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用于开发新型农药的木脂素的合成及其构效关系

Syntheses and structure-activity relationship of lignans to develop novel pesticides.

作者信息

Yamauchi Satoshi

机构信息

Graduate School of Agriculture, Ehime University.

出版信息

J Pestic Sci. 2024 Nov 20;49(4):311-320. doi: 10.1584/jpestics.J24-03.

DOI:10.1584/jpestics.J24-03
PMID:39882271
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11775267/
Abstract

The syntheses of stereoisomers of butane, butanediol, γ-butyrolactone, tri-substituted tetrahydrofuran (7,9'-epoxy), furofuran, tetra-substituted tetrahydrofuran (7,7'-epoxy and 7,8'-epoxy-8,7'-neolignan), benzylidene, coumarin, indan, and pyran type lignans were achieved. All the stereoisomers of the butane type lignans showed larvicidal activity and anti-phytopathogenic fungal activity. The γ-butyrolactone lignan showed stereospecific cytotoxicity against insect cells. Stereo/enantiospecific plant growth inhibitory activity was observed in tri-substituted tetrahydrofuran, tetra-substituted tetrahydrofuran (7,7'-epoxy), coumarin, and pyran type lignans. The furofuran lignan both inhibited and promoted growth in plants. Stereo/enantiospecific anti-phytopathogenic fungal activity was observed in tetra-substituted tetrahydrofuran (7,7'-epoxy) and -benzylidene lignans.

摘要

实现了丁烷、丁二醇、γ-丁内酯、三取代四氢呋喃（7,9'-环氧）、呋喃并呋喃、四取代四氢呋喃（7,7'-环氧和7,8'-环氧-8,7'-新木脂素）、亚苄基、香豆素、茚和吡喃型木脂素立体异构体的合成。所有丁烷型木脂素的立体异构体均表现出杀幼虫活性和抗植物病原真菌活性。γ-丁内酯木脂素对昆虫细胞表现出立体特异性细胞毒性。在三取代四氢呋喃、四取代四氢呋喃（7,7'-环氧）、香豆素和吡喃型木脂素中观察到立体/对映体特异性植物生长抑制活性。呋喃并呋喃木脂素对植物生长既有抑制作用又有促进作用。在四取代四氢呋喃（7,7'-环氧）和亚苄基木脂素中观察到立体/对映体特异性抗植物病原真菌活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/a3552261198a/jps-49-4-J24-03-scheme07.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/2bc1b19d0935/jps-49-4-J24-03-figure01.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/e9b922326004/jps-49-4-J24-03-figure02.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/47179207b8d0/jps-49-4-J24-03-scheme01.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/7b4a49eac6d8/jps-49-4-J24-03-figure03.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/2addd93bf383/jps-49-4-J24-03-scheme02.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/feb2db93bc3b/jps-49-4-J24-03-scheme03.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/d9eb5384f3cf/jps-49-4-J24-03-figure04.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/584c280a4ab8/jps-49-4-J24-03-scheme04.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/88af20aae21a/jps-49-4-J24-03-scheme05.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/a7ed5e627016/jps-49-4-J24-03-scheme06.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/a3552261198a/jps-49-4-J24-03-scheme07.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/2bc1b19d0935/jps-49-4-J24-03-figure01.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/e9b922326004/jps-49-4-J24-03-figure02.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/47179207b8d0/jps-49-4-J24-03-scheme01.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/7b4a49eac6d8/jps-49-4-J24-03-figure03.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/2addd93bf383/jps-49-4-J24-03-scheme02.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/feb2db93bc3b/jps-49-4-J24-03-scheme03.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/d9eb5384f3cf/jps-49-4-J24-03-figure04.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/584c280a4ab8/jps-49-4-J24-03-scheme04.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/88af20aae21a/jps-49-4-J24-03-scheme05.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/a7ed5e627016/jps-49-4-J24-03-scheme06.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0972/11775267/a3552261198a/jps-49-4-J24-03-scheme07.jpg

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