ent-Clavilactone J and Its Quinone Derivative, Meroterpenoids from the Fungus Resupinatus sp

J Nat Prod. 2023 Nov 24;86(11):2580-2584. doi: 10.1021/acs.jnatprod.3c00174. Epub 2023 Nov 6.

Abstract

Metabolites 1 and 2, isolated from cultures of the basidiomycete Resupinatus sp. BCC84615, collected in a tropical forest in northeastern Thailand, showed weak antibiotic activity against Bacillus subtilis and Staphylococcus aureus and cytotoxicity against cancer cell lines. Their planar structures were elucidated by high-resolution electrospray ionization mass spectrometry and NMR spectroscopy as clavilactone J, known from the basidiomycete Ampulloclitocybe clavipes, and its new 1,4-benzoquinone derivative. A detailed analysis of the ROESY correlations in 1 confirmed the recent revision of the relative configuration of clavilactone J. However, specific rotation and Cotton effects observed by electronic circular dichroism were contrary to those of the clavilactones; thus, we assigned a rare antipodal absolute configuration.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Basidiomycota* / chemistry
  • Benzoquinones / pharmacology
  • Circular Dichroism
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Quinones

Substances

  • Anti-Bacterial Agents
  • Benzoquinones
  • Quinones