期刊
JOURNAL OF NATURAL PRODUCTS
卷 83, 期 9, 页码 2727-2736出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.0c00668
关键词
-
资金
- MIUR [PRIN2017, WN73PL]
- INDENA SpA
Cannabitwinol (CBDD, 3), the second member of a new class of dimeric phytocannabinoids in which two units are connected by a methylene bridge, was isolated from a hemp (Cannabis sativa L.) industrial extract. The structural characterization of cannabitwinol, complicated by broadening of H-1 NMR signals and lack of expected 2D NMR correlations at room temperature, was fully carried out in methanol-d(4) at -30 degrees C. All the attempts to prepare CBDD by reaction of CBD with formaldehyde or its iminium analogue (Eschenmoser salt) failed, suggesting that this sterically congested dimer is the result of enzymatic reactions on the corresponding monomeric acids. Analysis of the cannabitwinol profile of transient receptor potential (TRP) modulation evidenced the impact of dimerization, revealing a selectivity for channels activated by a decrease of temperature (TRPM8 and TRPA1) and the lack of significant affinity for those activated by an increase of temperature (e.g., TRPV1). The putative binding modes of cannabitwinol with TRPA1 and TRPM8 were investigated in detail by a molecular docking study using the homology models of both channels.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据