Periconiastone A, an Antibacterial Ergosterol with a Pentacyclo[8.7.0.01,5.02,14.010,15]heptadecane System from Periconia sp. TJ403-rc01

Org Lett. 2019 Oct 18;21(20):8469-8472. doi: 10.1021/acs.orglett.9b03270. Epub 2019 Oct 3.

Abstract

Periconiastone A (1), an ergosterol with an unprecedented pentacyclo[8.7.0.01,5.02,14.010,15]heptadecane system, was isolated from Periconia sp. TJ403-rc01. Its structure was assigned by extensive spectroscopic analyses and quantum-chemical 13C NMR and ECD calculations. A vinylogous α-ketol rearrangement and an aldol condensation reaction during biosynthesis were proposed as key steps for the formation of 1. Compound 1 showed antibacterial activity against Gram-positive S. aureus and E. faecalis with MIC values of 4 and 32 μg/mL, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Ascomycota / chemistry*
  • Ergosterol / chemical synthesis
  • Ergosterol / chemistry
  • Ergosterol / pharmacology*
  • Escherichia / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Staphylococcus aureus / drug effects*
  • Stereoisomerism

Substances

  • Anti-Bacterial Agents
  • periconiastone A
  • Ergosterol

Supplementary concepts

  • Escherichia faecalis