期刊
JOURNAL OF NATURAL PRODUCTS
卷 83, 期 1, 页码 88-98出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.9b00876
关键词
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资金
- UNIHEMP research project Use of iNdustrIal Hemp biomass for Energy and new biocheMicals Production - Fondo Europeo di Sviluppo Regionale (FESR) [ARS01_00668]
- Fondo Europeo di Sviluppo Regionale (FESR) (within the PON RI) [CUP B76C18000520005, CUP E53C17000720005]
- Military Chemical Pharmaceutical Institute of Florence
The butyl homologues of Delta(9)-tetrahydrocannabinol, Delta(9)-tetrahydrocannabutol (Delta(9)-THCB), and cannabidiol, cannabidibutol (CBDB), were isolated from a medicinal Cannabis sativa variety (FM2) inflorescence. Appropriate spectroscopic and spectrometric characterization, including NMR, UV, IR, ECD, and HRMS, was carried out on both cannabinoids. The chemical structures and absolute configurations of the isolated cannabinoids were confirmed by comparison with the spectroscopic data of the respective compounds obtained by stereoselective synthesis. The butyl homologue of Delta(9)-THC, Delta(9)-THCB, showed an affinity for the human CB1 (K-i = 15 nM) and CB2 receptors (K-i = 51 nM) comparable to that of (-)-trans-Delta(9)-THC. Docking studies suggested the key bonds responsible for THC-like binding affinity for the CB1 receptor. The formalin test in vivo was performed on Delta(9)-THCB in order to reveal possible analgesic and anti-inflammatory properties. The tetrad test in mice showed a partial agonistic activity of Delta(9)-THCB toward the CB1 receptor.
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