Isolation, antimicrobial activity, and absolute configuration of the furylidene tetronic acid core of pestalotic acids A-G

Org Biomol Chem. 2012 Jul 21;10(27):5307-14. doi: 10.1039/c2ob25469g. Epub 2012 Jun 11.

Abstract

Natural products possessing the 3-(furan-2(5H)-ylidene)furan-2,4(3H,5H)-dione (furylidene tetronic acid) skeleton are rare and were encountered only as fungal metabolites. The configurational assignment of the furylidene tetronic acid core using conventional approaches remained a challenge. Pestalotic acids A-G (1-7) are new furylidene tetronic acid derivatives isolated from a plant endophyte Pestalotiopsis yunnanensis. The structure of 1 was elucidated by combination of NMR experiments, X-ray crystallography, and ECD calculations. Compounds 3 and 7 showed significant antimicrobial activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Circular Dichroism
  • Furans / chemistry*
  • Furans / isolation & purification
  • Furans / pharmacology
  • Microbial Viability / drug effects
  • Molecular Conformation
  • Staphylococcus aureus / drug effects
  • Streptococcus pneumoniae / drug effects

Substances

  • Anti-Bacterial Agents
  • Furans
  • tetronic acid