Ingenines A and B, Two New Alkaloids from the Indonesian Sponge Acanthostrongylophora ingens

Drug Res (Stuttg). 2015 Jul;65(7):361-5. doi: 10.1055/s-0034-1384577. Epub 2014 Jul 22.

Abstract

As a continuation of the work on EtOAc fraction of the Indonesian sponge Acanthostrongylophora ingens, 2 new alkaloids: one pyrimidine-β-carboline alkaloid named ingenine A (2) and one pyrimidine-γ-carboline alkaloid named ingenine B (3), along with annomontine (1) were isolated. Their structures were unambiguously established on the basis of NMR spectroscopy ((1) H, (13)C, (1) H-(1) H COSY, HMQC, and HMBC) and mass spectral data. This is the first report of isolation pyrimidine-γ-carboline alkaloid from natural source. Compounds 1 and 3 showed pronounced cytotoxicity against the murine lymphoma L5178Y cancer cell line with ED50 7.8 and 9.1 μg/mL respectively, while compound 2 showed weak activity.

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Carbolines / chemistry
  • Carbolines / isolation & purification*
  • Carbolines / pharmacology
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Mice
  • Molecular Structure
  • Porifera / chemistry*
  • Pyrimidines / chemistry
  • Pyrimidines / isolation & purification*
  • Pyrimidines / pharmacology

Substances

  • Alkaloids
  • Antineoplastic Agents
  • Carbolines
  • Pyrimidines
  • annomontine
  • ingenine A