RRC ID 33192
Author Yan Q, Kanegae A, Miyachi T, Naka H, Tatsuta H, Ando T.
Title Female sex pheromones of two Japanese saturniid species, Rhodinia fugax and Loepa sakaei: identification, synthesis, and field evaluation.
Journal J. Chem. Ecol.
Abstract While 11 species in the family Saturniidae are found in Japan, no sex pheromones of the native species had been investigated previously. We collected larvae of Rhodinia fugax in Nagano and Tottori Prefecture, and of Loepa sakaei in Okinawa Prefecture, and extracted sex pheromones of these two species from virgin female moths. In gas chromatography-electroantennogram detection (GC-EAD) analyses, male antennae of each species responded to one component in the respective pheromone extracts of conspecific females. Chemical analyses of the extracts by GC/mass spectrometry revealed that the EAD-active compounds of R. fugax and L. sakaei were a hexadecadienal and a tetradecadienyl acetate, respectively. The two species belong to the subfamily Saturniinae, and the mass spectra of both were similar to that of the 6,11-hexadecadienyl acetate identified from Antheraea polyphemus, classified in the same subfamily, suggesting the same 6,11-dienyl structure for the C16 aldehyde and a 4,9-dienyl structure for the C14 acetate. Based on this assumption, four geometrical isomers of each dienyl compound were stereoselectively synthesized via acetylene intermediates, compared to the natural products, and tested in the field. Male catches confirmed the pheromone structures of the two Japanese saturniid species as (6E,11Z)-6,11-hexadecadienal for R. fugax and (4E,9Z)-4,9-tetradecadienyl acetate for L. sakaei. The compounds have a characteristic 1,6-dienyl motif common to the pheromones of Saturniinae species.
Volume 41(1)
Pages 1-8
Published 2015-1
DOI 10.1007/s10886-014-0538-6
PMID 25533776
MeSH Acetates / analysis Acetates / chemistry Alkadienes / analysis Alkadienes / chemistry Animals Female Gas Chromatography-Mass Spectrometry Japan Male Molecular Structure Moths / chemistry* Moths / drug effects Pheromones / analysis Pheromones / chemistry Sex Attractants / analysis Sex Attractants / chemical synthesis Sex Attractants / chemistry* Sex Attractants / pharmacology*
IF 2.447
Times Cited 3
WOS Category ECOLOGY BIOCHEMISTRY & MOLECULAR BIOLOGY
Resource
Silkworms Rhodinia fugax