Semiochemicals containing lepidopteran sex pheromones: Wonderland for a natural product chemist

Abstract

Since the first identification of bombykol, sex pheromones of about 700 moth species have been elucidated. Additionally, field evaluations of synthetic pheromones and their related compounds have revealed the male attraction of another 1,300 species. These pheromones and attractants are listed on the web-sites, "Pheromone Database, Part I. " Pheromone components are classified according to their chemical structures into two major groups (Types I and II) and miscellaneous. Based on our previous review published in 2004, studies reported during the last two decades are highlighted here to provide information on the structure characteristics of newly identified pheromones, current techniques for structure determination, new enantioselective syntheses of methyl-branched pheromones, and the progress of biosynthetic research. Besides the moth sex pheromones, various pheromones and allomones from many arthropod species have been uncovered. These semiochemicals are being collected in the "Pheromone Database, Part II. " The chemical diversity provides a wonderland for natural product chemists.

Identification of a unique three‐component sex pheromone produced by the tea black tussock moth, Dasychira baibarana (Lepidoptera: Erebidae: Lymantriinae)

“…The 11‐desaturation is a key step in compound II of D. baibarana (Z3,Z6,epo9,E11‐21:H), as Z3,Z6,Z9,E11‐19:H and Z3,Z6,Z9,Z11‐19:H from Alsophila pometaria of the Geometridae 26 and the 11,12‐epoxide of Z6,Z9,E11‐21:H produced by Orgyia postica of the Lymantriinae 20 . Type II epoxy pheromone components are derived from their corresponding unsaturated hydrocarbons, 25 which are processed in oenocytes and transported to the pheromone gland via the hemolymph 27‐30 . In the case of D. baibarana , we proposed that Z3,Z6,Z9,E11‐21:H is a biosynthetic precursor of Z3,Z6,epo9,E11‐21:H and the double bond at the 9‐position is selectively oxidized.…”

“…20 Type II epoxy pheromone components are derived from their corresponding unsaturated hydrocarbons, 25 which are processed in oenocytes and transported to the pheromone gland via the hemolymph. [27][28][29][30] In the case of D. baibarana, we proposed that Z3,Z6,Z9,E11-21:H is a biosynthetic precursor of Z3,Z6,epo9,E11-21:H and the double bond at the 9-position is selectively oxidized. Z3,Z6,epo9-21:H and Z3,Z6-21:11-one were detectable from 1 μL of the (20 FE) extract, but a more concentrated extract 1 μL of (180 FE) was required to detect an analyzable mass spectrum of Z3,Z6,epo9, E11-21:H because of its low content.…”

(Z, Z, Z)-3,6,9-nonadecadiene, a potential inhibitor of sex pheromone ofEctropis grisescensWarren (Lepidoptera: Geometridae): electroantennogram test, wind tunnel, and in silico study

“…Nowadays, sex pheromone technology has been extensively used in many regions as an efficient and environmentally sound method for pest control. [6][7][8][9] Attempts to identify sex pheromones of Ectropis obliqua began 30 yr ago, but the components still have not been accurately identified. 10 In recent studies, sex pheromones of E. grisescens was reidentified, which revealed the distinction of sex pheromones components between E. obliqua and E. grisescens.…”

Developments in Fatty Acid-Derived Insect Pheromone Production Using Engineered Yeasts

“…Type-II sex pheromones comprise odd polyunsaturated hydrocarbons (C17-C23) with two or three double bonds at positions three, six, or nine, in addition to their corresponding epoxide derivatives ( Matsumoto, 2010 ; Sun et al, 2019 ; Yang et al, 2020 ). The miscellaneous groups of sex pheromones comprise secondary alcohols with short-chain fatty acids (C7 and C9) and can be further classified as Type-0, while those with methyl-branched compounds are classified as Type-III ( Ando and Yamamoto, 2020 ).…”