Literature DB >> 11248677

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

M Fellermeier1, W Eisenreich, A Bacher, M H Zenk.   

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.

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Year:  2001        PMID: 11248677     DOI: 10.1046/j.1432-1033.2001.02030.x

Source DB:  PubMed          Journal:  Eur J Biochem        ISSN: 0014-2956


  35 in total

1.  Gene Networks Underlying Cannabinoid and Terpenoid Accumulation in Cannabis.

Authors:  Jordan J Zager; Iris Lange; Narayanan Srividya; Anthony Smith; B Markus Lange
Journal:  Plant Physiol       Date:  2019-05-28       Impact factor: 8.340

2.  Application of 3D NMR for Structure Determination of Peptide Natural Products.

Authors:  Fan Zhang; Navid Adnani; Emmanuel Vazquez-Rivera; Doug R Braun; Marco Tonelli; David R Andes; Tim S Bugni
Journal:  J Org Chem       Date:  2015-08-21       Impact factor: 4.354

3.  Crystallization and preliminary X-ray diffraction studies of polyketide synthase-1 (PKS-1) from Cannabis sativa.

Authors:  Chiho Taguchi; Futoshi Taura; Taro Tamada; Yoshinari Shoyama; Yukihiro Shoyama; Hiroyuki Tanaka; Ryota Kuroki; Satoshi Morimoto
Journal:  Acta Crystallogr Sect F Struct Biol Cryst Commun       Date:  2008-02-29

4.  Influence of mevinolin on chloroplast terpenoids in Cannabis sativa.

Authors:  Hakimeh Mansouri; Fatemeh Salari
Journal:  Physiol Mol Biol Plants       Date:  2014-02-26

Review 5.  Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects.

Authors:  Ethan B Russo
Journal:  Br J Pharmacol       Date:  2011-08       Impact factor: 8.739

6.  Acyl-lipid thioesterase1-4 from Arabidopsis thaliana form a novel family of fatty acyl-acyl carrier protein thioesterases with divergent expression patterns and substrate specificities.

Authors:  Ian P Pulsifer; Christine Lowe; Swara A Narayaran; Alia S Busuttil; Sollapura J Vishwanath; Frédéric Domergue; Owen Rowland
Journal:  Plant Mol Biol       Date:  2013-11-10       Impact factor: 4.076

7.  Cannabinoids as anticancer therapeutic agents.

Authors:  Olga Kovalchuk; Igor Kovalchuk
Journal:  Cell Cycle       Date:  2020-04-05       Impact factor: 4.534

8.  Characterization of leachianone G 2"-dimethylallyltransferase, a novel prenyl side-chain elongation enzyme for the formation of the lavandulyl group of sophoraflavanone G in Sophora flavescens Ait. cell suspension cultures.

Authors:  Ping Zhao; Kenichiro Inoue; Isao Kouno; Hirobumi Yamamoto
Journal:  Plant Physiol       Date:  2003-10-09       Impact factor: 8.340

9.  Cloning and characterization of naringenin 8-prenyltransferase, a flavonoid-specific prenyltransferase of Sophora flavescens.

Authors:  Kanako Sasaki; Kouji Mito; Kazuaki Ohara; Hirobumi Yamamoto; Kazufumi Yazaki
Journal:  Plant Physiol       Date:  2008-01-24       Impact factor: 8.340

10.  Identification of candidate genes affecting Delta9-tetrahydrocannabinol biosynthesis in Cannabis sativa.

Authors:  M David Marks; Li Tian; Jonathan P Wenger; Stephanie N Omburo; Wilfredo Soto-Fuentes; Ji He; David R Gang; George D Weiblen; Richard A Dixon
Journal:  J Exp Bot       Date:  2009-07-06       Impact factor: 6.992

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