Stereochemical determination of new cytochalasans from the plant endophytic fungus Trichoderma gamsii

Fitoterapia. 2014 Jul:96:115-22. doi: 10.1016/j.fitote.2014.04.009. Epub 2014 Apr 18.

Abstract

Three new cytochalasans, trichalasins E (1), F (2) and H (7), together with four known analogues, trichalasin C (3), aspochalasin K (4), trichalasin G (5) and aspergillin PZ (8), were isolated from one endophytic fungus Trichoderma gamsii inhabiting in the traditional medicinal plant Panax notoginseng (BurK.) F.H. Chen. Trichalasins E (1) contains a unique hydroperoxyl group, which is the first report in all known analogues, whereas trichalasin H (7) possesses the rare 6/5/6/6/5 pentacyclic skeleton with 12-oxatricyclo [6.3.1.0(2,7)] moiety as that of aspergillin PZ (8). The relative configurations of the new compounds were characterized by analysis of coupling constants and ROESY correlations, and the absolute configurations of trichalasins E (1), H (7) and aspergillin PZ (8) were determined by modified Mosher's reaction. In addition, compounds 1-5, 7 and 8 were tested cytotoxic activities against several cancer cell lines.

Keywords: Cytochalasans; Endophytes; Stereochemistry; Trichoderma gamsii.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Cytochalasins / chemistry
  • Cytochalasins / isolation & purification*
  • Cytochalasins / pharmacology
  • Endophytes
  • Humans
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification
  • Indole Alkaloids / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plants / microbiology
  • Trichoderma / chemistry*

Substances

  • Antineoplastic Agents
  • Cytochalasins
  • Indole Alkaloids
  • aspergillin PZ
  • aspochalasin K