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Plant and Cell Physiology Advance Access originally published online on October 14, 2008
Plant and Cell Physiology 2008 49(12):1767-1782; doi:10.1093/pcp/pcn150
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© The Author 2008. Published by Oxford University Press on behalf of Japanese Society of Plant Physiologists. All rights reserved. For permissions, please email: journals.permissions@oxfordjournals.org

PKS Activities and Biosynthesis of Cannabinoids and Flavonoids in Cannabis sativa L. Plants

Isvett Josefina Flores-Sanchez and Robert Verpoorte*

Pharmacognosy Department/Metabolomics, Institute of Biology, Gorlaeus Laboratories, PO Box 9502, 2300 RA Leiden University, Leiden, The Netherlands

*Corresponding author: E-mail, verpoort{at}chem.leidenuniv.nl; Fax, +31-71-52-74 511.


  Abstract

Polyketide synthase (PKS) enzymatic activities were analyzed in crude protein extracts from cannabis plant tissues. Chalcone synthase (CHS, EC 2.3.1.74 [EC] ), stilbene synthase (STS, EC 2.3.1.95 [EC] ), phlorisovalerophenone synthase (VPS, EC 2.3.1.156 [EC] ), isobutyrophenone synthase (BUS) and olivetol synthase activities were detected during the development and growth of glandular trichomes on bracts. Cannabinoid biosynthesis and accumulation take place in these glandular trichomes. In the biosynthesis of the first precursor of cannabinoids, olivetolic acid, a PKS could be involved; however, no activity for an olivetolic acid-forming PKS was detected. Content analyses of cannabinoids and flavonoids, two secondary metabolites present in this plant, from plant tissues revealed differences in their distribution, suggesting a diverse regulatory control for these biosynthetic fluxes in the plant.

Keywords: Cannabinoids - Cannabis sativa - Flavonoids - Glandular trichomes - Olivetol synthase - Polyketide synthase

Abbreviations: APCI, atmospheric pressure chemical ionization; BAS, benzalacetone synthase; BBS, bibenzyl synthase; BUS, isobutyrophenone synthase; CBCA, cannabichromenic acid; CBD, cannabidiol; CBDA, cannabidiolic acid; CBG, cannabigerol; CBGA, cannabigerolic acid; CBN, cannabinodiol; CHS, chalcone synthase; {Delta}8-THC, {Delta}8-tetrahydrocannabinol; {Delta}9-THC, {Delta}9-tetrahydrocannabinol; {Delta}9-THCA, {Delta}9-tetrahydrocannabinolic acid; {Delta}9-THVA, {Delta}9-tetrahydrocannabivarinic acid; DMSO, dimethylsulfoxide; DOXP/MEP, deoxyxylulose phosphate/methyl-erythritol phosphate; DTT, dithiothreitol; GPP, geranyl diphosphate; HEDS/HvCHS, homoeriodictyol/eriodictyol synthase; LC-MS, liquid chromatography–mass spectrometry; PiBP, phlorisobutyrophenone; PiVP, phlorisovalerophenone; PKS, polyketide synthase; PVPP, polyvinylpolypyrrolidone; Rt, retention time; STCS, stilbene carboxylate synthase; STS, stilbene synthase; TFA, trifluoroacetic acid; VPS, phlorisovalerophenone synthase

(Received July 2, 2008; Accepted October 7, 2008)
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