Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451
Organic Chemistry
Structural Confirmation of 15-Norlubiminol and 15-Norepilubiminol, Isolated from Solanum aethiopicum, by Chemical Conversion from Lubimin and Epilubimin, and their Antifungal Activity
Ayako WATANABE, Hiroaki TOSHIMA, Hiroshi NAGASE, Toshinori NAGAOKA, Teruhiko YOSHIHARA
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2001 年 65 巻 8 号 p. 1805-1811

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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.
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© 2001 by Japan Society for Bioscience, Biotechnology, and Agrochemistry
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