Cytochalasins and orsellinic acid derivatives with cytotoxicity from the soil-derived fungus Trichocladium asperum

Phytochemistry. 2025 Mar:231:114340. doi: 10.1016/j.phytochem.2024.114340. Epub 2024 Nov 26.

Abstract

Four undescribed cytochalasins (1-4), three undescribed orsellinic acid derivatives (5-7) and two known metabolites including methyl lecanorate (8) and methyl orsellinate (9) were isolated from the solid-state cultivation of a soil-derived fungus Trichocladium asperum SQ2-3 collected in Qinghai-Tibet Plateau. Their structures were elucidated by analysis of NMR (1D and 2D) and mass spectrometry data. The absolute configurations of 1-7 were assigned by a combination of the modified Mosher's method, microscale derivatization and Mo2(OAc)4-induced circular dichroism experiment. Compounds 1, 2, 3 and 6 showed significant cytotoxicity against HL-60, A3494, SMMC-7721, MDA-MB-231 and SW480 cell lines with IC50 values ranging from 4.74 to 15.84 μM, respectively. Meanwhile, compound 1 could obviously damage mitochondrial membrane potential and induce G2/M cell cycle arrest in A549 cells.

Keywords: Cytochalasins; Cytotoxicity; Orsellinic acid derivatives; Soil-derived fungus; Trichocladium asperum.

MeSH terms

  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / isolation & purification
  • Antineoplastic Agents* / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cytochalasins* / chemistry
  • Cytochalasins* / isolation & purification
  • Cytochalasins* / pharmacology
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor*
  • Humans
  • Hypocreales / chemistry
  • Membrane Potential, Mitochondrial / drug effects
  • Molecular Structure
  • Oleanolic Acid / analogs & derivatives
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / isolation & purification
  • Oleanolic Acid / pharmacology
  • Resorcinols / chemistry
  • Resorcinols / isolation & purification
  • Resorcinols / pharmacology
  • Soil Microbiology
  • Structure-Activity Relationship

Substances

  • Cytochalasins
  • orsellinic acid
  • Antineoplastic Agents
  • Resorcinols
  • Oleanolic Acid