BIOSYNTHESIS OF MONOTERPENES AND SESQUITERPENES IN LARIX-LEPTOLEPIS CALLUS FROM DEUTERATED MEVALONATES

Callus cultures from the seedling leaves of Larix leptolepis were able to synthesize p-cymene [1], sesquiterpene hydrocarbons, and some oxygenated sesquiterpenes. Deuterium atoms from RS-[6,6,6-2H3]-, RS-[5,5-2H2]-, and RS-[4,4-2H2]-mevalonate were extensively incorporated into p-cymene [1], α-cedrene [2], 6E-β-farnesene [3], and farnesol [4] by the calli. The isopentenyl origins of these lower terpenoids were confirmed by gc-ms analysis, and no preferential labeling of the isopentenyl-pyrophosphate-derived portions of the molecules was noted. The labeling patterns confirmed on the basis of these ms spectra indicate a 1,2-hydride shift in α-cedrene [2] formation and the loss of the expected hydrogen atom in 6E-β-farnesene [3] formation. © 1990, American Chemical Society. All rights reserved.