Two New Phenol Derivatives from the Cold Seep-Derived Fungus Aspergillus insuetus SD-512

Chem Biodivers. 2021 Oct;18(10):e2100512. doi: 10.1002/cbdv.202100512. Epub 2021 Sep 16.

Abstract

Two new phenol derivatives, namely insphenol A (1) and acetylpeniciphenol (2), along with seven known analogs (3-9), were isolated from the deep-sea cold seep-derived fungus, Aspergillus insuetus SD-512. The structures of 1 and 2 were established by extensive interpretation of NMR and mass spectroscopic data. The absolute configuration of 1 was determined by the combination of coupling constant analysis and acid hydrolysis. Among the isolated compounds, insphenol A (1) represents the first example of isopentenyl phenol derivative with a unique 1-glycosylation from the species Aspergillus insuetus. The isolated new compounds were evaluated for antibacterial activities against six human or aquatic pathogens, while compound 2 exhibited inhibitory effect against Edwardsiella tarda, Vibrio alginolyticus, and V. vulnificus, with MIC values of 4, 8, and 8 μg/mL, respectively.

Keywords: Aspergillus insuetus; antibacterial activity; cold seep-derived fungus; marine natural products.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Aspergillus / chemistry*
  • Edwardsiella tarda / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Phenols / chemistry
  • Phenols / isolation & purification
  • Phenols / pharmacology*
  • Vibrio / drug effects*

Substances

  • Anti-Bacterial Agents
  • Phenols

Supplementary concepts

  • Aspergillus insuetus