A general protocol for the selective mono-O-methylation of resorcinyl phytocannabinoids was developed. The availability of semi-synthetic monomethyl analogues of cannabigerol (CBG), cannabidiol (CBD), and cannabidivarin (CBDV) (1a-3a, respectively) made it possible to quantify these minor phytocannabinoids in about forty different chemotypes of fiber hemp. No chemotype significantly accumulated mono-O-methyl CBD (2b) or its lower homologue 3b, while at least three chemotypes containing consistent amounts (> 400 mg/Kg) of O-methyl CBG (1b) were identified. O-methylation of alkyl phytocannabinoids 1b-3b does not significantly change the activity on PPARs, in contrast to what reported for phenethyl analogues.
O-Methyl Phytocannabinoids: Semi-synthesis, Analysis in Cannabis Flowerheads, and Biological Activity / Caprioglio, D., Allegrone, G., Pollastro, F., Valera, S., Lopatriello, A., Collado, J.A., Munoz, E., Appendino, G., Taglialatela-Scafati, O.. - In: PLANTA MEDICA. - ISSN 0032-0943. - 85:11-12(2019), pp. 981-986. [10.1055/a-0883-5383]
O-Methyl Phytocannabinoids: Semi-synthesis, Analysis in Cannabis Flowerheads, and Biological Activity
Lopatriello A.Membro del Collaboration Group
;Taglialatela-Scafati O.
Supervision
2019
Abstract
A general protocol for the selective mono-O-methylation of resorcinyl phytocannabinoids was developed. The availability of semi-synthetic monomethyl analogues of cannabigerol (CBG), cannabidiol (CBD), and cannabidivarin (CBDV) (1a-3a, respectively) made it possible to quantify these minor phytocannabinoids in about forty different chemotypes of fiber hemp. No chemotype significantly accumulated mono-O-methyl CBD (2b) or its lower homologue 3b, while at least three chemotypes containing consistent amounts (> 400 mg/Kg) of O-methyl CBG (1b) were identified. O-methylation of alkyl phytocannabinoids 1b-3b does not significantly change the activity on PPARs, in contrast to what reported for phenethyl analogues.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
