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

    11 Citations (Scopus)
    134 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

    ASJC Scopus subject areas

    • Drug Discovery
    • Analytical Chemistry
    • Molecular Medicine
    • Complementary and alternative medicine
    • Pharmacology
    • Pharmaceutical Science
    • Organic Chemistry

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