Biosynthesis of cannabinoids. Incorporation experiments with (13)C-labeled glucoses

Eur J Biochem. 2001 Mar;268(6):1596-604. doi: 10.1046/j.1432-1033.2001.02030.x.

Abstract

The biosynthesis of cannabinoids was studied in cut sprouts of Cannabis sativa by incorporation experiments using mixtures of unlabeled glucose and [1-(13)C]glucose or [U-(13)C(6)]glucose. (13)C-labeling patterns of cannabichromenic acid and tetrahydrocannabinolic acid were analyzed by quantitative NMR spectroscopy. (13)C 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cannabinoids / biosynthesis*
  • Cannabinoids / metabolism
  • Cannabis / metabolism
  • Carbon Isotopes
  • Glucose / metabolism*
  • Nuclear Magnetic Resonance, Biomolecular

Substances

  • Cannabinoids
  • Carbon Isotopes
  • Glucose