Bioactive steroid derivatives and butyrolactone derivatives from a gorgonian-derived Aspergillus sp. fungus

Chem Biodivers. 2015 Sep;12(9):1398-406. doi: 10.1002/cbdv.201400321.

Abstract

Six steroid derivatives, 1-6, and five butyrolactone derivatives, 7-11, were isolated from the fermentation broth of a gorgonian-derived Aspergillus sp. fungus. Their structures were elucidated on the basis of NMR and MS spectral data. Compound 1 is a new, highly conjugated steroid. The NMR and MS data of 7 and 8 are reported for the first time, as their structures were listed in SciFinder Scholar with no associated reference. Compounds 1, 4, 5, and 8-11 inhibited the larval settlement of barnacle Balanus amphitrite with EC50 values ranging from 0.63 to 18.4 μg ml(-1) . Butyrolactone derivatives 7 and 8 showed pronounced antibacterial activities against Staphylococcus aureus with the same MIC values as the positive control ciprofloxacin (MIC 1.56 μM for all three compounds).

Keywords: Antibacterial activity; Antifouling activity; Aspergillus; Butyrolactone derivatives; Fungi; Steroid derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / isolation & purification
  • 4-Butyrolactone / pharmacology
  • Animals
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Aspergillus / chemistry*
  • Biofouling / prevention & control
  • Humans
  • Larva / drug effects
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Staphylococcal Infections / drug therapy
  • Staphylococcus aureus / drug effects
  • Steroids / chemistry*
  • Steroids / isolation & purification
  • Steroids / pharmacology
  • Thoracica / drug effects

Substances

  • Anti-Bacterial Agents
  • Steroids
  • 4-Butyrolactone