Bisindole alkaloids

• Main Authors: Kam, Toh Seok, Choo, Yeun Mun
• Format: Article
• Published: Elsevier 2006
• Subjects: Q Science (General); QD Chemistry
• Online Access: http://eprints.um.edu.my/1621/; https://doi.org/10.1016/S1099-4831(06)63004-6

This chapter provides an overview on bisindole alkaloids. The indole–indole and tryptamine–tryptamine type, and related alkaloids are discussed. Tryptamine–tryptamine type with an additional monoterpene unit and related alkaloids are briefly discussed. Corynanthe–tryptamine is constituted from the union of a tryptamine unit and a corynanthe moiety. They are found mainly in plants of the genus Strychnos, but have also been isolated from other genera of the Apocynaceae, Rubiaceae, and Loganiaceae families. The bisindole alkaloid longicaudatine, first detected in various Strychnos species by its characteristic reaction with ferric chloride or Ce(IV) reagents, was obtained in a number of instances with its isomer, bisnorC-alkaloid H (284), which also showed the same chromatographic and chromogenic properties. Alstonia sphaerocapitata and A. undulata provided undulatine and deformylundulatine, respectively. The alkaloids are constituted from the union of a cabucraline unit and a N-methylpericyclivine unit, via C(10) of the former to C(6′) of the latter. The structures were elucidated on the basis of mass spectral and NMR data. The absolute configuration of vincristine is established by X-ray analysis of its methiodide derivative, from which the configurations of the stereocenters in vinblastine were inferred from the known relationship between the two compounds.