TY - JOUR
T1 - A Nrf-2 Stimulatory Hydroxylated Cannabidiol Derivative from Hemp (Cannabis sativa)
AU - Chianese, Giuseppina
AU - Sirignano, Carmina
AU - Benetti, Emanuele
AU - Marzaroli, Vittoria
AU - Collado, Juan A
AU - de la Vega, Lauren
AU - Appendino, Giovanni
AU - Muñoz, Eduardo
AU - Taglialatela-Scafati, Orazio
N1 - Funding Information:
This research was funded by MIUR, research grant PRIN2017, Project WN73PL (Bioactivity-directed exploration of the phytocannabinoid chemical space).
Copyright © 2022 The Authors. Published by American Chemical Society and American Society of Pharmacognosy.
PY - 2022/4/22
Y1 - 2022/4/22
N2 - A phytochemical analysis of mother liquors obtained from crystallization of CBD from hemp (Cannabis sativa), guided by LC-MS/MS and molecular networking profiling and completed by isolation and NMR-based characterization of constituents, resulted in the identification of 13 phytocannabinoids. Among them, anhydrocannabimovone (5), isolated for the first time as a natural product, and three new hydroxylated CBD analogues (1,2-dihydroxycannabidiol, 6, 3,4-dehydro-1,2-dihydroxycannabidiol, 7, and hexocannabitriol, 8) were obtained. Hexocannabitriol (8) potently modulated, in a ROS-independent way, the Nrf2 pathway, outperforming all other cannabinoids obtained in this study and qualifying as a potential new chemopreventive chemotype against cancer and other degenerative diseases.
AB - A phytochemical analysis of mother liquors obtained from crystallization of CBD from hemp (Cannabis sativa), guided by LC-MS/MS and molecular networking profiling and completed by isolation and NMR-based characterization of constituents, resulted in the identification of 13 phytocannabinoids. Among them, anhydrocannabimovone (5), isolated for the first time as a natural product, and three new hydroxylated CBD analogues (1,2-dihydroxycannabidiol, 6, 3,4-dehydro-1,2-dihydroxycannabidiol, 7, and hexocannabitriol, 8) were obtained. Hexocannabitriol (8) potently modulated, in a ROS-independent way, the Nrf2 pathway, outperforming all other cannabinoids obtained in this study and qualifying as a potential new chemopreventive chemotype against cancer and other degenerative diseases.
KW - Cannabidiol/pharmacology
KW - Cannabinoids/chemistry
KW - Cannabis/chemistry
KW - Chromatography, Liquid
KW - Tandem Mass Spectrometry/methods
UR - http://www.scopus.com/inward/record.url?scp=85127649183&partnerID=8YFLogxK
U2 - 10.1021/acs.jnatprod.1c01198
DO - 10.1021/acs.jnatprod.1c01198
M3 - Article
C2 - 35316044
SN - 0163-3864
VL - 85
SP - 1089
EP - 1097
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 4
ER -
