Isolation and structure of novel autoregulators from Streptomyces griseus.

Gräfe, U.; Reinhardt, G.; Schade, Wolfgang; Krebs, D.; Eritt, I.; Fleck, W. F.; Heinrich, Eugen

doi:10.7164/antibiotics.35.609

Cited by 67 publications

(26 citation statements)

References 13 publications

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“…This appears not to be the case in N. vitripennis since virgin females were also attracted by (4S,5S)-HDL, which is not released by males. (4S,5R)-HDL has been described among the fermentation products of Streptomyces griseus (Graefe et al, 1982). (+)Vernolic acid (9Z,12S,13R)-12,13-epoxyoctadec-9-enoic acid) has been shown to be the precursor of HDL stereoisomers in microorganisms (Garbe and Tressl, 2003).…”

Section: Discussionmentioning

confidence: 99%

A male sex pheromone in a parasitic wasp and control of the behavioral response by the female's mating status

Rüther

Stahl

Steiner

et al. 2007

Journal of Experimental Biology

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SUMMARY Male insects may increase their chance of successful reproduction by releasing pheromones that attract females or elicit sexual acceptance. In parasitic wasps, male pheromones have been suggested for a few species but no chemicals have been identified so far. Here we report the first identification of a male sex pheromone in parasitic Hymenoptera. In abdomens of male jewel wasps, Nasonia vitripennis Walker, we found a mixture of(4R,5R)- and(4R,5S)-5-hydroxy-4-decanolide (HDL), which was released intermittently and attracted virgin females, but no males, in an olfactometer bioassay. However, only a few minutes after copulation mated females avoided the male-derived pheromone. Neither preference nor avoidance was shown by mated females after 24 h and even after they had been allowed to oviposit for 6 days. Nasonia vitripennis females normally mate only once. Thus,their variable response to the sex attractant depending on the mating status makes sense from an evolutionary perspective. Firstly, it increases the chance of virgins to be inseminated. Secondly, by terminating the response or even avoiding the male pheromone, mated females decrease the probability of encountering males and being disturbed by their courtship activities when searching for new oviposition sites.

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Section: Discussionmentioning

confidence: 99%

A male sex pheromone in a parasitic wasp and control of the behavioral response by the female's mating status

Rüther

Stahl

Steiner

et al. 2007

Journal of Experimental Biology

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“…During the fermentation of Streptomyces griseus, the enantiomer (4S,5R)-2 occurs temporarily before the antibiotic production and is known as L-factor in the literature [11] [12]. Due to the biological activity of 2, many contributions have been published concerning the chemical and chemoenzymatic synthesis of the four isomers of 2 [13 ± 17].…”

mentioning

confidence: 99%

Metabolism of Deuterated Isomeric 6,7‐Dihydroxydodecanoic Acids in Saccharomyces cerevisiae – Diastereo‐ and Enantioselective Formation and Characterization of 5‐Hydroxydecano‐4‐lactone (=4,5‐Dihydro‐5‐(1‐hydroxyhexyl)furan‐2(3H)‐one) Isomers

Garbe

Tressl

2003

Helvetica Chimica Acta

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The chemical synthesis of deuterated isomeric 6,7‐dihydroxydodecanoic acid methyl esters 1 and the subsequent metabolism of esters 1 and the corresponding acids 1a in liquid cultures of the yeast Saccharomyces cerevisiae was investigated. Incubation experiments with (6R,7R)‐ or (6S,7S)‐6,7‐dihydroxy(6,7‐2H2)dodecanoic acid methyl ester ((6R,7R)‐ or (6S,7S)‐(6,7‐2H2)‐1, resp.) and (±)‐threo‐ or (±)‐erythro‐6,7‐dihydroxy(6,7‐2H2)dodecanoic acid ((±)‐threo‐ or (±)‐erythro‐(6,7‐2H2)‐1a, resp.) elucidated their metabolic pathway in yeast (Tables 1–3). The main products were isomeric 2H‐labeled 5‐hydroxydecano‐4‐lactones 2. The absolute configuration of the four isomeric lactones 2 was assigned by chemical synthesis via Sharpless asymmetric dihydroxylation and chiral gas chromatography (Lipodex ® E). The enantiomers of threo‐2 were separated without derivatization on Lipodex ® E; in contrast, the enantiomers of erythro‐2 could be separated only after transformation to their 5‐O‐(trifluoroacetyl) derivatives. Biotransformation of the methyl ester (6R,7R)‐(6,7‐2H2)‐1 led to (4R,5R)‐ and (4S,5R)‐(2,5‐2H2)‐2 (ratio ca. 4 : 1; Table 2). Estimation of the label content and position of (4S,5R)‐(2,5‐2H2)‐2 showed 95% label at C(5), 68% label at C(2), and no 2H at C(4) (Table 2). Therefore, oxidation and subsequent reduction with inversion at C(4) of 4,5‐dihydroxydecanoic acid and transfer of 2H from C(4) to C(2) is postulated. The 5‐hydroxydecano‐4‐lactones 2 are of biochemical importance: during the fermentation of Streptomyces griseus, (4S,5R)‐2, known as L‐factor, occurs temporarily before the antibiotic production, and (−)‐muricatacin (=(4R,5R)‐5‐hydroxy‐heptadecano‐4‐lactone), a homologue of (4R,5R)‐2, is an anticancer agent.

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“…(4R,5R)-5-Hydroxy-4-decanolide (1a; Fig. )isone such g-butyrolactone which was recently found in male Nasonia vitripennis as an additional pheromone compound differing only in its configuration from the previously described (4R,5S)-5-hydroxy-4decanolide (1b) [7].T he enantiomers of these two compounds,( 4 S,5S)-and (4S,5R)isomers 1c and 1d,were also natural compounds,named as L-factors,isolated from the cultures of Streptomyces griseus,w hich reveal autoregulatory properties [8]. Due to their notable bioactivity,t he synthesis of L-factors has receiveda ttention of organic chemists and accordingly variouss trategies have been developed [9].…”

mentioning

confidence: 80%

Alkyne‐Mediated Approach to the Synthesis of (4R,5R)‐5‐Hydroxy‐4‐decanolide and (−)‐Muricatacin

Reddy

Suman

Rao

2015

Helvetica Chimica Acta

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Isolation and structure of novel autoregulators from Streptomyces griseus.

Cited by 67 publications

References 13 publications

A male sex pheromone in a parasitic wasp and control of the behavioral response by the female's mating status

A male sex pheromone in a parasitic wasp and control of the behavioral response by the female's mating status

Metabolism of Deuterated Isomeric 6,7‐Dihydroxydodecanoic Acids in Saccharomyces cerevisiae – Diastereo‐ and Enantioselective Formation and Characterization of 5‐Hydroxydecano‐4‐lactone (=4,5‐Dihydro‐5‐(1‐hydroxyhexyl)furan‐2(3H)‐one) Isomers

Alkyne‐Mediated Approach to the Synthesis of (4R,5R)‐5‐Hydroxy‐4‐decanolide and (−)‐Muricatacin

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