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New oxygenated himachalenes in male-specific odor of the Chinese windmill butterfly, Byasa alcinous alcinous

Author:
Ômura, Hisashi, Noguchi, Taro, Nehira, Tatsuo
Source:
Natural product research 2016 v.30 no.4 pp. 406-411
ISSN:
1478-6427
Subject:
eclosion, sexual maturity, sesquiterpenoids, acetates, nuclear magnetic resonance spectroscopy, males, Papilionidae, solvents, windmills, butterflies, odors, hydrolysates, adults
Abstract:
Male adults of the Chinese windmill Byasa alcinous alcinous (Papilionidae) are well known to have a strong musk-like odor, in which two oxygenated himachalene compounds, together with six sesquiterpene hydrocarbons, were newly discovered. γ-Himachalen-4-yl acetate (1) was the predominant compound isolated from the solvent extract of the males. The structure of 1 was determined using MS and NMR, and its relative configuration was established as 1 S *,4 R *,6 R * by NOE analysis with the help of quantum mechanical computation. Interestingly, the amount of 1 in males increased until 7 days after eclosion, suggesting that this compound is involved in sexual maturation for mating. Another new compound was identified as γ-himachalen-4-ol (2) by comparison with the retention time and mass spectrum of the hydrolysate of 1 . Since males of other papilionid species have general volatiles omnipresent in plants and insects, the presence of species-specific volatiles in males is characteristic of B. alcinous alcinous .
Agid:
4790436