Bioactive xanthoquinodins and epipolythiodioxopiperazines from Chaetomium globosum 7s-1, an endophytic fungus isolated from Rhapis cochinchinensis (Lour.) Mart

Nat Prod Res. 2020 Feb;34(4):494-502. doi: 10.1080/14786419.2018.1489392. Epub 2018 Nov 19.

Abstract

A new xanthoquinodin B9 (1), together with two known xanthoquinodins, xanthoquinodin A1 (2) and xanthoquinodin A3 (3), three epipolythiodioxopiperazines, chetomin (4), chaetocochin C (5) and dethio-tetra(methylthio)chetomin (6), and four other compounds, chrysophanol (7), emodin (8), alatinone (9), and ergosterol (10) were isolated from the endophytic fungus Chaetomium globosum 7s-1, isolated from Rhapis cochinchinensis (Lour.) Mart. All isolated structures were established based on their spectroscopic data analyses. Compounds 1-6 showed antibacterial activity against Gram positive bacteria with MICs ranging from 0.02 pM to 10.81 µM. Compounds 1-6 also exhibited cytotoxicity against KB, MCF-7 and NCI-H187 cancer cell lines (IC50 0.04-18.40 µM). However, they were cytotoxic towards a normal cell line (Vero cell) with IC50 values ranging from 0.04 to 3.86 µM.

Keywords: Chaetomium globosum; antibacterial; cytotoxicity; epipolythiodioxopiperazine; xanthoquinodin.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Chaetomium / chemistry*
  • Chlorocebus aethiops
  • Chromones / chemistry
  • Chromones / isolation & purification*
  • Cytotoxins / chemistry
  • Cytotoxins / isolation & purification*
  • Cytotoxins / pharmacology
  • Disulfides / isolation & purification
  • Ergosterol / chemistry
  • Ergosterol / isolation & purification
  • Humans
  • Indole Alkaloids / isolation & purification
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Piperazine / chemistry
  • Piperazine / isolation & purification*
  • Piperazines / isolation & purification
  • Vero Cells

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Chromones
  • Cytotoxins
  • Disulfides
  • Indole Alkaloids
  • Piperazines
  • chaetocochin C
  • chetomin
  • Piperazine
  • Ergosterol