Angustifonines A and B, cytotoxic bisindole alkaloids from Bousigonia angustifolia

J Nat Prod. 2014 Jan 24;77(1):57-62. doi: 10.1021/np4005823. Epub 2014 Jan 13.

Abstract

Two new bisindole alkaloids, angustifonines A (1) and B (2), comprising the union of a rearranged monoterpenoid quinoline and an aspidospermine alkaloid, as well as 27 known indole alkaloids were isolated from the twigs and leaves of Bousigonia angustifolia. Their structures and absolute configurations were elucidated by a combination of MS, NMR, and computational methods. Angustifonines A and B exhibited cytotoxicity against various human cancer cell lines with IC50 values of 2.71-16.22 μM. A possible biosynthesis pathway toward the new bisindole alkaloids 1 and 2 is presented.

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
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • Female
  • HL-60 Cells
  • Humans
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification*
  • Indole Alkaloids / pharmacology*
  • Inhibitory Concentration 50
  • MCF-7 Cells
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Plant Stems / chemistry
  • Quinolines

Substances

  • Antineoplastic Agents, Phytogenic
  • Drugs, Chinese Herbal
  • Indole Alkaloids
  • Quinolines
  • angustifonine A
  • angustifonine B
  • aspidospermine