Department of Pharmaceutical Sciences, Faculty of Science, Tshwane University of Technology, Private Bag X680, Pretoria, 0001, South Africa.
Department of Pharmaceutical Sciences, Faculty of Science, Tshwane University of Technology, Private Bag X680, Pretoria, 0001, South Africa; SAMRC Herbal Drugs Research Unit, Faculty of Science, Tshwane University of Technology, Private Bag X680, Pretoria, 0001, South Africa.
Phytochemistry. 2019 Oct;166:112061. doi: 10.1016/j.phytochem.2019.112061. Epub 2019 Jul 9.
(-)-Mesembrine is a chiral alkaloid that features an aryloctahydroindole skeleton and is most commonly found in species of the succulent genus Sceletium. Several Sceletium species are used by various ethnic groups in South Africa to manage disorders of the central nervous system. Binding assays have revealed that mesembrine is a more potent inhibitor of the serotonin transporter (SERT) than fluoxetine (Prozac) which has prompted the commercialization of mesembrine-containing consumer products. The congested all carbon quaternary stereocenter present at the bridgehead of mesembrine has rendered it a compound of interest for research in synthetic chemistry, which has assisted in the absolute configuration of the naturally occurring isomer to be assigned. Accordingly, this review will cover the recent literature pertaining to the distribution, structural elucidation, chemotaxonomy, biosynthesis, organic synthesis, as well as the biological activities of (-)-mesembrine. Recent synthetic procedures of the non-natural enantiomer as well as the racemate are also considered.
(-)-Mesembrine 是一种手性生物碱，具有芳基八氢吲哚骨架，最常见于肉质属 Sceletium 的物种中。几种 Sceletium 物种被南非的不同族群用于治疗中枢神经系统紊乱。结合实验表明，mesembrine 是一种比氟西汀（百忧解）更有效的 5-羟色胺转运蛋白（SERT）抑制剂，这促使含有 mesembrine 的消费产品商业化。mesembrine 桥位上拥挤的全碳季碳立体中心使其成为合成化学研究的关注焦点，这有助于确定天然异构体的绝对构型。因此，本综述将涵盖有关 (-)-mesembrine 的分布、结构阐明、化学分类学、生物合成、有机合成以及生物活性的最新文献。最近还考虑了非天然对映异构体和外消旋体的合成方法。
