Ibogan, Aspidosperman, Vincamine, and Bisindole Alkaloids from a Malayan Tabernaemontana corymbosa: Iboga Alkaloids with C-20α Substitution

Journal of Natural Products
2016.0

Abstract

Ten new indole alkaloids (1-10) comprising five ibogan, two aspidosperman, one vincamine, and two bisindole alkaloids, in addition to 32 known alkaloids, were isolated from the stem-bark extract of a Malayan Tabernaemontana corymbosa. The structures of these alkaloids were determined based on analysis of the NMR and MS data and, in five instances (1, 3, 5, 6, 8), confirmed by X-ray diffraction analysis. Two of the iboga alkaloids, conodusines B (2) and C (3), and the iboga-containing bisindole tabernamidine B (10) are notable for the presence of an α-substituted acetyl group at C-20 of the iboga carbon skeleton. The iboga alkaloid (+)-conodusine E (5) had MS and NMR data that were identical to those of (-)-ervatamine I, recently isolated from Ervatamia hainanensis. Establishment of the absolute configuration of (+)-conodusine E (5) was based on analysis of the ECD data, correlation with (-)-heyneanine, and X-ray analysis, which showed that (+)-5 belongs to the same enantiomeric series as exemplified by (-)-coronaridine. The configuration at C-20' of the previously reported Tabernaemontana bisindole alkaloid 19'-oxotabernamine (renamed tabernamidine B) required revision based on the present results. Several of the bisindoles showed pronounced in vitro growth inhibitory activity against drug-sensitive and vincristine-resistant KB cells.

Knowledge Graph

Similar Paper

Ibogan, Aspidosperman, Vincamine, and Bisindole Alkaloids from a Malayan <i>Tabernaemontana corymbosa</i>: Iboga Alkaloids with C-20α Substitution
Journal of Natural Products 2016.0
Five New Iboga Alkaloids from <i>Tabernaemontana corymbosa</i>
Journal of Natural Products 2002.0
New Bisindole Alkaloids from <i>Tabernaemontana </i><i>corymbosa</i>
Journal of Natural Products 2003.0
Ibogan, Tacaman, and Cytotoxic Bisindole Alkaloids from <i>Tabernaemontana</i>. Cononusine, an Iboga Alkaloid with Unusual Incorporation of a Pyrrolidone Moiety
Journal of Natural Products 2015.0
Ibogan, Tacaman, and Cytotoxic Bisindole Alkaloids from <i>Tabernaemontana</i>. Cononusine, an Iboga Alkaloid with Unusual Incorporation of a Pyrrolidone Moiety
Journal of Natural Products 2015.0
New Bisindole Alkaloids from Tabernaemontana corymbosa
Journal of Natural Products 2003.0
Five New Iboga Alkaloids from Tabernaemontana corymbosa
Journal of Natural Products 2002.0
A Hexacyclic, Iboga-Derived Monoterpenoid Indole with a Contracted Tetrahydroazepine C-Ring and Incorporation of an Isoxazolidine Moiety, a Seco-Corynanthean, an Aspidosperma-Aspidosperma Bisindole with Anticancer Properties, and the Absolute Configuration of the Pyridopyrimidine Indole Alkaloid, Vernavosine
Journal of Natural Products 2016.0
Vobasine, vincamine, voaphylline, tacaman, and iboga alkaloids from Tabernaemontana corymbosa
Phytochemistry 2022.0
Taburnaemines A–I, Cytotoxic Vobasinyl-Iboga-Type Bisindole Alkaloids from <i>Tabernaemontana corymbosa</i>
Journal of Natural Products 2018.0