Jenamidines A to C: unusual alkaloids from Streptomyces sp. with specific antiproliferative properties obtained by chemical screening

J Antibiot (Tokyo). 2003 Sep;56(9):747-54. doi: 10.7164/antibiotics.56.747.

Abstract

Three new naturally occurring bicyclic alkaloids, jenamidines A (1), B (2) and C (3), were discovered and isolated from the culture broth of Streptomyces sp. (strain HKI0297) via the chemical screening approach. Fermentation, isolation, structure and biological activities of these three new secondary metabolites are reported. The jenamidines have an unusual octahydro-pyrido[1,2-a]pyrimidine skeleton. Jenamidine A (1) shows antiproliferative effects against the chronic myeloid leukaemic cell line K-562. In addition, the new tricyclic sesquiterpenoid, africantriol (4) was isolated from the same strain.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / metabolism
  • Alkaloids / pharmacology*
  • Animals
  • Antibiotics, Antineoplastic / chemistry
  • Antibiotics, Antineoplastic / isolation & purification*
  • Antibiotics, Antineoplastic / metabolism
  • Antibiotics, Antineoplastic / pharmacology*
  • Bridged-Ring Compounds / chemistry
  • Bridged-Ring Compounds / isolation & purification
  • Bridged-Ring Compounds / metabolism
  • Bridged-Ring Compounds / pharmacology
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Fermentation
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Structure
  • Pyridines / chemistry
  • Pyridines / isolation & purification
  • Pyridines / metabolism
  • Pyridines / pharmacology
  • Pyrimidinones / chemistry
  • Pyrimidinones / isolation & purification
  • Pyrimidinones / metabolism
  • Pyrimidinones / pharmacology
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / metabolism
  • Sesquiterpenes / pharmacology
  • Streptomyces / growth & development
  • Streptomyces / metabolism*

Substances

  • Alkaloids
  • Antibiotics, Antineoplastic
  • Bridged-Ring Compounds
  • Pyridines
  • Pyrimidinones
  • Sesquiterpenes
  • africantriol
  • jenamidine A
  • jenamidine B
  • jenamidine C