title: New cytotoxic indole alkaloids from Tabernaemontana calcarea from the Madagascar rainforest.
abstract: Bioassay-directed fractionation of the alkaloid portion of a CH(2)Cl(2)-MeOH extract of Tabernaemontana calcarea resulted in the isolation of the three new cytotoxic indole alkaloids, 1-3, and the 12 known alkaloids voacangine (4), isovoacangine (5), coronaridine (6), 11-hydroxycoronaridine (7), voacristine (8), 19-epi-voacristine (9), isovoacristine (10), ibogamine (11), 10-methoxyibogamine (12), 11-methoxyibogamine (13), heyneanine (14), and 19-epi-heyneanine (15). The structures of the new compounds 1-3 were elucidated on the basis of extensive 1D and 2D NMR spectroscopic interpretation. All the compounds exhibited cytotoxic activity against the A2780 ovarian cancer cell line.
authors.affiliation: Department of Chemistry, M/C 0212, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061, USA.
authors.forename: V S
authors.initials: VS
authors.lastname: Prakash Chaturvedula
authors.forename: Shannon
authors.initials: S
authors.lastname: Sprague
authors.forename: Jennifer K
authors.initials: JK
authors.lastname: Schilling
authors.forename: David G I
authors.initials: DG
authors.lastname: Kingston
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008270:Madagascar; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010051:Ovarian Neoplasms; D010946:Plants, Medicinal / Q000737:chemistry*; D030014:Tabernaemontana / Q000737:chemistry*; D014407:Tumor Cells, Cultured / Q000187:drug effects
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D026121:Indole Alkaloids