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

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

  • Planta Med. 2019 Aug;85(11-12):981-986. doi: 10.1055/a-0883-5383.
Diego Caprioglio 1,  Gianna Allegrone 1,  Federica Pollastro 1,  Stefano Valera 1,  Annalisa Lopatriello 2,  Juan A Collado 3,  Eduardo Munoz 3,  Giovanni Appendino 1,  Orazio Taglialatela-Scafati 2
Affiliations

Affiliations

  • 1 Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale, Novara, Italy.
  • 2 Dipartimento di Farmacia, Università di Napoli Federico II, Napoli, Italy.
  • 3 Maimonides Biomedical Research Institute of Córdoba; Department of Cellular Biology, Physiology and Immunology, University of Córdoba; University Hospital Reina Sofía, Córdoba, Spain.
PMID: 30934093 DOI: 10.1055/a-0883-5383
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.

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