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  • Analytical Chemistry and Spectroscopy  (16)
  • Organic Chemistry  (13)
  • Drosophilidae  (4)
  • 1
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 12 (1986), S. 1037-1055 
    ISSN: 1573-1561
    Keywords: Drosophila ; Diptera ; Drosophilidae ; yeasts ; cactus ; community ecology ; mutualism ; coadaptation ; evolution ; alkaloids ; fatty acids ; sterols
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The mutualistic interactions of cactophilicDrosophila and their associated yeasts in the Sonoran Desert are studied as a system which has evolved within the framework of their host cactus stem chemistry. Because theDrosophila-yeast system is saphrophytic, their responses are not thought to directly influence the evolution of the host. Host cactus stem chemistry appears to play an important role in determining where cactophilicDrosophila breed and feed. Several chemicals have been identified as being important. These include sterols and alkaloids of senita as well as fatty acids and sterol diols of agria and organpipe cactus. Cactus chemistry appears to have a limited role in directly determining the distribution of cactus-specific yeasts. Those effects which are known are due to unusual lipids of organpipe cactus and triterpene glycosides of agria and organpipe cactus.Drosophilayeast interactions are viewed as mutualistic and can take the form of (1) benefits to theDrosophila by either direct nutritional gains or by detoxification of harmful chemicals produced during decay of the host stem tissue and (2) benefits to the yeast in the form of increased likelihood of transmission to new habitats. Experiments on yeast-yeast interactions in decaying agria cactus provide evidence that the yeast community is coadapted. This coadaptation among yeasts occurs in two manners: (1) mutualistic increases in growth rates (which are independent of the presence ofDrosophila larvae) and (2) stabilizing competitive interactions when growth reaches carrying capacity. This latter form is dependent on larval activity and results in benefits to the larvae present. In this sense, the coadapted yeast community is probably also coadapted with respect to itsDrosophila vector.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 13 (1987), S. 2069-2081 
    ISSN: 1573-1561
    Keywords: Drosophila ; D. mojavensis ; D. nigrospiracula ; D. mettleri ; Diptera ; Drosophilidae ; cactus ; alkaloids ; viability ; development ; longevity ; host-plant relationships
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Drosophila mettleri is a soil-breeding, cactophilic drosophilid which lives in the Sonoran Desert. Several chemical constituents of cacti in this region have been identified as having major roles in insect-host plant relationships involvingDrosophila. For example, isoquinoline alkaloids, which are present in senita cactus, have been shown to be toxic to seven of the nine species tested. The two tolerant species areD. pachea, the normal resident, andD. mettleri. Necroses of senita cacti are often used as feeding substrates byD. mettleri adults, but this species has never been reared from senita rots. Soil, which have been soaked by juice from saguaro and cardón rots, are the typical breeding substrates of this species. The tissues of both of these cacti also contain alkaloids, chemically related to those in senita, but at much lower concentrations. Alkaloid concentration in saguaro-soaked soil was found to be 1.4–27 times the average concentration in fresh tissue. Alkaloids were extracted from saguaro tissue and used in tests of larva-to-adult viability, developmental rate, and adult longevity. Elevated concentrations of saguaro alkaloids had no significant effect on the longevity ofD. mettleri, but significantly reduced the longevity ofD. nigrospiracula andD. mojavensis, two nonsoil breeding cactophilic species. Viability and developmental rates of all three species were affected, but the effect onD. nigrospiracula was comparatively greater. It is argued that the adaptations that allowD. mettleri to utilize the saguaro soil niche also convey tolerance to alkaloids present in senita tissue. The ability to utilize senita necroses as feeding substrates represents an ecological advantage to D. mettleri, in that the density of potential feeding sites is increased as compared to species which are more specific in their host-plant relationships.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 20 (1994), S. 1893-1906 
    ISSN: 1573-1561
    Keywords: Drosophila ; Diptera ; Drosophilidae ; cytochrome P-450 ; poly-substrate monooxygenase ; cactus ; alkaloids ; resistance
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The cytochrome P-450 monooxygenase system has been implicated in plant utilization by at least three species ofDrosophila (D. nigrospiracula, D. mettleri, andD. mojavensis) that are endemic to the Sonoran Desert of the southwestern United States and northwestern Mexico. Basal and induced levels of total cytochrome P-450 were determined for third-instar and decapitated 2- to 5-day post eclosion adults of the three desert species. Total P-450 levels, both basal and induced for all species assayed, were significantly higher for adults than for larvae by up to 20-fold. On a per organism basis, the levels of in vitro metabolism of the cactus alkaloid, carnegine, and patterns of response to induction by cactus tissue for adult desertDrosophila approximated those of larvae. Induction by phenobarbital, however, resulted in levels of in vitro carnegine metabolism that were up to 5.6-fold higher in adults than in larvae.
    Type of Medium: Electronic Resource
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  • 4
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A novel antibiotic, PD 121,222, was isolated from a complex of pluramycin-like compounds containing mostly kidamycin and neopluramycin. Spectral analyses showed that this compound is the 14,16-dihydroxy analog of rubiflavin A.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 78 (1995), S. 292-300 
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthetic (+)-makomakine (6) was transformed in six steps into (+)-17R,18R)-17,18-dihydrohobartine-17,18-diol ((+)-5) with an overall yield of 38% (Scheme 2). This compound was shown to be identical with natural hobartinol, a monoterpene indole alkaloid from Aristotelia australasica, originally believed to be the (17S)-epimer 1. At the same time, the synthesis of (+)-5 delineates the hitherto unknown absolute configuration of this metabolite.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Biomedical Chromatography 1 (1986), S. 155-158 
    ISSN: 0269-3879
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Medicine
    Notes: Endogenous opioid receptoractive peptides in the cerebrospinal fluid (CSF) of human controls and in those patients diagnosed as having senile dementia of the Alzheimer's type (SDAT) are measured with a radioreceptorassay following HPLC separation. [3H]Etorphine is the ligand used to detect in the HPLC fractions the presence of those endogenous peptides that preferentially interact with several opioid receptors. The RRA uses a receptor-rich P2 fraction extracted from a canine limbic system. The total opioid peptide content found in the HPLC fractions 6-20 (to avoid salts in fractions 1-5) of SDAT CSF (383 ± 187 pmol ME-equivalents per ml CSF) is significantly higher than the corresponding total from patients with no known neurological disorders (89.1 ± 46.3 pmol ME-equivalents per ml).
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 15 (1989), S. 663-676 
    ISSN: 1573-1561
    Keywords: Drosophila ; Diptera ; Drosophilidae ; triterpene glycosides ; cactus ; fitness components ; host-plant relationships
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The effects of pentacyclic triterpene glycosides extracted from agria and organ pipe cacti on three fitness parameters of the cactophilic fruit fly,Drosophila mojavensis were tested. Triterpene glycosides from organ pipe increased development time and reduced larval viability while those from agria produced smaller adults (reduced fecundity). In addition, the microbial communities in the organ pipe saponin media were less dense than those in the media to which agria saponins had been added. The role of cactus triterpene glycosides in the ecology of thisDrosophila species is discussed.
    Type of Medium: Electronic Resource
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  • 8
    Electronic Resource
    Electronic Resource
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 5 (1993), S. 150-153 
    ISSN: 0899-0042
    Keywords: aminoacyl adenylate esters ; hydrolytic stabilization by intramolecular interaction ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Studies of the properties of aminoacyl derivatives of 5′-AMP are aimed at understanding the origin of the process of protein synthesis. Aminoacyl (2′,3′) esters of 5′-AMP can serve as models of the 3′-terminus of aminoacyl tRNA. We report here on the relative rates of hydrolysis of AC-D- and L-Phe AMP esters as a function of pH. At all pHs above 3, the rate constant of hydrolysis of the AC-L-Phe ester is 1.7 to 2.1 times that of AC-D-Phe ester. The D-isomer seems partially protected from hydrolysis by a stronger association with the adenine ring of the 5′-AMP. © 1993 Wiley-Liss, Inc.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 9
    Electronic Resource
    Electronic Resource
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 5 (1993), S. 428-435 
    ISSN: 0899-0042
    Keywords: enantiomeric pharmacokinetics ; benzamides ; gastroprokinetic agents ; prochirality ; chiral sulfoxidation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ML-1035, 4-amino-5-chloro-2-[2-(methylsulfinyl)ethoxy]-N-[2-(diethylamino)ethyl]benzamide, is a sulfoxide compound and a racemic gastroprokinetic agent with a chiral center at the sulfur atom. We have investigated the disposition kinetics of (R)-ML-1035 sulfoxide (R) and (S)-ML-1035 sulfoxide (S) after the single enantiomers and the racemic mixture were administered to rats in separate experiments. There was no noticeable chiral inversion after either enantiomer dose. Both enantiomers were rapidly absorbed. After dosing with enantiomers or with the racemate, the resulting plasma concentration-time curve of R was closely parallel to that of S in both intravenous and oral experiments, suggesting that the two enantiomers have approximately the same disposition kinetics. After intravenous enantiomer doses, only S underwent conversion to sulfide, suggesting that sulfidation in the liver is enantioselective. However, the enantioselective sulfidation after intravenous dosing did not introduce a difference in the global plasma disposition profiles between R and S, since the reduction reaction is a minor metabolic process. Other metabolic reactions such as sulfonation and mono-N-desethylations were not enantioselective. After oral administration, conversion to sulfide was observed for both enantioners, implicating the existence of a nonhepatic pathway in sulfidation. Administration of a prochiral sulfide dose was associated with an enantioselective sulfoxidation, in which the R/S concentration ratios increased as a function of time. In addition, enantiomeric interaction causing changes in pharmacokinetic parameters was observed after the oral racemate dose, while the interaction is negligible after an intravenous racemate dose, indicating a route dependency in enantiomeric interaction. © 1993 Wiley-Liss, Inc.
    Additional Material: 4 Ill.
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  • 10
    Electronic Resource
    Electronic Resource
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 4 (1991), S. 125-134 
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: Ab initio MO methods have been used to study the structures and energetics of dicyandiamide, [(NH2)2C=N—C≡N], its isomers, protonated species, radical anions, transition structures for internal conformational change and transition structures for isomerization. Structures were optimized at the HF/STO-3G, HF/3-21G and HF/6-31G* levels; selected barrier heights for smaller analogues were also computed at the MP4SDTQ/6-31G* level. The most stable isomer of dicyandiamide has the cyano group on the imine nitrogen [1, (NH2)2C=NC≡N]; the other isomer [2, HN=C(NH2)NH—C≡N] lies 12.8 kcal mol-1 higher. Inversion at the imino nitrogen proceeds by a linear, in plane process with a barrier of 32.5 kcal mol-1. The amino rotation barriers are 19 kcal mol-1 (single NH2) and 40 kcal mol-1 (both NH2 in a conrotaory or a disrotatory fashion; if the NH2 groups are allowed to pyramidalize the disrotatory barrier drops to 20 kcal mol)-1. Protonation occurs preferentially on the imine nitrogen (PA = 219.7 kcal mol-1 for 1); the proton affinities PA of the amino nitrogens are 25-30 kcal mol-1 lower. Isomerization between 2 and 1 would go via a 1,3-sigmatropic hydrogen shift, but the barrier is high (48.3 kcal mol-1); protonation reduces the hydrogen shift barrier by ca 15 kcal mol-1. However, the most likely mechanism for isomerization involves protonation of the imine nitrogen in 2 followed by deprotonation of the cyano-substituted nitrogen to form 1, circumventing the energetically costly 1,3-sigmatropic hydrogen shift. When an electron is transferred to dicyandiamide, a sizeable fraction of the resonance stabilization of the guanidine moiety is lost.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
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