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Studies on the Biosynthesis of γ–Decalactone in Sporobolomyces odorus

Albrecht, Wolfgang; Tressl, Roland

Incubation of racemic ethyl [2,2-2H2]-(E)-3,4-epoxydecanoate and the corresponding acid with intact cells of Sporobolomyces odorus led to the formation of deuterium labeled γ-decalaetone. The detection of labeled 2-decen-4-olide and 4-oxodecanoic acid made it possi­ble to propose the biogenetic sequence leading to γ-decalactone. The determination of the en­ antiomeric ratio of the lactone revealed an unspecific metabolism of the precursor. In contrast to the (E)-isomer, after administration of ethyl [5,6-2H2]-(Z)-3,4-epoxydeeanoate no transfor­mation could be detected. These results indicate that (E)-3,4-epoxydecanoic acid, formed from (E)-3-decenoyl-CoA , an intermediate of the β-oxidation of linoleic acid, is the genuine precur­sor in the biosynthesis of γ-decalactone.
Published in: Zeitschrift für Naturforschung C, 10.1515/znc-1990-3-411, De Gruyter