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Erinacine Q, a New Erinacine from Hericium erinaceum , and its Biosynthetic Route to Erinacine C in the Basidiomycete

2002; Oxford University Press; Volume: 66; Issue: 3 Linguagem: Inglês

10.1271/bbb.66.571

1347-6947

Hiromichi Kenmoku, Takashi Shimai, Tomonobu Toyomasu, Nobuo Kato, Takeshi Sassa,

Phytochemistry and Biological Activities

Erinacines as cyathane-xylosides are known to have potent stimulating activity for nerve-growth-factor synthesis. Our search for new cyathane metabolites from a liquid culture of Hericium erinaceum YB4-6237 resulted in the isolation of a new erinacine named erinacine Q (1). NMR spectrometry and a chemical derivation from erinacine P (2) determined the compound to be a derivative in which the formyl group of erinacine P had been reduced to the hydroxymethyl group. To clarify the biosynthetic relationship between erinacine Q and the others, [1′-13C]erinacine Q ([1′-13C]-1) was chemically derived from [1′-13C]erinacine P ([1′-13C]-2) which had been prepared by feeding [1-13C]-D-glucose to the basidiomycete. The biotransformation of labeled erinacine Q into [1′-13C]erinacine C ([1′-13C]-5) via [1′-13C]erinacine P in this basidiomycete was demonstrated by NMR spectrometry.