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Acidichromism and Ionochromism of Luteolin and Apigenin, the Main Components of the Naturally Occurring Yellow Weld: A Spectrophotometric and Fluorimetric Study

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Abstract

Luteolin and apigenin, extracted from Reseda luteola L., were spectrophotometrically and fluorimetrically studied. The spectra were investigated as a function of pH in methanol/water solutions (1/2, v/v) in the 2–12 pH range. The absorption spectra markedly shifted to the red by increasing the pH. Three acid–base dissociation steps were detected for luteolin (pK a = 6.9; 8.6; 10.3) and two for apigenin (pK a = 6.6; 9.3). Fluorescence emission was very weak or undetectable (Φ F < 10−4) in acidic solution, but increased in intensity with increasing the pH. Both molecules exhibited a great propensity towards complex formation with metal ions, with association constants on the order of 105–107 for the first complexation step; in the presence of excess Al3+ ions, multiple equilibria were detected. A marked fluorescence enhancement was observed upon complexation with Al3+ ions (Φ F ∼ 1 for luteolin and ∼10−2 for apigenin).

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Acknowledgements

The research was funded by the Ministero per l’Università e la Ricerca Scientifica e Tecnologica (Rome) and the University of Perugia. One of us (V.V.) is grateful to the Italian Consiglio Nazionale delle Ricerche for a fellowship NATO CNR OUTREACH.

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Authors and Affiliations

  1. Department of Chemistry, University of Perugia, 06123, Perugia, Italy

    G. Favaro, C. Clementi & A. Romani

  2. Department of Analytical and Environmental Chemistry, Vilnius University, 03225, Vilnius, Lithuania

    V. Vickackaite

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  1. G. Favaro
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  2. C. Clementi
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  3. A. Romani
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  4. V. Vickackaite
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Correspondence to G. Favaro.

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Favaro, G., Clementi, C., Romani, A. et al. Acidichromism and Ionochromism of Luteolin and Apigenin, the Main Components of the Naturally Occurring Yellow Weld: A Spectrophotometric and Fluorimetric Study. J Fluoresc 17, 707–714 (2007). https://doi.org/10.1007/s10895-007-0222-0

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  • DOI: https://doi.org/10.1007/s10895-007-0222-0

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