Journal
EUROPEAN JOURNAL OF BIOCHEMISTRY
Volume 268, Issue 6, Pages 1596-1604Publisher
WILEY
DOI: 10.1046/j.1432-1327.2001.02030.x
Keywords
biosynthesis; cannabinoid; deoxyxylulose; NMR spectroscopy; polyketide
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The biosynthesis of cannabinoids was studied in cut sprouts of Cannabis sativa by incorporation experiments using mixtures of unlabeled glucose and [1-C-13]glucose or [U-C-13(6)]glucose. C-13-labeling patterns of cannabichromenic acid and tetrahydrocannabinolic acid were analyzed by quantitative NMR spectroscopy. C-13 enrichments and coupling patterns show that the C-10-terpenoid moiety is biosynthesized entirely or predominantly (> 98%) via the recently discovered deoxyxylulose phosphate pathway. The phenolic moiety is generated by a polyketide-type reaction sequence. The data support geranyl diphosphate and the polyketide, olivetolic acid, as specific intermediates in the biosynthesis of cannabinoids.
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