Jump to main content
Jump to site search

Issue 19, 1970
Previous Article Next Article

Terpene biosynthesis. Part II. Biosynthesis of thujane derivatives in Thuja, Tanacetum, and Juniperus species

Abstract

(–)-Thujone, (+)-isothujone, and (+)-sabinene were biosynthesised from [2-14C]mevalonic acid by certain Thuja, Tanacetum, and Juniperus species with from 90 to more than 99% of the incorporated tracer in that part of the skeleton derived from isopentenyl pyrophosphate. The part hypothetically derived from 3,3-dimethylallyl pyrophosphate was essentially unlabelled. The tracer pattern in (+)-sabinyl acetate was similar, but the acetate group contained ten times more tracer than the terpenoid portion, presumably as a result of degradation of mevalonic acid releasing tracer to the C2-pool.

These results are not consistent with the accepted view that isopentenyl and 3,3-dimethylallyl pyrophosphates, which condense to form monoterpenes, are both directly derived from mevalonic acid. They may be rationalised by: (a) the existence of a metabolic pool of isotopically normal 3,3-dimethylallyl pyrophosphate (or its structural equivalent) that reacted with labelled isopentenyl pyrophosphate of mevalonoid origin; (b) compartmentation effects; or (c) the formation of 3,3-dimethylallyl pyrophosphate from a source such as the monoterpene pool.

The locations of tracer in all compounds were in accord with Ruzicka's hypothetical schemes for the biogenesis of bicyclic monoterpenes but were inconsistent with alternative mechanisms that have been proposed on the basis of incomplete degradations of thujone and α-pinene biosynthesised in Thuja and Pinus species.

Back to tab navigation

Article information


J. Chem. Soc. C, 1970, 2689-2693
Article type
Paper

Terpene biosynthesis. Part II. Biosynthesis of thujane derivatives in Thuja, Tanacetum, and Juniperus species

D. V. Banthorpe, J. Mann and K. W. Turnbull, J. Chem. Soc. C, 1970, 2689 DOI: 10.1039/J39700002689

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.


Search articles by author

Spotlight

Advertisements