1 ハエドクソウ殺虫成分の構造決定・合成及び活性(ポスター発表の部)

概要

論文の詳細を見る
The analytical and insecticidal assays with the extract of the herbaceous perennial plant, Phryma leptostachya L., have been conducted, including the isolation, structure elucidation and total syntheses of the active plant components, as well as derivation of congeners and analysis of structural requirements for the biological activity. So far, novel insecticidal sesquilignans such as HAEDOXAN A, C-acetate, D, F-acetate, G-acetate, and H-acetate, of which content totally below 5% of the extract, were revealed to be responsible for the peculiar flaccid paralysis followed by the insect death. In association with piperonyl butoxide, haedoxan A showed very high insecticidal activity against housefly as comparable with deltamethrin. The synthetic studies clarified the activity is tightly linked with the absolute configuration (1S, 2R, 5R, 6S, 2"R, 3"R) among the 32 stereoisomers. The molecule could take a conformation as the opened 15-crown-5, suggesting the ability to chelate with metal ions such as Ca^<+2>, Mg^<+2>, and Na^<+1> in the nervous system of insects. The discussions will be focused on the total synthesis and absolute configuration of (+)-haedoxan D as well as the structure-activity relationship concerning with about 50 congeners of haedoxan obtained by the isolation and syntheses. The previous assignment of the absolute configuration of (1S, 2S, 5R, 6S)-(+)-phrymarolin I and (1S, 2S, 5R, 6S,2"R,3"R)-(+)-haedoxan D, depending on the large acetylation shift of 2-H in their molecules, have been revised to (1S, 2R, 5R, 6S) and (1S, 2R, 5R, 6S, 2"R, 3"R), respectively, based on their NOESY spectra.
天然有機化合物討論会の論文
1988-09-26

1 ハエドクソウ殺虫成分の構造決定・合成及び活性(ポスター発表の部)

スポンサーリンク

概要

著者

関連論文

スポンサーリンク