29. BC環開環型ストリゴラクトンアナログの合成とAM菌および根寄生雑草に対する活性評価(口頭発表,植物化学調節学会第46回大会)

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It has been demonstrated that all tested natural and synthetic strigolactones (SLs) with a tricyclic ABC lactone coupled to a methylbutenolide via an enol ether bond showed hyphal branching activity in the AM fungus Gigaspora margarita, and that truncation of the A- and AB-rings in the tricyclic lactone resulted in a drastic reduction in hyphal branching activity. In this study, we synthesized the BC-ring-opening SL analogues and evaluated their biological activity on G. margarita and the root parasitic weed Orobanche minor. Alcoholysis of formyl Meldrum's acid by either benzyl alcohol, o-, m-, p-methylbenzyl alcohol, or cyclohexanemethanol followed by alkylation with racemic 4-bromo-2-methyl-2-buten-4-olide provided trans- and diester BC-ring-opening SL analogues. Among the analogues synthesized, the cyclohexanemethanol-derived diester and trans-analogues showed the most potent activity on G. margarita and O. minor, respectively.
2011-10-03