Graphiumins, new thiodiketopiperazines from the marine-derived fungus Graphium sp. OPMF00224

J Antibiot (Tokyo). 2015 Oct;68(10):620-7. doi: 10.1038/ja.2015.41. Epub 2015 Apr 22.

Abstract

Eight new thiodiketopiperazines, designated as graphiumins A to H (1-8), were isolated along with bisdethiobis(methylthio)-deacetylaranotin (9) and bisdethiobis(methylthio)-deacetylapoaranotin (10) from the culture broth of the marine-derived fungus Graphium sp. OPMF00224. The structures of the graphiumins were elucidated based on spectroscopic analyses (1D and 2D NMR data, ROESY correlations and CD data) and chemical methods. The absolute configuration of the common (3S)-3-hydroxy-octanoyl acid residue in 1, 3 and 4 was determined by hydrolysis, benzoyl derivatization and HPLC analysis using a chiral column. Five graphiumins moderately inhibited yellow pigment production by methicillin-resistant Staphylococcus aureus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Ascomycota / chemistry*
  • Fermentation
  • Hydrolysis
  • Magnetic Resonance Spectroscopy
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Piperazines / chemistry
  • Piperazines / pharmacology*
  • Seawater / microbiology
  • Spectrometry, Mass, Electrospray Ionization
  • Sulfhydryl Compounds / chemistry
  • Sulfhydryl Compounds / pharmacology*
  • Water Microbiology

Substances

  • Anti-Bacterial Agents
  • Piperazines
  • Sulfhydryl Compounds
  • graphiumins