从大麻中分离出的一种新型植物大麻素，其体内模拟大麻活性高于 Δ9-四氢大麻酚：Δ9-四氢大麻酚。,Scientific Reports

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从大麻中分离出的一种新型植物大麻素，其体内模拟大麻活性高于 Δ9-四氢大麻酚：Δ9-四氢大麻酚。
Scientific Reports ( IF 3.8 ) Pub Date : 2019-12-30 , DOI: 10.1038/s41598-019-56785-1
Cinzia Citti _{1,

2,

3} , Pasquale Linciano ₃ , Fabiana Russo ₃ , Livio Luongo ₄ , Monica Iannotta ₄ , Sabatino Maione ₄ , Aldo Laganà _{2,

5} , Anna Laura Capriotti ₅ , Flavio Forni ₃ , Maria Angela Vandelli ₃ , Giuseppe Gigli ₂ , Giuseppe Cannazza _{2,

3}

Affiliation

(-)-反式-Δ9-四氢大麻酚 (Δ9-THC) 是造成大麻中毒活性的主要化合物。侧烷基链的长度影响这种大麻素的生物活性。特别是，具有较长侧链的 Δ9-THC 的合成类似物已显示出远高于 Δ9-THC 本身的大麻模拟特性。在尝试定义表征药用大麻品种的植物大麻素概况时，鉴定了一种具有与 Δ9-THC 相同结构但具有七项烷基侧链的新植物大麻素。分离并充分表征了天然化合物，并通过与立体选择性合成获得的相同化合物匹配来确定其立体化学构型。这种新的植物大麻素被称为 (-)-反式-Δ9-四氢大麻酚 (Δ9-THCP)。与 Δ9-THCP 一起，还分离了相应的具有七项侧烷基链 (CBDP) 的大麻二酚 (CBD) 同系物，并通过与其合成对应物匹配来明确鉴定。Δ9-THCP 在体外对人 CB1 受体的结合活性 (Ki = 1.2 nM) 与 CP55940 (Ki = 0.9 nM)（一种有效的完全 CB1 激动剂）相似。在大麻素四联体药理学测试中，Δ9-THCP 引起运动减退、镇痛、僵直和直肠温度降低，表明具有类似 THC 的大麻模拟活性。这种新植物大麻素的存在可以解释某些大麻品种的药理特性，而这些特性很难通过单一 Δ9-THC 的存在来解释。

"点击查看英文标题和摘要"

A novel phytocannabinoid isolated from Cannabis sativa L. with an in vivo cannabimimetic activity higher than Δ9-tetrahydrocannabinol: Δ9-Tetrahydrocannabiphorol.

(-)-Trans-Δ9-tetrahydrocannabinol (Δ9-THC) is the main compound responsible for the intoxicant activity of Cannabis sativa L. The length of the side alkyl chain influences the biological activity of this cannabinoid. In particular, synthetic analogues of Δ9-THC with a longer side chain have shown cannabimimetic properties far higher than Δ9-THC itself. In the attempt to define the phytocannabinoids profile that characterizes a medicinal cannabis variety, a new phytocannabinoid with the same structure of Δ9-THC but with a seven-term alkyl side chain was identified. The natural compound was isolated and fully characterized and its stereochemical configuration was assigned by match with the same compound obtained by a stereoselective synthesis. This new phytocannabinoid has been called (-)-trans-Δ9-tetrahydrocannabiphorol (Δ9-THCP). Along with Δ9-THCP, the corresponding cannabidiol (CBD) homolog with seven-term side alkyl chain (CBDP) was also isolated and unambiguously identified by match with its synthetic counterpart. The binding activity of Δ9-THCP against human CB1 receptor in vitro (Ki = 1.2 nM) resulted similar to that of CP55940 (Ki = 0.9 nM), a potent full CB1 agonist. In the cannabinoid tetrad pharmacological test, Δ9-THCP induced hypomotility, analgesia, catalepsy and decreased rectal temperature indicating a THC-like cannabimimetic activity. The presence of this new phytocannabinoid could account for the pharmacological properties of some cannabis varieties difficult to explain by the presence of the sole Δ9-THC.

更新日期：2019-12-30

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