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Structural implications on color, fluorescence, and antiradical activity in betalains

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Abstract

Betalains are water-soluble pigments with high antiradical capacity which bestow bright colors on flowers and fruits of most plants of the order Caryophyllales. They are classified as betacyanins, exhibiting a violet coloration, and betaxanthins, which exhibit yellow coloration. Traditionally, betalains have been defined as condensation products of betalamic acid with different amines and amino acids, but the implication of the pigment structure for their properties has not been investigated. This paper explores different structural features of the betalains, revealing the clues for the switch from yellow to violet color, and the loss of fluorescence. A relevant series of 15 betalain-related compounds (both natural and novel semisynthetic ones) is obtained and characterized by chromatography, UV-vis spectrophotometry, fluorescence, and electrospray ionization mass spectroscopy. Antiradical properties of individual pure compounds in a broad pH range are studied under the ABTS•+ radical assay. Relevance of specific bonds is studied, and differences between betaxanthins and betacyanins are used to explore in depth the structure–antiradical activity relationships in betalains.

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Abbreviations

ABTS:

2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)

DOPA:

Dihydroxyphenylalanine

LDL:

Low density lipoproteins

PDA:

Photodiode array

TEAC:

Trolox equivalent antiradical capacity

TFA:

Trifluoroacetic acid

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Acknowledgments

This work was supported by AGL2007-65907 (MCINN, FEDER, Spain) and by Programa de ayudas a Grupos de Excelencia de la Región de Murcia, de la Fundación Séneca, Agencia de Ciencia y Tecnología de la Región de Murcia (Plan Regional de Ciencia y Tecnología 2007/2010). F. G.-H. holds a contract with the “Programa Ramón y Cajal” (MCINN, FEDER, Spain). The authors declare that they have no conflict of interest.

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  1. Unidad Docente de Biología, Departamento de Bioquímica y Biología Molecular A, Facultad de Veterinaria, Universidad de Murcia, 30100, Espinardo, Murcia, Spain

    Fernando Gandía-Herrero, Josefa Escribano & Francisco García-Carmona

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  1. Fernando Gandía-Herrero
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  2. Josefa Escribano
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  3. Francisco García-Carmona
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Correspondence to Fernando Gandía-Herrero.

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Gandía-Herrero, F., Escribano, J. & García-Carmona, F. Structural implications on color, fluorescence, and antiradical activity in betalains. Planta 232, 449–460 (2010). https://doi.org/10.1007/s00425-010-1191-0

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