Isolation, analysis and structures of phototoxic fagopyrins from buckwheat

Food Chem. 2014 Jan 15;143:432-9. doi: 10.1016/j.foodchem.2013.07.118. Epub 2013 Aug 9.

Abstract

Buckwheat products are commonly used in health foods and food supplements. However, public awareness regarding the presence of photodynamic naphthodianthrones fagopyrins that can cause photosensitization is low. At least two additional compounds with structures similar to that of fagopyrin are known to exist; however, the structures of these compounds have never been determined. In this work, we improved the extraction procedure and the chromatographic analysis of fagopyrins by developing a simple, sensitive and high-resolution high performance liquid chromatography (HPLC) analytical method using fluorescence detection. We observed at least six fagopyrin derivatives, which were isolated and characterized via UV-Vis absorption, NMR spectroscopy and mass spectrometry. We determined the structures of two new derivatives (fagopyrin A and fagopyrin E) and proved the existence of protofagopyrins that can transform into fagopyrins upon light exposure. Our methods complement the existing knowledge regarding fagopyrins and will allow for their further analysis, isolation and investigation of their biological activity.

Keywords: Buckwheat analysis; Fagopyrin derivatives; Fagopyrum sp.; Fluorescence; Naphthodianthrone; Photodynamic.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fagopyrum / chemistry*
  • Fagopyrum / radiation effects
  • Light / adverse effects
  • Molecular Structure
  • Photosensitizing Agents / chemistry*
  • Photosensitizing Agents / isolation & purification*
  • Plant Extracts / chemistry*
  • Plant Extracts / isolation & purification*
  • Quinones / chemistry*
  • Quinones / isolation & purification*
  • Seeds / chemistry
  • Seeds / radiation effects

Substances

  • Photosensitizing Agents
  • Plant Extracts
  • Quinones
  • fagopyrin