Trichophycin A, a Cytotoxic Linear Polyketide Isolated from a Trichodesmium thiebautii Bloom

Mar Drugs. 2017 Jan 6;15(1):10. doi: 10.3390/md15010010.

Abstract

In an effort to isolate and characterize bioactive secondary metabolites from Trichodesmium thiebautii blooms, collected cyanobacteria biomass was subjected to bioassay-guided extraction and fractionation using the human colon cancer cell line HCT-116, resulting in the isolation and subsequent structure characterization of a linear polyketide trichophycin A (1). The planar structure of 1 was completed using 1D and 2D NMR spectroscopy and high-resolution electrospray ionization mass spectrometry (HRESIMS). Trichophycin A was moderately toxic against the murine neuroblastoma cell line Neuro-2A (EC50: 6.5 μM) and HCT-116 cells (EC50: 11.7 μM). Trichophycin A was significantly more cytotoxic than the previously isolated polyketides trichotoxin A and trichotoxin B. These cytotoxicity observations suggest that toxicity may be related to the polyol character of these polyketide compounds.

Keywords: Trichodesmium thiebautii blooms; polyketide; polyol; secondary metabolite.

MeSH terms

  • Animals
  • Antimicrobial Cationic Peptides
  • Cell Line, Tumor
  • Cyanobacteria / chemistry*
  • HCT116 Cells
  • Humans
  • Magnetic Resonance Spectroscopy / methods
  • Mice
  • Neuroblastoma / drug therapy
  • Peptides / chemistry
  • Peptides / pharmacology
  • Polyketides / chemistry*
  • Polyketides / pharmacology
  • Spectrometry, Mass, Electrospray Ionization / methods
  • Trichodesmium / chemistry*

Substances

  • Antimicrobial Cationic Peptides
  • Peptides
  • Polyketides
  • trichotoxin