Unstable Tetramic Acid Derivatives from the Deep-Sea-Derived Fungus Cladosporium sphaerospermum EIODSF 008

Mar Drugs. 2018 Nov 15;16(11):448. doi: 10.3390/md16110448.

Abstract

Seven new unstable tetramic acid derivatives, cladosporiumins I-O (17), together with the known analogue cladodionen (8) were isolated from the extract of the deep-sea-derived fungus Cladosporium sphaerospermum EIODSF 008. Their structures were elucidated by spectroscopic analysis, quantum chemical calculations and ECD spectra. Compound 4 was a Mg complex of tetramic acid derivative. In acidic solvent, 4 could change to 1 and 6, and 7 could change to 5. In addition, 1, 5 and 8 existed as two exchangeable isomers, respectively. The structures of cladosporiumins E-H were reassigned as their Na complexes. The antibacterial and cytotoxic activities of 18 were also evaluated. However, because of their instability, all of the isolated compounds did not show significant antibacterial activity as the preliminary EtOAc extracts of the fungal strain.

Keywords: Cladosporium sphaerospermum; cladosporiumins I-O; deep-sea-derived fungus; tetramic acid.

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
  • Aquatic Organisms / chemistry*
  • Bacteria / drug effects
  • Cladosporium / chemistry*
  • Drug Stability
  • HL-60 Cells
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Pyrrolidinones / chemistry*
  • Pyrrolidinones / isolation & purification
  • Pyrrolidinones / pharmacology
  • Solvents / chemistry

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Pyrrolidinones
  • Solvents
  • tetramic acid