Abstract
The biosynthesis of the furanic labdane diterpene marrubiin has been studied in plantlets and shoot cultures of Marrubium vulgare (Lamiaceae). The use of [2-14C]acetate, [2-14C]pyruvate, [2-14C]mevalonic acid and [U-14C]glucose incorporation experiments showed that the labelling of sterols in etiolated shoot cultures of M. vulgare was in accordance with their biosynthesis via the acetate-mevalonate pathway. In contrast, the incorporation rates of these precursors into the diterpene marrubiin could not be explained by biosynthesis of this compound via the acetate-mevalonate pathway. Cultivation of etiolated shoot cultures of M. vulgare on medium containing [1-13C]glucose and subsequent 13C-NMR spectroscopy of marrubiin led to the conclusion that the biosynthesis of marrubiin follows a non-mevalonate pathway. All isoprenic units of 13C-labelled marrubiin were enriched in those carbons that correspond to positions 1 and 5 of a putative precursor isopentenyl diphosphate. This labelling pattern from [1-13C]glucose is consistent with an alternative pathway via trioses, which has already been shown to occur in Eubacteria and Gymnospermae. The labdane skeleton is a precursor of many other skeletal types of diterpenes. Therefore it becomes obvious that in connection with the few known examples of a non-mevalonate pathway to isoprenoids the formation of some isoprenoids in plants via a non-mevalonate pathway might be quite common.
Full Text
The Full Text of this article is available as a PDF (281.8 KB).
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Bach T. J. Some new aspects of isoprenoid biosynthesis in plants--a review. Lipids. 1995 Mar;30(3):191–202. doi: 10.1007/BF02537822. [DOI] [PubMed] [Google Scholar]
- Breccia A., Badiello R. The role of general metabolites in the biosynthesis of natural products. I. The terpene marrubiin. Z Naturforsch B. 1967 Jan;22(1):44–49. [PubMed] [Google Scholar]
- Eisenreich W., Menhard B., Hylands P. J., Zenk M. H., Bacher A. Studies on the biosynthesis of taxol: the taxane carbon skeleton is not of mevalonoid origin. Proc Natl Acad Sci U S A. 1996 Jun 25;93(13):6431–6436. doi: 10.1073/pnas.93.13.6431. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Knöss W., Reuter B. Biosynthesis of [14C]geranylgeranyldiphosphate by a prenyl transferase system from a mutant strain of Gibberella fujikuroi. Anal Biochem. 1996 Aug 1;239(2):208–212. doi: 10.1006/abio.1996.0316. [DOI] [PubMed] [Google Scholar]
- Lichtenthaler H. K., Schwender J., Disch A., Rohmer M. Biosynthesis of isoprenoids in higher plant chloroplasts proceeds via a mevalonate-independent pathway. FEBS Lett. 1997 Jan 6;400(3):271–274. doi: 10.1016/s0014-5793(96)01404-4. [DOI] [PubMed] [Google Scholar]
- Loreto F., Ciccioli P., Brancaleoni E., Cecinato A., Frattoni M., Sharkey T. D. Different sources of reduced carbon contribute to form three classes of terpenoid emitted by Quercus ilex L. leaves. Proc Natl Acad Sci U S A. 1996 Sep 3;93(18):9966–9969. doi: 10.1073/pnas.93.18.9966. [DOI] [PMC free article] [PubMed] [Google Scholar]
- RUZICKA L. The isoprene rule and the biogenesis of terpenic compounds. Experientia. 1953 Oct 15;9(10):357–367. doi: 10.1007/BF02167631. [DOI] [PubMed] [Google Scholar]
- Rohmer M., Knani M., Simonin P., Sutter B., Sahm H. Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate. Biochem J. 1993 Oct 15;295(Pt 2):517–524. doi: 10.1042/bj2950517. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Schwender J., Seemann M., Lichtenthaler H. K., Rohmer M. Biosynthesis of isoprenoids (carotenoids, sterols, prenyl side-chains of chlorophylls and plastoquinone) via a novel pyruvate/glyceraldehyde 3-phosphate non-mevalonate pathway in the green alga Scenedesmus obliquus. Biochem J. 1996 May 15;316(Pt 1):73–80. doi: 10.1042/bj3160073. [DOI] [PMC free article] [PubMed] [Google Scholar]