Microchimica Acta

, Volume 169, Issue 3, pp 327–334

The role of glycosides in the light-stabilization of 3-hydroxyflavone (flavonol) dyes as revealed by HPLC

  • Xian Zhang
  • Dominique Cardon
  • José Luis Cabrera
  • Richard Laursen
Original Paper

DOI: 10.1007/s00604-010-0361-x

Cite this article as:
Zhang, X., Cardon, D., Cabrera, J.L. et al. Microchim Acta (2010) 169: 327. doi:10.1007/s00604-010-0361-x

Abstract

Before the advent of synthetic dyes, textiles were colored primarily with extracts of plants, many of which, in the case of yellow colors, were flavonoids. One important Asian yellow dye source was buds from the pagoda tree (Sophora japonica). Using reversed phase HPLC to separate the flavonoid components of plants and of dyed textiles, and UV/Visible and mass spectrometry to detect and identify them, we have shown that the buds of pagoda trees (Sophora japonica) contain an enzyme that converts light-stable rutin, the 3-O-rutinoside of quercetin, to light-unstable quercetin. This work provides an explanation for why 3-O-substituted, rather than unsubstituted, 3-hydroxyflavones, are generally, in our experience, found in extracts of historical textiles; it also shows how, i.e., by heat inactivation of glycosidases, 3-O-substituted hydroxyflavones could have been selected for. Some other dye-producing plants, e.g., Reseda luteola and Flaveria haumanii, also appear to contain glycosidases. The need for proper processing of dyestuffs, e.g., by heat treatment, was probably recognized by dyers in ancient times, even if the processes were not understood.

Keywords

HPLC, mass spectrometryDye analysis3-HydroxyflavoneSophora japonicaGlycosidase

Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  • Xian Zhang
    • 1
  • Dominique Cardon
    • 2
  • José Luis Cabrera
    • 3
  • Richard Laursen
    • 1
  1. 1.Department of ChemistryBoston UniversityBostonUSA
  2. 2.CIHAM/UMR 5648, 18, quai Claude-BernardCNRSLyons Cedex 07France
  3. 3.Departamento de Farmacia, Facultad de Ciencias QuímicasUniversidad Nacional de CórdobaCórdobaArgentina