Voacangine (12-methoxyibogamine-18-carboxylic acid methyl ester) is an alkaloid found predominantly in the root bark of the Voacanga africana tree, as well as in other plants such as Tabernanthe iboga, Tabernaemontana africana, Trachelospermum jasminoides, Tabernaemontana divaricata and Ervatamia yunnanensis.
[8] Under UV-A and UV-B light its crystals fluoresce blue-green, and it is soluble in ethanol.
[17] The late-stage biosynthesis of (-)-voacangine in Tabernanthe iboga, a (-)-ibogamine-type alkaloid, has been elucidated via homology-guided transcriptome mining.
The biosynthesis of stemmadenine acetate has been characterized in C. roseus[19] but remains uncharacterized in T. iboga.
Stereochemical divergence occurs during the cyclization step, whereby T. iboga coronaridine synthase (TiCorS), a catharanthine synthase (CS) homologue, catalyzes a stereoselective formal Diels-Alder reaction on dehydrosecodine (4) to form coronaridine iminium (5).