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01606502
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  • 6
    Electronic Resource
    Electronic Resource
    Ultrastructural abnormalities of mitochondria and deficiency of myocardial cytochromec oxidase in a patient with ventricular tachycardia (1991)
    Springer
    Virchows Archiv 419 (1991), S. 63-68 
    Details
    ISSN: 1432-2307
    Keywords: Mitochondrial cardiomyopathy ; Ultrastructure ; Cytochromec oxidase deficiency ; Ventricular tachycardia
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary A 30-year-old woman presented with lifethreatening ventricular tachycardia without overt heart disease. Ultrastructural investigation of endomyocardial biopsy disclosed abnormally structured and often enlarged mitochondria. Morphometry revealed the ratio of volume density of mitochondria to myofibrils to be markedly increased to 0.667 as compared with five controls (mean: 0.46; range: 0.445–0.479). Investigation of mitochondrial respiratory chain enzymes revealed a 90% reduction in activity of cytochromec oxidase. Our data suggest that mitochondrial cardiomyopathy may induce malignant ventricular arrhythmias.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01600154
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  • 7
    Electronic Resource
    Electronic Resource
    Varicocele in the rat: a new experimental model (1991)
    Springer
    Urological research 19 (1991), S. 319-322 
    Details
    ISSN: 1434-0879
    Keywords: Varicocele ; Rat, Histology ; Ultrastructure ; Temperature ; Infertility
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary With no consistent animal prototype for the study of varicocele, we set out to create a model in the rat by complete ligation of the main branch of left spermatic vein (MBSV) or by partial ligation of the left renal vein. Three months later, the histology, ultrastructure and temperature of the testis and epididymis were studied. Microscopically, spermatogenic arrest was the most frequent anomaly seen. The most frequently noted ultrastructural change of the testis was distension of smooth endoplasmic reticula in Sertoli cells. The microvilli of columnar epithelia in epididymis were sparse and showed local defects. Lesions and increased temperatures in the testis and epididymis induced by the ligation of the left MBSV were similar to those seen in partial ligation of the left renal veins, with no significant differences between left and right. Significant differences were found, however, on comparison with the controls.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00299069
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  • 8
    Electronic Resource
    Electronic Resource
    Morphology of the synovium during its differentiation and development in the mouse knee joint (1991)
    Springer
    Anatomy and embryology 183 (1991), S. 537-544 
    Details
    ISSN: 1432-0568
    Keywords: Synovial membrane ; Development ; Ultrastructure ; Scanning electron microscopy ; Mouse
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The prenatal and postnatal development of the mouse knee joint was investigated by transmission and scanning electron microscopy. In the prenatal stage, following the appearance of a narrow intercellular cleft between two skeletal elements on the 16th fetal day, clefting extended into the lateral synovial mesenchyme. In some regions, the extension of the cleft was very rapid, but in a certain region (future fat pad region), it was somewhat slower. Macrophage-like cells appeared in the synovial mesenchyme on the 16th fetal day, and then increased in number, and were distributed as if they were clustering around the presumptive clefting zone in the future fat pad region on the 17th–18th fetal day. This suggests that macrophage-like cells may participate in joint development, as they phagocytize and remove some kinds of solid extracellular matrix, and facilitate the cleft extension. In the early postnatal stage, scanning electron microscopic observations showed that there were two different types of cell in the synovial lining. One of them exhibited a surface morphology corresponding to that of macrophages: a spherical cell body and numerous pseudopodia. The other type of cell exhibited various cell shapes with many cytoplasmic processes extending along the synovial surface.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00187902
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  • 9
    Electronic Resource
    Electronic Resource
    Endothelial heterogeneity in the chick wing bud: A morphometric study (1991)
    Springer
    Anatomy and embryology 184 (1991), S. 47-53 
    Details
    ISSN: 1432-0568
    Keywords: Wing bud ; Endothelial cell ; Development ; Ultrastructure ; Morphometry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The microvascular endothelium of the chick wing bud at stages 22, 27, and 32 was evaluated by ultrastructural morphometry. The rationale for this study is based on the hypothesis that endothelial cells exhibit variation in structure and function during cytodifferentiation. The microvessels had a luminal diameter range such that they were classified as capillaries. The thin continuous endothelium was devoid of a basal lamina. The endothelium had a very small number of plasmalemmal vesicles; vacuoles were however present for all stages and in some cases were abundant. The temporal findings were that endothelial cell thickness increases, plasmalemmal vesicle densities decrease, and the densities of cytoplasmic vacuoles increase. The spatial results were that endothelial cells in proximal regions of the limb have a greater thickness, contain fewer vesicles and have more vacuoles than those in distal regions. In general, these results indicate that endothelial ultrastructural heterogeneity occurs within a 31/2 day timespan of wing bud development. The discussion considers the results with regard to recent reports on endothelial cell heterogeneity.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01744260
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  • 10
    Electronic Resource
    Electronic Resource
    Development of taste organs inRana temporaria (1991)
    Springer
    Anatomy and embryology 184 (1991), S. 363-369 
    Details
    ISSN: 1432-0568
    Keywords: Taste organs ; Amphibia ; Development ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary In tadpoles ofRana temporaria two successive generations of taste organs: taste buds (TBs) and taste disks were studied. The TBs are located in the apices of oral premetamorphic papillae. Each TB consists of vertically elongated receptor cells (probably taste) and supporting cells. No basal (Merkel) cells were observed there. Morphologically, two types of receptor cells have been distinguished in a TB. Complete synaptic structures were observed in the TBs between the 30th and 41st of Gosner's (1960) developmental stages, though synaptic vesicles occur already at stage 26. The taste disks consist of taste cells, supporting cells and basal cells. Dense-core synaptic vesicles occur in the gustatory cells at stage 41, but complete synaptic structures were not observed earlier than at stage 45. Synaptic junctions observed at some of the gustatory cells seem to be reciprocal (bidirectional).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00957898
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  • 11
    Electronic Resource
    Electronic Resource
    The anatomy and fine structure of the echidnaTachyglossus aculeatus snout with respect to its different trigeminal sensory receptors including the electroreceptors (1991)
    Springer
    Anatomy and embryology 184 (1991), S. 371-393 
    Details
    ISSN: 1432-0568
    Keywords: Tachyglossus aculeatus (echidna) ; Echidna bill ; Sensory receptors ; Electroreceptor ; Mechanoreceptor ; Trigeminal nerve ; Monotreme ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The gross anatomy and nerve supply of the bill of echidna (Tachyglossus aculeatus) is described in relation to its function as an outstanding sensory organ. The sensory innervation of the skin of the echidna snout was investigated by means of frontal serial sections, after decalcification of the specimens. A comprehensive light and electron microscopic description of the location and fine structure of cutaneous sensory receptors of the trigeminal system was made by this means. The encapsulated and non-encapsulated Ruffini receptors, the types of other free receptors in the connective tissue and the Merkel cell receptor do not differ morphologically from those of higher mammals, whereas the pacinian-like corpuscle shows a unique organization of its outer core. This is composed of large perineural cells containing a unique reticulum of parallel-orientated endoplasmic membranes. Lamellated corpuscles, seen in isolation or in association with push rods, are numerous in the snout and in the tip of the tongue of echidna. Push rod receptor organs occur in the hairless skin of the bill with a very dense array at its rostral end and in the pseudopalatal ridges. Gland duct receptors are restricted to the skin adjacent to the nostrils and the mouth opening, including the pseudopalatal plates. Only about one quarter of the total number of 400 seromucous glands receive a sensory innervation of their intraepidermal duct segment. Within each innervated gland two types of receptor terminals are identified. The distributions of the different receptor types are mapped for different regions of the skin, the mucous membrane of the nasal and oral vestibule and the tip of the tongue. The fine structure of nerve terminals is discussed from a comparative anatomical point of view, and some speculations are made about possible transduction processes that underlie the known electrophysiological properties. The sensory organs such as the “push rod” and “gland duct receptor”, and most of their sensory terminals, are less differentiated in echidna snout than in the platypus (Ornithorhynchus anatinus) bill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00957899
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  • 12
    Electronic Resource
    Electronic Resource
    Immunocytochemical and ultrastructural studies of hyaline inclusions in sporadic motor neuron disease (1991)
    Springer
    Acta neuropathologica 82 (1991), S. 295-301 
    Details
    ISSN: 1432-0533
    Keywords: Hyaline inclusions ; Motor neuron disease ; Amyotrophic lateral sclerosis ; Immunocytochemistry ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary We investigated hyaline inclusion bodies (HI) immunocytochemically and ultrastructurally in six cases of sporadic motor neuron disease (MND). All HI contained large amounts of ubiquitin and some HI were stained at the core or the center with anti-neurofilament antibody, with the surrounding halo unstained. No HI were stained with antibodies raised against cytoskeletal proteins such as high-molecular weight microtubule-associated proteins and phosphorylated tau. Ultrastructurally, HI were chiefly composed of filaments measuring about 20 nm in diameter thicker than neurofilaments, and contained fine granules and frequently one or more of four characteristic profiles, i.e., small electron-dense materials resembling Bunina bodies, bundles of tubular filaments measuring approximately 20 nm in diameter, large electron-dense cores, and focal accumulations of randomly arranged neurofilaments. Hyaline inclusions can be regarded as one of the characteristic markers for sporadic MND as well as familial amyotrophic lateral sclerosis. Hyaline inclusions have a markedly heterogeneous ultrastructure and, therefore, differences in immunoreactivity with antineurofilament antibodies are not unexpected.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00308815
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  • 13
    Electronic Resource
    Electronic Resource
    Meningiomas differentiating to arachnoid trabecular cells: a proposal for histological subtype “arachnoid trabecular cell meningioma” (1991)
    Springer
    Acta neuropathologica 82 (1991), S. 327-330 
    Details
    ISSN: 1432-0533
    Keywords: Meningioma ; Microcystic meningioma ; Vacuolated meningioma ; Arachnoid trabecular cell ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Three cases of meningiomas which had abundant small vacuoles in the tumor tissue are reported. By electron microscopy, the tumor cells exhibited long and thin processes, the tips of which were united by desmosomes. The tumor tissue was revealed to have wide extracellular spaces which corresponded to the vacuoles observed by light microscopy. In previous literature, various terms have been used when referring to this meningioma, such as microcystic meningioma or vacuolated meningioma. Since the ultrastructure of the tumor showed similarity to that of normal arachnoid trabecular cells, we propose to call the tumor “arachnoid trabecular cell meningioma” denoting its morphological nature clearly.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00296542
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  • 14
    Electronic Resource
    Electronic Resource
    Galactosialidosis: neuropathological findings in a case of the late-infantile type (1991)
    Springer
    Acta neuropathologica 82 (1991), S. 331-339 
    Details
    ISSN: 1432-0533
    Keywords: Galactosialidosis ; Neuronal storage disease ; Neuropathology ; Ultrastructure ; Neuronal loss
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The neuropathological findings in a 13-year-old Japanese male showing decrease of sialidase and β-galactosidase activities are reported. The patient was the product of normal pregnancy to consanguineous parents. He started to sit at 8 months, stand at 20 months and walk at the age of 2; mental retardation, visual disturbance, cerebellar ataxia, myoclonus and epilepsy developed by the age of 10, and he died at 13. Neuropathological investigation revealed neuronal loss and storage. Severe loss of neurons was observed in the thalamus, globus pallidus, lateral geniculate body, gracile nucleus, Purkinje and retinal ganglion cells. Marked ballooning was seen in the Betz cells and neurons in the basal forebrain, the motor neurons in the cranial nerve nuclei and spinal cord, and in the trigeminal and spinal ganglia. The storage material varied in staining from region to region and from neuron to neuron. Electron microscopic investigation revealed a variety of intracytoplasmic and intranuclear inclusions: membranous cytoplasmic bodies, parallel, wavy-lamellar or tortuous tubular structures, lipofuscin-like irregular-shaped pleomorphic bodies, and cytoplasmic vacuoles with fine granules and lamellar materials. The severity of the neuronal loss did not seem to correlate with the amount of the storage materials, but with the presence of tortuous tubular inclusion.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00296543
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  • 15
    Electronic Resource
    Electronic Resource
    Intramedullary secretory gangliocytoma (1991)
    Springer
    Acta neuropathologica 82 (1991), S. 402-407 
    Details
    ISSN: 1432-0533
    Keywords: Gangliocytoma ; Ultrastructure ; Catecholamines ; Hypertension ; Spinal cord
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary An 8-year-old boy developed severe systemic hypertension during resection of an intramedullary tumor. The histological, ultrastructural and immunocytochemical characteristics of the tumor are those of a gangliocytoma. Based on the demonstration of tyrosine hydroxylase in neuronal tumor cells, it is postulated that catecholamine secretion was responsible for the systemic hypertension.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00296552
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  • 16
    Electronic Resource
    Electronic Resource
    Immunocytochemical and ultrastructural studies of Werdnig-Hoffmann disease (1991)
    Springer
    Acta neuropathologica 81 (1991), S. 408-417 
    Details
    ISSN: 1432-0533
    Keywords: Werdnig-Hoffmann disease ; Immunocytochemistry ; Ultrastructure ; Cytoskeleton ; Ubiquitin
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Neuronal alterations in two cases of Werdnig-Hoffmann disease (WH) were investigated immunocytochemically and ultrastructurally. Ballooned neurons (BNs) were found in anterior horn, Clarke's column, dorsal root ganglion and thalamus. Anti-phosphorylated neurofilament antibodies preferentially stained the peripheral perikarya and proximal neuronal processes of BNs, whereas anti-ubiquitin antibodies preferentially stained the central perikarya of BNs. Ultrastructurally, BNs showed degenerative changes ranging from a diffuse increase of neurofilaments to a centrally accentuated accumulation of mitochondria and vesicular or membranous profiles. Our studies suggest that ubiquitinated degradation products accumulate in the center of the BN's perikaryon and displace aberrantly phosphorylated neurofilaments to the periphery. BNs in WH probably reflect an intrinsic alteration in the metabolism of neurofilaments that is associated with regressive changes in the neuron and eventually neuronal death.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00293462
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  • 17
    Electronic Resource
    Electronic Resource
    The effect of denervation on the morphology of regenerating rat soleus muscles (1991)
    Springer
    Acta neuropathologica 82 (1991), S. 21-32 
    Details
    ISSN: 1432-0533
    Keywords: Muscle ; Regeneration ; Denervation ; Ultrastructure ; Snake toxin
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary This study examines the level to which muscle regeneration proceeds in the absence of innervation. Regeneration was monitored in rat soleus muscles following localised injection of a snake toxin, notexin. Muscles which had been concomittantly denervated were compared with those that were normally innervated. Until 3–4 days following toxin administration regeneration is identical in both groups. The muscles contain new myotubes in place of the degenerated “parent” fibres. Thereafter, the non-denervated muscles grow rapidly and by 28 days their myofibres attain the size of those from the contralateral controls. Growth of denervated regenerating muscles, however, is retarded and is superseded by a gradual atrophy. In such muscles we further identify ultrastructural abnormalities from 7 days post-injection. These a re loss of individual myosin filaments and the presence of immature and abnormal configurations of the transverse system and triads. We, thus, conclude that innervation is an obligatory requirement for the restoration of normal myofibrillar and sarcotubular morphology, as well as growth, but is not necessary for the neo-formation of myofibres.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00310919
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  • 18
    Electronic Resource
    Electronic Resource
    Bone marrow transplant in a case of mucopolysaccharidosis I Scheie phenotype: skin ultrastructure before and after transplantation (1991)
    Springer
    Acta neuropathologica 82 (1991), S. 33-38 
    Details
    ISSN: 1432-0533
    Keywords: MPS I-S ; Skin biopsy ; Ultrastructure ; Bone marrow transplant
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary An 11-year-old girl with mucopolysaccharidosis I Scheie phenotype (MPS I-S) received a bone marrow transplant (BMT) from her heterozygous HLA-identical LMC-non-reactive mother. Multidisciplinary studies were carried out and results evaluated 21 months after transplantation. Herein we report the ultrastructural findings pre-and post-BMT in skin. Multidisciplinary studies are commonly used to evaluate the benefits of metabolic correction following BMT in some MPS and other inherited metabolic disorders, and changes in morphology have been described in liver and few other tissues. In this case, we elected skin, since connective tissue is universally involved in MPS and is safely and easily obtainable. Comparison of skin biopsy specimens taken before and after BMT showed a considerable change in dermal fibroblast morphology, with marked reduction in cell size and the number and size of abnormal lysosomes, thus indicating the clearance of storage. Our results demonstrate that dermal cells respond to enzyme replacement therapy in MPS I-S, with the clearance of glycosaminoglycan lysosomal accumulation in connective tissue fibroblasts, which had near-normal morphology 21 months after BMT. Therefore, the practice of skin biopsy after BMT in MPS and other metabolic disorders in which dermal cells are involved should be encouraged.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00310920
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  • 19
    Electronic Resource
    Electronic Resource
    Idiopathic prolactin cell hyperplasia of the pituitary mimicking prolactin cell adenoma: a morphological study including immunocytochemistry, electron microscopy, and in situ hybridization (1991)
    Springer
    Acta neuropathologica 82 (1991), S. 147-151 
    Details
    ISSN: 1432-0533
    Keywords: Hyperplasia ; Pituitary ; Pathology ; Prolactin ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Prolactin cell adenoma is the most frequently found lesion in surgically removed pituitaries of patients with hyperprolactinemia. However, in several instances, instead of prolactin cell adenoma, other lesions are encountered by morphological investigation. We report here the morphological findings in a patient with hyperprolactinemia who underwent transsphenoidal pituitary surgery for suspected prolactin cell adenoma. A morphological diagnosis of tumor could not be confirmed and massive diffuse prolactin cell hyperplasia was identified. The aim of this publication is to describe the lesion by histology, immunocytochemistry, electron microscopy, and in situ hybridization and to call attention to primary prolactin cell hyperplasia which can mimic prolactin cell adenoma.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00293958
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  • 20
    Electronic Resource
    Electronic Resource
    Fulminant blastomycosis with blastomycotic infection of a cerebral glioma (1991)
    Springer
    Acta neuropathologica 82 (1991), S. 420-424 
    Details
    ISSN: 1432-0533
    Keywords: Blastomycosis ; North American Blastomy-cosis ; Brain tumor ; Opportunistic infection ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Except for isolated case reports, blastomycosis has not been identified as a significant problem in immunosuppressed patients. We describe an unusual case with blastomycotic infection of a cerebral glioma in a 56-year-old man who underwent radiotherapy for his tumor and died of fulminant blastomycotic pneumonia. This is believed to be the first reported case of Blastomyces dermatitidis infection of a cerebral glioma. The light microscopic and ultrastructural features of B. dermatitidis, the giant forms of which were encountered in our patient, are described, and the role of immuno-suppression due to steroid therapy in the pathogenesis of this fulminant infection are reviewed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00296555
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  • 21
    Electronic Resource
    Electronic Resource
    Scrapie inoculation of mice: light and electron microscopy of the superior colliculi (1991)
    Springer
    Acta neuropathologica 81 (1991), S. 562-571 
    Details
    ISSN: 1432-0533
    Keywords: Scrapie ; Ultrastructure ; Vacuolation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Ultrastructural examination of the superior colliculi of mice intraocularly inoculated with the ME7 strain of scrapie showed vacuolation early in the course of infection. Brains were examined between 85–260 days after monocular inoculation with scrapie. The mean incubation period for the development of clinical disease was 302 days. Vacuolation was seen initially in the contralateral superior colliculus and subsequently in the ipsilateral colliculus. In coded trails light microscopical vacuolation was seen from 218 days but ultrastructural examination showed that sparse vacuoles were inconsistently present in either or both of the ipsilateral and contralateral colliculi from 85 days; frequent vacuoles were seen from 190 days. Scrapie-induced vacuoles were differentiated from vacuoles present in control tissue by the presence of loculation or by a limiting double membrane which showed protrusion or proliferation of the innermost lamella. Vacuolation was seen in neuronal perikarya, myelinated fibres, dendrites and axonal presynaptic terminals. Vacuoles of myelinated fibres were observed within myelin and possibly also in the inner tongue of oligodendroglial cytoplasm. Whorled membrane configurations were also seen. Tubulovesicular particles, 40 nm in diameter, were recognised in two scrapie-infected mice. It is suggested that some scrapie vacuoles arise as a result of incorporation of abnormal membrane into organelles, possibly mitochondria, in neuronal perikarya and neurites and probably also within oligodendroglial cytoplasm and myelin.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00310139
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  • 22
    Electronic Resource
    Electronic Resource
    Histopathogenesis of inflammatory linear verrucose epidermal naevus: histochemistry, immunohistochemistry and ultrastructure (1991)
    Springer
    Archives of dermatological research 283 (1991), S. 491-499 
    Details
    ISSN: 1432-069X
    Keywords: Inflammatory linear epidermal naevus ; Keratinization ; DACM ; Involucrin ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Skin lesions of three patients with inflammatory linear verrucose epidermal naevus (ILVEN) were examined. Histologically, orthokeratosis and parakeratosis were alternately seen in the acanthotic epidermis. By N-(7-dimethylamino-4-methyl-3-coumarinyl)maleimide staining, the horny cells in the parakeratotic epidermis showed a cytoplasmic SH pattern and a weak membranous SS pattern. The orthokeratotic epidermis revealed an increased involucrin expression, whereas the parakeratotic epidermis showed almost no involucrin expression. Ultrastructurally, in the parakeratotic epidermis, the living keratinocytes had prominent Golgi apparatuses and vesicles in the cytoplasm. In the intercellular spaces in the upper spinous layer through to the lower horny layer, an electron dense, homogeneous substance was deposited. The cytoplasm of the horny cells was filled with keratin filaments and contained remnants of nucleus and cytoplasmic membrane structures, and some lipid droplets. The marginal band formation was incomplete. Most of these ultrastructural abnormalities were not found in the orthokeratotic epidermis. There are both similarities and differences in histopathogenesis of the parakeratotic epidermis between ILVEN and psoriasis. A unique finding was the lack of involucrin expression in the ILVEN parakeratotic epidermis.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00371921
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  • 23
    Electronic Resource
    Electronic Resource
    The rhino mouse model: the effects of topically applied all-trans retinoic acid and CD271 on the fine structure of the epidermis and utricle wall of pseudocomedones (1991)
    Springer
    Archives of dermatological research 283 (1991), S. 100-107 
    Details
    ISSN: 1432-069X
    Keywords: Rhino mouse skin ; All-trans retinoic acid ; CD271 ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The histological and ultrastructural effects following 3 weeks' topical treatment with two agents (all-trans retinoic acid and a new synthetic retinoid-like substance, CD271) were evaluated on the epidermis and the epithelial wall of the pseudocomedones in rhino mouse skin. The comedolytic effects of these drugs were similar, and consisted of a reduction of the utricular diameter, with normalization of follicular units. Morphological examinations revealed a hyperplastic response with an increase in the number of cell layers of both epidermis and follicular epithelium, and modifications in keratinocyte differentiation. Ultrastructural changes in the epidermis and epithelial wall were observed mainly in the granular and horny layers, with increased desquamation, and a decrease in the cohesiveness of corneocytes. During the first week of treatment, some cutaneous toxic effects were noticed, but they normalized within two weeks. On the other hand, a fine granular material persisted in the intercellular spaces. It is confirmed that the skin of the rhino mouse is a good model for the evaluation of the comedolytic effects of drugs. Moreover, it reveals the specific effects of retinoids on epidermal differentiation. We have demonstrated that topically applied CD271 induces modifications similar to those obtained with all-trans retinoic acid. It is thus concluded that CD271 is a potentially effective anti-acne agent.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00371617
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  • 24
    Electronic Resource
    Electronic Resource
    Ultrastructural study of the skin in Sjögren — Larsson syndrome (1991)
    Springer
    Archives of dermatological research 283 (1991), S. 141-148 
    Details
    ISSN: 1432-069X
    Keywords: Sjögren ; Larsson syndrome ; Ichthyosis ; Ultrastructure ; Lamellar body ; Keratinization
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The ichthyosiform skin and the uninvolved skin of a 5-year-old Japanese female with Sjögren — Larsson syndrome were examined by light and electron microscopy to elucidate the keratinization disorder. Light microscopically, the epidermis of the ichthyosiform skin showed acanthosis, papillomatosis and hyperkeratosis. The horny cells had a basket-weave appearance. The granular cell layer was slightly thickened. Slight round cell infiltration and vascular dilatation were seen in the upper dermis. The uninvolved skin was histologically normal. Electron microscopically, in both ichthyosiform and uninolved skin, abnormal lamellar or membranous inclusions were present in the cytoplasm of horny cells of the epidermis. These inclusions appeared to be derived from some of the lamellar bodies and/or abnormal membranous structures found in the cytoplasm of spinous and granular cells. Mitochondria in the epidermal basal cells were more numerous in the ichthyosiform skin than in the uninvolved skin. These findings indicate that, whether the skin is involved or not, the epidermis of the patient with this disorder may always have a structural abnormality, which may be genetically determined. Local environmental factors may play a role in inducing the acanthosis and papillomatosis of the epidermis.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00372053
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  • 25
    Electronic Resource
    Electronic Resource
    Are accessory nuclei involved in the establishment of developmental gradients in hymenopteran oocytes? (1991)
    Springer
    Development genes and evolution 199 (1991), S. 423-426 
    Details
    ISSN: 1432-041X
    Keywords: Oogenesis ; Accessory nuclei ; Developmental gradients ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary In the oocytes ofTenthredo olivacea, accessory nuclei (AN) are formed by budding from the nuclear envelope of the oocyte nucleus. Newly formed AN contain electron-dense material of nuclear origin and are surrounded by a double envelope devoid of pores. Such structures are subsequently transported to the peripheral ooplasm (periplasm), where they grow to reach a final diameter of 5 µm. In the envelopes of advanced AN nuclear pores arise. Through these pores “nuage” material is extruded into the surrounding periplasm. These findings are discussed with respect to a possible involvement of AN in the establishment of developmental gradients in hymenopteran oocytes.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01705853
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  • 26
    Electronic Resource
    Electronic Resource
    The origin of the nascent blastocoele in preimplantation mouse embryos ultrastructural cytochemistry and effect of chloroquine (1991)
    Springer
    Development genes and evolution 200 (1991), S. 77-85 
    Details
    ISSN: 1432-041X
    Keywords: Lysosomes ; Ultrastructure ; Chloroquine ; Blastocyst ; Mouse
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Mouse morulae are known to undergo cavitation as soon as some external cells have entered the sixth cell cycle (Garbutt et al. 1987). Since the early cytological features of cavitation are still unclear, we undertook a careful ultrastructural analysis of late morulae-nascent blastocysts. In addition, since maturation of lysosomes might be involved in the first step of cavity formation, we focused our attention on these organelles by means of the cytochemical localization of trimetaphosphatase activity and by the study of the effects of chloroquine on precavitation embryos. Our results suggest that cavitation starts in a few external cells (presumably competent cells entering the sixth cell cycle), by the chloroquine-sensitive formation of degradative autophagic vacuoles engulfing lipid droplets and vacuoles containing osmiophilic material. These complex structures enlarge (as a result of lipid metabolism?) and so transform into intrablastomeric cavities which, by means of a membrane fusion process, very rapidly become extracellular cavities that coalesce. The abembryonic pole of the blastocyst is determined in this way. Moreover, we suggest that the juxtacoelic cytoplasmic processes covering the inner cell mass (ICM) cells, which are known to restrict the expression of their totipotency during early cavitation (Fleming et al. 1984), are the latest remnants of the walls of the growing intrablastomeric cavities.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00637187
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  • 27
    Electronic Resource
    Electronic Resource
    Contributions of sodium and chloride to ultrastructural damage after dendrotomy (1991)
    Springer
    Experimental brain research 86 (1991), S. 60-72 
    Details
    ISSN: 1432-1106
    Keywords: Trauma ; Neuron ; Sodium ; Chloride ; Ultrastructure ; Mouse
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary To determine the contributions of sodium and chloride to ultrastructural changes after mechanical injury, we amputated primary dendrites of cultured mouse spinal neurons in low calcium medium in which sodium chloride had been replaced with either choline chloride or sodium isethionate or sodium propionate. Uninjured cultured neurons were also exposed to the sodium ionophore, monensin. A third set of neurons was injured in medium in which all sodium and calcium chloride had been replaced with sucrose. Neurons injured in low-calcium, low-sodium medium exhibited few ultrastructural changes, except very near the lesion, where there was some dilation of mitochondria and cisternae of the smooth endoplasmic reticulum (SER). Mitochondria in other regions of the neurons developed an electron opaque matrix, and those nearer to the lesion converted to the condensed configuration, characterized by expanded intracristal spaces as well as a dense matrix. If sodium but not chloride was present in the medium, there was some dilation of the Golgi cisternae after injury, as well as some increased electron opacity of the mitochondria. Monensin treated neurons also exhibited dilation of the Golgi cisternae. Neurons injured in sucrose-substituted medium showed none of the changes associated with injury in normal culture medium. These results indicate that sodium influx through the lesion is involved in the dilation of the SER, which is seen even in low-calcium medium, and that a permeant anion, such as chloride, is also involved. This dilation of the SER may result from uptake of calcium released from mitochondria in response to elevated cytosolic sodium. Dilation of the Golgi cisternae appears to be a response only to elevated intracellular sodium. Condensation of the mitochondria after injury is thought to be due to increased demands for ATP synthesis and may involve a “futile cycling” of calcium across the mitochondrial membrane, involving sodium-mediated calcium release in response to elevated intracellular calcium.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00231040
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  • 28
    Electronic Resource
    Electronic Resource
    Secretory tapetum of Brassica oleracea L.: polarity and ultrastructural features (1991)
    Springer
    Sexual plant reproduction 4 (1991), S. 28-35 
    Details
    ISSN: 1432-2145
    Keywords: Tapetal cells ; Brassica oleracea L ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary The ultrastructure of the secretory, binucleate tapetum of Brassica oleracea in the micro spore mother cell (MMC) stage through to the mature pollen stage is reported. The tapetal cells differentiate as highly specialized cells whose development is involved in lipid accumulation in their final stage. They start breaking down just before anther dehiscence. Nuclei with dispersed chromatin, large nucleoli and many ribosomes in the cytoplasm characterize the tapetal cells. The wall-bearing tapetum phase ends at the tetrade stage. The dissolution of tapetal walls begins from the inner tangential wall oriented towards the loculus and proceeds gradually along the radial walls to the outer tangential one. The plasmodesmata transversing the radial walls between tapetal cells persist until the mature microspore, long after loss of the inner tangential wall. After wall dissolution, the tapetal protoplasts retain their integrity and position within the anther locule. The tapetal cell membrane is in direct contact with the exine of the microspores/pollen grains and forms tubular evaginations that increase its surface area and appear to be involved in the translocation of solutes from the tapetal cells to the microspores/ pollen grains. The tapetal cells exhibit a polarity expressed by spatial differentiation in the radial direction.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00194568
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  • 29
    Electronic Resource
    Electronic Resource
    Brassica napus pollen development during generative cell and sperm cell formation (1991)
    Springer
    Sexual plant reproduction 4 (1991), S. 176-181 
    Details
    ISSN: 1432-2145
    Keywords: Pollen ; Brassica napus ; Mitoses ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Brassica napus pollen development during the formation of the generative cell and sperm cells is analysed with light and electron microscopy. The generative cell is formed as a small lenticular cell attached to the intine, as a result of the unequal first mitosis. After detaching itself from the intine, the generative cell becomes spherical, and its wall morphology changes. Simultaneously, the vegetative nucleus enlarges, becomes euchromatic and forms a large nucleolus. In addition, the cytoplasm of the vegetative cell develops a complex ultrastructure that is characterized by an extensive RER organized in stacks, numerous dictyosomes and Golgi vesicles and a large quantity of lipid bodies. Microbodies, which are present at the mature stage, are not yet formed. The generative cell undergoes an equal division which results in two spindle-shaped sperm cells. This cell division occurs through the concerted action of cell constriction and cell plate formation. The two sperm cells remain enveloped within one continuous vegetative plasma membrane. One sperm cell becomes anchored onto the vegetative nucleus by a long extension enclosed within a deep invagination of the vegetative nucleus. Plastid inheritance appears to be strictly maternal since the sperm cells do not contain plastids; plastids are excluded from the generative cell even in the first mitosis.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00190001
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  • 30
    Electronic Resource
    Electronic Resource
    Ultrastructure of the micropyle and its relationship to pollen tube growth and synergid degeneration in sunflower (1991)
    Springer
    Sexual plant reproduction 4 (1991), S. 166-175 
    Details
    ISSN: 1432-2145
    Keywords: Helianthus annuus ; Ultrastructure ; Micropyle ; Pollen tube ; Synergid degeneration
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Ultrastructural studies made on the micropyle of sunflower before and after pollination resulted in the following observations. (1) The micropyle is closed instead of a hole or canal. The inner epidermis of the integument on both sides of the micropyle is in close contact at the apex of the ovule. The boundary between the two sides consists of two layers of epidermal cuticle. (2) The micropyle contains a transmitting tissue. The micropyle is composed of an intercellular matrix produced by the epidermal cells of the integument. (3) The micropyle is asymmetrical, and is much wider on the side proximal to the funicle. On the funicle side the cells adjacent to the micropyle are similar to those of the transmitting tissue: they have large amounts of intercellular matrix and contain abundant dictyosomes, rough ER, and starch grains, and provide an appropriate environment for growth of the pollen tubes. The cells distal to the funicle are rich in rough ER and lipid bodies; they lack large intercellular spaces. (4) The micropyle is variable in the axial direction, i.e., it is much larger and more asymmetric at the level distal to the embryo sac than at a level close to the embryo sac. After pollination, one to four pollen tubes are seen in a micropyle. During their passage through the micropyle, most pollen tubes are restricted to the side proximal to the funicle. There is a greater tendency (81%) for the degenerate synergid to be located toward the funicle, i.e., at the same side as the pollen tube pathway. The data indicate a close relationship between micropyle organization, orientation of pollen tube growth, and synergid degeneration.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00190000
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  • 31
    Electronic Resource
    Electronic Resource
    Sperm cells of the pollen tubes of Brassica: Ultrastructure and isolation (1991)
    Springer
    Sexual plant reproduction 4 (1991), S. 226-234 
    Details
    ISSN: 1432-2145
    Keywords: Male germ unit ; Sperm cells ; Isolation ; Pollen tubes ; Brassica napus ; Pollen-tube inner plasma membrane ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Sperm cells of pollen tubes grown both in vivo and in vitro form a male germ unit. Extensions from both sperm cells of each pollen tube are closely associated with the tube nucleus. A high yield (2.7 × 104. 20 mg−1 pollen grains germinated) of intact sperm cells was obtained following release by osmotic shock from pollen tubes grown in vitro. Structural integrity of isolated sperm was maintained by isolation at low temperature in an osmotically balanced medium. At 4° C many isolated sperm pairs were still enclosed within the pollentube inner plasma membrane. Sperm cells not enclosed within this membrane no longer remained connected as a pair. During isolation vesicles formed on the sperm cell surface from disruption of the fibrillar components bridging the periplasmic space. Both in the pollen tube and after isolation the sperm nucleus is in close association with at least one region of the sperm plasma membrane. Sperm isolated at room temperature showed the presence of nucleopores, and nuclei were euchromatic, instead of heterochromatic as in intact sperm in the pollen tube.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00190009
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  • 32
    Electronic Resource
    Electronic Resource
    Microsporogenesis and tapetal development in fertile and cytoplasmic male-sterile sugar beet (Beta vulgaris L.) (1991)
    Springer
    Sexual plant reproduction 4 (1991), S. 215-225 
    Details
    ISSN: 1432-2145
    Keywords: Cytoplasmic male sterility ; Beta vulgaris ; Microsporogenesis ; Tapetum ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary The development of sporogenous and tapetal cells in the anthers of male-fertile and cytoplasmic male-sterile sugar beet (Beta vulgaris L.) plants was studied using light and transmission electron microscopy. In general, male-sterile anthers showed a much greater variability in developmental pattern than male-fertile anthers. The earliest deviation from normal anther development was observed to occur in sterile anthers at meiotic early prophase: there was a degeneration or irregular proliferation of the tapetal cells. Other early aberrant events were the occurrence of numerous small vesicles in the microspore mother cells (MMC) and a disorganized chromatin condensation. Deviations that occurred in sterile anthers at later developmental stages included: (1) less distinct inner structures in the mitochondria of both MMC and tapetal cells from middle prophase onwards. (2) dilated ER and nuclear membranes at MMC prophase, in some cases associated with the formation of protein bodies. (3) breakdown of cell walls in MMCs and tapetal cells at late meiotic prophase. (4) no massive increase in tapetal ER at the tetrad stage. (5) a general dissolution of membranes, first in the MMC, then in the tapetum. (6) abortion of microspores and the occurrence of a plasmodial tapetum in anthers reaching the microspore stage. (7) no distinct degeneration of tapetal cells after microspore formation. Thus, it seems that the factors that lead to abortive microsporogenesis are structurally expressed at widely different times during anther development. Aberrant patterns are not restricted to the tetrad stage but occur at early prophase.
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    URL: http://dx.doi.org/10.1007/BF00190008
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  • 33
    Electronic Resource
    Electronic Resource
    Fluoride effects on leaf cell ultrastructure of olive trees growing in the vicinity of the Aluminium Factory of Greece (1991)
    Springer
    Trees 5 (1991), S. 83-89 
    Details
    ISSN: 1432-2285
    Keywords: Air pollutants ; Chloroplasts ; Fluoride ; Olive tree leaves ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition
    Notes: Summary Leaves of olive trees growing in the vicinity of the Aluminium Factory of Greece were ultrastructurally investigated in order to determine any malformations caused by environmental air pollutants, especially hydrogen fluoride, in comparison with control samples and normal seasonal senescence. Estimation of some elements accumulated by these leaves showed that they contained high amounts of F and Al attributable to the operation of the nearby factory. The most seriously effected cell components were found to be the mesophyll chloroplasts that show a dilation of the intrathylakoid space, increase of the number of plastoglobuli, discoloration of plastoglobuli, accumulation of large starch grains and an overall disorganized appearance of the organelle. The nuclear crystalloid inclusions have unusual shapes, while the vacuoles contain a fibrillar/granular material that increases their electron density. It is concluded that the ultrastructural malformations are caused by a combination of environmental stresses and air pollutants.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00227489
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  • 34
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    Electronic Resource
    Different epithelia in the distal human male urethra (1991)
    Springer
    Cell & tissue research 264 (1991), S. 23-32 
    Details
    ISSN: 1432-0878
    Keywords: Male urethra ; Urethral epithelium ; Immunocytochemistry ; Ultrastructure ; Man
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary The distal segment of the human male urethra, in particular the fossa navicularis, was studied with light- and electron microscopy as well as by means of histochemical and immunocytochemical methods. The fossa navicularis of the urethra contains a circumscribed zone of extremely thick, non-keratinized stratified squamous epithelium composed of cells containing a large amount of glycogen. These cells lack acid phosphatase activity and lysozyme-like immunoreactivity, both of which can be demonstrated to varying extents in the other zones of the distal male urethra. These glycogen-rich cells are considered to be the substrate for an endogenous flora of lactobacteria, whereas the acid-phosphatase activity and the lysozyme-like immunoreactivity indicate the presence of macrophages and the secretion of bactericidal agents at the epithelial surface. These observations suggest that the different zones with heterogeneous properties in the distal male urethra probably represent a defense system against the invasion of pathogenic microorganisms. Moreover, the glycogen-rich zone, which resembles the glycogen-rich epithelium of the vagina, is estrogen-dependent. This is demonstrated in cases of sex reversal in which after long-lasting estrogen treatment the glycogen-rich zone becomes extremely extended by displacement of the neighbouring epithelium.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00305719
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  • 35
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    Electronic Resource
    Ultrastructure of melatonin-responsive cells in the ovine pars tuberalis (1991)
    Springer
    Cell & tissue research 263 (1991), S. 529-534 
    Details
    ISSN: 1432-0878
    Keywords: Melatonin ; Pituitary gland, pars tuberalis ; Secretory cells ; Cyclic AMP ; Ultrastructure ; Cell culture ; Sheep
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary Functional receptors for melatonin have been localized and characterized on the pars tuberalis (PT) of a number of mammalian species, but the cell-type responsive to melatonin is unknown. The ultrastructure of the ovine pars tuberalis has been examined and these findings correlated with the functional response of the gland to melatonin. This study revealed that two secretory cell types predominate in the ovine PT, which differ in the abundance of dense-core granules. The most abundant of the cells are either agranular or very sparsely granulated and represent 90% of the total population, with the remaining 10% being composed of cells with abundant dense-core vesicles. Few follicular cells were observed. This ratio of secretory cell-types persisted in primary culture, with the two types non-separable by Percoll gradient centrifugation. Using forskolin, as a non-specific stimulant of adenylate cyclase, melatonin was shown to inhibit the formation of cyclic AMP by 80–90% in cells both before and after Percoll centrifugation. The results demonstrate that the agranular secretory cells of the ovine pars tuberalis are the melatonin responsive cell-type of this gland.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00327285
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  • 36
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    Electronic Resource
    Ultrastructure and distribution of somatostatin-like immunoreactive neurons and nerve fibres in the coeliac ganglion of cats (1991)
    Springer
    Cell & tissue research 263 (1991), S. 567-572 
    Details
    ISSN: 1432-0878
    Keywords: Somatostatin ; Coeliac ganglion ; Autonomic innervation ; Ultrastructure ; Cat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary Somatostatin-like immunoreactivity was localized in nerve cell bodies and nerve terminals in the cat coeliac ganglion. Two types of somatostatin-immunoreactive cell bodies were revealed, the first being large (diameter 35 μm), numerous and weakly labelled, where—as the second was considerably smaller (diameter 10.4 μm), sparsely distributed and heavily stained. The immunoreactive nerve terminals were in synaptic contact with many immunonegative large neurons and dendrites. However, in a few cases, somatostatin-immunoreactive nerve terminals could also be observed on the surface of lightly stained neurons. Transection of vagal or mesenteric nerve failed to affect the distribution or density of somatostatin-like immunoreactive nerve terminals. These results demonstrate the existence of a synaptic input to the principal neurons of the coeliac ganglion of the cat by somatostatin-containing nerve terminals and suggest that this peptide may act as a neuromodulator or neurotransmitter. It is proposed that somatostatin-positive neurons provide intrinsic projections to other somatostatin-positive and to somatostatin-negative neurons throughout the coeliac ganglion, thereby creating a complex interneuronal system.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00327290
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  • 37
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    Electronic Resource
    Islets of preadipocytes highly committed to differentiation in cultures of adherent rat adipocytes (1991)
    Springer
    Cell & tissue research 264 (1991), S. 243-251 
    Details
    ISSN: 1432-0878
    Keywords: Preadipocytes ; Adipocyte precursor cells ; Adipose tissue ; Differentiation-cell cultures ; Ultrastructure ; Rat (Fischer 344)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary Cultures of adherent mature adipocytes, obtained from collagenase-digests of adipose tissue of the rat, invaribly contain rapidly proliferating, fibroblastlike cells despite the washing and centrifugation procedures empolyed during isolation of the fat cells. Such spindle-like cells originate from low-density structures, which we term “islets”, that are present, together with the mature adipocytes, in the floating layer of the digest of adipose tissue. Islets are found in preparations from adult (3–4 months old) as well as aging (17–24 months old) rats. By light-and electron microscopy, the islets appear as clusters of closely associated cells containing a variable amount of lipid-like material. Cells of endothelial or pericytic origin are also present in the islets. Within a few hours of culture, the islets give rise to those spindle-like cells that have been seen to proliferate in the cultures. By 36–48 hours, such cells begin to accumulate lipid droplets and, by 150 hours, assume the morphology of small mature adipocytes (diameter 20–35 μm) with a large central lipid droplet. The pattern of differentiation of these cells recalls that of preadipocytes derived from the stromal-vascular fraction of adipose tissue digests. Nonetheless, the extent and rapidity of their adipose conversion, as well as the culture conditions necessary for differentiation, are different and suggest that these cells are a substantially uniform subpopulation of adipocyte-precursor cells highly committed to differentiation.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00313961
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    Postnatal changes in the ultrastructure of the rat olfactory epithelium: the supranuclear region of the supporting cells (1991)
    Springer
    Cell & tissue research 265 (1991), S. 193-196 
    Details
    ISSN: 1432-0878
    Keywords: Postnatal development ; Olfactory epithelium ; Supporting cells ; Receptor cell dendrites ; Ultrastructure ; Rat (Wistar)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary The present electron-microscopical study reports ultrastructural changes occurring in the supranuclear region of the supporting cells of the rat olfactory epithelium during the first 16 days of postnatal life. These changes are concerned with the enclosure of receptor cell dendrites and an increase in the amount of smooth endoplasmic reticulum, which has a specific distribution in the supporting cell. An increase in microvillous projections at the free cell surface is also observed. Moreover, this report demonstrates that the cytoarchitecture of the apical portion of the olfactory epithelium at the 16th day of postnatal life is similar, with respect to the relationship between supporting cells and receptor cell dendrites, to that of adult animals.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00318154
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  • 39
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    Diversity of ultrastructure in different phenotypes of cultured microvessel endothelial cells isolated from bovine corpus luteum (1991)
    Springer
    Cell & tissue research 266 (1991), S. 37-49 
    Details
    ISSN: 1432-0878
    Keywords: Microvessel endothelial cells ; Cell culture ; Corpus luteum ; Ultrastructure ; Cow
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary Five different types of cultured microvessel endothelial cells defined by use of light microscopy and scanning electron microscopy in a preceding study were investigated by transmission electron microscopy. Type-1 cells displayed a deep invagination of the cell membrane or a single cilium. Granules of low electron density were abundant. A perinuclear ring of intermediate filaments occurred. Cultures of type-2 cells were subdivided into phenotype A, reminiscent of cell-type 1, and into phenotype B, assumed to be vascular smooth muscle cells. Many highly electron-dense granules appeared in late postconfluent cultures of both phenotypes. Cell-type 3 was conspicuous because of a large intracytoplasmic vacuole. Lysosomes with curvilinear bodies were found in cell-types 3 and 4. Both cell types developed a peripheral regular network of microfilaments. Cell-type 5 showed vesiculation of the rough endoplasmic reticulum, lipid droplets and a peripheral felt-like belt of microfilaments. Tubular forms seen in late postconfluent cultures of cell-types 1 to 3 displayed a core of extracellular matrix. Pseudotubular forms of cell-type 4 contained apoptotic bodies. Thus, as seen at the ultrastructural level, different features are maintained by cultured microvessel endothelial cells, suggesting that they have different inherent properties.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00678709
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  • 40
    Electronic Resource
    Electronic Resource
    Effect of cytokines on thymic hematopoietic precursors (1991)
    Springer
    Cell & tissue research 264 (1991), S. 369-375 
    Details
    ISSN: 1432-0878
    Keywords: Thymus ; CD4- ; CD8- ; thymocyte ; Thymic hematopoietic precursors ; Cytokines ; Ultrastructure ; Mouse (DBA/2, H-2d)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary We have previously shown that the interaction of thymocytes with thymic accessory cells (macrophages and/or interdigitating cells) is one of the factors required for thymocyte activation. Precursors of both thymic accessory cell and thymocytes are included in the CD4- CD8- Mac-1- Ia- subpopulation, and their respective maturation and/or activation may be modulated by granulocyte-macrophage colony-stimulating factor, interleukin 1 and interleukin 2. When CD4- CD8- thymic cells are activated with granulocyte-macrophage colony-stimulating factor plus interleukin 2, both macrophages and interdigitating-like cells are present, as shown by electron microscopy. When activated with interleukin 1 plus interleukin 2, the interdigitating-like cells is the only accessory cell present. In both culture conditions, large clusters are formed between interdigitating cells and lymphoid cells. These results have led us to propose two-step signals for thymocyte proliferation: first, the maturation of macrophages under granulocyte-macrophage colony-stimulating factor control and the production of interleukin 1, and secondly, the maturation of interdigitating cells under interleukin 1 control, their clustering with thymocytes which are then activated.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00313976
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  • 41
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    Electronic Resource
    The fine structure of lamellate cells in the brain of amphioxus (Branchiostoma lanceolatum, Cephalochordata) (1991)
    Springer
    Cell & tissue research 263 (1991), S. 597-600 
    Details
    ISSN: 1432-0878
    Keywords: Lamellate cell ; Ultrastructure ; Ciliary photoreceptors ; Nervous system, prochordates ; Branchiostoma lanceolatum (Acrania)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary The lamellate cells of amphioxus have round nuclei, and cytoplasm with many mitochondria and a large amount of glycogen. Each of these cells projects a highly modified, branched cilium into the central canal, where it characteristically forms lamellar structures. Primary branches and secondary lamellae often contain accessory microtubules that are not derived from the axonema. The functional and evolutionary significance of this cell type is discussed in relation to the ciliary photoreceptors found in other chordates.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00327295
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  • 42
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    Cell types in the fetal pars tuberalis of the human adenohypophysis at mid-gestation (1991)
    Springer
    Cell & tissue research 264 (1991), S. 161-165 
    Details
    ISSN: 1432-0878
    Keywords: Adenohypophysis ; Pars tuberalis ; Ultrastructure ; Immunohistochemistry ; Fetal ; Human
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary The pars tuberalis of the adenohypophysis was investigated in three human fetuses at mid-gestation by electron microscopy or immunohistochemistry. In addition to gonadotrophs and thyrotrophs, identified by immunohistochemistry and ultrastructural morphology, electron microscopy revealed the existence of an additional differentiated cell type closely resembling “pars tuberalis-specific” cells known from other species. The role of this cell type in the human endocrine regulation remains to be elucidated.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00305734
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  • 43
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    Effect of 1,10-phenanthroline on ultrastructure of pea leaves (1991)
    Springer
    Protoplasma 161 (1991), S. 23-30 
    Details
    ISSN: 1615-6102
    Keywords: 1,10-Phenanthroline ; Photodynamic herbicides ; Pisum sativum ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary We have examined ultrastructural changes of mesophyll cells in pea leaves induced by the photodynamic herbicide 1,10-phenanthroline (Phe). Dark incubation of pea plants did not cause any damage in plants or changes in the ultrastructure of mesophyll cells. Two hours of illumination after pretreatment with Phe caused photooxidative damage in plant but was not sufficient to markedly change the ultrastructure, although dilation of endoplasmic reticulum (ER) cisternae occurred. Illumination for 12 h caused inhibition of grana formation in pretreated plants. These ultrastructural changes and the inhibition of chlorophyll (Chl) accumulation may be due to the inhibition of transport of certain proteins to the plastids, diminished accumulation of chlorophyll proteins (e.g., LHCP) and a decrease in activity of the chlorophyll synthetase.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01328894
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  • 44
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    Electronic Resource
    Intercellular permeability inAbutilon nectary trichomes (1991)
    Springer
    Protoplasma 161 (1991), S. 150-159 
    Details
    ISSN: 1615-6102
    Keywords: Abutilon ; Lucifer Yellow ; Microinjection ; Nectary ; Transport ; Trichome ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Intercellular transport was examined in nectary hairs ofAbutilon slriatum var.thompsonii using dye-uptake and microinjection followed by fluorescence and electron microscopy. Dye-uptake experiments demonstrated that both Lucifer Yellow CH (LYCH) and diaminobenzidine (DAB) move centrifugally along an apoplastic pathway from the sepellary tissue towards the tip cell. Further, fluorescence of LYCH could also be detected inside the cells of the nectary trichome. When LYCH or LYCH/DAB were microinjected into the tip cell, the dye spread in a centripetal direction towards the stalk cell. Electron microscopical investigations of microinjected nectary hairs revealed numerous electron-opaque globules in the cytoplasm of the nectary hair cells. In addition, multivesicular bodies, nuclei with opaque regions and changes in the rough endoplasmic reticulum (RER) were seen in nectary hair cells even at very low concentrations of injected dye. Ultrastructural investigations provided evidence for cytological changes in microinjected nectary hairs.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01322727
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  • 45
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    Ultrastructure of the vegetative organisation and initial stages of silica plate deposition in the soil testate amoebaCorythion dubium (1991)
    Springer
    Protoplasma 163 (1991), S. 136-144 
    Details
    ISSN: 1615-6102
    Keywords: Corythion dubium ; Silica deposition ; Testate amoeba ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary The siliceous body plates ofCorythion dubium are bound by a band of organic cement which is thickest at the lateral margins. The anterior vacuolar cytoplasm is separated by a pigment zone, which forms a dark band in the mid-body region, from the compact posterior region containing a typical vesicular nucleus surrounded by a region of dense endoplasmic reticulum. A pellicular basket of microtubules surrounds the posterior cytoplasm. The large Golgi complex lies between the nucleus and the fundus. Numerous coated and uncoated vesicles from the Golgi cisternae are seen in the peripheral cytoplasm alongside developing plates. These small siliceous plates are enclosed in silicon deposition vesicles lying in surface ruffles of the plasmalemma, often in association with a pair of microtubules. Observations are made on the formation of these vesicles and the early stages of silica deposition. A comparison is drawn between silica deposition inC. dubium and choanoflagellates where there is a similar association between silicon deposition vesicles and microtubules.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01323337
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  • 46
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    Effects of heat shock and thermoadaptation on the ultrastructure of cowpea (Vigna unguiculata) cells (1991)
    Springer
    Protoplasma 163 (1991), S. 125-135 
    Details
    ISSN: 1615-6102
    Keywords: Cowpea ; Heat shock ; Thermoadaptation ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Suspension culture cells of cowpea (Vigna unguiculata) were examined using transmission electron microscopy to characterize morphological changes associated with hyperthermal stress. Cultures maintained at 26°C (unadapted cells) and 38°C (thermoadapted cells) were examined before and after exposure to elevated temperatures of 34°C and 45°C, respectively. Observations indicate that while there were significant ultrastructural differences between unadapted and thermoadapted cells, the following structural modifications in response to heat stress were observed in cells of both cultures: (a) almost a complete loss of polyribosomes, rough ER, and dictyosomes, (b) migration of intracellular waste material (presumably proteinaceous in composition) into the cell vacuole, (c) swelling of the nucleolus with assumed accumulation of preribosomal RNP granules, and (d) retraction of the tonoplast from the cytoplasm into the vacuoles of some cells. Heat shock granules (two size classes) were observed in the cytoplasm of stressed thermoadapted cells along with hollow-cored granules within the leucoplasts. Apart from a few minor differences, the morphological modifications that were made in apparent response to hyperthermal stress were remarkably similar in both cultures.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01323336
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  • 47
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    Ontogeny and ultrastructure of spontaneous nodules in alfalfa (Medicago sativa) (1991)
    Springer
    Protoplasma 162 (1991), S. 1-11 
    Details
    ISSN: 1615-6102
    Keywords: Rhizobium meliloti ; Development ; Symbiosis ; Nitrogen fixation ; Ultrastructure ; Spontaneous nodule
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary The development of spontaneous nodules, formed in the absence ofRhizobium and combined nitrogen, on alfalfa (Medicago sativa L. cv. Vernal) was investigated at the light and electron microscopic level and compared to that ofRhizobium-induced normal nodules. Spontaneous nodules were initiated from cortical cell divisions in the inner cortex next to the endodermis, i.e., the site of normal nodule development. These nodules, on uninoculated roots, were white multilobed structures, histologically composed of nodule meristems, cortex, endodermis, central zone and vascular strands. Nodules were devoid of intercellular or intracellular bacteria confirming microbiological tests. Early development of spontaneous nodules was initiated by series of anticlinal followed by periclinal divisions of dedifferentiated cells in the inner cortex of the root. These cells formed the nodular meristem from which the nodule developed. The cells in the nodule meristems divided unequally and differentiated into two distinct cell types, one larger type being filled with numerous membrane-bound starch grains, and the other smaller type with very few starch grains. There were no infection threads or bacteria in the spontaneous nodules at any stage of development. This size differentiation is suggestive of the different cell sizes seen inRhizobium-induced nodules, where the larger cell type harbours the invading bacteria and the smaller type is essential in supportive metabolic roles. The ontogenic studies further support the claim that these structures are nodules rather than aberrant lateral roots, and that plant possess all the genetic information needed to develop a nodule with distinct cell types. Our results suggest that bacteria and therefore theirnod genes are not necessarily involved in the ontogeny and morphogenesis of spontaneous and normal nodules in alfalfa.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01403895
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  • 48
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    The occurrence and ultrastructure of a mechanoreceptor in the human cricopharyngeus muscle (1991)
    Springer
    European archives of oto-rhino-laryngology and head & neck 248 (1991), S. 144-146 
    Details
    ISSN: 1434-4726
    Keywords: Cricopharyngeus muscle ; Golgi tendon organ ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary An encapsulated nerve structure resembling the Golgi tendon organ was found in a human cricopharyngeus muscle near the cricoid cartilage where muscle fibers terminate. The capsule consisted of lamellated flattened cells with a basal lamina. Capsular cells separated the lumen into small compartments which contained myelinated and/or nonmyelinated nerve fibers. Nonmyelinated nerve fibers were also found in the interlamellar spaces of the capsular cells. Some nonmyelinated nerve fibers were dilated and contained abundant mitochondria, being partly surrounded by a Schwann cell sheath and embedded in collagen bundles. These features indicate that the nerve structure is a mechanoreceptor similar to the Golgi tendon organ. Its location and structure indicate that it is placed to detect the tension of the cricopharyngeus muscle.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00178924
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  • 49
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    A New General Synthesis of 2,2-Dialkyl-2,3-dihydro-4H-pyran-4-ones and Their Application for the in situ Preparation of Electron-Rich Dienes in Carbonyl-Alkyne Exchange Reactions with AcetylenesPresented in part at the autumn meeting of the Swiss Chemical Society in Bern on October 20, 1989. (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 27-46 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The substituted 2,2-dialkyl-2,3-dihydro-4H-pyran-4-ones of type II and III have been prepared by acid-catalyzed cyclization of the corresponding substituted acetylenic ketones I in good to excellent yields (Scheme 1). These 2,2-dialkyl-2,3-dihydro-4H-pyran-4-ones II and III have been used for the in situ preparation of highly reactive dienes of type IV-VI (Scheme 2) in carbonyl-alkyne exchange reactions with electron-poor alkynes VII to yield the highly substituted aromatic compounds VIII and IX. These reactions proceed in good yields and with excellent degree of regioselectivity. Aryl-substituted 2,2-dialkyl-2,3-dihydro-4H-pyran-4-ones III (R1 = Ar) subsequently yield highly substituted biaryls. Reaction mechanisms are presented for the formation of the 2,2-dialkyl-2,3-dihydro-4H-pyran-4-ones as well as for the carbonyl-alkyne exchange reactions with electron-poor acetylenes.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740106
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  • 50
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    Structural and Luminescence Study of the 3:2 Complex between Europium Nitrate and the B Isomer of Dicyclohexyl-18-crown-6Part 40 of the series ‘Complexes of Lanthanoid Salts with Macrocyclic Ligands’; Part 39 [1]. (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 65-78 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The crystal and molecular structure of bis[dinitrato-(2,4,8,15,18,21-hexaoxatricyclo[20.4.0.09,14]hexacosane)europium(III)]pentakis(nitrato)europiate(III) [Eu(NO3)2LB]2([Eu(NO3)5]), has been determined at 170 K from single-crystal X-ray diffraction. The complex crystallizes in the monoclinic space group P21/n (ITC No. 14): a = 16.338(3) Å, b = 15.704(3) Å, c = 24.474(4) Å, β = 97.73(1)°, Z = 4. The structure was refined to a final R value of 0.058 (Rw = 0.060). The asymmetric unit contains three independent ions lying on general positions: [Eu(NO3)5]2- and two distinct [Eu(NO3)2LB]+ cations with the macrocyclic ligand in the cis-anti-cis conformation (B-isomer). The EuIIIions are 10-coordinate with the following mean bond lengths: Eu-O(nitrate) = 2.48(2) Å in the anion and 2.45(2) Å in the two cations, Eu-O(ether) = 2.56(8) and 2.55(5) Å. Small but significant differences are observed between the two complex cations, especially with respect to the positions of the cyclohexyl substituent. A conformational analysis performed on the six O-atoms of the complex cations confirms the predictions of a simple model. The metal ion sites of the complex have been probed by high-resolution excitation and emission spectra at 296 and 77 K. The 5D0←7F0 excitation spectrum displays two main bands along with several other minor components. A detailed analysis of the corresponding and selectively excited emission spectra leads to the observation of three types of spectra corresponding to the three crystallographically different EuIII ions. Moreover, three minor sites are identified, one anionic and two cationic, with a population equal to ca. 10% of the population of the main sites. We interpret this finding as reflecting the presence of molecules with slightly different conformations.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740109
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    Asymmetric Diels-Alder Cycloadditions with C2-Symmetrical Chiral Carbamoylnitroso Dienophiles (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 103-109 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The C2-symmetrical chiral pyrrolidines 2 and 3 are of opposite helicity. The corresponding N-acylnitroso dienophiles 6 and 7 react in good yield with cyclohexadiene, leading thereby with excellent diastereoisomeric excess to the expected Diels-Alder cycloadducts (see Scheme). The [2.2.2] bicyclic moieties of the major diastereoisomers 9 and 11 proved to be of opposite configuration, as expected. Their configuration is best explained by assuming the acylnitroso dienophile to be in the s-cis conformation in the transition state, the approach of the diene being endo (see Fig.).
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740112
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  • 52
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    2,3- and 4,5-Secodopa, the Biosynthetic Intermediates Generated from L-Dopa by an Enzyme System Extracted from the Fly Agaric, Amanita muscaria L., and Their Spontaneous Conversion to Muscaflavin and Betalamic Acid, Respectively, and Betalains (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 124-140 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An enzyme is extracted from the red peel of Amanita muscaria which cleaves the C(2)-C(3) and the C(4)-C(5) bond of the aromatic ring of L-dopa (1) to form a mixture of 4,5-secodopa (= salt of 6-amino-2-hydroxy-4-(2′-oxoethylidene)hept-2-enedioic acid; 2) and 2,3-secodopa ( = salt of 7-amino-5-formyl-2-hydroxyocta-2,4-dienedioic acid; 3), two hitherto hypothetical biosynthetic intermediates (see Scheme). Though isolation of these products has not been possible, structural evidence is inferred from reaction products, kinetics, and spectroscopical characteristics in comparison with known compounds. Secodopas 2 and 3 are characterized in dilute solution by HPLC and UV/VIS spectroscopy (anions; λmax 424 and 414 nm, resp., ∊420 = 25500; on acidification, shift to 380 and 372 nm, resp.). They cyclize without enzyme catalysis, optimally at pH 4.5-5; 3 produces muscaflavin (5) and 2 betalamic acid (4). The products arc identified by direct comparison with authentic samples in HPLC, by 1H-NMR of 5, and by condensation of 4 with L-proline to form the well known betalain indicaxanthin (7). The enzymatic conversion of L-dopa (1) via 2 to betalamic acid (4; (S)) and its condensation with L-proline leads to pure natural indicaxanthin (7; (2S,115)); correspondingly, the enzymatic conversion of D-dopa to (R)-betalamic acid and its condensation with L-proline produces isoindicaxanthin ((2S,11R)) which is unknown in nature. Particularly relevant is the fact that the same enzyme cleaves pyrocatechol to produce a solution of the enolate form of the known 2-hydroxy-6-oxohexa-2,4-dienoate (secopyrocatechol; 9; see Fig. 5). Dissociation constants of the corresponding enolic functions in the cleavage products are determined by spectrometric titration and compared to those of known systems.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740115
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  • 53
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    Photochemical Reactions of Tetrahydroquinoxalin-2(1H)-ones and Related Compound (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 225-231 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Photochemical behaviors of the pyrazinone derivatives 5,6,7,8-tetrahydroquinoxalin-2(1H)-ones 1a-c and 1,5,6,7,8,9-hexahydro-2H-cyclohepta[b]pyrazin-2-one 1d were investigated. Dye-sensitized photo-oxygenation of 1a-c gave the 1:1 adducts 5a-c of the corresponding 3,8a-epidioxy-3,5,6,7,8,8a-hexahydroquinoxalin-2(1H)-one 4 and H2O, whereas 1d gave 3,9a-epidioxy-1,3,5,6,7,8,9,9a-octahydro-2H-cyclohepta[b]pyrazin-2-one 4d (Scheme 2). The different kind of products was interpreted as being the result of the ring strain and steric hindrance of endoperoxides produced from 1a-d with singlet oxygen. Irradiation of 1a-b in the presence of alkenes gave tricyclic azetidine derivatives 9 by [2 + 2] cycloaddition of the C=N bond of 1 to the alkene.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740122
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  • 54
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    Analogues of Sialic Acids as Potential Sialidase Inhibitors. Synthesis of C6 and C7 Analogues of N-Acetyl-6-amino-2,6-dideoxyneuraminic Acid (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 343-369 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The piperidines 12-18, piperidmose analogues of Neu5Ac (1) with a shortened side chain, were synthesized from N-acetyl-D-glucosamine via the azidoalkene 32 and tested as inhibitors of Vibrio cholerae sialidase. Deoxygenation at C(4) of the uronate 22, obtained from the known D-GlcNAc derivative 20, was effected by β-elimination (→ 23), exchange of the AcO at C(3) with a (t-Bu)Me2SiO group and hydrogenation (→ 26; Scheme 1). Chain extension of 26 by reaction with Me3SiCH2MgCl gave the D-ido-dihydroxysilane 28, which was transformed into the unsaturated L-xylo-mesylate 29 and further into the L-lyxo-alcohol 30, the mesylate 31, and the L-xylo-azide 32. The derivatives 29-31 prefer a sickle zig-zag and 32 mainly an extended zig-zag conformation (Fig. 2). The piperidinecarboxylate 15 was obtained from 32 by ozonolysis (→ 33), intramolecular reductive animation (→ 34), and deprotection, while reductive animation of 34 with glycolaldehyde (→ 35) and deprotection gave 16 (Scheme 2). An intramolecular azide-olefin cycloaddition of 32 yielded exclusively the fused dihydrotriazole 36, while the lactone 39 did not cyclize (Scheme 3). Treatment of 36 with AcOH (→ 37) followed by hydrolysis (→ 38) and deprotection led to the amino acid 18. To prepare the (hydroxymethyl)piperidinecarboxylates 12 and 17, 32 was first dihydroxylated (Scheme 4). The L-gluco-diol 40 was obtained as the major product, in agreement with Kishi's rule. Silylation of 40 (→ 42), oxidation with periodinane (→ 44), and reductive animation gave the L-gluco-piperidine 45. It was, on the one hand, deprotected to the amino acid 12 and, on the other hand, N-phenylated (→ 46) and deprotected to 17. While 45 and 12 adopt a 2C5 conformation, the analogous N-Ph derivatives 46 and 17 adopt a 5C2 and a B3,6 conformation, respectively, on account of the allylic 1,3-strain. The conformational effects of this 1,3-strain are also evident in the carbamate 47, obtained from 45 (Scheme 5), and in the C(2)-epimerized bicyclic ether 48, which was formed upon treatment of 47 with (diethylamino)sulfur trifluoride (DAST). Fluorination of 40 with DAST (→ 49) followed by treatment with AcOH led to the D-ido-fluorohydrin 50. Oxidation of 50 (→ 51) followed by a Staudinger reaction and reduction with NaBH3CN afforded the (fluoromethyl)piperidine 52, while reductive amination of 51 with H2/Pd led to the methylpiperidine 55, which was similarly obtained from the keto tosylate 54 and from the dihydrotriazole 36. Deprotection of 52 and 55 gave the amino acids 13 and 14, respectively. The aniline 17 does not inhibit V. cholerae sialidase; the piperidines 12-16 and 18 are weak inhibitors, evidencing the importance of an intact 1,2,3-trihydroxypropyl side chain.
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    Synthese von Monomorin I, einem Spurpheromon der Pharao-Ameise (Monomorium pharaonis) (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 438-444 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of Monomorin I, a Trail Pheromone of the Pharao Ant (Monomorium pharaonis)Katalytic hydrogenation of the 4-nitroalkanone 5 yielded the cis-pyrrolidine ester 6 (Scheme). The preparation of 5 was accomplished by ethanolysis of the nitrocyclohexanone derivative 4. Iodination at C(α) of 6, followed by cyclization, gave a nearly 5:6 mixture of the two C(5)-epimers 10/9 of octahydroindolizine. Epimerisation of the undesired 10 to 9 and subsequent transformation of the latter gave racemic monomorine I (1; 34% yield from 5).
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    Masthead (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991) 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
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    URL: http://dx.doi.org/10.1002/hlca.19910740301
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    Structure cristalline d'une thiazolorifamycine: rifamycine P (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 326-330 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Crystal Structure of a Thiazolorifamycine: Rifamycine PThe crystal structure of a natural thiazolorifamycin, rifamycin P, as an adduct with EtOH and H2O, has been determined by X-ray crystallography by a combination of direct methods and Patterson techniques. Block-diagonal least-squares refinement using 5996 independent reflections and 1475 parameters led to an R factor of 0.092 (two independent molecules of rifamycin P). The middle part of the ansa chain, essential for activity against the bacterial DNA-dependent RNA polymerase (DDRP) resembles that of active rifamycins. The four OH groups lie on the same side of the molecule and are almost in the same plane. Interatomic distances between the O-atoms agree well with a spatial model derived from X-ray studies, performed on semisynthetic active rifamycins.
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    Synthesis of 4-{{[(Isopropyloxy)methylphosphoryloxy]imino}methyl}-1-methylpyridinium Iodide and Its Characterisation (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 331-335 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Oximes are used in the therapy of organophosphate poisoning. They form an interaction product with the organophosphate which is claimed to be more toxic than the organophosphate itself. We have synthesized one of these compounds which would be formed by the reaction of pyridine-4-carbaldehyde oxime methiodide with sarin (GB). Thus, reaction of oxime 1 with sarin chloridate (2), yielded 4-{{[(isopropyloxy)methylphosphoryloxy]-imino}methyl}-1-methylpyridinium iodide (4) which was characterized by NMR spectroscopy and X-ray crystallography.
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    Transformations in the Isoxazole Series: Synthesis of Substituted 2-AminothiazolesDedicated to Prof. Dr. Oskar Jeger (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 531-542 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Substitued N-(isoxazol-4-yl)thioureas 1 undergo a transformation in the presence of hexacarbonylmolybdenum and acid to yield functionalized thiazoles 3 in a one-pot reaction. In a few cases, 1,4,5-trisubstituted dihydroimidazolethiones 4 are also isolated as side products. Mechanistic considerations are outlined and scope and limitations of this new methodology discussed.
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    Biosynthesis of the Spermine Alkaloid Aphelandrine (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 565-571 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Aphelandrine (1) is shown to be biosynthesized in the root cells of Aphelandra tetragona (VAHL) NEES from labelled putrescine (4), spermidine (5), and cinnamic acid (3). Whether spermine (6) and the (p-hydroxycinnamoyl)spermidine 8 are precursors of 1 is uncertain, since the latter is hydrolysed to a large extent before incorporation, and the former is metabolized to 4 and 5. Methionine (7) is the source of the 3-aminopropyl unit of 5 and 6.
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    Glycosylidene Carbenes. Part 3. Synthesis of SpirocyclopropanesPresented at the ‘XVIth International Carbohydrate Symposium’, Yokohama, Japan, 12th-17th August 1990, Abstr. PL-05. (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 585-593 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Thermolysis of the glycosylidene-derived O-benzylated diazirine 1 in the presence of N-phenylmaleimide (2), acrylonitrile (3), dimethyl fumarate (4), or dimethyl maleate (5) led in good yields to mixtures of the spirocyclopropanes 6/7, 8-11, 12/13, and 12/13/16/17. The diastereoselectivity depends upon the alkene. The cycloaddition of 1 to 5 is not diastereospecific, in keeping with previous results. Deprotection of 12, 13, 16, and 17 yielded the tetrols 14,15, 18, and 19, respectively.
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    Lithium-Salt Effects in Peptide Synthesis. Part II. Improvement of Degree of Resin Swelling and of Efficiency of Coupling in Solid-Phase Synthesis (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 628-643 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The course of solid-phase peptide-coupling reactions as well as the swelling properties of a peptide-resin are influenced by the addition of inorganic salts (LiCl, LiBr, LiClO4, KSCN). Used as additives, these salts can (i) improve coupling yields (e.g., for Fmoc-(Ala)5-Phe-resin → Fmoc-(AIa)6-Phe-resin in DMF/CH2Cl2 1:1 from 89.4 to 97.1% (for polyethylene oxide) on polystyrene (= PEO-PS) resin) or from 77.5 to 93.8% (for poly-(N,N′-dimethylacrylamide) on ‘Kieselgur’ (=PDMAA-KG) resin) without and with 0.4M LiCl, respectively), (ii) increase resin swelling (e.g. for Fmoc-(Ala)5-Phe-(polystyrene resin) from 2.42- to 5.73-fold in 1-methylpyrrolidin-2-one (=NMP) without and with LiCl, (respectively), and (iii) change coupling rates. Example;; of coupling reactions and swelling behaviour (degree and rate) in different solvents (DMF, DMF/CH2Cl2 1:1, THF, NMP, N,N-dimethylpropyleneurea (= DMPU) with and without salts) using different resins (polystyrene (PS); PEO-PS, and PDMAA-KG) and an improved analysis of alanine oligomers up to Ala12-Phe by HPLC and FAB-MS are reported.
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    On the Methyl-Transfer Reaction in Crystalline Methyl 2-(Methylthio)benzenesulfonate: a Thermally Induced Non-Topochemical Solid-State Reaction (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 662-669 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The rearrangement of methyl 2-(methylthio)benzenesulfonate (1) to the zwitterionic 2-(dimethyl-sulfonium)benzenesulfonate (2) is known to proceed in solution by intermolecular Me transfers. The same rearrangement has been observed to occur in crystalline 1, but the crystal structure shows that the molecular packing is not conducive to intermolecular Me transfer. The reaction has been carried out with mixed crystals composed of 1 and deuteriomethylated (D6)-l. By fast-atom-bombardment mass spectroscopy, it has been shown that the product consists of a 1:2:1 mixture of the non-, tri-, and hexadeuterated species, the mixture expected, if the solid-state reaction proceeds by intermolecular Me transfers. From this result, together with the slower rates of conversion in the single crystal compared with the melt, it can be concluded that the reaction must occur not topochemically but rather at defects such as microcavities, surfaces, and other irregularities in the ordered crystal arrangement.
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    Syntheses and Crystal Structures of 4,5-Dihydro-2-(2′-hydroxyphenyl)oxazole-Containing Metal Complexes (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 717-726 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of the complexes 3 of various metals ligated to chiral 4,5-dihydro-2-(2′-oxidophenyl-ϰO)oxazoles-ϰN is described (Scheme). Three of them, i.e. 3a, 3e, and 3f containing CuII, ZnII and NiII, respectively, were analyzed by X-ray diffraction studies. A series of CuII complexes (6a-d) with differently substituted dihydrooxazoles have been synthesized.
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    1-(2′-Deoxy-β-D-xylofuranosyl)thymine Building Blocks for Solid-Phase Synthesis and Properties of Oligo(2′-Deoxyxylonucleotides) (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 748-760 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1-(2′-Deoxy-β-D-threo-pentofuranosyl)thymine (= 1-(2′-deoxy-β-D-xylofuranosyl)thymine; xTd; 2) was converted into its phosphonate 3b as well as its 2-cyanoethyl phosphoramidite 3c. Both compounds were used for solid-phase synthesis of d[(xT)12-T] (5), representing the first DNA fragment build up from 3′-5′-linked 2′-deoxy--β-D-xylonucleosides. Moreover, xTd was introduced into the innermost part of the self-complementary dodecamer d(G-T-A-G-A-A-xT-xT-C-T-A-C)2 (9). The CD spectrum of d[(xT)12-T] (5) exhibits reversed Cotton effects compared to d(T12) (6; see Fig. 1), implying a left-handed single strand. With d(A12) (7) it could be hybridized to form a propably Left-handed double strand d(A12) · d[(xT)12-T] (7·5) which was confirmed by melting experiments in combination with temperature-dependent CD spectroscopy. While 5 was hydrolyzed by snake-venom phosphodiesterase, it was resistant towards calf-spleen phosphodiesterase. The modified, self-complementary duplex 9 was hydrolyzed completely by snake-venom phosphodiesterase, at a twelvefold slower rate compared to unmodified 8; calf-spleen phosphodiesterase hydrolyzed 9 only partially.
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    Conformational Analysis of Marine Polyhalogenated β-Chamigrenes Through Temperature-Dependent NMR SpectraPresented in part by G.G. at both CISCI 90, S. Benedetto del Tronto, 30 September-5 October 1990, and the Congresso Nazionale di Risonanze Magnetiche, Pisa, 22-24 October 1990. (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 774-786 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Temperature-dependent 1H- and 13C-NMR spectra reveal that polyhalogenated marine β-chamigrenes or synthetic derivatives thereof which are trans-diequatorially, substituted at C(8) and C(9), such as rogiolol ((-)-2), obtusol ((+)-3), and their acetates (+)-1 and (-)-4, undergo slow ring-A chair-chair inversion. Conformational equilibria and kinetics are investigated with the aid of synthetic model compounds and molecular-mechanics calculations. Thus, steric repulsions between Brax-C(2) and Heq-C(7) are seen to disfavour thermodynamically conformers 1b, 2b, 3b, and 4b, which can only be detected through cross-saturation transfer, while additional steric repulsions between Meax-C(1) and OHax-C(3) make conformer 8b of obtusol epimer so scarcely populated that it can not be detected. In agreement, with (+)-9 and (+)-10, which have a trigonal C(2), two conformers can be directly observed by NMR. The kinetic barriers, which are seen to arise mainly from steric repulsions between Hax-C(14) and the axial H or halogen atoms at C(8) and C(10), are calculated and discussed with respect to well documented exocycliemethylidene-substituted cyclohexane(ene) systems. This helps to rationalize why in rogiolol acetate ((+)-1) ring B is unusually inert towards Zn/Et2O/AcOH which causes bromohydrine-group elimination from ring A.
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    Cycloviolaxanthin (= (3S,5R,6R,3′S,5′R,6′R)-3,6:3′,6′-Diepoxy-5,6,5′,6′-tetrahydro-β,β-carotin-5,5′-diol), ein neues Carotinoid aus Paprika (Capsicum annuum) (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 819-824 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cycloviolaxanthin (= (3S,5R,6R,3′S,5′R,6′R)-3.6:3′,6′-Diepoxy-5,6,5′,6′-tetrahydro-β,β-carotene-5,5′-diol), a Novel Carotenoid from Red Paprika (Capsicum annuum)From red paprika (Capsicum annuum var. longum nigrum) cycloviolaxanthin was isolated as a minor carotenoid and, based on spectral data, assigned the symmetrical structure 8.
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    Studies Directed Towards the Biosynthesis of the C7N Unit of Rifamycin B: A New Synthesis of Quinic Acid from Shikimic Acid (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 807-818 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of quinic acid (4) via epoxide 13, starting from shikimic acid (5), is described (Scheme 1). Treatment of 13 with thiophenol yielded not only 17, but also the γ-lactones 18 and 19 as result of migration of silyl groups within a cis- and trans-diol system. The conversion provides a direct stereoselective epoxidation of a shikimic-acid derivative as well as an alternative pathway for the preparation of 4. A shorter approach via the disilylated epoxide 22 was unsuccessful because the γ-lactone 25 was obtained in place of the desired α-hydroxy ester 24 (Scheme 2).
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    Nucleotides. Part XXXVIPart XXXV:[1]. Syntheses and biological characterization of phosphorothioate analogues of (3′-5′)adenylate trimer (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 892-898 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The four protected diastereoisomcrs 7a/7b and 8a/8b P-thioadenylyl-(3′-5′)-P-thioadenylyI-(3′-5′)-adenosine were synthesized, separated, and deblocked to the free oligonucleotides (Scheme). Biochemical characterization of these (3′-5′)phosphorothioate analogues of adenyiate trimer indicate that these compounds, and the corresponding 5′-monophosphates, neither bind to nor activate RNase L, and are considered to be valuable control compounds in screening experiments.
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    Double-Diamond Inclusion Compounds of 2,6-Dimethylydeneadamantane-1,3,5,7-tetracarboxylic Acid (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 825-877 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The crystal structures of four inclusion compounds of 2,6-dimethylideneadamantane-1,3,5,7-tetracarboxylic acid (4) are described, which involve the following guest species: (a) a mixture of 4-methylpent-3-en-2-one, 2,6-dimethylhepta-2,5-dien-4-one, and mesitylene (condensation products of acetone); (b) mesitylene; (c) a mixture of 4-methylpent-3-en-2-one and mesitylene; (d) (tert-butyl)benzene. In all four cases, the host architectures consist of two interpenetrating super-diamond networks built up by the tetra-acid molecules via pairwise H-bonds between the tetrahedrally directed COOH groups. In the first three cases (tetragonal crystal symmetry), the two diamond-like host lattices interpenetrate symmetrically, in the fourth case (monoclinic) asymmetrically. This asymmetry is brought about by the increased steric bulk of the (tert-butyl)benzene guest molecules. Attempts to enforce an inclusion compound of 4 with a single, extremely hollow diamond-like host lattice by offering still bulkier guest molecules have as yet not been met with success. The generally very high propensity of 4 to form inclusion compounds was envisaged and designed beforehand by appropriate evaluation and modulation of the crystal structure of the parent adamantane-1,3,5,7-tetracarboxylic acid, which represents a fivefold diamond-like self-inclusion compound. Crystals of the free, uncomplexed 4 appear to be extremely unstable and could so far not be obtained. On the other hand, from aqueous solution a very stable monohydrate of 4 may be crystallized (4-H2O), which was also subjected to X-ray analysis. The (triclinic) crystal structure of 4·H2O involves an interesting dichotomy inasmuch its pattern of H-bonding may be rationalized either in terms of a double, cross-linked super-zincblende (sphalerite) architecture, or as a system of porous, puckered 4-connected sheets, which interpenetrate each other pairwise and are cross-linked by the H2O molecules. Various structure and (space group) symmetry characteristics of the supramolecular solid-state complexes reported here are highlighted by pointing out analogies with comparable structures retrieved from the literature.
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    Masthead (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991) 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740501
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    Novel Antifungal Tetracyclic Compounds from Bauhinia rufescens LAM.Presented in part at the Meeting of the Swiss Chemical Society, Bern, 19th October 1990. (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 791-799 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: As the root bark CH2Cl2 extract of Bauhinia rufescens showed antifungal activity in a bioassay with the plant pathogenic fungus Cladosporium cucumerinum, a phytochemical investigation was undertaken on material collected in Niger. Activity-guided fractionation of this extract, using different preparative chromatographic methods, allowed the isolation of the four new antifungal tetracyclic compounds 1-4. Their structures were established by 1H- and 13C-NMR data, and single-crystal X-ray analyses were used to confirm the structures of 1 and 3. The isolated compounds seem to be biogenetically related to a stilbene.
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    URL: http://dx.doi.org/10.1002/hlca.19910740413
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  • 73
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    Versatile Stereoselective Synthesis of Completely Protected Trifunctional α-Methylated α-Amino Acids Starting from Alanine (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 800-806 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new route to completely protected α-methylated α-amino acids starting from alanine is described (see Scheme). These derivatives, which are obtained via base-catalyzed opening of the oxazolidinones (2S,4R)- and (2R,4S)-2, can be directly employed in peptide synthesis. The synthesis of both enantiomers of Z-protected α-methylaspartic acid β-(tert-butyl)ester (O4-(tert-butyl) hydrogen 2-methylaspartates (R) or (S)-4a), α-methyl-glutamic acid γ-(tert-butyl) ester (O5-(tert-butyl) hydrogen 2-methylglutamate (R)- or (S)-4b), and of Nε-bis-Boc-protected α-methyllysine (N6,N6-bis[(tert-butyloxy)carbonyl]-2-methyllysine (R)- or (S)-4c) is described in full detail.
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  • 74
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    Nucleotides. Part XXXVPart XXXV:[1]. Synthesis of 3′-deoxyadenylyl-(2′-5′)-3′-deoxyadenyIyl-(2′-ω)-9-(ω-hydroxyalkyl)adenines (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 887-891 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Via the phosphotriester approach, new structural analogs of (2′-5′)oligoadenyiates, namely 3′-deoxyadenylyl-(2′-5′)-3′-dcoxyadenylyl-(2′-ω)-9-(ω-hydroxyalkyl)adenines 18-21, have been synthesized (see Scheme) which should preserve biological activity and show higher stability towards phosphodiesterases. The newly synthesized oligonucleotides 18-21 have been characterized by 1H-NMR spectra, TLC, and HPLC analysis.
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    URL: http://dx.doi.org/10.1002/hlca.19910740419
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  • 75
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    Mitteilungen (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 905-906 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740423
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  • 76
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    [5-Leucin]enkephalin-Related Glycoconjugates: Structurally Novel Agents Effective against HIV-1 (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 951-955 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of [Leu5]enkephalin-related glycoconjugates with an ester-, ether-, or amide-type linkage were synthesized and evaluated for antiviral activity against HIV-1 in a cell-culture system using peripheral blood lymphocytes. All tested glycoconjugates exhibited a certain antiviral activity which was significantly higher than the activity of the parent peptide compound itself. These results indicate that synthetic glycoconjugates of opioid peptides are good candidates for the development of anti-HIV agents.
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    URL: http://dx.doi.org/10.1002/hlca.19910740505
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  • 77
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    Synthesis, Isolation, and Full Spectroscopic Characterization of Eleven (Z)-Isomers of (3R,3′R)-Zeaxanthin (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 969-982 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Developmental efforts to improve the yield of the chemical synthesis of (3R,3′R)-zeaxanthin resulted in the isolation, partly by chromatography from reaction mixtures, and full spectroscopic characterization by 1H-NMR, UV/VIS, and CD spectrosocpy of eleven (Z/E)-isomers of zeaxanthin: (7Z)-, (9Z), (13Z)-, (15Z)-, (7Z,7′Z)-, (9Z,9′Z)- (7Z,9Z,7Z)-, (7Z,11Z,7′Z)-, (9Z,13Z,9′Z)-, (7Z,9Z,7′Z,9′Z)-, and (7Z,9Z,11Z,7′Z,9′Z)-zeaxanthin. Five of these isomers were obtained by specific synthesis, namely the (7Z)-, (7Z,7′Z)-, (9Z,9′Z)-, (7Z,9Z,7′Z)-, and (7Z,9Z,7′Z-9Z)-isomers.
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  • 78
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    Ringerweiterung von 1,2-Thiazol-3(2H)-on-1,1-dioxiden und 3-Amino-2H-azirinen zu 4H-1,2,5-Thiadiazocin-6-on-1,1-dioxiden (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1002-1010 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ring Enlargement of 1,2-Thiazol-3(2H)-one-1,1-dioxides and 3-Amino-2H-azirines to 4H-1,2,5-Thiadiazocin-6-one-1,1-dioxidesReaction of 3-amino-2H-azirines 2 with the 1,1-dioxides 4 and 7 of 1,2-thiazol-3(2H)-ones and 1,2-thiazoli-din-3-ones, respectively, in i-PrOH at room temperature leads to 4H-1,2,5-thiadiazocin-6(5H)-one-1,1-dioxides 5 (Scheme 2, Table) and the corresponding 7,8-dihydro derivatives 8 (Scheme 4), respectively. The structure of some of the new 8-membered heterocycles as well as the structure of the minor by-product 6 (Scheme 3) have been established by X-ray crystallography (Chapt. 4). The proposed reaction mechanism for the ring expansion to 5 and 8 (Scheme 2) is in accordance with previously published results of reactions of 2 and NH-acidic heterocycles and is further supported by the results of the reaction of 4a and the (1-15N)-labelled aminoazirine 2a*.
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  • 79
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    Zur Oxidation von 1,2-Thiazolen: Ein einfacher Zugang zu 1,2-Thiazol-3(2H)-on-1,1-dioxidenHerrn Prof. Dr. Siegfried Hauptmann zum 60. Geburtstag gewidmet (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1059-1070 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Oxidation of 1,2-Thiazoles; A Convenient Approach to 1,2-Thiazol-3(2H)-one 1,1-DioxidesThe 1,2-thiazoles obtained from 3-chloroalk-2-enals and ammonium thiocyanate (7 → 9, Scheme 1) are easily transformed to 1,2-thiazol-3(2H)-one 1,1-dioxidcs 10 on treatment with H2O2 in AcOH at 80°. Hydrogenation of 10 in AcOH yields the corresponding saturated 1,2-thiazolidin-3-one 1,1-dioxides 16 (Scheme 3). Cycloalka[c]-1,2-thiazoles 18 are prepared from 2-[(thiocyanato)methyliden]cycloalkan-1-ones and ammonia (Scheme 4). Surprisingly, oxidation of 18a with H2O2 in AcOH yields the tricyclic oxaziridine 19.
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    URL: http://dx.doi.org/10.1002/hlca.19910740515
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  • 80
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    Zur Synthese von Derivaten des Pyrido[1,2-a]azepinsProf. Horst Prinzbach zum 60. Geburtstag gewidmet (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1095-1101 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: On the Synthesis of Derivatives of Pyrido[1,2-a]lazepineThe conjugated pyridinium ylides of type 4 undergo 8π -electrocyclisation affording the heterobicyclic allenes 5 which, in the presence of H2O and H2O2, are subsequently transformed into the substituted pyrido[1,2-a]-azepinones 6, a novel heterocyclic system. The chemical behaviour of 6a,b is dominated by cleavage of the lactam bond and subsequent reaction to pyridinc and isoquinoline derivatives, respectively; e.g. reaction of 6a, b with 4,5-dihydro-4-methyl-3H-1,2,4-triazole-3,5-dione affords the cycloadducts 11 and 12 almost quantitatively. The successful transformation of 6b into 15 is described, the latter being the first representative of the presently unknown, potentially antiaromatic pyrido[1,2-a]azepine (1).
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    URL: http://dx.doi.org/10.1002/hlca.19910740519
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  • 81
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    Mitteilungen (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1156-1156 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740525
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  • 82
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    Regioselectivity, Stereoselectivity, and Isotopically Sensitive Branching in the Fe(I)-Mediated Dehydrogenation of Octane-1,8-diol in the Gas PhaseDedicated to Prof. Jürgen Sauer on the occasion of his 60th birthday (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1127-1134 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Regio- and stereospecific labeling experiments are conducted to unravel the mechanistic features of the Fe+-induced dehydrogenation of octane-1,8-diol in the gas phase. With regard to the regioselectivity, ca. 20% of molecular hydrogen originates from the C(3)/C(4) or the equivalent C(5)/C(6) positions. The remaining 80% are, provided by the C(4)/C(5) methylene units. The steps, preceding the reductive elimination of hydrogen, are irreversible, and the overall reaction follows a 1,2-elimination mode. The loss of HD from C(3)/C(4) is associated with a kinetic isotope effect KH2/KHD = 1.68. Formation of D2 from the positions C(4)/C(5) has an isotope effect of KH2/KD2 = 4.7; this figure is slightly dependent on the configuration at C(4)/C(5). Most interesting is the finding that the configuration at C(4)/C(5) in [4,5-D2]octane-1,8-diol, i.e. 5c vs. 5d, plays a pivotal role in the dehydrogenation of the central C(4)/C(5) part. This unexpected and unprecedented result is explained in terms of conformational analysis. A staggered-like conformation serves as a precursor to generate a trans-fused bicyclic intermediate 6. It is this very intermediate from which most of the molecular hydrogen is eliminated. Of minor importance is the as-fused chelate 7, which is formed from an eclipsed-like conformation of the octane-1,8-diol/Fe+ complex. The contribution of 6 and 7 to the product formation is controlled by the relative configuration at the labeled positions C(4)/C(5). For the D,L-form 5c, we estimate a ratio of ca. 9:1 for the contribution of 6 vs. 7; due to an isotope effect, this ratio drops to 1:85:1 for the meso-form 5d. This finding constitutes the first example for the existence of isotopically sensitive branching (‘metabolic switching’) in gas-phase organometallic chemistry.
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    URL: http://dx.doi.org/10.1002/hlca.19910740522
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  • 83
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    Crystal Structures of the Lanthanum(III), Europium(III), and Terbium(III) Cryptates of Tris(bipyridine) Macrobicyclic Ligands (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1163-1170 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The crystal structures of the LaIII, EuIII, and TbIII complexes of macrobicyclic [bpy.bpy.bpy] ligands, [La3+ ⊂ 1]3 Cl- ( = 3-La), [Tb3+ ⊂ 1]3 Cl- ( = 3-Tb), and [Eu3+ ⊂ 2]3 C1- ( = 3-Eu), have been determined. They confirm the cryptate nature of these species, the cations being bound to the eight N-sites of the ligand. The macrobicycle presents two open faces, thus allowing additional coordination of two species, Cl- ions or H2O molecules, to the bound cations. These data provide structural support for the photophysical studies of the luminescent properties of the EuIII and TbIII cryptates, which indicated residual coordination of H2O molecules.
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    URL: http://dx.doi.org/10.1002/hlca.19910740603
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  • 84
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    Biphenyltetrols and Dibenzofuranones from Oxidative Coupling of Resorcinols with 4-Alkylpyrocatechols: New Ciues to the Mechanism of Insect Cuticle Sclerotization (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1205-1212 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Oxidation of 4-alkylpyrocatechols 2 by means of an insect diphenoloxidase (laccase) or K3 [Fe(CN)6] yields, in the presence of resorcinols 1 (R2 = H), complex mixtures of products from which biphenyltetrols 3 (R3 = H) and dibenzofuranones 5 and 6 were isolated. It is suggested that similar homo-coupling products are formed from pyrocatechols 2b and 2c in insects during cuticle sclerotization.
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    URL: http://dx.doi.org/10.1002/hlca.19910740607
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  • 85
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    Quantitative Formation in Water of [Ru(CO)(H2O)5]2+ from Hexaaquaruthenium(II) and Carbon Monoxide (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1236-1238 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: High-pressure 17O- and 13C-NMR show that [Ru(H2O)6]2+ reacts quantitatively with carbon monoxide (50 bar) in water to form [Ru(CO)(H2O)5]2+.
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    URL: http://dx.doi.org/10.1002/hlca.19910740611
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  • 86
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    Synthese von ‘Push-Pull’-Oligoacetylenen24. Miteilung über Aminoacryl-Derivate. 23. Mitteilung: [1]Kurzmitteilung: [2] (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1264-1272 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of ‘Push-Pull’-OligoAcetylenes‘Push-pull’ triacetylenes 11a, b, c, as well as ‘push-pull’ tetraacetylene 13b have been prepared by reaction of the corresponding trichloroene(oligoinyl)amines 9 and 10 with 2 mol-equiv. of BuLi followed by acylation. The sequences (Schemes 3 and 4) are very simple and straightforward, they could in principle be applied to the synthesis of ‘push-pull’ pentaAcetylenes 15 and hexaacetylenes 17 (Scheme 5). Main limitations are the moderate yields as well as the low thermal stability of push-pull oligoacetylenes.
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    URL: http://dx.doi.org/10.1002/hlca.19910740614
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  • 87
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    Metabolic products of microorganisms. Part 262Part 261: [1].. The absolute configuration of sphydrofuran, a widespread metabolite from streptomycetes (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1281-1286 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Sphydrofuran (1) was isolated from the culture filtrate of Streptomyces sp. (strain Gö 28 and Tü 3616) by chemical screening methods. Metabolite 1 is an anomeric and ring-chain tautomeric mixture and could easily be transformed into the stable furan derivative 2 under acidic conditions. The constitution and relative configuration of 1 was established by X-ray crystallography of its 8-O-methyl derivative 3a. The absolute configuration at C(4) of 1 and thus of the whole molecule (3R,4S,5S) could be determined starting from 2 using the Helmchen method.
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    URL: http://dx.doi.org/10.1002/hlca.19910740617
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    Structure and reactivity of xanthocorrinoids. Part VPart IV, [1].. Formation of trans-diol derivatives of 5,6-dihydrocobyrinic acid from xanthocorrinoids under acidic conditions (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1287-1295 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: On treatment with H2SO4/MeOH, epimerization of hexamethyl cis-5,6-dihydroxycobyrinate c,8-lactam (3) takes place quantitatively at C(6), yielding the corresponding trans-diol 4. The corresponding lactone 7, whose structure has been established by X-ray analysis, is obtained from xanthocorrinoids 5 and 6 under similar conditions.
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    URL: http://dx.doi.org/10.1002/hlca.19910740618
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  • 89
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    Alternative Strategies for the Fmoc Solid-Phase Synthesis of O4-Phospho-L-tyrosine-Containing Peptides (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1314-1328 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A number of biologically relevant O4-phospho-L-tyrosine-containing peptides have been synthesized by either the global phosphorylation of the side-chain-unprotected L-tyrosine moiety in presynthesized resin-bound peptides or alternatively by the incorporation of suitably protected O4-phospho-L-tyrosine building blocks in the continuous-flow method of Fmoc solid-phase peptide synthesis. Different phosphate-protecting groups have been applied.
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    URL: http://dx.doi.org/10.1002/hlca.19910740621
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  • 90
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    Stereoselektive Synthese von Pyrrolizidin-Alkaloiden aus NitroalkanonenHerrn Professor Dr. C. H. Eugster zurn 70. Geburtstag gewidmet (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1352-1361 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Stereoselective Synthesis von Pyrrolizidin Alkaloids from NitroalkanonesReduction of 5-nitropentadecane-2,8-dione (11), synthesized by a Michael reaction from nitromethane, methyl vinyl ketone, and dec-1-en-3-one, gave, depending on the conditions, two epimeric 3-heptyl-2,3,5,6,7,7a-hexahydro-5-methyl-1H-pyrrolizines as the main products: Catalytic hydrogenation (Pd/C) afforded the expected 7aα-hydro epimer 1b with cis-orieted H-atoms at C(3), C(5), and C(7a). NaBH3CN/NH4OAc reduction of the nitrodione 11 yielded all four diastereoisomers with the 7aβ-hydro epimer 1a as the predominant component; 1a is a pheromone of the cryptic thief ant Solenopsis sp. The N-atom of the pyrrolizidine ring stems from NH4OAc exclusively as shown by reduction of 11 with NaBH3CN/(15N)H4OAc.
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    URL: http://dx.doi.org/10.1002/hlca.19910740624
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    Glycosylidene Carbenes. Part 4. Synthesis of Spirocyclopropanes from Acetamidoglycosylidene-Derived Diazirines (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1362-1372 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of the first glycosylidene-derived 2-acetamido-2-deoxydiazirine 4 from N-acetylglucosamine 6 is described. Thus, 6 was transformed into the 3-O-mesylglucopyranoside 9 by glycosidation with allyl alcohol, benzylidenation, and mesylation (Scheme 2). Solvolysis of 9 gave the allopyranoside 10 which, upon benzylation and glycoside cleavage, yielded the hemiacetals 12. Using our established method (via the lactone oxime 14 and the diaziridines 16), 12 gave the diazirine 4. Thermolysis of this diazirine in the presence of i-PrOH gave the dihydro-1,3-oxazole 5 (Scheme 1); in the presence of acrylonitrile, the four diastereoisomeric spirocyclopropanes 17-20 and the acetamidoallal 21 were obtained and separated by prep. HPLC (Scheme 3). Assignment of the configuration of 17-20 is based on NOE measurements and on the effect of diamagnetic anisotropy of the CN group. The ratio of the four cyclopropanes, which is in keeping with earlier results, is rationalized.
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  • 92
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    Mammalian alkaloids: Synthesis and O-methylation of (S)- and (R)-3′-hydroxycoclaurine and their N-methylated analogues with S-adenosyl-L-[methyl-14C]methionine in presence of mammalian catechol O-methyltransferase (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1399-1411 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: O-Methylation of the optically active 3′-hydroxycoclaurines 3a and 3b and of the N-methylated analogs 5a,b with S-adenosyl-L-[methyl-14C]methionine in presence of mammalian COMT was investigated in vitro. The N-unsubstituted (1S)- and (1R )-isomers 3a and 3b, respectively, afforded almost equal amounts of the corresponding N-norreticuline 4 and N-nororientaline 19, besides two unknown by-products (see Fig. and Table 1). The N-methylated (1S)-isoquinoline 5a, on the other hand, afforded largely (S)-orientaline ((S)-19), while an almost equal mixture of (R)-reticuline (6b) and (R)-orientaline ((R)-19) was obtained from the (1R)-enantiomer 5b. The isoquinolines 3a,b and 5a,b were prepared by a Bischler-Napieralski cyclization yielding O-benzyl-protected isoquinoline 10 (Scheme 1). The optical resolution of 10 was accomplished with 2′-bromotartranilic acid. The N-methylated isoquinolines were prepared by N-formylation of 10a,b and reduction of the formamides 13a,b with diborane (→ 14a,b). Deblocking of the benzyl-ether moieties of 10a,b and 14a,b was accomplished by catalytic hydrogenation in presence of HCl, affording directly 3a,b·HCl and 5a,b·HCl, respectively.
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    URL: http://dx.doi.org/10.1002/hlca.19910740704
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  • 93
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    A Novel, Degraded Polyketidic Lactone, Leptosphaerolide, and Its Likely Diketone Precursor, Leptosphaerodione. Isolation from Cultures of the Marine Ascomycete Leptosphaeria oraemaris (LINDER)Presented in part by A. G. at the ‘Giornate di chimica delle Sostanze Naturali’ meeting, Maratea (Potenza), on June 3, 1991. (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1445-1450 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Acetone extraction of cultures of the marine ascomycete Leptosphaeria oraemaris (LINDER) on cornmeal disk gave the novel polyketide derivative leptosphaerolide ( = (+)-7-[(1E)-l,3-dimethylpent-1-enyl]-10-hydroxy-3-methoxybenzo[1,2-b:5,4-c′]dipyran-2(9H)-one; (4+)-8) besides the o-dihydroquinone 3-[(1E)-1,3-dimethylpent-1-euyl]-8,10-dihydroxy-7-methoxy-8-(2-oxopropyl)-1H-naphtho[2,3-c]pyran-9(8H)-one (1) as a 10:9 mixture of epimers. retro-Aldol reaction of 1 gave leptosphaerodione ( = (-)-3-[(1E)-1,3-dimethylpent-1-enyl]-10-hydroxy-7-methoxy-1H-naphtho[2,3-c]pyran-8,9(8H)-dione; (-)-6) which was also present in small amounts in the extracts and which gave 1 on reaction with acetone. It is thus likely that 1 is an artefact of the extraction by acetone. Biogenetically (+)-8 might derive from (-)-6 via an unusual oxidation with loss of CO2.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740707
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  • 94
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    1,2-Stereoinduction in Radical Reactions: Stereoselective Synthesis of 2-Alkyl-3-hydroxybutanoates (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1600-1607 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Radical addition to 2-cyclohexyl-5-methylidene-6-methyl-1,3-dioxan-4-one (2) affords stereoselectively 5,6-trans-products trans-3. The size of the radical has no influence on the selectivity. These trans-acetals are converted into threo-3-hydroxy-butanoates 4. Methyl 2-methylidene-3-[(tert-butyl)diphenylsilyloxy]butanoate (5), treated under the same conditions, leads mainly to the erythro-isomer of 4 after deprotection. An influence of the steric bulkyness of the radical is observed. The stereochemical course of the reactions is discussed.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740722
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  • 95
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    Electronic Resource
    Gas-Phase Chemistry of Ti+ to Zn+ with Butyl Isothiocyanate (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1609-1621 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Using a complete set of 2H-labeled isotopomers, the gas-phase reactions of Ti+ to Zn+ with butyl isothio-cyanate are studied. The main product for most of the metal ions is MHNCS+ formed by an ion/dipole mechanism. Exceptions are Cr+, which yields significant amounts of H2 and H2S loss, Mn+, which is the only ion that does not form MHNCS+ at all but produces mainly C2H4 and C3H6, and Zn+, which predominantly reacts by charge transfer.
    Additional Material: 6 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740802
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  • 96
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    1,3-Oxathiolan-Synthese: Spirocyclische 1,3-Oxathiolane aus der Lewis-Säure-katalysierten Umsetzung von cyclischen Trithiocarbonaten und OxiranenHerrn Professor Dr. C. H. Eugster zum 70. Geburtstag gewidmet (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1500-1510 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1,3-Oxathiolanc Synthesis: Spirocyclic 1,3-Oxathiolanes from the Lewis-Acid-Catalyzed Reaction of Cyclic Trithiocarbonates and OxiranesThe cyclic trithiocarbonates 1.3-dithiolane-2-thione (4) and 1,3-dithiole-2-thione (9) in 1,2-dichloroethane and MeCN, respectively, react with alkyl- and phenyl-substituted oxiranes 2 in the presence of Lewis acids to give 1-oxa-4,6,9-trithiaspiro[4.4]nonanes 5 and 6 (Scheme 2) and 1-oxa-4,6,9-trithiaspiro[4.4]non-7-enes 10 and 11 (Scheme 3), respectively. The reactions proceed regioselectively yielding 2-alkyl (5, 10) and 3-phenyl derivatives (6, 11) as the main products. From the reaction of 4 and 2-phenyloxirane (2e) with TiCl4, 2-phenyl-1,4,6,9-tetrathia-spiro[4.4]nonane (7) is isolated as a minor product. The molecular structures of 5a, 6e, and 7 are established by X-ray crystallography.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740714
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  • 97
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    2D-NMR ConformationaL Studies of ChiraL Functionalized Ferrocenylphosphine Ligands for the Gold(I)-Catalyzed Aldol Reaction (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1533-1543 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The conformations in solution of six selected chiral 1,1′-bis (diphenylphosphino)ferrocenyl ligands bearing functionalized side chains, the diastercoisomers 4 and 5 and 6-9, have been elucidated by 2D-NMR methods (COSY, TOCSY, NOESY, and 1H,31P and 1H,13C correlations). The possible relationship between the preferred conformation and the stereoselectivity observed in the gold(I)-catalyzed asymmetric aldol condensation in the presence of these ligands is discussed.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740717
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  • 98
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    Crystal Structure and ESR Study of a Bimetallic Copper/Iron Crown Ether Inclusion Complex (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1591-1599 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Bimetallic inclusion complexes have been synthesized by a secondary coordination interaction between the guest complex [Fe(η5-C5H5)(CO)2(NH3)][PF6] and copper(II) complex 1a or nickel(II) complex lb containing crown-ether hosts. The X-ray crystal-structure analysis established that the Cu,Fe inclusion complex 2 crystallize as a centrosymmetric dimer with a Cu—Cu separation of 3.73 Å and a novel out-of-plane Cu—N interaction. The magnetic parameters for 2 were obtained by ESR and ENDOR spectroscopy. ESR susceptibility measurements down to 6 K exclude the presence of any antiferromagnetic coupling interaction between the CuIIcenters of the dimer.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740721
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  • 99
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    Synthesis of Aristotelia-type alkaloids. Part VIIIPart VII: [1].. Synthesis of (±)-aristolasicone (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1636-1642 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The revised structure of the indole alkaloid aristolasicone (2) was confirmed through a convergent total synthesis of the racemic form of this metabolite. The key step involves a one-pot condensation/cyclization reaction between 1-(4-methoxyphenylsulfonyl)-1H-indole-2-acetaldehyde (9) and (±)-trans-5-(2,6-difluorobenzyloxy)-p-menth-l-en-8-amine ((±)-7). The resulting allohobartine derivative (±)-13, obtained in 84% yield, was deprotected and oxidized to (±)-alloscrratenone ((±)-15) which cyclized smoothly to the target molecule (±)-2 upon exposure to BF3 · Et2O.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740804
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  • 100
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    From 1-(Silyloxy)Butadiene to 4-Amino-4-Deoxy-DL-Erythrose and to 1-Amino-1-Deoxy-DL-Erythritol Derivatives via Hetero-Diels-Alder Reactions with Acylnitroso Dienophiles (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1653-1670 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Acylnitroso dienophiles 4 reacted instantly with 1-(silyloxy)butadiene 5α and led in good yield to the regioisomeric cycloadducts 6 (major) and 7 (minor; Scheme 2, Table 1). cis-Hydroxylation of these primary cycloadducts with OsO4 (catalyst) occurred stereospecifically and in high yield (→8 and 9, resp.; Scheme 2). It was followed by reductive ring cleavage to give either 1-amino-1-deoxy-DL-erythritol or 4-amino-4-deoxy-DL-erythrose derivatives 10 and 14, respectively, depending on the nature of the reducing agent (Schemes 3 and 4).
    Additional Material: 7 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740806
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