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

Diego Caprioglio; Gianna Allegrone; Federica Pollastro; Stefano Valera; Annalisa Lopatriello; Juan A. Collado; Eduardo Munoz; Giovanni Appendino; Orazio Taglialatela-Scafati

doi:10.1055/a-0883-5383

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

Diego Caprioglio
, Gianna Allegrone
, Federica Pollastro
, Stefano Valera
, Annalisa Lopatriello
, Juan A. Collado
, Eduardo Munoz
, Giovanni Appendino
, Orazio Taglialatela-Scafati

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	981-986
Number of pages	6
Journal	Planta Medica
Volume	85
Issue number	11-12
DOIs	https://doi.org/10.1055/a-0883-5383
Publication status	Published - 2019

Keywords

Cannabaceae
Cannabis sativa
O-methylation
PPAR
meroterpenoids
phytocannabinoids

Access to Document

10.1055/a-0883-5383

Cite this

@article{6eb1974226c247c0b0b5c7b15df23be2,

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

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.",

keywords = "Cannabaceae, Cannabis sativa, O-methylation, PPAR, meroterpenoids, phytocannabinoids",

author = "Diego Caprioglio and Gianna Allegrone and Federica Pollastro and Stefano Valera and Annalisa Lopatriello and Collado, \{Juan A.\} and Eduardo Munoz and Giovanni Appendino and Orazio Taglialatela-Scafati",

note = "Publisher Copyright: {\textcopyright} 2019 Georg Thieme Verlag KG Stuttgart · New York.",

year = "2019",

doi = "10.1055/a-0883-5383",

language = "English",

volume = "85",

pages = "981--986",

journal = "Planta Medica",

issn = "0032-0943",

publisher = "Georg Thieme Verlag",

number = "11-12",

}

TY - JOUR

T1 - O-Methyl Phytocannabinoids

T2 - Semi-synthesis, Analysis in Cannabis Flowerheads, and Biological Activity

AU - Caprioglio, Diego

AU - Allegrone, Gianna

AU - Pollastro, Federica

AU - Valera, Stefano

AU - Lopatriello, Annalisa

AU - Collado, Juan A.

AU - Munoz, Eduardo

AU - Appendino, Giovanni

AU - Taglialatela-Scafati, Orazio

PY - 2019

Y1 - 2019

N2 - 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.

AB - 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.

KW - Cannabaceae

KW - Cannabis sativa

KW - O-methylation

KW - PPAR

KW - meroterpenoids

KW - phytocannabinoids

UR - https://www.scopus.com/pages/publications/85070548897

U2 - 10.1055/a-0883-5383

DO - 10.1055/a-0883-5383

M3 - Article

SN - 0032-0943

VL - 85

SP - 981

EP - 986

JO - Planta Medica

JF - Planta Medica

IS - 11-12

ER -

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this