Anastrephin and epianastrephin, novel lactone components isolated from the sex pheromone blend of male caribbean and mexican fruit flies

✍ Scribed by Merle A Battiste; Lucjan Strekowski; David P Vanderbilt; Melean Visnick; Roy W King; James L Nation

• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 253 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)87958-7

✦ Synopsis

Anastrephin and epianastrephin, novel lactone components isolated from the male produced pheromone of two Anastrepha fruit fly species (Caribbean and Mexican) are assigned the structure and relative stereochemistry 1 and 2, respectively, on the basis of spectroscopic and chemical evidence including synthesTs. Courting male Caribbean fruit flies, AlzQstrepha suspensa (Loew), produce and release a four-component sex pheromone2 which in addition to attracting females for mating also acts as an aggregation pheromone for both sexes in the field.3 Chromatography of male A. suspensa extracts on silver nitrate-impregnated silicic acid afforded four individually bioactive components (I-IV) each isolated in >95% purity. Components I and II are Cg unsaturated alcohols 26 and were readily identified as Z-3-nonen-l-01 and Z,Z-3,6-nonadien-l-01, respectively. 4 Synthetic samples of I and II were also shown to have behavioral activity in laboratory bioassays with lo-day-old female flies. 4 Components III and IV, henceforth referred to as anastrephin and epianastrephin, constitute the major fraction, by weight, of the extracted pheromone blend and have now been identified as the diastereoisomeric trans-fused bicyclic y-lactones ,I_ and 2, respectively.5 In this paper we report the structure elucidation of lactones 1 and 2 by spectroscopic means as well as chemical synthesis. In addition we describe the results of a companion study which convincingly demonstrates the presence of lactones 1. and 2, along with Z-3-nonen-l-01 and Z,Z-3,6-nonadien-l-01, in the extracts of males of the closely related Mexican fruit fly, Anastrepha Zudens (Loew).

As such these results constitute the first structural identification of the multi-component pheromone blends of fruit flies of the species Anastrepha.