Impact of Lignosulfonates on the Thermodynamic and Kinetic Parameters of Malvidin-3- O-glucoside in Aqueous Solutions

Paula Araújo; Nuno Basílio; Ana Fernandes; Nuno Mateus; Victor de Freitas; Fernando Pina; Joana Oliveira

doi:10.1021/acs.jafc.8b02273

Impact of Lignosulfonates on the Thermodynamic and Kinetic Parameters of Malvidin-3- O-glucoside in Aqueous Solutions

Paula Araújo, Nuno Basílio, Ana Fernandes, Nuno Mateus, Victor de Freitas, Fernando Pina, Joana Oliveira

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

The interaction of malvidin-3-O-glucoside (1) and a lignosulfonate was studied by UV-visible spectroscopy, and the results obtained showed the formation of a complex between the negatively charged lignosulfonate and the flavylium cation form (AH⁺) of this anthocyanin at pH 1. The thermodynamic and kinetic parameters of 1 in the presence of a lignosulfonate were determined by UV-visible spectroscopy and stopped-flow techniques. The main differences were observed in the flavylium cation (AH⁺)/quinoidal base (A) equilibrium, the AH⁺ form being more stabilized than A (pK_a1 = 4.4 ± 0.1) compared with 1 in the absence of the lignosulfonate (pK_a1 = 3.9 ± 0.1). Furthermore, comparing the hydration (k_h = 0.028 s^-1) and dehydration (k_-h = 40 M^-1 s^-1) processes of 1 in the presence of the lignosulfonate with the processes of 1 (k_h = 0.12 s^-1 and k_-h = 35 M^-1 s^-1) show that the hydration process is slower while the dehydration process is practically unaffected in the presence of the lignosulfonate.

Original language	English
Pages (from-to)	6382-6387
Number of pages	6
Journal	Journal of Agricultural and Food Chemistry
Volume	66
Issue number	25
DOIs	https://doi.org/10.1021/acs.jafc.8b02273
Publication status	Published - 27 Jun 2018

Keywords

calcium lignosulfonate
copigmentation
flavylium cation stabilization
malvidin-3- O-glucoside
stopped-flow
UV-visible

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title = "Impact of Lignosulfonates on the Thermodynamic and Kinetic Parameters of Malvidin-3- O-glucoside in Aqueous Solutions",

abstract = "The interaction of malvidin-3-O-glucoside (1) and a lignosulfonate was studied by UV-visible spectroscopy, and the results obtained showed the formation of a complex between the negatively charged lignosulfonate and the flavylium cation form (AH+) of this anthocyanin at pH 1. The thermodynamic and kinetic parameters of 1 in the presence of a lignosulfonate were determined by UV-visible spectroscopy and stopped-flow techniques. The main differences were observed in the flavylium cation (AH+)/quinoidal base (A) equilibrium, the AH+ form being more stabilized than A (pKa1 = 4.4 ± 0.1) compared with 1 in the absence of the lignosulfonate (pKa1 = 3.9 ± 0.1). Furthermore, comparing the hydration (kh = 0.028 s-1) and dehydration (k-h = 40 M-1 s-1) processes of 1 in the presence of the lignosulfonate with the processes of 1 (kh = 0.12 s-1 and k-h = 35 M-1 s-1) show that the hydration process is slower while the dehydration process is practically unaffected in the presence of the lignosulfonate.",

keywords = "calcium lignosulfonate, copigmentation, flavylium cation stabilization, malvidin-3- O-glucoside, stopped-flow, UV-visible",

author = "Paula Ara{\'u}jo and Nuno Bas{\'i}lio and Ana Fernandes and Nuno Mateus and Freitas, {Victor de} and Fernando Pina and Joana Oliveira",

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T1 - Impact of Lignosulfonates on the Thermodynamic and Kinetic Parameters of Malvidin-3- O-glucoside in Aqueous Solutions

AU - Araújo, Paula

AU - Basílio, Nuno

AU - Fernandes, Ana

AU - Mateus, Nuno

AU - Freitas, Victor de

AU - Pina, Fernando

AU - Oliveira, Joana

N1 - info:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBPD%2F84805%2F2012/PT# info:eu-repo/grantAgreement/FCT/5876/147218/PT# SFRH/BPD/112465/2015. IF/00225/2015. PTDC/AGR-TEC/2789/2014 COMPETE POCI-01-0145-FEDER-016616, REDE/1517/RMN/2005. POCI/01/0145/FEDER/007265) from FCT/MEC through national funds and was cofinanced by FEDER, under the Partnership Agreement PT2020 and FEDER-Interreg Espana-Portugal Programme (project ref 0377_IBERPHENOL_6_E). Sem PDF conforme despacho.

PY - 2018/6/27

Y1 - 2018/6/27

N2 - The interaction of malvidin-3-O-glucoside (1) and a lignosulfonate was studied by UV-visible spectroscopy, and the results obtained showed the formation of a complex between the negatively charged lignosulfonate and the flavylium cation form (AH+) of this anthocyanin at pH 1. The thermodynamic and kinetic parameters of 1 in the presence of a lignosulfonate were determined by UV-visible spectroscopy and stopped-flow techniques. The main differences were observed in the flavylium cation (AH+)/quinoidal base (A) equilibrium, the AH+ form being more stabilized than A (pKa1 = 4.4 ± 0.1) compared with 1 in the absence of the lignosulfonate (pKa1 = 3.9 ± 0.1). Furthermore, comparing the hydration (kh = 0.028 s-1) and dehydration (k-h = 40 M-1 s-1) processes of 1 in the presence of the lignosulfonate with the processes of 1 (kh = 0.12 s-1 and k-h = 35 M-1 s-1) show that the hydration process is slower while the dehydration process is practically unaffected in the presence of the lignosulfonate.

AB - The interaction of malvidin-3-O-glucoside (1) and a lignosulfonate was studied by UV-visible spectroscopy, and the results obtained showed the formation of a complex between the negatively charged lignosulfonate and the flavylium cation form (AH+) of this anthocyanin at pH 1. The thermodynamic and kinetic parameters of 1 in the presence of a lignosulfonate were determined by UV-visible spectroscopy and stopped-flow techniques. The main differences were observed in the flavylium cation (AH+)/quinoidal base (A) equilibrium, the AH+ form being more stabilized than A (pKa1 = 4.4 ± 0.1) compared with 1 in the absence of the lignosulfonate (pKa1 = 3.9 ± 0.1). Furthermore, comparing the hydration (kh = 0.028 s-1) and dehydration (k-h = 40 M-1 s-1) processes of 1 in the presence of the lignosulfonate with the processes of 1 (kh = 0.12 s-1 and k-h = 35 M-1 s-1) show that the hydration process is slower while the dehydration process is practically unaffected in the presence of the lignosulfonate.

KW - calcium lignosulfonate

KW - copigmentation

KW - flavylium cation stabilization

KW - malvidin-3- O-glucoside

KW - stopped-flow

KW - UV-visible

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U2 - 10.1021/acs.jafc.8b02273

DO - 10.1021/acs.jafc.8b02273

M3 - Article

C2 - 29870233

AN - SCOPUS:85048243760

SN - 0021-8561

VL - 66

SP - 6382

EP - 6387

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

IS - 25

ER -

Impact of Lignosulfonates on the Thermodynamic and Kinetic Parameters of Malvidin-3- O-glucoside in Aqueous Solutions

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Keywords

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