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O-Methyl Phytocannabinoids: Semi-synthesis, Analysis in Cannabis Flowerheads, and Biological Activity.

Planta medica (2019-04-02)
Diego Caprioglio, Gianna Allegrone, Federica Pollastro, Stefano Valera, Annalisa Lopatriello, Juan A Collado, Eduardo Munoz, Giovanni Appendino, Orazio Taglialatela-Scafati
ABSTRACT

A general protocol for the selective mono-O-methylation of resorcinyl phytocannabinoids was developed. The availability of semisynthetic monomethyl analogues of cannabigerol, cannabidiol, and cannabidivarin (1A: -3A: , respectively) made it possible to quantify these minor phytocannabinoids in about 40 different chemotypes of fiber hemp. No chemotype significantly accumulated mono-O-methyl cannabidiol (2B: ) or its lower homologue (3B: ), while at least three chemotypes containing consistent amounts (≥ 400 mg/kg) of O-methylcannabigerol (1B: ) were identified. O-Methylation of alkyl phytocannabinoids (1B: -3B: ) does not significantly change the activity on peroxisome proliferator-activated receptors in contrast to what was reported for phenethyl analogues.

MATERIALS
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Brand
Product Description

Sigma-Aldrich
Rosiglitazone, ≥98% (HPLC)