Capsaicin production by Alternaria alternata, an endophytic fungus from Capsicum annum; LC-ESI-MS/MS analysis

Phytochemistry. 2014 Feb:98:183-9. doi: 10.1016/j.phytochem.2013.12.001. Epub 2013 Dec 28.

Abstract

Alternaria alternata, an endophytic fungus capable of producing capsaicin (1) was isolated from Capsicum annum. The endophyte was found to produce capsaicin upto three generations. Upscaling of the fermentation broth led to the isolation of one known and one compound characterized as 2,4-di-tert-butyl phenol (2) and alternariol-10-methyl ether (3) respectively. Compound 1 and 3 were identified and quantified using liquid chromatography-electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS) system through multiple reaction monitoring (MRM). Furthermore, compound 3 displayed a range of cytotoxicity against a panel of human cancer cell lines and was found to induce apoptosis evidenced by Hoechst staining and loss of mitochondrial-membrane potential in HL-60 cells.

Keywords: (MRM)-LC–ESI–MS/MS; Alternaria alternata; Alternariol-10-methyl ether; Anti-cancer; Capsaicin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alternaria / chemistry*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Capsaicin / analogs & derivatives
  • Capsaicin / chemistry
  • Capsaicin / pharmacology*
  • Capsicum / chemistry*
  • Capsicum / microbiology
  • Cell Proliferation / drug effects
  • Chromatography, Liquid
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Fruit / chemistry*
  • Fruit / microbiology
  • HL-60 Cells
  • HeLa Cells
  • Humans
  • Membrane Potential, Mitochondrial / drug effects
  • Molecular Structure
  • Spectrometry, Mass, Electrospray Ionization
  • Structure-Activity Relationship
  • Tandem Mass Spectrometry
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents, Phytogenic
  • Capsaicin