Document Report Card

ID: ALA3044993

Journal: Biosci Biotechnol Biochem

Title: Structural confirmation of 15-norlubiminol and 15-norepilubiminol, isolated from Solanum aethiopicum, by chemical conversion from lubimin and epilubimin, and their antifungal activity.

Authors: Watanabe A, Toshima H, Nagase H, Nagaoka T, Yoshihara T.

Abstract: 15-Norlubiminol and 15-norepilubiminol were obtained from Solanum aethiopicum as an inseparable 1:1 mixture in a relatively poor yield to that of the major phytoalexins, lubimin and epilubimin. Their structures were confirmed by chemical conversion starting from lubimin and epilubimin. Baeyer-Villiger oxidation of the protected lubimins with m-chloroperoxybenzoic acid provided the desired formates. Deoxygenation with triphenylphosphine selenide and subsequent methanolysis provided 15-norlubiminols, whose 1H-NMR spectra were respectively identical with that of the corresponding isomer in the natural 15-norlubiminol mixture. The antifungal activity of 15-norlubiminols would be weaker than that of lubimins.

CiteXplore: 11577721

DOI: 10.1271/bbb.65.1805