Pheromone Biosynthesis in Lepidopterans: Desaturation and Chain Shortening

Bjostad, L. B.; Wolf, Walter A.; Roelofs, Wendell L.

doi:10.1016/b978-0-12-564485-3.50008-7

Cited by 106 publications

(112 citation statements)

References 54 publications

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“…The first desaturation step seems to be a less species-specific step that is presumably catalyzed by the Z11-desaturase commonly used in the pheromone biosyntheses of numerous moth species. In contrast, the second desaturation step is less common in that it generates a conjugated diene system through 1,4-elimination of two hydrogen atoms at the allylic positions of the double bond in the Z11-monoene C 16 intermediate (2). Similar 1,4-desaturation reactions involving monoene acyl precursors have only been observed in a handful of sex pheromone biosynthetic pathways (8)(9)(10).…”

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confidence: 85%

“…The first Z11-desaturation step is a prevalent one that has been described in many other moth species, whereas the second (E,Z)-10,12-desaturation step generates a conjugated diene system by means of 1,4-elimination of two allylic hydrogen atoms (2). In the present experiments designed to characterize the enzymes responsible for these two desaturation steps, we assumed that there would be two distinct desaturases acting sequentially.…”

Section: Discussionmentioning

confidence: 99%

“…A major class of sex pheromone components produced by these female moths has been characterized by the presence of straightchain C 10 -C 18 unsaturated aliphatic compounds containing an oxygenated functional group (aldehyde, alcohol, or acetate ester) derived from saturated C 16 or C 18 fatty acid (FA) intermediates that are synthesized de novo in the abdominal pheromone gland cells (2).…”

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confidence: 99%

“…The biosynthesis of bombykol from the intermediate palmitate (C16:acyl) is a rather simple procedure that eschews the common chain-shortening and hydroxyl group modification steps for three consecutive steps, i.e., Z11 desaturation, (E,Z)-10,12 desaturation, and fatty-acyl reduction (2,6). Among these steps, we have recently characterized the enzyme responsible for the fatty-acyl reduction, which we named pheromone gland fatty-acyl reductase (pgFAR) (7).…”

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Involvement of a bifunctional fatty-acyl desaturase in the biosynthesis of the silkmoth, Bombyx mori , sex pheromone

Moto

Suzuki

Hull

et al. 2004

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

114

116

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The straight-chain C10 to C18 unsaturated aliphatic compounds containing an oxygenated functional group (aldehyde, alcohol, or acetate ester) derived from saturated C 16 or C18 fatty acids are a major class of sex pheromone components produced by female moths. In the biosynthesis of these pheromone components, various combinations of limited chain-shortening and regio-and stereospecific desaturation reactions significantly contribute to the production of a vast number of the species-specific pheromone components in Lepidoptera. Biosynthesis of the silkmoth sex pheromone bombykol, (E,Z)-10,12-hexadecadien-1-ol, involves two consecutive desaturation steps, the second of which is unique in that it generates a conjugated diene system from the ⌬11-monoene C 16 intermediate. In experiments designed to characterize the acyl-CoA desaturases responsible for bombykol biosynthesis, we have cloned three cDNAs encoding desaturase family members from the pheromone gland of the inbred strain of the silkmoth, Bombyx mori. Transcript analyses by RT-PCR and subsequent functional assays using a Bac-to-Bac baculovirus expression system revealed that desat1 is the only desaturase gene prominently expressed during pheromonogenesis and that its gene product, B. mori Desat1, possesses both Z11 desaturation and ⌬10,12-desaturation activities. Consequently, we have concluded that B. mori Desat1 is not only a bifunctional desaturase involved in bombykol biosynthesis but that it is also the enzyme responsible for both desaturation steps.

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confidence: 85%

Section: Discussionmentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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Involvement of a bifunctional fatty-acyl desaturase in the biosynthesis of the silkmoth, Bombyx mori , sex pheromone

Moto

Suzuki

Hull

et al. 2004

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

114

116

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“…In this species, the genetic mechanism controlling the pheromone blend also seems to be similar to that of O. nubilalis Takanashi, unpublished data Evolution of sex pheromone biosynthesis system. The biosynthesis of 11-14:OAc is considered to follow the following steps; 16:Acyl is first chainshortened to 14:Acyl by limited β-oxidation, desaturated to 11-14:Acyl by 11-desaturase, reduced to 11-14:OH by acyl reductase, and acetylated to 11-14:OAc by acetyltransferase (Bjostad et al, 1987;Zhu et al, 1996). It seems that in O. latipennis, the enzyme that works in the final step of 11-14:OAc synthesis (acetyltransferase) is dysfunctional, and thereby E11-14:OH becomes the final product.…”

Section: Resultsmentioning

confidence: 99%

Ostrinia spp. in Japan: their host plants and sex pheromones

Ishikawa

Takanashi

Lee

et al. 1999

Entomologia Exp Applicata

109

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To contribute to the understanding of the genus Ostrinia (Lepidoptera; Pyralidae) in Japan, we collected larvae of Ostrinia spp. from known host plants and plants not recorded as hosts, and we examined the morphology and sex pheromones of the adults obtained. Consequently, the host plant ranges of the 7 Ostrinia spp. in Japan were clarified, and the sex pheromones of the 5 species O. scapulalis, O. zealis, O. zaguliaevi, O. palustralis and O. latipennis were identified in addition to that of the Asian corn borer O. furnacalis. The phylogenetic relationships of Japanese Ostrinia spp., with reference to the European corn borer O. nubilalis, are discussed based on these findings and results of molecular phylogenetic analyses.

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