title: Monoterpene Indole Alkaloids from the Fruit of Tabernaemontana litoralis and Differential Alkaloid Composition in Various Fruit Components.
abstract: 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.
authors.affiliation: Department of Biological Sciences and ‡Department of Chemistry, Brock University , 1812 Sir Isaac Brock Way, St. Catharines, Ontario L2S 3A1, Canada.
authors.forename: Yang
authors.initials: Y
authors.lastname: Qu
authors.affiliation: Department of Biological Sciences and ‡Department of Chemistry, Brock University , 1812 Sir Isaac Brock Way, St. Catharines, Ontario L2S 3A1, Canada.
authors.forename: Razvan
authors.initials: R
authors.lastname: Simonescu
authors.affiliation: Department of Biological Sciences and ‡Department of Chemistry, Brock University , 1812 Sir Isaac Brock Way, St. Catharines, Ontario L2S 3A1, Canada.
authors.forename: Vincenzo
authors.initials: V
authors.lastname: De Luca
mesh_terms: D030009:Aspidosperma / Q000737:chemistry; D005638:Fruit / Q000737:chemistry*; D006254:Hawaii; D026121:Indole Alkaloids; D019906:Nuclear Magnetic Resonance, Biomolecular; D011804:Quinolines; D046948:Secologanin Tryptamine Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D030014:Tabernaemontana / Q000737:chemistry*
chemical_list: D026121:Indole Alkaloids; D011804:Quinolines; D046948:Secologanin Tryptamine Alkaloids; C046117:stemmadenine; C009373:tabersonine