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Molecules 2016, 21(11), 1502; doi:10.3390/molecules21111502

Chemistry and Photochemistry of Anthocyanins and Related Compounds: A Thermodynamic and Kinetic Approach

LAQV, REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal
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Academic Editors: Arturo San Feliciano and Celestino Santos-Buelga
Received: 28 September 2016 / Revised: 2 November 2016 / Accepted: 3 November 2016 / Published: 10 November 2016
(This article belongs to the Special Issue Flavonoids: From Structure to Health Issues)

Abstract

Anthocyanins are identified by the respective flavylium cation, which is only one species of a multistate of different molecules reversibly interconverted by external inputs such as pH, light and temperature. The flavylium cation (acidic form) is involved in an apparent acid-base reaction, where the basic species is the sum of quinoidal base, hemiketal and cis- and trans-chalcones, their relative fraction depending on the substitution pattern of the flavylium cation. The full comprehension of this complex system requires a thermodynamic and kinetic approach. The first consists in drawing an energy level diagram where the relative positions of the different species are represented as a function of pH. On the other hand, the kinetic approach allows measuring the rates of the reactions that interconnect reversibly the multistate species. The kinetics is greatly dependent on the existence or not of a high cis-trans isomerization barrier. In this work, the procedure to obtain the energy level diagram and the rates of inter-conversion in the multistate in both cases (low or high isomerization barrier) are described. Practical examples of this approach are presented to illustrate the theory, and recently reported applications based on host–guest complexes are reviewed. View Full-Text
Keywords: anthocyanins; flavylium compounds; energy level diagram; multistate chemistry; cyclodextrins; cucurbiturils anthocyanins; flavylium compounds; energy level diagram; multistate chemistry; cyclodextrins; cucurbiturils
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Basílio, N.; Pina, F. Chemistry and Photochemistry of Anthocyanins and Related Compounds: A Thermodynamic and Kinetic Approach. Molecules 2016, 21, 1502.

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