Tubulin inhibitors from an endophytic fungus isolated from Cedrus deodara

J Nat Prod. 2013 Feb 22;76(2):194-9. doi: 10.1021/np3006666. Epub 2013 Feb 6.

Abstract

From an endophytic fungus, a close relative of Talaromyces sp., found in association with Cedrus deodara, four compounds including two new ones (2 and 4) were isolated and characterized. The structures of two compounds (1 and 4) were confirmed by X-ray crystallography. The compounds displayed a range of cytotoxicities against human cancer cell lines (HCT-116, A-549, HEP-1, THP-1, and PC-3). All the compounds were found to induce apoptosis in HL-60 cells, as evidenced by fluorescence and scanning electron microscopy studies. Also, the compounds caused significant microtubule inhibition in HL-60 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Apoptosis / drug effects
  • Ascomycota / chemistry*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / isolation & purification*
  • Bridged Bicyclo Compounds, Heterocyclic / pharmacology*
  • Cedrus / microbiology*
  • Crystallography, X-Ray
  • HCT116 Cells
  • HL-60 Cells
  • Humans
  • Isocoumarins / chemistry
  • Isocoumarins / isolation & purification*
  • Isocoumarins / pharmacology*
  • Molecular Conformation
  • Molecular Structure
  • Tubulin Modulators / chemistry
  • Tubulin Modulators / isolation & purification*
  • Tubulin Modulators / pharmacology*

Substances

  • (1S*,3R*,5R*)-3-methyl-2-oxa-bicyclo(3.3.1)nonan-7-one
  • (3S,4aR,7S)-7,8-dihydroxy-3-methyl-3,4,10,5,6,7-hexahydro-1H-isochromen-1-one
  • Bridged Bicyclo Compounds, Heterocyclic
  • Isocoumarins
  • Tubulin Modulators