New 1, 2-naphthoquinone-derived pigments from the mycobiont of lichen Trypethelium eluteriae Sprengel

Nat Prod Res. 2019 Jul;33(14):2044-2050. doi: 10.1080/14786419.2018.1484458. Epub 2018 Jun 20.

Abstract

A new yellow pigment trypethelonamide A (1), and a new dark violet-red pigment 5'-hydroxytrypethelone (2), as well as three known dark violet-red pigments (+)-8-hydroxy-7-methoxytrypethelone (3), (+)-trypethelone (4) and (-)-trypethelone (5) were isolated from the cultured lichenized fungus Trypethelium eluteriae. The structures of 1 and 2 were determined to be 1, 2-naphthoquinone derivatives by extensive spectroscopic analysis. The absolute configurations of 1 and 2 were assigned by quantum electronic circular dichroism (ECD) calculation. All isolated compounds were evaluated for cytotoxicities against A549, HepG2 and RKO cell lines, and antioxidant effects on DPPH. Compounds 1-5 showed moderate and weak cytotoxicities against RKO cell line with IC50 from 22.6 to 113.5 μM.

Keywords: ECD; Naphthoquinone; cytotoxicity; lichenized fungus; pigment.

MeSH terms

  • Antioxidants / pharmacology
  • Ascomycota
  • Cell Death / drug effects
  • Cell Line
  • Circular Dichroism
  • Coloring Agents / chemistry
  • Coloring Agents / isolation & purification
  • Humans
  • Lichens / chemistry*
  • Molecular Structure
  • Naphthoquinones / chemistry
  • Naphthoquinones / isolation & purification*
  • Polyketides / chemistry
  • Polyketides / isolation & purification
  • Spectrum Analysis

Substances

  • Antioxidants
  • Coloring Agents
  • Naphthoquinones
  • Polyketides
  • trypethelone