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1

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Effect of acetylsalicylic acid on secondary metabolism ofCatharanthus roseus tumor suspension cultures (1997)

Godoy-Hernández, Gregorio ; Loyola-Vargas, Victor M.

Springer

Plant cell reports 16 (1997), S. 287-290

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ISSN: 1432-203X

Keywords: Catharanthus roseus ; Acetylsalicylic acid ; Aspirin ; Alkaloids ; suspension cultures ; tumor

Source: Springer Online Journal Archives 1860-2000

Topics: Biology

Notes: Summary Addition of various concentrations (0.5–20 mM) of acetylsalicylic acid (ASA) to tumor lines ofCatharanthus roseus cultivatedin vitro and requiring corn starch as carbon source, produced remarkable effects on secondary metabolite production. An increase of 505% total alkaloids per culture (cells plus liquid medium), 1587% total phenolics (liquid medium), 612% total furanocoumarins (liquid medium) and 1476% total anthocyanins (liquid medium) was detected. 1 mM ASA in combination with other elicitors, such as homogenates ofAspergillus fumigatus or trans-cinnamic acid, did not further increase the metabolite content substantially. The results suggest that ASA could act as a new biotic elicitor of metabolite production inC. roseus cell suspension culture.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF01088282

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2

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Synthese und Konformation von Hexahydro-isochino[1,2-b][3]benzazepinen (1997)

Clemens, Martina ; Meise, Werner ; Himmel, Klaus ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1997 (1997), S. 447-457

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ISSN: 0947-3440

Keywords: Isoquino[1,2-b][3]benzazepines ; Iso-C-homoberbines ; Conformation analysis ; Bischler-Napieralski reaction ; Methyl ∊-hydroxycarboxylates ; Heterocycles ; Alkaloids ; Drug research ; Medicinal chemistry ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Synthesis and Conformation of Hexahydro-isoquino[1.2.-b][3]benzazepinesThe synthesis of the six hexahydro-isoquino[1,2-b][3]benzazepines 13a-f is described; their conformation is investigated by NMR spectroscopic methods, X-ray analysis and dehydrogenation with mercury(II) acetate.

Additional Material: 2 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199719970225

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3

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Enantiospecific Synthesis of 2,5-Disubstituted Piperidine Derivatives: Synthesis of (+)-Pseudoconhydrine (1997)

Dockner, Michael ; Sasaki, N. André ; Riche, Claude ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1997 (1997), S. 1267-1272

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ISSN: 0947-3440

Keywords: Alkaloids ; Enantiospecific synthesis ; Chiral building blocks ; 2,5-Disubstituted piperidines ; (+)-Pseudoconhydrine ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: A novel methodology for the synthesis of any one of the four stereoisomers of a 2,5-disubstituted piperidine in optically pure form is described, starting from readily available chiral building blocks 10 and 11 (or their antipodes). The utility of this approach is demonstrated in the total synthesis of (+)-pseudoconhydrine hydrochloride, the structure of which was confirmed by X-ray analysis.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199719970633

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4

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Dihydrocolchicine 8,12-Endoperoxide: A Novel Starting Material for Convenient Syntheses of the Allocolchicinoids N-Acetylcolchinol O-Methyl Ether and Androbiphenyline (1997)

Brecht, René ; Haenel, Frank ; Seitz, Gunther

Weinheim : Wiley-Blackwell

Liebigs Annalen 1997 (1997), S. 2275-2279

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ISSN: 0947-3440

Keywords: Semisynthetic colchicine analogues ; Endoperoxide transformations ; Colchicine-allocolchicine rearrangement ; Axial chirality ; Biaryls ; Alkaloids ; Colchicum autumnale ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Optically pure dihydrocolchicine-8,12-endoperoxide 2 is used as the starting material for the synthesis of some bioactive allocolchicinoids. Depending on the reaction conditions and reagents employed, different modifications of the C ring of colchicine (1) are achieved. Triphenylphosphane deoxygenation of 2 leads to the well known N-acetylcolchinol O-methyl ether (NCME, 6, 40% yield from 1). Treatment of the endoperoxide 2 with CH3OH/CH2Cl2/silica gel provides the plant alkaloid androbiphenyline (11) in a yield of 60% from 1. Triethylamine-catalysed transformation of 2 yields (-)-colchicine-8,12-dione (12) (17% yield), together with a mixture of interconverting tetracyclic hemiketals 8a and 8b. For the formation of the allo colchicinoids 6 and 11 plausible reaction pathways are suggested. In contrast to what is found in the literature, the assignment of the absolute configuration of natural (-)-colchicine (1), and the allo-congeners 6 and 11, should be (M,7S) or (aR,7S) instead of (aS,7S).

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199719971115

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5

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Biotransformation of Ergot Alkaloids by Haloperoxidase from Streptomyces aureofaciens: Stereoselective Acetoxylation and Propionoxylation (1997)

Křen, Vladimír ; Kawuloková, Libuše ; Sedmera, Petr ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1997 (1997), S. 2379-2383

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ISSN: 0947-3440

Keywords: Alkaloids ; Enzyme catalysis ; Oxidases ; Peroxides ; Acylations ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Agroclavine (1) was oxidized, by haloperoxidase from Streptomyces aureofaciens, to 2,3-dihydro-6,8-dimethyl-3β-acetoxy-8-ergolen-2-one (2) in the presence of sodium acetate and bromine ions. Acetate was incorporated into the above product during oxidation. In a propionate buffer, incorporation of propionate into the product was observed, yielding 2,3-dihydro-6,8-dimethyl-3β-propionoxy-8-ergolen-2-one (4). The biotransformation proceeded faster in the propionate buffer, affording also the higher oxidation product (4aS),(10bS)-7-amino-3,4,4a,5,6,10b-hexahydro-2,4-dimethyl-6-oxobenzo[f]quinoline (3).

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199719971129

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6

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Chemistry of Opium Alkaloids, XLIIIPart XLII. M. de Grauw, E. F. Muller, R. H. Woudenberg, L. Maat, Recl. Trav. Chim. Pays-Bas 1996, 115, 58. - A PM3 Computational Approach to the Selectivity in the Diels-Alder Reactions of Thebaine and Analogues with Methyl Propenoate (1997)

Baas, Jan M. A. ; Woudenberg, Richard H. ; Maat, Leendert

Weinheim : Wiley-Blackwell

Liebigs Annalen 1997 (1997), S. 13-19

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ISSN: 0947-3440

Keywords: 6-Demethoxythebaine ; Ethenoisomorphinans ; Ethenomorphinans ; Calculations, semiempirical ; Alkaloids ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Geometrically fully-optimized transition structures are calculated for the Diels-Alder adducts of methyl propenoate and the 3-demethoxy derivatives of the dienes thebaine, 6-demethoxythebaine, 5β-methylthebaine, and 5β-methyl-6-demethoxythebaine using the semiempirical PM3 method. The number of calculated forms is limited according to a search of the conformational space of methyl propenoate and of the dienes. The lengths of the incipient bonds in the transition structures vary from 2.0 to 2.4 Å, but the average value of the lengths of these two bonds in the same structure is much more constant: 2.18 ± 0.02 Å. The effects of the methoxycarbonyl group and of the 6-methoxy group on the lengths of the incipient bonds are in agreement with the relative magnitudes of the frontier orbital coefficients. Comparison of the energetic data with experimental results shows that the prediction of the stereo- and regioselectivities from the Gibbs energy of activation differences is good as far as it concerns the main products. The absence of minor products and the formation of the remarkably large amount of 8β-ethoxycarbonyl-6β,14β-ethenomorphinan from 5β-methyl-6-demethoxythebaine does not follow from the calculations.

Additional Material: 6 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199719970105

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7

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Solanum Alkaloids, 139 - Photolysis of N-Chlorospirosolanes (1997)

Quyen, Le Thi ; Himmelreich, Uwe ; Schreiber, Klaus

Weinheim : Wiley-Blackwell

Liebigs Annalen 1997 (1997), S. 1589-1592

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ISSN: 0947-3440

Keywords: Photolysis ; N-Chlorospirosolanes, photolysis of ; 23-Chloro- and 23,23-dichlorospirosolanes ; Steroids ; Alkaloids ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: UV irradiation of N-chlorosoladulcidine (2) in trifluoroacetic acid, followed by separation and hydrolysis of the obtained 3-O-trifluoroacetates affords (23R)-23-chlorosoladulcidine (5) and 23,23-dichlorosoladulcidine (7). Similar treatment of N-chlorotomatidine (9) affords 23,23-dichloro-22-isotomatidine (12).

Additional Material: 1 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199719970741

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8

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Synthesis of rac-Midpacamide and the spiro-Cyclization of Its Precursor (1997)

Lindel, Thomas ; Hoffmann, Holger

Weinheim : Wiley-Blackwell

Liebigs Annalen 1997 (1997), S. 1525-1528

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ISSN: 0947-3440

Keywords: Alkaloids ; Biomimetic synthesis ; spiro-Cyclization ; Marine sponges ; Natural products ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The alkylidene hydantoin 8 was synthesized as an analogue of the marine natural product oroidin (1) by employing a Horner-Wadsworth-Emmons reaction. Treatment of 8 with bromine in acetic acid induced a biomimetic spiro-cyclization forming the ACD ring system of dibromophakellin (2) in one step. rac-Midpacamide (10) was obtained from the same precursor through a chemoselective, ruthenium-catalyzed hydrogenation leaving the brominated pyrrole moiety intact.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199719970731

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9

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Capillary electrophoresis of natural products (1997)

Issaq, Haleem J.

Weinheim : Wiley-Blackwell

Electrophoresis 18 (1997), S. 2438-2452

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ISSN: 0173-0835

Keywords: Natural products ; Capillary electrophoresis ; Micellar electrokinetic capillary chromatography ; Chinese herbal preparations ; Alkaloids ; Toxins ; Illicit drugs ; Chemistry ; Biochemistry and Biotechnology

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Biology , Chemistry and Pharmacology

Notes: Capillary electrophoresis (CE) and micellar electrokinetic chromatography were used for the separation of widely different compounds from natural materials including antibiotics, humic substances, flavonoids, isoflavonoids, illicit drugs, coumarins, alkaloids, steroids, Chinese herbal preparations, nicotine, caffeine, amphetamines, toxins such as aflatoxins B1, B2, G1, G2, mycotoxins, heptapeptide aflatoxins and others, ephedrine compounds, mineral elements, and natural compounds in biological samples. A discussion of sample extraction and clean-up and the advantages of using CE is also presented.

Additional Material: 25 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/elps.1150181234

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10

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The Biosynthesis of Alkaloids IIPart I of this review appeared in Angew. Chem. Internet. Edit. 2, 341 (1963). (1963)

Mothes, K. ; Schütte, H. R.

Weinheim : Wiley-Blackwell

Angewandte Chemie International Edition in English 2 (1963), S. 441-458

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ISSN: 0570-0833

Keywords: Biosynthesis ; Alkaloids ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/anie.196304411

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The Biogenesis of Ergot AlkaloidsDedicated to Professor Hans von Euler on the occasion of his 90th birthday (1963)

Weygand, F. ; Floss, H.-G.

Weinheim : Wiley-Blackwell

Angewandte Chemie International Edition in English 2 (1963), S. 243-247

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ISSN: 0570-0833

Keywords: Ergot alkaloids ; Alkaloids ; Biosynthesis ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: In this article the biogenesis of the ergoline ring in lysergic acid derivatives and the clavines is discussed. T·yptophan and mevalonic acid are the precursors. The N-methyl group is supplied by formate or methionine. Concepts and results dealing with the manner in which the compounds are formed are discussed. Finally, the known biogenetic relationships among the ergot alkaloids are discussed in connection with their biogenesis.

Additional Material: 1 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/anie.196302431

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The Biosynthesis of Alkaloids IPart II of this review will appear in a subsequent issue of this journal.Dedicated to Professor Dr. Adolf Butenandt on the occasion of his 60th birthday (1963)

Mothes, K. ; Schütte, H. R.

Weinheim : Wiley-Blackwell

Angewandte Chemie International Edition in English 2 (1963), S. 341-357

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ISSN: 0570-0833

Keywords: Biosynthesis ; Alkaloids ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/anie.196303411

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