Vobatensines A-F, Cytotoxic Iboga-Vobasine Bisindoles from Tabernaemontana corymbosa

J Nat Prod. 2016 Apr 22;79(4):1048-55. doi: 10.1021/acs.jnatprod.5b01117. Epub 2016 Feb 26.

Abstract

Six new bisindole alkaloids of the iboga-vobasine type, vobatensines A-F (1-6), in addition to four known bisindoles (8-11), were isolated from a stem bark extract of a Malayan Tabernaemontana corymbosa. The structures of these alkaloids were determined based on analysis of the spectroscopic data and in the case of vobatensines A (1), B (2), and 16'-decarbomethoxyvoacamine (8) also confirmed by partial syntheses. Nine of these alkaloids (1-5, 8-11) showed pronounced in vitro growth inhibitory activity against human KB, PC-3, LNCaP, HCT 116, HT-29, MCF7, MDA-MB-231, and A549 cancer cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Drug Screening Assays, Antitumor
  • HCT116 Cells
  • HT29 Cells
  • Humans
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification*
  • Indole Alkaloids / pharmacology*
  • KB Cells
  • Malaysia
  • Molecular Structure
  • Plant Leaves / chemistry
  • Tabernaemontana / chemistry*

Substances

  • Antineoplastic Agents, Phytogenic
  • Indole Alkaloids
  • vobasine