TY - JOUR
T1 - (R,Z)-7,15-Hexadecadien-4-olide, sex pheromone of the yellowish elongate chafer, Heptophylla picea
AU - Leal, Walter Scares
AU - Kuwahara, Shigefumi
AU - Ono, Mikio
AU - Kubota, Sakae
N1 - Funding Information:
This work was supported in part by a special coordination fund for promoting science and technology (SCF) in the basic research core system by the Science and Technology Agency, Japan granted to WSL. MSD was on loan from Fuji Flavor Co. Ltd. We wish to thank Mrs Junko Iseda and Mr Toshihiro Imai, Japan Tobacco Inc., for the IR and CI-MS measurements, respectively. The logistical support of Mr Akio Tatara and Mr Shinsaku Saida in Shizuoka and Hokkaido, respectively, is acknowledged with pleasure. We are also indebted to Dr Shigeru Matsuyama, Tsukuba University, for his critical review
PY - 1996/3
Y1 - 1996/3
N2 - An active component of the sex pheromone system of the yellowish elongate chafer, Heptophylla picea was identified by GG-EAD. Mass spectral data and hydrogenation revealed that the active compound was a hexadecadien-4-olide. It was not possible to determine the double bond positions by direct DMDS derivatization of the pheromone, but partial hydrogenation (diimide) followed by DMDS derivatization showed that the double bonds were located in positions 7 and 15. FTIR (tracer) of the pheromone corroborated the lactone structure (1772 cm-1) and showed a band characteristic of a terminal double bond at 3073 cm-1, and one of a double bond in the cis-configuration at 3002 cm-1. Chiral resolution of the pheromone, after hydrogenation, demonstrated that the natural lactone had the (R)-stereochemistry. Synthetic (R,Z)-7,15-hexadecadien-4-olide, prepared from L-malic acid in 14 steps, was identical to the natural product in MS, IR, retention times and biological activity. This is the first fatty acid derivative compound found as a sex pheromone of a Melolonthinae species and as far as biosynthesis is concerned this is the most complex pheromone constituent of a scarab species.
AB - An active component of the sex pheromone system of the yellowish elongate chafer, Heptophylla picea was identified by GG-EAD. Mass spectral data and hydrogenation revealed that the active compound was a hexadecadien-4-olide. It was not possible to determine the double bond positions by direct DMDS derivatization of the pheromone, but partial hydrogenation (diimide) followed by DMDS derivatization showed that the double bonds were located in positions 7 and 15. FTIR (tracer) of the pheromone corroborated the lactone structure (1772 cm-1) and showed a band characteristic of a terminal double bond at 3073 cm-1, and one of a double bond in the cis-configuration at 3002 cm-1. Chiral resolution of the pheromone, after hydrogenation, demonstrated that the natural lactone had the (R)-stereochemistry. Synthetic (R,Z)-7,15-hexadecadien-4-olide, prepared from L-malic acid in 14 steps, was identical to the natural product in MS, IR, retention times and biological activity. This is the first fatty acid derivative compound found as a sex pheromone of a Melolonthinae species and as far as biosynthesis is concerned this is the most complex pheromone constituent of a scarab species.
KW - (R)-4-hexadecanolide
KW - (S)-4-hexadecanolide
KW - (S)-7,10-hexadecadien-4-olid e
KW - GC-EAD
KW - Scarabaeidae
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U2 - 10.1016/0968-0896(96)00008-9
DO - 10.1016/0968-0896(96)00008-9
M3 - Article
C2 - 8733609
AN - SCOPUS:0000674547
VL - 4
SP - 315
EP - 321
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
SN - 0968-0896
IS - 3
ER -