stemmadenine and tabersonine

Monoterpenoid indole alkaloids (MIAs) possess a diversity of alkaloid skeletons whose biosynthesis is poorly understood. A bioinformatic search of candidate genes, combined with their virus-induced gene silencing, targeted MIA profiling and in vitro/in vivo pathway reconstitution identified and functionally characterized six genes as well as a seventh enzyme reaction required for the conversion of 19

Topics: Aspidosperma; Carbolines; Catharanthus; Enzymes; Gene Expression Regulation, Plant; Gene Silencing; Indole Alkaloids; NADP; Plant Proteins; Quinolines; Strychnos; Tabernaemontana; Vinca Alkaloids

Vinblastine, a potent anticancer drug, is produced by

Topics: Antineoplastic Agents, Phytogenic; Catharanthus; Genes, Plant; Hydrolases; Indole Alkaloids; Quinolines; Vinblastine; Vinca Alkaloids

Two new monoterpene indole alkaloids, isoakuammiline (1) and 18-hydroxypseudovincadifformine (2), and five known alkaloids, coronaridine (3), heyneanine (4), 3,19-oxidocoronaridine (5), tabersonine, and strictosidine, were identified from the fruit of Tabernaemontana litoralis. The structures of the alkaloids were determined using NMR and MS data analyses. While 18-hydroxypseudovincadifformine (2) showed a new hydroxylation pattern, isoakuammiline (1) revealed a novel skeleton for monoterpene indole alkaloids. In spite of the isolation of stemmadenine from the fruit tissues in other Tabernaemontana species, this vital biosynthetic precursor of iboga, aspidosperma, and pseudoaspidosperma skeletons was not found in T. litoralis.

Topics: Aspidosperma; Fruit; Hawaii; Indole Alkaloids; Nuclear Magnetic Resonance, Biomolecular; Quinolines; Secologanin Tryptamine Alkaloids; Tabernaemontana