A new steroid with 7β,8β-epoxidation from the deep sea-derived fungus Aspergillus penicillioides SD-311

J Asian Nat Prod Res. 2021 Sep;23(9):884-891. doi: 10.1080/10286020.2020.1791096. Epub 2020 Jul 13.

Abstract

7β,8β-epoxy-(22E,24R)-24-methylcholesta-4,22-diene-3,6-dione (1), a new steroid, along with five known analogues (2-6), was isolated from the deep sea-derived fungus, Aspergillus penicillioides SD-311. Strikingly, 1 possessed a rare 7,8-epoxidation moiety. Meanwhile, this is the first time to report natural products from this fungus species. The structures were established by extensive spectroscopic analysis. The absolute configuration was determined by X-ray diffraction experiments. Compound 1 showed antibacterial activity against Vibrio anguillarum with MIC value of 32.0 µg/mL, while 2 displayed inhibitions against Edwardsiella tarda and Micrococcus luteus with MIC values both of 16 µg/mL.

Keywords: 7β,8β-epoxy steroid; Aspergillus penicillioides; deep sea-derived fungus; marine natural products.

MeSH terms

  • Anti-Bacterial Agents / pharmacology
  • Aspergillus
  • Fungi*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Steroids* / pharmacology
  • Vibrio

Substances

  • Anti-Bacterial Agents
  • Steroids

Supplementary concepts

  • Aspergillus penicillioides
  • Vibrio anguillarum