(E)-2-(2-Hydroxyethylidene)-6-methyl-5-heptenal (alpha-acariolal) and (E)-2-(2-hydroxyethyl)-6-methyl-2,5-heptadienal (beta-acariolal), two new types of isomeric monoterpenes from Caloglyphus polyphyllae (Acari: Acaridae).
The opisthonotal gland secretion of the acarid mite, Caloglyphus polyphyllae, contained two new monoterpenes, (E)-2-(2-hydroxyethylidene)-6-methyl-5-heptenal (1) and (E)-2-(2-hydroxyethyl)-6-methyl-2,5-heptadienal (2), to which we have given the trivial names alpha- and beta-acariolal in relation to alpha- and beta-acaridial (3 and 4), respectively. Elucidation of the structure of 1 was established mainly from 1H-NMR and GC/MS spectral data after partial purification, together with the fact that 1 was recovered in the more-polar fraction from a silica gel column than alpha- and beta-acaridial (3 and 4) present in the secretion. Compound 2 was obtained in the same fraction as a mixture with 1. Based on the facts that 2 had the same molecular weight by GC/MS and the same polarity as that of 1, compound 2 was assumed to be a structural analog of 1. The structures of compounds 1 and 2 were confirmed by their synthesis in nine and ten respective steps starting from alpha-bromo-gamma-butyrolactone.
Shimizu
Nobuhiro
N
Laboratory of Chemical Ecology, Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.
Tarui
Hirokazu
H
Mori
Naoki
N
Nishida
Ritsuo
R
Kuwahara
Yasumasa
Y
D040041:Acaridae / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D008401:Gas Chromatography-Mass Spectrometry; D007536:Isomerism; D007783:Lactones / Q000737:chemistry; D039821:Monoterpenes / Q000737:chemistry* / Q000302:isolation & purification; D019906:Nuclear Magnetic Resonance, Biomolecular
D000447:Aldehydes; D007783:Lactones; D039821:Monoterpenes