Armochaetoglobins A-J: Cytochalasan Alkaloids from Chaetomium globosum TW1-1, a Fungus Derived from the Terrestrial Arthropod Armadillidium vulgare

J Nat Prod. 2015 Jun 26;78(6):1193-201. doi: 10.1021/np500626x. Epub 2015 Jun 12.

Abstract

Ten new cytochalasan alkaloids, termed armochaetoglobins A-J (1-10), and four known chaetoglobosins (11-14) were isolated from a methanol extract of Chaetomium globosum TW1-1, a fungus isolated from the medicinal terrestrial arthropod Armadillidium vulgare. Their structures were elucidated by a combination of spectroscopy, single-crystal X-ray crystallography, and ECD calculations. Armochaetoglobins A-E (1-5) represented the first examples of seco-chaetoglobosins arising from an oxidative cleavage of C-19 and C-20. Among these compounds, armochaetoglobin A (1) features an unusual pyrrole ring. The cytotoxic activities of 2-10 were evaluated, and armochaetoglobin H (8) showed moderate inhibitory activities against five human cancer cell lines, with IC50 values ranging from 3.31 to 9.83 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Chaetomium / chemistry*
  • China
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • Humans
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification*
  • Indole Alkaloids / pharmacology
  • Inhibitory Concentration 50
  • Isopoda / microbiology*
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular

Substances

  • Antineoplastic Agents
  • Indole Alkaloids
  • chaetoglobosins