Isolation and characterization of 2-pyridone alkaloids and alloxazines from Beauveria bassiana

Nat Prod Res. 2017 Aug;31(16):1920-1929. doi: 10.1080/14786419.2016.1269091. Epub 2016 Dec 29.

Abstract

Two novel compounds bearing heterocyclic nitrogen, 2-pyridone alkaloid (1) and alloxazine derivative (2), along with the known pretenellin B (3), pyridovericin (4) and lumichrome (5) were isolated from a culture of the entomopathogenic fungal strain Beauveria bassiana. The chemical structures of 2-pyridone alkaloid and alloxazine derivative were established on the basis of the interpretation of spectroscopic data. The isolated compounds were evaluated in a panel of five cancer cell lines and pyridovericin exhibited cytotoxicity (IC50, μM) against cancer cell lines: HL-60 (25.9 ± 0.3), HCT8 (34.6 ± 3.6), MDA-MB435 (34.8 ± 3.8) and SF295 (31.1 ± 0.6). Considering that other pyridone compounds display good cytotoxic activity, it would be suggested to obtain new semi synthetic derivatives of pyridovericin, for the development of new cytotoxic chemical entities.

Keywords: Alloxazines; Beauveria bassiana; entomopathogenic fungus; pyridone alkaloids.

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Beauveria / chemistry*
  • Beauveria / metabolism
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Flavins / chemistry
  • Flavins / isolation & purification
  • Humans
  • Molecular Structure
  • Monosaccharides / chemistry
  • Pyridones / chemistry
  • Pyridones / isolation & purification
  • Pyridones / pharmacology
  • Secondary Metabolism

Substances

  • Alkaloids
  • Antineoplastic Agents
  • Flavins
  • Monosaccharides
  • Pyridones
  • pyridovericin
  • 7,8-dimethylalloxazine
  • isoalloxazine
  • 2-hydroxypyridine