Cytochathiazines A-C: Three Merocytochalasans with a 2 H-1,4-Thiazine Functionality from Coculture of Chaetomium globosum and Aspergillus flavipes

Org Lett. 2018 Nov 2;20(21):6817-6821. doi: 10.1021/acs.orglett.8b02942. Epub 2018 Oct 16.

Abstract

Cytochathiazines A-C (1-3), which represent a new type of merocytochalasan, were isolated from coculture of Chaetomium globosum and Aspergillus flavipes. Compounds 1-3 are the first natural products featuring an unprecedented 2 H-1,4-thiazine functionality. Plausible biosynthetic pathways for 1-3 with a chaetoglobosin and a dipeptide as the main constitutional units were proposed. Compound 2 induced apoptosis in leukemia cells through the activation of caspase-3 and the degradation of poly ADP-ribose polymerase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Apoptosis / drug effects
  • Aspergillus / chemistry*
  • Biosynthetic Pathways
  • Caspase 3 / metabolism
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Chaetomium / chemistry*
  • Coculture Techniques
  • Drug Screening Assays, Antitumor
  • Humans
  • Leukemia / pathology
  • Molecular Structure
  • Structure-Activity Relationship
  • Thiazines / chemistry*
  • Thiazines / pharmacology

Substances

  • Antineoplastic Agents
  • Thiazines
  • CASP3 protein, human
  • Caspase 3