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Effect of Temperature on Acidity and Hydration Equilibrium Constants of Delphinidin-3-O- and Cyanidin-3-O-sambubioside Calculated from Uni- and Multiwavelength Spectroscopic Data.
J Agric Food Chem. 2016 May 25; 64(20):4139-45.JA

Abstract

Delphinidin-3-O-sambubioside and cyanidin-3-O-sambubioside are the main anthocyanins of Hibiscus sabdariffa calyces, traditionally used to make a bright red beverage by decoction in water. At natural pH, these anthocyanins are mainly in their flavylium form (red) in equilibrium with the quinonoid base (purple) and the hemiketal (colorless). For the first time, their acidity and hydration equilibrium constants were obtained from a pH-jump method followed by UV-vis spectroscopy as a function of temperature from 4 to 37 °C. Equilibrium constant determination was also performed by multivariate curve resolution (MCR). Acidity and hydration constants of cyanidin-3-O-sambubioside at 25 °C were 4.12 × 10(-5) and 7.74 × 10(-4), respectively, and were significantly higher for delphinidin-3-O-sambubioside (4.95 × 10(-5) and 1.21 × 10(-3), respectively). MCR enabled the obtaining of concentration and spectrum of each form but led to overestimated values for the equilibrium constants. However, both methods showed that formations of the quinonoid base and hemiketal were endothermic reactions. Equilibrium constants of anthocyanins in the hibiscus extract showed comparable values as for the isolated anthocyanins.

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Authors+Show Affiliations

CIRAD , UMR 95 Qualisud, TA B-95/16, F-34398 Montpellier Cedex 5, France.

Montpellier SupAgro , UMR 95 Qualisud, TA B-95/16, F-34398 Montpellier Cedex 5, France.

CIRAD , UMR 95 Qualisud, TA B-95/16, F-34398 Montpellier Cedex 5, France.

CIRAD , UMR 95 Qualisud, TA B-95/16, F-34398 Montpellier Cedex 5, France.

CIRAD , UMR 95 Qualisud, TA B-95/16, F-34398 Montpellier Cedex 5, France.

CIRAD , UMR 95 Qualisud, TA B-95/16, F-34398 Montpellier Cedex 5, France.

UMR 408, University of Avignon, INRA , Safety and Quality of Plant Products, 84000 Avignon, France.

INRA-IPV , Unité de Recherche des Polymères et des Techniques Physicochimiques, 2 place Viala, 34060 Montpellier, France.

Montpellier SupAgro , UMR 95 Qualisud, TA B-95/16, F-34398 Montpellier Cedex 5, France.

MeSH

AnthocyaninsDisaccharidesFlowersHibiscusHydrogen-Ion ConcentrationKineticsPlant ExtractsSpectrum AnalysisTemperature

Pub Type(s)

Journal Article

Language

eng

PubMed ID

27124576

Citation

Vidot, Kévin, et al. "Effect of Temperature On Acidity and Hydration Equilibrium Constants of Delphinidin-3-O- and Cyanidin-3-O-sambubioside Calculated From Uni- and Multiwavelength Spectroscopic Data." Journal of Agricultural and Food Chemistry, vol. 64, no. 20, 2016, pp. 4139-45.

Vidot K, Achir N, Mertz C, et al. Effect of Temperature on Acidity and Hydration Equilibrium Constants of Delphinidin-3-O- and Cyanidin-3-O-sambubioside Calculated from Uni- and Multiwavelength Spectroscopic Data. J Agric Food Chem. 2016;64(20):4139-45.

Vidot, K., Achir, N., Mertz, C., Sinela, A., Rawat, N., Prades, A., Dangles, O., Fulcrand, H., & Dornier, M. (2016). Effect of Temperature on Acidity and Hydration Equilibrium Constants of Delphinidin-3-O- and Cyanidin-3-O-sambubioside Calculated from Uni- and Multiwavelength Spectroscopic Data. Journal of Agricultural and Food Chemistry, 64(20), 4139-45. https://doi.org/10.1021/acs.jafc.6b00701

Vidot K, et al. Effect of Temperature On Acidity and Hydration Equilibrium Constants of Delphinidin-3-O- and Cyanidin-3-O-sambubioside Calculated From Uni- and Multiwavelength Spectroscopic Data. J Agric Food Chem. 2016 May 25;64(20):4139-45. PubMed PMID: 27124576.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Effect of Temperature on Acidity and Hydration Equilibrium Constants of Delphinidin-3-O- and Cyanidin-3-O-sambubioside Calculated from Uni- and Multiwavelength Spectroscopic Data. AU - Vidot,Kévin, AU - Achir,Nawel, AU - Mertz,Christian, AU - Sinela,André, AU - Rawat,Nadirah, AU - Prades,Alexia, AU - Dangles,Olivier, AU - Fulcrand,Hélène, AU - Dornier,Manuel, Y1 - 2016/05/12/ PY - 2016/4/29/entrez PY - 2016/4/29/pubmed PY - 2017/4/7/medline KW - Hibiscus sabdariffa extract KW - MCR KW - UV−vis KW - anthocyanin KW - cyanidin-3-O-sambubioside KW - delphinidin-3-O-sambubioside KW - equilibrium constant KW - pH-jump SP - 4139 EP - 45 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 64 IS - 20 N2 - Delphinidin-3-O-sambubioside and cyanidin-3-O-sambubioside are the main anthocyanins of Hibiscus sabdariffa calyces, traditionally used to make a bright red beverage by decoction in water. At natural pH, these anthocyanins are mainly in their flavylium form (red) in equilibrium with the quinonoid base (purple) and the hemiketal (colorless). For the first time, their acidity and hydration equilibrium constants were obtained from a pH-jump method followed by UV-vis spectroscopy as a function of temperature from 4 to 37 °C. Equilibrium constant determination was also performed by multivariate curve resolution (MCR). Acidity and hydration constants of cyanidin-3-O-sambubioside at 25 °C were 4.12 × 10(-5) and 7.74 × 10(-4), respectively, and were significantly higher for delphinidin-3-O-sambubioside (4.95 × 10(-5) and 1.21 × 10(-3), respectively). MCR enabled the obtaining of concentration and spectrum of each form but led to overestimated values for the equilibrium constants. However, both methods showed that formations of the quinonoid base and hemiketal were endothermic reactions. Equilibrium constants of anthocyanins in the hibiscus extract showed comparable values as for the isolated anthocyanins. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/27124576/Effect_of_Temperature_on_Acidity_and_Hydration_Equilibrium_Constants_of_Delphinidin_3_O__and_Cyanidin_3_O_sambubioside_Calculated_from_Uni__and_Multiwavelength_Spectroscopic_Data_ DB - PRIME DP - Unbound Medicine ER -