(±)-Pestalachloride D, an antibacterial racemate of chlorinated benzophenone derivative from a soft coral-derived fungus Pestalotiopsis sp

Mar Drugs. 2013 Mar 28;11(4):1050-60. doi: 10.3390/md11041050.

Abstract

A new antibacterial chlorinated benzophenone derivative, (±)-pestalachloride D (1), along with a related analog, (±)-pestalachloride C (2), was recently isolated from the marine-derived fungus Pestalotiopsis sp. isolated from a soft coral Sarcophyton sp. collected from Yongxing Island in the South China Sea. Both chiral HPLC analysis and single-crystal X-ray data indicated that 1 is a racemic mixture. Interestingly, 1 did not exhibit any effect in the zebrafish embryo teratogenicity assay, while 2 led to abnormal growth. The potential impact on zebrafish embryo growth is discussed based on their crystal structures. The main difference of crystal structures between 1 and 2 is that the six-member non-aromatic ring (O4, C10, C9, C8, C2', and C3') in 1 exhibits a distorted chair conformation, while 2 shows a distorted boat conformation. Moreover, compounds 1 and 2 both exhibited moderate antibacterial activity.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / microbiology
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Anti-Bacterial Agents / toxicity
  • Benzofurans / isolation & purification
  • Benzofurans / pharmacology*
  • Benzofurans / toxicity
  • Benzophenones / isolation & purification
  • Benzophenones / pharmacology*
  • Benzophenones / toxicity
  • China
  • Chromatography, High Pressure Liquid
  • Crystallization
  • Crystallography, X-Ray
  • Indans / isolation & purification
  • Indans / pharmacology*
  • Indans / toxicity
  • Toxicity Tests
  • Xylariales / isolation & purification
  • Xylariales / metabolism*
  • Zebrafish

Substances

  • Anti-Bacterial Agents
  • Benzofurans
  • Benzophenones
  • Indans
  • pestalachloride C
  • pestalachloride D