Antimicrobial Sesquiterpenoid Derivatives and Monoterpenoids from the Deep-Sea Sediment-Derived Fungus Aspergillus versicolor SD-330

Mar Drugs. 2019 Sep 29;17(10):563. doi: 10.3390/md17100563.

Abstract

Two new antimicrobial bisabolane-type sesquiterpenoid derivatives, ent-aspergoterpenin C (compound 1) and 7-O-methylhydroxysydonic acid (2), and two new butyrolactone-type monoterpenoids, pestalotiolactones C (3) and D (4), along with a known monoterpenoid pestalotiolactone A (5) and four known bisabolane sesquiterpenoids (6-9), were isolated and identified from the deep-sea sediment-derived fungus Aspergillus versicolor SD-330. The structures of these compounds were elucidated on the basis of spectroscopic analysis, and the absolute configurations of the new compounds 1-4 were determined by the combination of NOESY and TDDFT-ECD calculations and X-ray crystallographic analysis. Additionally, we first determined and reported the absolute configuration of the known monoterpenoid pestalotiolactone A (5) through the X-ray crystallographic experiment. All of these isolated compounds were evaluated for antimicrobial activities against human and aquatic pathogenic bacteria. Compounds 1, 2, 6 and 9 exhibited selective inhibitory activities against zoonotic pathogenic bacteria such as Escherichia coli, Edwardsiella tarda, Vibrio anguillarum and V. harveyi, with MIC values ranging from 1.0 to 8.0 μg/mL.

Keywords: Aspergillus versicolor; antimicrobial activity; bisabolane-type sesquiterpenoids; deep-sea sediment-derived fungus; monoterpenoids.

MeSH terms

  • Animals
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / isolation & purification
  • Anti-Infective Agents / pharmacology*
  • Aspergillus / chemistry*
  • Crystallography, X-Ray
  • Edwardsiella tarda / drug effects
  • Escherichia coli / drug effects
  • Geologic Sediments / microbiology*
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Monoterpenes / chemistry
  • Monoterpenes / isolation & purification
  • Monoterpenes / pharmacology
  • Seawater / microbiology
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology
  • Vibrio / drug effects
  • Zoonoses / microbiology

Substances

  • Anti-Infective Agents
  • Monoterpenes
  • Sesquiterpenes

Supplementary concepts

  • Vibrio anguillarum
  • Vibrio harveyi