The role of glycosides in the light-stabilization of 3-hydroxyflavone (flavonol) dyes as revealed by HPLC (2025)

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.

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Acknowledgements

We wish to thank Drs. Tung-Feng Yeh for doing the Weather-O-meter® exposures for us, Recep Karadag for samples of dried Delphinium semibarbatum flowers, and Alvin Cohen, for guidance in finding Chinese bibliographic information.

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Authors and Affiliations

  1. Department of Chemistry, Boston University, Boston, MA, 02215, USA

    Xian Zhang&Richard Laursen

  2. CIHAM/UMR 5648, 18, quai Claude-Bernard, CNRS, 69365, Lyons Cedex 07, France

    Dominique Cardon

  3. Departamento de Farmacia, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, 5000, Córdoba, Argentina

    José Luis Cabrera

Authors

  1. Xian Zhang

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  2. Dominique Cardon

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  3. José Luis Cabrera

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  4. Richard Laursen

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Correspondence to Richard Laursen.

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Zhang, X., Cardon, D., Cabrera, J.L. et al. The role of glycosides in the light-stabilization of 3-hydroxyflavone (flavonol) dyes as revealed by HPLC. Microchim Acta 169, 327–334 (2010). https://doi.org/10.1007/s00604-010-0361-x

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  • DOI: https://doi.org/10.1007/s00604-010-0361-x

Keywords

  • HPLC, mass spectrometry
  • Dye analysis
  • 3-Hydroxyflavone
  • Sophora japonica
  • Glycosidase
The role of glycosides in the light-stabilization of 3-hydroxyflavone (flavonol) dyes as revealed by HPLC (2025)

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