Bingchamides A and B, two novel cyclic pentapeptides from the Streptomyces bingchenggensis: fermentation, isolation, structure elucidation and biological properties

J Antibiot (Tokyo). 2009 Sep;62(9):501-5. doi: 10.1038/ja.2009.60. Epub 2009 Jul 17.

Abstract

Two novel cyclic pentapeptides, bingchamides A (1) and B (2), have been isolated from the organic extracts of the mycelium of Streptomyces bingchenggensis. The structures of 1 and 2 were elucidated on the basis of extensive 1D and 2D NMR, as well as HRESI-MS, electrospray ionization-MS, UV and IR spectroscopic data analysis. Bingchamides A (1) and B (2) exhibited in vitro cytotoxicity toward human colon carcinoma cell line HCT-116 with the IC(50) values of 14.1 and 18.0 microg ml(-1), respectively. The bingchamides A (1) and B (2) scaffolds are probably promising structures for the development of new antitumor agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / metabolism
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Fermentation
  • Humans
  • Molecular Sequence Data
  • Mycelium / genetics
  • Mycelium / growth & development
  • Mycelium / metabolism
  • Peptides, Cyclic / biosynthesis
  • Peptides, Cyclic / chemistry*
  • Peptides, Cyclic / pharmacology
  • Streptomyces / genetics
  • Streptomyces / growth & development
  • Streptomyces / metabolism*

Substances

  • Antineoplastic Agents
  • Peptides, Cyclic
  • bingchamide A
  • bingchamide B

Associated data

  • GENBANK/DQ449953