Bile acid derivatives from a sponge-associated bacterium Psychrobacter sp

Arch Pharm Res. 2009 Jun;32(6):857-62. doi: 10.1007/s12272-009-1607-1. Epub 2009 Jun 26.

Abstract

In our search for bioactive metabolites from a marine sponge-associated bacterium Psychrobacter sp., a new bile acid derivative (1), which was assumed to be an artifact, were isolated along with six known (2-7) compounds by bioactivity-guided fractionation. Elucidation of the structure of the new compound was done using a combination of NMR ((1)H, (13)C, HMBC, HSQC, and COSY) and MS spectroscopy. Compound 1 exhibited moderate suppressive effects on both NO and IL-6 production at a concentration of 200 microM (87.3 microg/mL) without significant cytotoxicity against cells. Compounds 2-5 and 7 showed selective inhibitory activity against several human pathogenic bacterial strains at the low concentration of 30 microg/well. In a cytotoxicity evaluation, only compound 7 showed mild cytotoxicity against five human solid tumor cell lines (A-549, SK-OV-3, SK-MEL-2, XF-498, and HCT-15) with ED(50) values in the range of 11-14 microg/mL.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Bile Acids and Salts* / chemistry
  • Bile Acids and Salts* / isolation & purification
  • Bile Acids and Salts* / pharmacology
  • Cell Line
  • Cell Line, Tumor
  • Cholic Acids / chemistry
  • Cholic Acids / isolation & purification
  • Cholic Acids / pharmacology
  • Drug Screening Assays, Antitumor
  • Humans
  • Interleukin-6 / metabolism
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Mice
  • Models, Chemical
  • Molecular Structure
  • Nitric Oxide / metabolism
  • Porifera / microbiology*
  • Psychrobacter / chemistry*

Substances

  • 3-dimethoxy-12alpha-hydroxycholanic acid
  • Anti-Bacterial Agents
  • Anti-Inflammatory Agents
  • Antineoplastic Agents
  • Bile Acids and Salts
  • Cholic Acids
  • Interleukin-6
  • Nitric Oxide