Terretonin O: a new meroterpenoid from Aspergillus terreus

Nat Prod Res. 2020 Apr;34(7):965-974. doi: 10.1080/14786419.2018.1544977. Epub 2019 Jan 3.

Abstract

Terretonin O (1), a new meroterpenoid, was isolated individually from both methanolic extracts of thermophilic Aspergillus terreus TM8 and marine Aspergillus terreus LGO13. The recently reported terretonins M (2) and N (3) were further isolated from the fungus LGO13 along with nine known compounds, terrelumamide A (4), terrein (5), methyl-3,4,5-trimethoxyl-2-[2-(nicotinamide)benzamido] benzoate (6), butyrolactones I-III (7-9), aspulvinone O (10), ergosterol, ergost-4-ene-3-one and methyl linoleate. Structure of terretonin O (1) was established on the bases of HRESIMS, 1D and 2D NMR spectra and comparison with its analogues in literatures. The relative stereochemistry of 1 was assigned on the basis of NOESY spectra and comparison with reported configuration of its congener compounds 2 and 3. The antimicrobial and cytotoxic activities of the fungal extracts and obtained compounds were assayed using a set of microorganisms, and cervix carcinoma cell line (KB-3-1), respectively. Isolation and taxonomical characterization of the producing strains are reported.

Keywords: Aspergillus terreus; bioactive metabolites; biological activities; terretonin O.

MeSH terms

  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / isolation & purification
  • Anti-Infective Agents / metabolism
  • Anti-Infective Agents / pharmacology
  • Aspergillus / chemistry*
  • Cell Line, Tumor
  • Cytotoxins / chemistry
  • Cytotoxins / isolation & purification
  • Cytotoxins / pharmacology
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Stereoisomerism
  • Terpenes / chemistry
  • Terpenes / isolation & purification*
  • Terpenes / pharmacology

Substances

  • Anti-Infective Agents
  • Cytotoxins
  • Terpenes