Control of the sex pheromone biosynthetic pathway in Thaumetopoea pityocampa by the pheromone biosynthesis activating neuropeptide

Fabriás, Gemma; Barrot, M.; Camps, Francisco

doi:10.1016/0965-1748(95)00003-e

Cited by 44 publications

(30 citation statements)

References 30 publications

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“…The processionary moth sex pheromone, (Z)-13-hexadecen-11-ynyl acetate, is biosynthesized from palmitic acid by sequential ⌬ 11 desaturation, ⌬ 11 acetylenation and ⌬ 13 desaturation, followed by final reduction and acetylation (13)(14)(15)(16)(17). This biosynthetic pathway suggested that three different desaturases were involved in the process.…”

Section: Discussionmentioning

confidence: 99%

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A multifunctional desaturase involved in the biosynthesis of the processionary moth sex pheromone

Serra

Piña

Abad

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

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The sex pheromone of the female processionary moth, Thaumetopoea pityocampa, is a unique C16 enyne acetate that is biosynthesized from palmitic acid. Three consecutive desaturation reactions transform this saturated precursor into the triunsaturated fatty acyl intermediate: formation of (Z)-11-hexadecenoic acid, acetylenation to 11-hexadecynoic acid, and final ⌬ 13 desaturation to (Z)-13-hexadecen-11-ynoic acid. By using degenerate primers common to all reported insect desaturases, a single cDNA sequence was isolated from total RNA of T. pityocampa female pheromone glands. The full-length transcript of this putative desaturase was expressed in elo1⌬/ole1⌬ yeast mutants (both elongase 1 and ⌬ 9 desaturase-deficient) for functional assays. The construct fully rescued the ⌬ole1 yeast phenotype, confirming its desaturase activity. Analysis of the unsaturated products from transformed yeast extracts demonstrated that the cloned enzyme showed ⌬ 11 desaturase, ⌬ 11 acetylenase, and ⌬ 13 desaturase activities. Therefore, this single desaturase may account for the three desaturation steps involved in the sex pheromone biosynthetic pathway of the processionary moth.acetylene ͉ cloning ͉ enyne ͉ Thaumetopoea pityocampa ͉ yeast

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Section: Discussionmentioning

confidence: 99%

“…This compound is further ⌬ 13 desaturated to give the enynoic immediate pheromone precursor ( Fig. 1), which is finally reduced and acetylated (13)(14)(15)(16)(17).…”

mentioning

confidence: 99%

A multifunctional desaturase involved in the biosynthesis of the processionary moth sex pheromone

Serra

Piña

Abad

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

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“…In the most studied genus, Thaumetopoea, the ability to form the acetylenic compounds 7A and 7B is not universal. The pheromone pathway is regulated by the Pheromone Biosynthesis Activating Neuropeptide (PBAN), whose presence allows the conversion of the enynoic acid to the acetylated pheromone [91]. While labeling experiments have shown that Thaumetopoea pityocampa Δ 11 -desaturates 16:0, installs the acetylenic bond, and then dehydrogenates C-13:14 in strict sequence prior to the modifications at the carboxylate group, Thaumetopoea processionea was found to produce only the corresponding 11,13-dienyl esters [92,93].…”

Section: 14mentioning

confidence: 99%

“…Acetylenic pheromone biosynthesis in insects. In T. pityocampa, the transformation of the acetylenic fatty acid to the pheromone 7B is blocked in the absence of the hormone PBAN [91]. Stereochemistry of acetylenase/desaturase activities.…”

Section: Future Directionsmentioning

confidence: 99%

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

296

228

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Polyacetylenic natural products are a substantial class of often unstable compounds containing a unique carbon-carbon triple bond functionality, that are intriguing for their wide variety of biochemical and ecological functions, economic potential, and surprising mode of biosynthesis. Isotopic tracer experiments between 1960 and 1990 demonstrated that the majority of these compounds are derived from fatty acid and polyketide precursors. During the past decade, research into the metabolism of polyacetylenes has swiftly advanced, driven by the cloning of the first genes responsible for polyacetylene biosynthesis in plants, moss, fungi, and actinomycetes, and the initial characterization of the gene products.The current state of knowledge of the biochemistry and molecular genetics of polyacetylenic secondary metabolic pathways will be presented together with an up-to-date survey of new terrestrial and marine natural products, their known biological activities, and a discussion of their likely metabolic origins.

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“…In several species (Tang et al, 1989;Jacquin et al, 1994;Jurenka et al, 1991a;Zhao et al, 2002), PBAN influences a step in fatty acid synthesis, probably the conversion of acetyl-CoA to malonyl-CoA by the enzyme acetyl CoA carboxylase. In other species, it influences the metabolism of fatty acids including their reduction (Martinez et al, 1990, Fabrias et al, 1995, Ozawa and Matsumoto, 1996 or acetylation following reduction (Mas et al, 2000). One other study (Fang et al, 1996) suggested that PBAN may control the mobilization of pheromone precursor fatty acids from TGs.…”

Section: Introductionmentioning

confidence: 94%

Regulation of pheromone biosynthesis in the “Z strain” of the European corn borer, Ostrinia nubilalis

Eltahlawy

Buckner

Foster

2007

Arch Insect Biochem Physiol

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The regulation of pheromone biosynthesis by the neuropeptide PBAN in the Z strain of the European corn borer, Ostrinia nubilalis, was investigated using labeled intermediates. Injection of radiolabeled acetate showed PBAN did not influence the de novo synthesis of saturated fatty acids in the gland. When deuterium-labeled myristic acid was topically applied to the gland, females injected with PBAN produced more labeled pheromone than did control females, indicating that PBAN controls one of the later steps of pheromone biosynthesis. Although more myristic acid was Delta11-desaturated in the gland in the presence of PBAN, this was counterbalanced by less Delta11-desaturation of palmitic acid, indicating that desaturase activity did not change overall. This change in flux of myristic acid through to pheromone was shown to be caused by increased reduction of fatty acid pheromone precursors occurring in the presence of PBAN.

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Control of the sex pheromone biosynthetic pathway in Thaumetopoea pityocampa by the pheromone biosynthesis activating neuropeptide

Cited by 44 publications

References 30 publications

A multifunctional desaturase involved in the biosynthesis of the processionary moth sex pheromone

A multifunctional desaturase involved in the biosynthesis of the processionary moth sex pheromone

Biosynthesis and function of polyacetylenes and allied natural products

Regulation of pheromone biosynthesis in the “Z strain” of the European corn borer, Ostrinia nubilalis

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