Planta Med 2019; 85(11/12): 981-986
DOI: 10.1055/a-0883-5383
Biological and Pharmacological Activities
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

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

Diego Caprioglio
1   Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale, Novara, Italy
,
Gianna Allegrone
1   Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale, Novara, Italy
,
Federica Pollastro
1   Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale, Novara, Italy
,
Stefano Valera
1   Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale, Novara, Italy
,
Annalisa Lopatriello
2   Dipartimento di Farmacia, Università di Napoli Federico II, Napoli, Italy
,
Juan A. Collado
3   Maimonides Biomedical Research Institute of Córdoba; Department of Cellular Biology, Physiology and Immunology, University of Córdoba; University Hospital Reina Sofía, Córdoba, Spain
,
Eduardo Munoz
3   Maimonides Biomedical Research Institute of Córdoba; Department of Cellular Biology, Physiology and Immunology, University of Córdoba; University Hospital Reina Sofía, Córdoba, Spain
,
Giovanni Appendino
1   Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale, Novara, Italy
,
Orazio Taglialatela-Scafati
2   Dipartimento di Farmacia, Università di Napoli Federico II, Napoli, Italy
› Author Affiliations
Further Information

Publication History

received 01 February 2019
revised 18 March 2019

accepted 20 March 2019

Publication Date:
01 April 2019 (online)

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 (1a3a, 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 (1b3b) does not significantly change the activity on peroxisome proliferator-activated receptors in contrast to what was reported for phenethyl analogues.

* Dedicated to Professor Dr. Cosimo Pizza 70th birthday in recognition of his outstanding contribution to natural product research.


 
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