Issue 24, 1995

Sesqui- and di-terpene biosynthesis from 13C labelled acetate and mevalonate in cultured cells of Heteroscyphus planus

Abstract

Cultured cells of the liverwort, Heteroscyphus planus, accumulate a wide variety of sesquiterpenes and diterpenes of the clerodane type. 13C Atoms of [2-13C]acetate and [2-13C]- and [4,5-13C2]-mevalonates (MVAs) are incorporated into sesquiterpenes more extensively than into diterpenes by cultured cells of H. planus. (1S)-7-Methoxy-1,2-dihydrocadalene, a predominant sesquiterpene, and heteroscyphic acid A, a main diterpene, incorporating 13C labelled precursors were analysed by 13C NMR spectroscopy. Preferential labelling of the farnesyl diphosphate (FPP)-derived portion of heteroscyphic acid A was confirmed by 13C enriched peaks and 13C–13C couplings, while sesquiterpenes were labelled equivalently. From these results, it appears that separate sites for sesquiterpene and diterpene biosynthesis exist in cultured cells of H. planus as could be observed in higher plants. Since the same type of nonequivalent labelling was observed in the phytyl side chain of chlorophyll by other experiments, it is suggested that all compounds, which are formed from GGPP within chloroplasts, are biosynthesized partly via the condensation of FPP derived from exogenous MVA with endogenous isopentenyl diphosphate in chloroplasts. A 1,2-methyl migration of the methyl group originating at C-3 of MVA is also confirmed in the biosynthesis of the trans-clerodane skeleton.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1995, 3111-3115

Sesqui- and di-terpene biosynthesis from 13C labelled acetate and mevalonate in cultured cells of Heteroscyphus planus

K. Nabeta, T. Ishikawa and H. Okuyama, J. Chem. Soc., Perkin Trans. 1, 1995, 3111 DOI: 10.1039/P19950003111

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.

Spotlight

Advertisements