The biogenesis of cannabinoids in Cannabis sativa

Kajima, Masahiro; Piraux, M.

doi:10.1016/0031-9422(82)80016-2

Cited by 34 publications

(23 citation statements)

References 9 publications

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“…This is supported by the fact that the content of CBNRA in the CBDA strain is much lower than that of CBGA (0.08 versus 2.8 mg/g of rapidly expanding leaves). 2 Kinetic properties similar to those of CBDA synthase have been described for limonene synthase, which mediates the formation of limonene with higher V max and lower K m values for geranyl pyrophosphate as compared with neryl pyrophosphate (18). However, the cyclization catalyzed by limonene synthase is not accompanied by oxidation (16 ) suggests that CBDA synthase also may require some cofactors, we could not demonstrate either cofactors or coenzymes that activate the enzyme activity.…”

Section: Figmentioning

confidence: 50%

“…Several groups have attempted to confirm this hypothesis by feeding experiments, although they could not obtain unequivocal results owing to the low incorporation of labeled precursors into CBDA (15,18). To definitively establish the biosynthetic mechanism of CBDA, we directly investigated the enzyme (CBDA synthase) that catalyzes the formation of CBDA.…”

Section: Discussionmentioning

confidence: 99%

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Purification and Characterization of Cannabidiolic-acid Synthase from Cannabis sativa L.

Taura

Morimoto

Shoyama

1996

Journal of Biological Chemistry

162

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We identified a unique enzyme that catalyzes the oxidocyclization of cannabigerolic acid to cannabidiolic acid (CBDA) in Cannabis sativa L. (CBDA strain). The enzyme, named CBDA synthase, was purified to apparent homogeneity by a four-step procedure: ammonium sulfate precipitation followed by chromatography on DEAE-cellulose, phenyl-Sepharose CL-4B, and hydroxylapatite. The active enzyme consists of a single polypeptide with a molecular mass of 74 kDa and a pI of 6.1. The NH 2 -terminal amino acid sequence of CBDA synthase is similar to that of ⌬ 1 -tetrahydrocannabinolic-acid synthase. CBDA synthase does not require coenzymes, molecular oxygen, hydrogen peroxide, and metal ion cofactors for the oxidocyclization reaction. These results indicate that CBDA synthase is neither an oxygenase nor a peroxidase and that the enzymatic cyclization does not proceed via oxygenated intermediates. CBDA synthase catalyzes the formation of CBDA from cannabinerolic acid as well as cannabigerolic acid, although the k cat for the former (0.03 s ؊1

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Section: Figmentioning

confidence: 50%

Section: Discussionmentioning

confidence: 99%

Purification and Characterization of Cannabidiolic-acid Synthase from Cannabis sativa L.

Taura

Morimoto

Shoyama

1996

Journal of Biological Chemistry

162

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“…La première étape consiste en une réaction de condensation du pyrophosphate de géranyle avec l'acide olivétolique pour former le cannabigérol (CBG) lui-même précurseur du cannabichromène (CBC), du cannabidiol (CBD) ou du A-9-tétrahydrocannabinol (A-9-THC) (2)(3)(4)(5)(6)(7)(8)(9)(10)(11). A chaque étape, des enzymes catalysent la réaction (12)(13)(14).…”

Section: Introductionunclassified

Santhica 23 et 27 : deux variétés de chanvre (Cannabis sativa L.) sans Δ-9-THC

Fournier¹,

Beherec²,

Bertucelli³

2004

Ann Toxicol Anal

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“…This explanation suggests that the enzymes are either combined or closely located to each other so that the olivetolic acid is placed directly into the site responsible for prenylation. This hypothesis has still to be proven, but supports the fact that olivetolic acid cannot be found in Cannabis extracts [35].…”

Section: Biochemistry and Biosynthesismentioning

confidence: 80%

“…Here the incorporation of radioactive labeled olivetol has been detected in very low amounts and olivetolic acid in high amounts. These reactions were performed in planta, whereas the previous reactions were performed in vitro [35]. It still remains unclear which structure, olivetol or olivetolic acid, is really preferred.…”

Section: Biochemistry and Biosynthesismentioning

confidence: 99%