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

[Image: see text] 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 phytoca...

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Autores principales: Chianese, Giuseppina, Sirignano, Carmina, Benetti, Emanuele, Marzaroli, Vittoria, Collado, Juan A., de la Vega, Lauren, Appendino, Giovanni, Muñoz, Eduardo, Taglialatela-Scafati, Orazio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society and American Society of Pharmacognosy 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9040056/
https://www.ncbi.nlm.nih.gov/pubmed/35316044
http://dx.doi.org/10.1021/acs.jnatprod.1c01198
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author Chianese, Giuseppina
Sirignano, Carmina
Benetti, Emanuele
Marzaroli, Vittoria
Collado, Juan A.
de la Vega, Lauren
Appendino, Giovanni
Muñoz, Eduardo
Taglialatela-Scafati, Orazio
author_facet Chianese, Giuseppina
Sirignano, Carmina
Benetti, Emanuele
Marzaroli, Vittoria
Collado, Juan A.
de la Vega, Lauren
Appendino, Giovanni
Muñoz, Eduardo
Taglialatela-Scafati, Orazio
author_sort Chianese, Giuseppina
collection PubMed
description [Image: see text] 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.
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spelling pubmed-90400562022-04-27 A Nrf-2 Stimulatory Hydroxylated Cannabidiol Derivative from Hemp (Cannabis sativa) Chianese, Giuseppina Sirignano, Carmina Benetti, Emanuele Marzaroli, Vittoria Collado, Juan A. de la Vega, Lauren Appendino, Giovanni Muñoz, Eduardo Taglialatela-Scafati, Orazio J Nat Prod [Image: see text] 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. American Chemical Society and American Society of Pharmacognosy 2022-03-22 2022-04-22 /pmc/articles/PMC9040056/ /pubmed/35316044 http://dx.doi.org/10.1021/acs.jnatprod.1c01198 Text en © 2022 The Authors. Published by American Chemical Society and American Society of Pharmacognosy https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Chianese, Giuseppina
Sirignano, Carmina
Benetti, Emanuele
Marzaroli, Vittoria
Collado, Juan A.
de la Vega, Lauren
Appendino, Giovanni
Muñoz, Eduardo
Taglialatela-Scafati, Orazio
A Nrf-2 Stimulatory Hydroxylated Cannabidiol Derivative from Hemp (Cannabis sativa)
title A Nrf-2 Stimulatory Hydroxylated Cannabidiol Derivative from Hemp (Cannabis sativa)
title_full A Nrf-2 Stimulatory Hydroxylated Cannabidiol Derivative from Hemp (Cannabis sativa)
title_fullStr A Nrf-2 Stimulatory Hydroxylated Cannabidiol Derivative from Hemp (Cannabis sativa)
title_full_unstemmed A Nrf-2 Stimulatory Hydroxylated Cannabidiol Derivative from Hemp (Cannabis sativa)
title_short A Nrf-2 Stimulatory Hydroxylated Cannabidiol Derivative from Hemp (Cannabis sativa)
title_sort nrf-2 stimulatory hydroxylated cannabidiol derivative from hemp (cannabis sativa)
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9040056/
https://www.ncbi.nlm.nih.gov/pubmed/35316044
http://dx.doi.org/10.1021/acs.jnatprod.1c01198
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