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

DIEGO CAPRIOGLIO; G. Allegrone; Federica POLLASTRO; STEFANO VALERA; A. Lopatriello; J. A. Collado; E. Munoz; G. Appendino; O. Taglialatela-Scafati

doi:10.1055/a-0883-5383

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

DIEGO CAPRIOGLIO, G. Allegrone, Federica POLLASTRO, STEFANO VALERA, A. Lopatriello, J. A. Collado, E. Munoz, G. Appendino, O. Taglialatela-Scafati

Dipartimento di Scienze del Farmaco

Risultato della ricerca: Contributo su rivista › Articolo in rivista › 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.

Lingua originale	Inglese
pagine (da-a)	981-986
Numero di pagine	6
Rivista	Planta Medica
Volume	85
Numero di pubblicazione	11-12
DOI	https://doi.org/10.1055/a-0883-5383
Stato di pubblicazione	Pubblicato - 2019

Keywords

Cannabaceae
Cannabis sativa
O-methylation
PPAR
meroterpenoids
phytocannabinoids

Accesso al documento

10.1055/a-0883-5383

http://hdl.handle.net/11579/106887

Altri file e collegamenti

handle

Cita questo

@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, Cannabaceae, Cannabis sativa, O-methylation, PPAR, meroterpenoids, phytocannabinoids",

author = "DIEGO CAPRIOGLIO and G. Allegrone and Federica POLLASTRO and STEFANO VALERA and A. Lopatriello and Collado, \{J. A.\} and E. Munoz and G. Appendino and O. 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: Semi-synthesis, Analysis in Cannabis Flowerheads, and Biological Activity

AU - CAPRIOGLIO, DIEGO

AU - Allegrone, G.

AU - POLLASTRO, Federica

AU - VALERA, STEFANO

AU - Lopatriello, A.

AU - Collado, J. A.

AU - Munoz, E.

AU - Appendino, G.

AU - Taglialatela-Scafati, O.

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

KW - Cannabaceae

KW - Cannabis sativa

KW - O-methylation

KW - PPAR

KW - meroterpenoids

KW - phytocannabinoids

UR - https://iris.uniupo.it/handle/11579/106887

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

Accesso al documento

Altri file e collegamenti

Fingerprint

Cita questo