Biosynthesis of cannabinoids. Incorporation experiments with (13)C-labeled glucoses.
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.
Biozentrum-Pharmazie, Universität Halle, Halle/Saale, Germany. zenk@biozentrum.uni-halle.de
M
M
Fellermeier
W
W
Eisenreich
A
A
Bacher
M H
MH
Zenk
D002186:Cannabinoids / Q000096:biosynthesis* / Q000378:metabolism; D002188:Cannabis / Q000378:metabolism; D002247:Carbon Isotopes; D005947:Glucose / Q000378:metabolism*; D019906:Nuclear Magnetic Resonance, Biomolecular
D002186:Cannabinoids; D002247:Carbon Isotopes; D005947:Glucose