Structure-activity relationships of trichothecenes against COLO201 cells and Cochliobolus miyabeanus: The role of 12-epoxide and macrocyclic moieties

  • Bioorg Med Chem Lett. 2019 Apr 15;29(8):982-985. doi: 10.1016/j.bmcl.2019.02.015.
Manami Matsumoto  1 ,  Mami Nishiyama  1 ,  Hayato Maeda  1 ,  Akio Tonouchi  1 ,  Katsuhiro Konno  2 ,  Masaru Hashimoto  3
Affiliations
  • 1. Faculty of Agriculture and Life Science, Hirosaki University, 3-Bunkyo-cho, Hirosaki 036-8561, Japan.
  • 2. Institute of Natural Medicine, University of Toyama, Toyama 930-0194, Japan.
  • 3. Faculty of Agriculture and Life Science, Hirosaki University, 3-Bunkyo-cho, Hirosaki 036-8561, Japan. Electronic address: [email protected].
PMID: 30797671 DOI: 10.1016/j.bmcl.2019.02.015
Abstract

The novel trichothecene 12-deoxytrichodermin (3) was isolated from the fungus Trichoderma sp. 1212-03, and included with Other known natural trichothecenes in a structure-activity relationship investigation against a human colon Cancer cell line (COLO201) and filamentous fungus Cochliobolus miyabeanus. This revealed that the 12-epoxide functionality is critical for the cytotoxicity of simple trichothecenes trichodermin (4) and deoxynivalenol (2), while not critical for the cytotoxicity of roridin J (6) and epiisororidin E (8). In contrast, 12-epoxide is essential for the Antifungal activity.

Keywords
12-Deoxytrichothecenes; Cytotoxicity; Structure-activity relationship; Trichothecenes.