Department of Pharmacy, School of Medicine and Surgery, University of Naples Federico II, Via D. Montesano 49, 80131 Napoli, Italy.
Institute of Biomolecular Chemistry, National Research Council (ICB-CNR), Via Campi Flegrei 34, 80078, Pozzuoli (NA), Italy.
J Nat Prod. 2024 Apr 26;87(4):722-732. doi: 10.1021/acs.jnatprod.3c00831. Epub 2024 Feb 26.
The first detailed phytochemical analysis of the cannabigerol (CBG)-rich chemotype IV of L. resulted in the isolation of the expected cannabigerolic acid/cannabigerol (CBGA/CBG) and cannabidiolic acid/cannabidiol (CBDA/CBD) and of nine new phytocannabinoids (-), which were fully characterized by HR-ESIMS and 1D and 2D NMR. These included mono- or dihydroxylated CBGA/CBG analogues, a congener with a truncated side chain (), cyclocannabigerol B (), and the CBD derivatives named cannabifuranols ( and ). Cyclocannabigerol B and cannabifuranols are characterized by a novel phytocannabinoid structural architecture. The isolated phytocannabinoids were assayed on the receptor channels TRPA1 and TRPM8, unveiling a potent dual TRPA1 agonist/TRPM8 antagonist profile for compounds , , and . Chiral separation of the two enantiomers of resulted in the discovery of a synergistic effect of the two enantiomers on TRPA1.
首次对富含大麻萜酚（CBG）的大麻素化学型 IV 的详细植物化学分析导致分离出预期的大麻二酚酸/大麻萜酚（CBGA/CBG）和大麻二酚酸/大麻二酚（CBDA/CBD）以及 9 种新的植物大麻素（-），通过高分辨率电喷雾电离质谱（HR-ESIMS）和 1D 和 2D NMR 对其进行了全面表征。这些包括单或二羟基化的 CBGA/CBG 类似物、具有截断侧链的同系物（）、环大麻萜酚 B（）和命名为大麻呋喃醇的 CBD 衍生物（和）。环大麻萜酚 B 和大麻呋喃醇具有新型植物大麻素结构架构。分离出的植物大麻素在受体通道 TRPA1 和 TRPM8 上进行了测定，揭示了化合物、、对 TRPA1 具有双重 TRPA1 激动剂/TRPM8 拮抗剂的特性。对 的两种对映异构体进行手性分离发现，两种对映异构体对 TRPA1 具有协同作用。
