Isolation of undescribed cladosporols and spirobisnaphthalenes from a plant pathogen Cladosporium cladosporioides F-10-2-A

Phytochemistry. 2024 Jun:222:114073. doi: 10.1016/j.phytochem.2024.114073. Epub 2024 Mar 31.

Abstract

Two undescribed cladosporol derivatives, cladosporols J-K (1-2), and three previously unreported spirobisnaphthalenes, urnucratins D-F (3-5), as well as eleven known cladosporols (6-16), were characterized from Cladosporium cladosporioides (Cladosporiaceae), a common plant pathogen isolated from the skin of Chinese toad. Cladosporols J-K (1-2) with a single double bond have been rarely reported, while urnucratins D-F (3-5) featured an unusual benzoquinone bisnaphthospiroether skeleton, contributing to an expanding category of undiscovered natural products. Their structures and absolute configurations were determined using extensive spectroscopic methods, including NMR, HRESIMS analyses, X-ray single crystal diffraction, as well as through experimental ECD analyses. Biological assays revealed that compounds 1 and 2 exhibited inhibitory activity against A549 cells, with IC50 values of 30.11 ± 3.29 and 34.32 ± 2.66 μM, respectively.

Keywords: Cladosporiaceae; Cladosporium cladosporioides; Cladosporols; Cytotoxicity; Plant pathogen; Spirobisnaphthalenes.

MeSH terms

  • A549 Cells
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Cell Proliferation / drug effects
  • Cladosporium* / chemistry
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Naphthalenes* / chemistry
  • Naphthalenes* / isolation & purification
  • Naphthalenes* / pharmacology
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification
  • Spiro Compounds / pharmacology
  • Structure-Activity Relationship

Substances

  • Naphthalenes
  • Spiro Compounds
  • Antineoplastic Agents