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

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dc.contributor.authorChianese, Giuseppina
dc.contributor.authorSirignano, Carmina
dc.contributor.authorBenetti, Emanuele
dc.contributor.authorMarzaroli, Vittoria
dc.contributor.authorCollado, Juan A
dc.contributor.authorde la Vega, Lauren
dc.contributor.authorAppendino, Giovanni
dc.contributor.authorMuñoz, Eduardo
dc.contributor.authorTaglialatela-Scafati, Orazio
dc.contributor.funderMIUR
dc.date.accessioned2023-05-03T15:22:57Z
dc.date.available2023-05-03T15:22:57Z
dc.date.issued2022-03-22
dc.description.abstractA 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.
dc.description.sponsorshipThis research was funded by MIUR, research grant PRIN2017, Project WN73PL (Bioactivity-directed exploration of the phytocannabinoid chemical space). LC-MS experiments were run at the LAS (Laboratorio di Analisi Strumentale). The assistance of Dr. Chiara Cassiano is acknowledged. O.T.S. thanks Indena SpA for financial support.
dc.identifier.citationChianese G, Sirignano C, Benetti E, Marzaroli V, Collado JA, de la Vega L, et al. A Nrf-2 Stimulatory Hydroxylated Cannabidiol Derivative from Hemp (Cannabis sativa). J Nat Prod. 2022 Apr 22;85(4):1089-1097
dc.identifier.doi10.1021/acs.jnatprod.1c01198
dc.identifier.essn1520-6025
dc.identifier.pmcPMC9040056
dc.identifier.pmid35316044
dc.identifier.pubmedURLhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9040056/pdf
dc.identifier.unpaywallURLhttps://discovery.dundee.ac.uk/files/74584444/acs.jnatprod.1c01198.pdf
dc.identifier.urihttp://hdl.handle.net/10668/22593
dc.issue.number4
dc.journal.titleJournal of natural products
dc.journal.titleabbreviationJ Nat Prod
dc.language.isoen
dc.organizationHospital Universitario Reina Sofía
dc.organizationInstituto Maimónides de Investigación Biomédica de Córdoba-IMIBIC
dc.page.number1089-1097
dc.publisherAmerican Chemical Society
dc.pubmedtypeJournal Article
dc.pubmedtypeReview
dc.pubmedtypeResearch Support, Non-U.S. Gov't
dc.relation.projectIDPRIN2017
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/acs.jnatprod.1c01198
dc.rightsAttribution 4.0 International
dc.rights.accessRightsopen access
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subjectCannabidiol
dc.subjectCannabinoids
dc.subjectCannabis
dc.subjectNF-E2-related factor 2
dc.subject.decsCromatografía liquida
dc.subject.decsEspectrometría de masas en tándem
dc.subject.decsCromatografía liquida
dc.subject.decsEspecies reactivas de oxígeno
dc.subject.meshChromatography, liquid
dc.subject.meshTandem mass spectrometry
dc.subject.meshReactive oxygen species
dc.subject.meshLiquid chromatography-mass spectrometry
dc.subject.meshChromatography, liquid
dc.titleA Nrf-2 Stimulatory Hydroxylated Cannabidiol Derivative from Hemp (Cannabis sativa).
dc.typeresearch article
dc.type.hasVersionVoR
dc.volume.number85
dspace.entity.typePublication

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