Mesembrine: The archetypal psycho-active Sceletium alkaloid

• Published in: Phytochemistry (Oxford) 2019-10, Vol.166, p.112061-112061, Article 112061
• Main Authors: Makolo, Felix, Viljoen, Alvaro, Veale, Clinton G.L.
• Format: Article
• Language: English
• Subjects: Alkaloid; Congested quaternary carbon; Mesembrine; Mood elevation; Sceletium tortuosum
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2019.112061

(−)-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. [Display omitted] •This review concisely covers the botanical distribution, structure and stereochemistry, biosynthesis, bench top synthesis and biological activity of the Sceletium alkaloid mesembrine.