Biogenesis of sex pheromones in the female olive fruit-fly

Hungerford, Natasha L.; Hübener, Achim; Fletcher, Mary T.; DeVoss, James J.; Kitching, William; Mazomenos, B. E.; Κωνσταντοπούλου, Μαρία; Krokos, F.; Haniotakis, G. E.; Moore, Christopher

doi:10.1039/a800691a

Cited by 13 publications

(15 citation statements)

References 11 publications

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“…64 As determination of the biosynthetic origin of the C 9 unit is impeded by excessive metabolism of fatty acid precursors, subsequent biosynthetic investigations have focused on possible advanced precursors of 5. 64,77,78 Similarly, feeding of [ 2 H 4 ]-33 and [ 2 H 4 ]-52 to B. cacuminata males also resulted in significant deuterium incorporation into 5 and its hydroxylated derivatives (3R,6R)-30, (3S,6R)-30 and (4S,6S)-31. 67 Thus, both species could apparently biosynthesise their hydroxy spiroacetals from direct hydroxylation of the major spiroacetal, as had previously been observed with the hydroxylated derivatives of exo-brevicomin in pine bark beetles.…”

Section: Introductionmentioning

confidence: 96%

“…79 Indeed, when both species were fed [ 2 H 4 ]-5, their respective hydroxy spiroacetals were produced with the same absolute stereochemistry and very similar enantiomeric excesses to those observed naturally. 64,67,77,78 However, it is conceivable that the hydroxy spiroacetals could arise from a pathway utilising an epoxide as a trihydroxyketone equivalent. Administration of deuterium labelled 6-but-3-enyl-3,4-dihydro-2H-pyran ([ 2 H 3 ]-54) to B. oleae 64,77 resulted in the production of labelled (3S,6S)-30, (3S,6R)-30, (2S,5S)-32 and (2S,5R)-32, but these exhibited enantiomeric profiles significantly different from those of the natural components (Scheme 11).…”

Section: Introductionmentioning

confidence: 99%

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Biosynthesis of insect spiroacetals

2009

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The volatile secretions of numerous species of Coleoptera (beetles), Hymenoptera (wasps, bees) and Diptera (true flies) contain complex blends of spiroacetals. In several species, a certain number of them appear to function as sex pheromones. The structure of insect-derived spiroacetals will be summarised and the techniques useful for their identification and the investigation of their biogenesis will be discussed. Progress in the study and delineation of likely biosynthetic pathways to these spiroacetals in Dipteran (Bactrocera) and Hymenopteran (Megarhyssa) species will be reviewed, and the validity of these pathways as a general paradigm for spiroacetal generation in the wider insect world will be assessed.

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Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

Biosynthesis of insect spiroacetals

2009

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“…The fact that the abundances of (F) and (G) in the natural sample are very different (ca 8:1) is not an unusual state of affairs with such epimeric spiroacetals in insects. 2,3,12 Speculation on the biosynthesis of insect spiroacetals has been presented elsewhere, 2,29 and the origin of the component (B) and (C) may be associated with either propionate or even amino acid intervention. Because of the novelty of (B) and (C) and the latter's predominance in the secretion, such incorporation studies are planned.…”

Section: Components (C) (D) (F) (G) and (H)mentioning

confidence: 99%

Synthesis and Stereochemistry of Insect Derived Spiroacetals with Branched Carbon Skeletons

Tu¹,

Hübener²,

Zhang³

et al. 2000

Synthesis

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About thirty constitutionally different spiroacetals have been characterised from insects but only three have branched carbon skeletons. Two are based on the 1,7-dioxaspiro[5.5]undecane system and are certain stereoisomers of the 2,4,8-trimethyl derivative, from the aposematic shield bug, Cantao parentum (White), and a 2,2,8-trimethyl derivative from the rove beetle, Ontholestes murinus (L). The 1,6-dioxaspiro[4.5]decane system is represented by a stereoisomer of the 2,3,7-trimethyl derivative in the Cantao species. The elucidation of their structures and stereochemistry by spectroscopy, synthesis and enantioselective gas chromatography is described.

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“…We generated transcriptomes from dissected antennae and rectal glands from both male and female adults. Rectal glands are involved in potential sex pheromone production in Bactrocera species [47, 48]. Moreover, members of the chemosensory multigene families are expressed in pheromone glands in Lepidoptera where they are involved in pheromone product process [49–53].…”

Section: Introductionmentioning

confidence: 99%

Candidates for chemosensory genes identified in the Chinese citrus fly, Bactrocera minax, through a transcriptomic analysis

Kang

et al. 2019

BMC Genomics

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Background The males of many Bactrocera species (Diptera: Tephritidae) respond strongly to plant-derived chemicals (male lures) and can be divided into cue lure/raspberry ketone (CL/RK) responders, methyl eugenol (ME) responders and non-responders. Representing a non-responders, Bactrocera minax display unique olfactory sensory characteristics compared with other Bactrocera species. The chemical senses of insects mediate behaviors that are associated with survival and reproduction. Here, we report the generation of transcriptomes from antennae and the rectal glands of both male and female adults of B. minax using Illumina sequencing technology, and annotated gene families potentially responsible for chemosensory. Results We developed four transcriptomes from different tissues of B. minax and identified a set of candidate genes potentially responsible for chemosensory by analyzing the transcriptomic data. The candidates included 40 unigenes coding for odorant receptors (ORs), 30 for ionotropic receptors (IRs), 17 for gustatory receptors (GRs), three for sensory neuron membrane proteins (SNMPs), 33 for odorant-binding proteins (OBPs), four for chemosensory proteins (CSPs). Sex- and tissue-specific expression profiles for candidate chemosensory genes were analyzed via transcriptomic data analyses, and expression profiles of all ORs and antennal IRs were investigated by real-time quantitative PCR (RT-qPCR). Phylogenetic analyses were also conducted on gene families and paralogs from other insect species together. Conclusions A large number of chemosensory genes were identified from transcriptomic data. Identification of these candidate genes and their expression profiles in various tissues provide useful information for future studies towards revealing their function in B. minax. Electronic supplementary material The online version of this article (10.1186/s12864-019-6022-5) contains supplementary material, which is available to authorized users.

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Biogenesis of sex pheromones in the female olive fruit-fly

Cited by 13 publications

References 11 publications

Biosynthesis of insect spiroacetals

Biosynthesis of insect spiroacetals

Synthesis and Stereochemistry of Insect Derived Spiroacetals with Branched Carbon Skeletons

Candidates for chemosensory genes identified in the Chinese citrus fly, Bactrocera minax, through a transcriptomic analysis

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