Biosynthesis of (-)-β-barbatene from 13C- and 2H-labelled acetate, mevalonate and glycerol

The H-2 and C-13 enrichment, C-13-C-13 coupling patterns and beta-H-2 isotope shifts observed in beta-barbatanol prepared from (-)-beta-barbatene incorporating variously H-2- and C-13-labelled mevalonates, acetates and glycerol verifies a 1,4-hydrogen shift and a double 1,2-methyl migration in the formation of beta-barbatene in cultured cells of Heteroscyphus planus, and also indicates the diversity of regulation and the sole operation of the mevalonate pathway in extrachloroplastidic sesquiterpene biosynthesis.