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Biomedical subjects

J Meinwald

Publications and source records attributed to J Meinwald.

At least 55 records · Page 3Linked to original sources
PubMed1995

The chemistry of sexual selection.

The moth Utetheisa ornatrix (Lepidoptera: Arctiidae) is protected against predation by pyrrolizidine alkaloids that it sequesters as a larva from its foodplants. At mating, the male transfers alkaloid to the female with the spermatophore, a gift that the female supplements with alkaloid of her own and transmits to the eggs. Eggs are protected as a result. The male produces a pheromone, hydroxydanaidal, that he derives from the alkaloid and emits from a pair of extrusible brushes (coremata) during precopulatory interaction with the female. Males rendered experimentally alkaloid-free fail to produce the pheromone and are less successful in courtship. The male produces the pheromone in proportion both to his alkaloid load and to the amount of alkaloid he transfers to the female. The pheromone could thus serve as an indication of male "worth" and provide a basis for female choice. Utetheisa females are promiscuous and therefore are able to accrue multiple nuptial gifts (alkaloid and nutrient, both transmitted with the spermatophore). They use sperm selectively, favoring those of larger males. Larger males in nature are also richer in alkaloid. Females therefore reinforce after copulation the choice mechanism they already exercise during courtship.

Alkaloids↗
PubMed1995

Stereoselective metabolism of enflurane by human liver cytochrome P450 2E1.

The toxicity of the chiral fluorinated volatile anesthetics halothane, enflurane, and isoflurane is closely related to their metabolism by hepatic cytochrome P450. Although individual anesthetic enantiomers have been shown to exhibit a difference in anesthetic efficacy, metabolism of anesthetic enantiomers has not been reported. Human liver enflurane metabolism to difluoromethoxydifluoroacetic acid (DFMDFA) and inorganic fluoride is catalyzed in vivo and in vitro by cytochrome P450 2E1. The purpose of this investigation was to characterize enflurane racemate and enantiomer metabolism to test the hypothesis that fluorinated ether anesthetic metabolism by cytochrome P450 2E1 exhibits substrate stereoselectivity. Enflurane metabolism by microsomes from three human livers and by microsomes containing cDNA-expressed human P450 2E1 was measured at saturating enflurane concentrations. DFMDFA was quantitated with gas chromatography-mass spectrometry by detection of the ethanolamide derivative. In microsomes from all three livers, (R)-enflurane metabolism was significantly greater than that of (S)-enflurane, whereas rates of racemic enflurane metabolism were generally between those seen for the R- and S-enantiomers. The ratio of (R)-enflurane to (S)-enflurane metabolism in the three livers studied was 2.1:1, 1.9:1, and 1.4:1. (R)-, (S)-, and racemic enflurane were all metabolized by expressed P450 2E1. The ratio of (R)-enflurane to (S)-enflurane metabolism was 1.9:1. The metabolic enantiomeric selectivity of human liver P450 2E1 for (R)-enflurane suggests that enflurane metabolism by P450 2E1 occurs by direct substrate oxidation, rather than indirectly through the generation of a P450-dependent reactive oxygen species, and supports the hypothesis that the P450 2E1 active site is somewhat restrictive and capable of stereochemical discrimination.

Anesthetics, Inhalation↗
PubMed1994

Biosynthesis of a defensive insect alkaloid: epilachnene from oleic acid and serine.

The biosynthesis of the azamacrolide epilachnene by the coccinellid beetle Epilachna varivestis has been studied with 2H-labeled oleic acid, 2H-labeled L-serine, and 13C,15N-labeled L-serine. The incorporation of these precursors into epilachnene defines the origin of the alkaloid's entire carbon/nitrogen skeleton. GC/MS and GC/IR studies of alkaloid produced by Epilachna fed with deuteriated oleic acid show that oleic acid loses four carbon atoms from its carboxyl end during the biosynthesis. Other details, including the mechanism of carbon-nitrogen bond formation between the fatty acid and amino acid moieties, remain to be established.

Alkaloids↗
PubMed1994

Genetic differences affecting the potency of stereoisomers of halothane.

The mechanism of action of volatile anesthetics is the subject of some debate. Much of the controversy has centered on whether the site of such actions is purely lipid in nature or may contain a protein target. This report studies the interaction of stereoisomers of halothane on the wild type and on a variety of genetic mutants of Caenorhabditis elegans. The mutants studied have previously been shown to have altered sensitivities to volatile anesthetics. In one mutant, fc34, (R)-halothane [the (+) isomer] was 3 times more potent than its S (-) isomer. Other mutants and wild-type animals displayed more modest differences in sensitivity to the enantiomers. The results indicate that a genetic pathway exists in C. elegans controlling sensitivity to halothane and that both lipid and protein targets may mediate halothane's effects.

Animals↗
PubMed1994

Defensive use of an acquired substance (carminic acid) by predaceous insect larvae.

Larvae of two insects, a coccinellid beetle (Hyperaspis trifurcata) and a chamaemyiid fly (Leucopis sp.), feed on cochineal insects and appropriate their prey's defensive chemical, carminic acid, for protective purposes of their own. H. trifurcata discharges the chemical with droplets of blood (hemolymph) that it emits when disturbed; Leucopis sp. ejects the compound with rectal fluid. Ants are thwarted by these defenses, which are compared with the previously-described defense of a pyralid caterpillar (Laetilia coccidivora) that disgorges carminic acid-laden crop fluid. The defensive fluid of all three larvae contains carminic acid at concentrations spanning a range (0.2-6.2%) proven deterrent to ants. Many insects are known to appropriate defensive substances from plants. Insects that acquire defensive chemicals from animal sources may be relatively rare.

Animals↗
PubMed1993

Determination of double-bond position in some unsaturated terpenes and other branched compounds by alkylthiolation.

The electron-impact mass spectra of alpha, beta-bis(methylthio) derivatives of certain terpenes and other compounds with branched alkenyl groups contain diagnostic peaks that can be used for locating the position of the double bond in the parent compound. In contrast to the spectra of dimethyl disulfide (DMDS) derivatives obtained from compounds containing CH=CH type double bonds, which show two predominant fragment ions, most of the compounds examined in the current investigation showed only one predominant fragment ion, arising from that part of the molecule which possesses the more substituted carbon of the original double bond. For example, all the derivatives from compounds with an isopropylidene moiety showed a base peak at m/z89 which can be attributed to the formation of a [(CH3)2C=SCH3]+ fragment. The application of the DMDS procedure to naturally occurring terpenes is discussed.

Animals↗
PubMed1993

Relevance of chemistry to conservation of isolated populations: the case of volatile leaf components of Dicerandra mints.

Chemical analysis of the essential oils of four congeneric species of mint plant (Dicerandra spp.) endemic to Florida revealed a pattern of chemical similarity and dissimilarity that would not have been predicted on morphological or geographic criteria. Dicerandra christmanii differs fundamentally from its congeners in that it produces fewer compounds and lacks the acyclic components. Yet D. christmanii is more closely similar to Dicerandra frutescens than to other Dicerandra species in morphological characters and geographic range. We conclude that the potential chemical value of a species should not be prejudged on the basis of nonchemical characters and that designation of surplus plant populations by conservationists should be resisted unless such populations have also been chemically studied.

Conservation of Natural Resources↗
PubMed1993

Insect pheromone biosynthesis: stereochemical pathway of hydroxydanaidal production from alkaloidal precursors in Creatonotos transiens (Lepidoptera, Arctiidae).

The mechanism by which the moth Creatonotos transiens produces its male pheromone, (7R)-hydroxydanaidal, from heliotrine, an alkaloidal precursor of opposite (7S) stereochemistry, was investigated. Specifically deuteriated samples of heliotrine and epiheliotrine were prepared and fed to C. transiens larvae, and the steps in the biosynthetic process were monitored by gas chromatography/mass spectrometry. These analyses indicate that heliotrine is initially epimerized to (7S)-epiheliotrine by oxidation to the corresponding ketone followed by stereospecific reduction. The order of the subsequent steps is (i) aromatization of the dihydropyrrole ring, (ii) ester hydrolysis, and (iii) oxidation of the resulting primary alcohol to the final aldehyde. The ecological implications of this insect's ability (and the inability of another moth, Utetheisa ornatrix) to use representatives of two stereochemical families of alkaloids as pheromone precursors are discussed.

Journal Article↗
PubMed1993

Azamacrolides: a family of alkaloids from the pupal defensive secretion of a ladybird beetle (Epilachna varivestis).

Defensive droplets from glandular hairs of the pupa of the Mexican bean beetle, Epilachna varivestis, contain a group of structurally novel alkaloids, the azamacrolides. The major constituent of this secretion, epilachnene, is shown to be (5Z)-11-propyl-12-azacyclotetradec-5-en-14-olide. The secretion also contains an epilachnadiene and trace amounts of three closely related components.

Alkaloids↗
PubMed1993

Pregnanes from defensive glands of a belostomatid bug.

The aquatic bug Abedus herberti (Hemiptera: Belostomatidae) secretes a mixture containing four pregnanes (desoxycorticosterone (I), pregnenolone (II), progesterone (III), and 3 alpha-hydroxy-pregn-5-en-20-one (IV)) from its cephalic glands. Pregnanes had previously been characterized from the defensive glands of aquatic beetles (Dytiscidae) and shown to be deterrent to fish. It may be specifically under predation pressure from fish that A. herberti and Dytiscidae evolved their comparable defenses.

Animals↗
PubMed1993

Defensive secretion of the millipede Floridobolus penneri.

Six quinones were identified from the defensive secretion of the millipede Floridobolus penneri. The two major components, 2-methyl-1,4-benzoquinone [1] and 2-methoxy-3-methyl-1,4-benzoquinone [3], previously characterized, comprise 95% of the secretion. One of the minor compounds, 2,5-dimethyl-3-methoxy-1,4-benzoquinone [4], is a new natural product. Another, 2-hydroxy-3-methyl-1,4-benzoquinone [2], had been tentatively characterized from a microbial source. The other two components are 2,3-dimethoxy-1,4-benzoquinone [5] and 2,3-dimethoxy-5-methyl-1,4-benzoquinone [6]. No sex difference in the composition of the secretion was noted.

Animals↗
PubMed1991

Pheromonal advertisement of a nuptial gift by a male moth (Utetheisa ornatrix).

Male Utetheisa ornatrix produce a courtship pheromone (hydroxydanaidal) that they derive from systemic pyrrolizidine alkaloid of plant origin. Pheromone titers in males correlate with systemic levels of alkaloid and with the quantity of alkaloid transmitted to the female at mating. The male's emission of pheromone during courtship may therefore communicate his possession of protective alkaloids and his capacity to provision the female. By mating preferentially with males endowed with hydroxydanaidal, females may ensure their acquisition of an alkaloidal gift for use in egg defense.

Animals↗
PubMed1991

Sexual dimorphism in the defensive secretion of a carabid beetle.

The defensive secretions of male and female Oodes americanus display striking qualitative differences. Altogether 13 carboxylic acids were identified in the secretions of the two sexes. Methacrylic, crotonic, and tiglic acids are produced exclusively by the female; the male lacks these unsaturated components, but produces their saturated analogs. 2-Methylbutyric acid is a major component produced by both sexes. Shared components also include hexanoic, (E)-2-hexenoic, benzoic, and (E)-2-octenoic acid, of which the latter two had not previously been reported from carabid beetles.

Animals↗
PubMed1991

Inhalational anesthetics stereochemistry: optical resolution of halothane, enflurane, and isoflurane.

Halothane (I), enflurane (II), and isoflurane (III), which are among the most important inhalation anesthetics, are currently administered as racemic mixtures. The pure enantiomers have not been described, and no analytical method for resolving the commercially available racemic mixtures has been reported. Complete optical resolution of (+/-)-I and (+/-)-III on per-n-pentylated alpha-cyclodextrin (Lipodex A) and of (+/-)-II and (+/-)-III on octakis(6-O-methyl-2,3-di-O-pentyl)-gamma-cyclodextrin capillary columns has been achieved, making rapid and convenient determination of enantiomeric ratios in samples of all three of these anesthetics possible.

Chromatography↗
PubMed1988

Biparental defensive endowment of eggs with acquired plant alkaloid in the moth Utetheisa ornatrix.

The eggs of Utetheisa ornatrix contain pyrrolizidine alkaloids. These compounds are contributed by both parents, who sequester them as larvae from their food plants. Females receive alkaloid from the males at mating, apparently by seminal infusion, and transmit this alkaloid together with alkaloid of their own to the eggs. Field and laboratory tests showed that the alkaloids protect eggs from predators. The alkaloidal contribution of the male, although smaller than that of the female, itself provides significant egg protection. A previously identified pheromone, derived by the male from the alkaloid and emitted during precopulatory behavior, may announce the male alkaloidal worth to the female.

Animals↗