Acremosides A-G, Sugar Alcohol-Conjugated Acyclic Sesquiterpenes from a Sponge-Derived Acremonium Species

J Nat Prod. 2024 Apr 26;87(4):1059-1066. doi: 10.1021/acs.jnatprod.4c00015. Epub 2024 Apr 1.

Abstract

Seven new sugar alcohol-conjugated acyclic sesquiterpenes, acremosides A-G (1-7), were isolated from the cultures of the sponge-associated fungus Acremonium sp. IMB18-086 cultivated with heat-killed Pseudomonas aeruginosa. The structures were determined by comprehensive analyses of 1D and 2D NMR spectroscopic data. The relative configurations were established by J-based configuration analysis and acetonide derivatization. The absolute configurations were elucidated by the Mosher ester method and ECD calculations. The structures of acremosides E-G (5-7) featured the linear sesquiterpene skeleton with a tetrahydrofuran moiety attached to a sugar alcohol. Acremosides A (1) and C-E (3-5) showed significant inhibitory activities against hepatitis C virus (EC50 values of 4.8-8.8 μM) with no cytotoxicity (CC50 of >200 μM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acremonium* / chemistry
  • Animals
  • Antiviral Agents / chemistry
  • Antiviral Agents / isolation & purification
  • Antiviral Agents / pharmacology
  • Hepacivirus / drug effects
  • Humans
  • Molecular Structure
  • Porifera / chemistry
  • Pseudomonas aeruginosa / drug effects
  • Sesquiterpenes* / chemistry
  • Sesquiterpenes* / isolation & purification
  • Sesquiterpenes* / pharmacology

Substances

  • Sesquiterpenes
  • Antiviral Agents