A Nrf-2 Stimulatory Hydroxylated Cannabidiol Derivative from Hemp (Cannabis sativa)

Giuseppina Chianese, Carmina Sirignano, Emanuele Benetti, Vittoria Marzaroli, Juan A Collado, Lauren de la Vega, Giovanni Appendino, Eduardo Muñoz, Orazio Taglialatela-Scafati (Lead / Corresponding author)

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)
46 Downloads (Pure)

Abstract

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.

Original languageEnglish
Pages (from-to)1089-1097
Number of pages9
JournalJournal of Natural Products
Volume85
Issue number4
Early online date22 Mar 2022
DOIs
Publication statusPublished - 22 Apr 2022

Keywords

  • Cannabidiol/pharmacology
  • Cannabinoids/chemistry
  • Cannabis/chemistry
  • Chromatography, Liquid
  • Tandem Mass Spectrometry/methods

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