The biosynthesis of (+)-α-pinene in Pinus species

Abstract

1. The degradation of (+)-α-pinene biosynthesized from 3RS-[2-14C]mevalonate by Pinus radiata or Pinus nigra revealed an asymmetrical labelling pattern whereby the moiety derived from isopentenyl pyrophosphate contained at least 90% of the incorporated tracer. This pattern differed both in asymmetry and position of labelling from previous results obtained with P. nigra, but is consistent with the generally accepted hypothetical mechanism for the biosynthesis of the pinane skeleton. 2. (+)-α-Pinene biosynthesized in Pinus attenuata and in the previously named two species from 3RS-[2-14C,(4R)-4-3H1]mevalonate and its (4S)-isomer retained all the 4R hydrogen atoms (within the experimental error) but lost all the 4S hydrogen atoms of the precursor. This stereospecificity of hydrogen loss is the same as that previously found for the formation of geraniol and nerol in other plant species, and the result may be reasonably inferred to be general for monoterpenes.