Laboratory of Chemical Ecology, Graduate School of Agriculture, Kyoto University, Kitashirakawa, Sakyo-ku, Kyoto, Japan.
Department of Plant Pathology and Entomology, Okinawa Prefectural Agricultural Research Center, Itoman, Okinawa, Japan.
Biosci Biotechnol Biochem. 2021 Nov 24;85(12):2360-2367. doi: 10.1093/bbb/zbab166.
A series of 3-oxygenated α-ionone analogs have been developed as highly specific male lures for the solanaceous fruit fly Bactrocera latifrons, a pest of solanaceous fruits. We compared the attractant and phagostimulant activities of analogs with or without (i) unsaturations at the 4,5- and/or 7,8-positions and (ii) oxygen moieties at the 3- and/or 9-positions of the ionone molecule. Since naturally occurring vomifoliol (V2) was found to induce a highly potent phagostimulant activity in B. latifrons males, related analogs including dehydrovomifoliol (V1), 6-hydroxy-α-ionone (U1), and 6-hydroxy-α-ionol (U2) were synthesized to evaluate their attractant and phagostimulant activities. Synthetic V1, V2, U1, and U2 exhibited low attractant activity, but their phagostimulant activity was relatively high. Optical isomers of 3-oxo-7,8-dihydro-α-ionone (P3) and V1 were prepared to examine the stereochemical specificity of attractants. (+)-(6R)-P3 and (+)-(6S)-V1 exhibited the corresponding activities, while their respective antipodal enantiomers were found entirely inactive.
我们合成了一系列 3-位含氧的 α-紫罗兰酮类似物，作为茄科实蝇 Bactrocera latifrons 的高特异性雄虫引诱剂，B. latifrons 是茄科果实的一种害虫。我们比较了具有或不具有（i）4,5-和/或 7,8-位不饱和键以及（ii）3-和/或 9-位含氧基团的类似物的引诱和取食刺激活性。由于天然存在的vomifoliol（V2）被发现能诱导 B. latifrons 雄虫产生很强的取食刺激活性，因此合成了相关的类似物，包括脱氢vomifoliol（V1）、6-羟基-α-紫罗兰酮（U1）和 6-羟基-α-紫罗兰醇（U2），以评估它们的引诱和取食刺激活性。合成的 V1、V2、U1 和 U2 表现出较低的引诱活性，但它们的取食刺激活性相对较高。还制备了 3-氧代-7,8-二氢-α-紫罗兰酮（P3）和 V1 的光学异构体，以检验引诱剂的立体化学特异性。(+)-(6R)-P3 和 (+)-(6S)-V1 表现出相应的活性，而它们各自的对映异构体则完全没有活性。
