Secondary metabolites from the fermented rice of the fungus Monascus purpureus and their bioactivities

Nat Prod Res. 2019 Dec;33(24):3541-3550. doi: 10.1080/14786419.2018.1488698. Epub 2018 Dec 5.

Abstract

Phytochemical investigation of the EtOAc-soluble fraction of the ethanolic extract of a yellow mutant of the fungus Monascus purpureus BCRC 38110 (Eurotiaceae) grown on rice resulted in the isolation of one new azaphilone derivative, monapurpureusone (1), one acetophenone metabolite isolated for the first time from natural source, monapurpureusin (2), along with four known compounds, TW94a (3), ergosterol (4), monascin (5), and ankaflavin (6). The structures and relative configurations of these compounds were elucidated by spectroscopic analyses, including 1D- and 2D-NMR spectroscopy and mass spectrometry, and by the comparison of their NMR data with those of related compounds. Some phytochemicals were evaluated for both anti-inflammatory activity through the measurement of nitric oxide (NO) production levels in lipopolysaccharide (LPS)-stimulated murine-derived macrophages RAW264.7 cell lines and antioxidant activities.

Keywords: Eurotiaceae; acetophenone; anti-inflammatory; antioxidant activities; azaphilone.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology
  • Antioxidants / isolation & purification*
  • Antioxidants / pharmacology
  • Benzopyrans / isolation & purification
  • Ergosterol / isolation & purification
  • Ergosterol / metabolism
  • Fermentation*
  • Flavins / isolation & purification
  • Heterocyclic Compounds, 3-Ring / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Structure
  • Monascus / chemistry*
  • Monascus / metabolism
  • Oryza / microbiology*
  • Pigments, Biological / isolation & purification
  • RAW 264.7 Cells / microbiology*

Substances

  • Anti-Inflammatory Agents
  • Antioxidants
  • Benzopyrans
  • Flavins
  • Heterocyclic Compounds, 3-Ring
  • Pigments, Biological
  • ankaflavin
  • azaphilone
  • monascin
  • Ergosterol