The European grapevine moth, Lobesia botrana, uses (E,Z)-7,9-dodecadienyl acetate as its major sex pheromone component. Through in vivo labeling experiments we demonstrated that the doubly unsaturated pheromone component is produced by ∆11 desaturation of tetradecanoic acid, followed by chain shortening of (Z)-11-tetradecenoic acid to (Z)-9-dodecenoic acid, and subsequently introduction of the second double bond by an unknown ∆7 desaturase, before final reduction and acetylation. By sequencing and analyzing the transcriptome of female pheromone glands of L. botrana, we obtained 41 candidate genes that may be involved in sex pheromone production, including the genes encoding 17 fatty acyl desaturases, 13 fatty acyl reductases, 1 fatty acid synthase, 3 acyl-CoA oxidases, 1 acetyl-CoA carboxylase, 4 fatty acid transport proteins and 2 acyl-CoA binding proteins. A functional assay of desaturase and acyl-CoA oxidase gene candidates in yeast and insect cell (Sf9) heterologous expression systems revealed that Lbo_PPTQ encodes a ∆11 desaturase producing (Z)-11-tetradecenoic acid from tetradecanoic acid. Further, Lbo_31670 and Lbo_49602 encode two acyl-CoA oxidases that may produce (Z)-9-dodecenoic acid by chain shortening (Z)-11-tetradecenoic acid. The gene encoding the enzyme introducing the E7 double bond into (Z)-9-dodecenoic acid remains elusive even though we assayed 17 candidate desaturases in the two heterologous systems.

欧洲葡萄蛾Lobesia botrana使用 ( E , Z )-7,9-十二碳烯基乙酸酯作为其主要性信息素成分。通过 体内 标记实验，我们证明了双不饱和信息素成分是由十四烷酸的 Δ11 去饱和，随后 ( Z )-11-十四碳烯酸链缩短为 ( Z )-9-十二碳烯酸，随后引入在最终还原和乙酰化之前，未知的 Δ7 去饱和酶生成第二个双键。通过对植物药材雌性信息素腺体转录组的测序分析，我们获得了41个可能参与性信息素产生的候选基因，包括编码17个脂肪酰基去饱和酶、13个脂肪酰基还原酶、1个脂肪酸合酶、3个酰基辅酶A氧化酶、1个乙酰辅酶A羧化酶、4个脂肪酸转运的基因蛋白质和 2 种酰基辅酶 A 结合蛋白。酵母和昆虫细胞 (Sf9) 异源表达系统中去饱和酶和酰基辅酶 A 氧化酶候选基因的功能分析表明，Lbo_PPTQ 编码一种从十四烷酸产生 ( Z )-11-十四碳烯酸的 ∆11 去饱和酶。此外，Lbo_31670 和 Lbo_49602 编码两种酰基辅酶 A 氧化酶，它们可以通过链缩短 ( Z )-11-十四碳烯酸产生 ( Z )-9-十二碳烯酸。编码将 E7 双键引入 (即使我们在两个异源系统中检测了 17 种候选去饱和酶，Z )-9-十二碳烯酸仍然难以捉摸。