Ophiobolins P-T, five new cytotoxic and antibacterial sesterterpenes from the endolichenic fungus Ulocladium sp

Fitoterapia. 2013 Oct:90:220-7. doi: 10.1016/j.fitote.2013.08.002. Epub 2013 Aug 13.

Abstract

Five ophiobolane sesterterpenes, ophiobolins P-T, and three known compounds, 6-epi-21,21-O-dihydroophiobolin G, 6-epi-ophiobolin G and 6-epi-ophiobolin K, were isolated from the acetone extract of the endolichenic fungus Ulocladium sp. by using OSMAC method. Their structures were elucidated on the basis of spectroscopic analysis. The absolute configuration of the 18,19-diol moieties in ophiobolin Q was assigned using the Frelek's method. The cytotoxic effects on KB and HepG2 cell lines, antibacterial activity against Bacillus subtilis, methicillin-resistant Staphylococcus aureus, and Bacille Calmette-Guerin were evaluated for all isolated compounds. Ophiobolin T and 6-epi-ophiobolin G exhibited the most potent cytotoxic activity against HepG2 with IC₅₀ of 0.24 and 0.37 μM, respectively. In antibacterial assay, ophiobolins P and T showed moderate antibacterial activity against B. subtilis and meticillin-resistant S. aureus. Ophiobolin T also displayed moderate antibacterial activity against the Bacille Calmette-Guerin strain.

Keywords: Antibacterial activity; Cytotoxicity; Endophytic fungi; Ophiobolane sesterterpenes; Ulocladium sp..

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Antineoplastic Agents / therapeutic use
  • Ascomycota / chemistry*
  • Bacillus subtilis / drug effects
  • Bacteria / drug effects*
  • Biological Products / chemistry
  • Biological Products / pharmacology*
  • Biological Products / therapeutic use
  • Hep G2 Cells
  • Humans
  • KB Cells
  • Lichens / chemistry*
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Mycobacterium bovis / drug effects
  • Neoplasms / drug therapy*
  • Sesterterpenes / chemistry
  • Sesterterpenes / isolation & purification
  • Sesterterpenes / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Biological Products
  • Sesterterpenes
  • ophiobolins