Terpenoid Biosynthesis from 1-Deoxy-D-Xylulose in Higher Plants by Intramolecular Skeletal Rearrangement

The incorporation of [1-13C]- [2,3,4,5-13C4]1-deoxy-D-xylulose into β -carotene, lutein, phytol, and sitosterol in a cell culture of Catharanthus roseus was analyzed by NMR spectroscopy. The labeling patterns of the isoprene precursors, isopentenyl pyrophosphate and dimethylallyl pyrophosphate, were...

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Published in:Proceedings of the National Academy of Sciences - PNAS 1997-09, Vol.94 (20), p.10600-10605
Main Authors: Arigoni, Duilio, Sagner, Silvia, Latzel, Christoph, Eisenreich, Wolfgang, Bacher, Adelbert, Zenk, Meinhart H.
Format: Article
Language:English
Subjects:
Atoms
Biochemistry
Biological Sciences
Biosynthesis
Carbon
Carotenoids
Cells, Cultured
Chlorophylls
Diphosphates
Flowers & plants
Magnetic Resonance Spectroscopy
Metabolites
Plant Cells
Plants - metabolism
Sitosterols
Spectroscopy
Terpenes - chemistry
Terpenes - metabolism
Terpenoids
Xylulose - analogs & derivatives
Xylulose - metabolism
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Summary:The incorporation of [1-13C]- [2,3,4,5-13C4]1-deoxy-D-xylulose into β -carotene, lutein, phytol, and sitosterol in a cell culture of Catharanthus roseus was analyzed by NMR spectroscopy. The labeling patterns of the isoprene precursors, isopentenyl pyrophosphate and dimethylallyl pyrophosphate, were obtained from the terpenes by a retrobiosynthetic approach.13C Enrichment and13C13C coupling patterns showed conclusively that 1-deoxy-D-xylulose and not mevalonate is the predominant isoprenoid precursor of phytol, β -carotene, and lutein. Label from 1-deoxyxylulose was also diverted to phytosterols to a minor extent (6% relative to carotene and phytol formation). The data demonstrate that the formation of isopentenyl pyrophosphate from pentulose occurs strictly by an intramolecular rearrangement process.
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.94.20.10600