Investigation of the difference in color enhancement effect on cyanidin-3-O-glucoside by phenolic acids and the interaction mechanism

被引:9
作者
Cao, Yan [1 ]
Zhao, Baofu [2 ]
Li, Yougui [3 ]
Gao, Haiyan [1 ]
Xia, Qile [1 ]
Fang, Zhongxiang [4 ]
机构
[1] Zhejiang Acad Agr Sci, Food Sci Inst, State Key Lab Managing Biot & Chem Threats Qual &, Key Lab Postharvest Handling Fruits,Minist Agr & R, Hangzhou 310021, Peoples R China
[2] Shaanxi Univ Sci & Technol, Sch Food & Biol Engn, Xian 710021, Peoples R China
[3] Zhejiang Acad Agr Sci, Sericultural Res Inst, Hangzhou 310021, Peoples R China
[4] Univ Melbourne, Sch Agr & Food, Parkville, VIC 3010, Australia
基金
中国国家自然科学基金;
关键词
Cyanidin-3-O-glucoside; Phenolic acids; Stability; Co-pigmentation effect; Molecular docking; RED WINE; PREFERMENTATIVE ADDITION; DEGRADATION KINETICS; MODEL SOLUTIONS; COPIGMENTATION; ANTHOCYANINS; MALVIDIN-3-O-GLUCOSIDE;
D O I
10.1016/j.foodchem.2023.135409
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Co-pigmentation effect of phenolic acids on cyanidin-3-O-glucoside (C3G) and the mechanisms were investi-gated. Sinapic acid (SIA), ferulic acid (FA), p-coumaric acid (p-CA) and syringic acid (SYA) significantly enhanced C3G stability (P < 0.05), whereas vanillic acid (VA) and gallic acid (GA) showed no influence (P > 0.05). Among these phenolic acids, SIA and FA had higher binding coefficient with C3G (48.83 and 43.38), reduced degradation rate constant by 40.0 -50.0 %, prolonged half-life by 74.6 -94.7 % at 323 K, and significantly inhibited C3G hydration reaction (pKh = 2.87 and 2.80, P < 0.05). Molecular docking revealed that C3G and co-pigments were connected by hydrogen bond and 7L-7L stacking interaction. Hydroxycinnamic acids of SIA, FA and p-CA bound with ring B and ring C of C3G, while hydroxybenzoic acids of SYA, VA and GA hardly interacted with ring C. Generally, the protection effect of hydroxycinnamic acids on C3G was better than that of hydroxybenzoic acids, exhibiting stronger hyperchromic effect.
引用
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页数:7
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共 35 条
[11]   Grape pectic polysaccharides stabilization of anthocyanins red colour: Mechanistic insights [J].
Fernandes, Ana ;
Raposo, Filomena ;
Evtuguin, Dmitry V. ;
Fonseca, Fatima ;
Ferreira-da-Silva, Frederico ;
Mateus, Nuno ;
Coimbra, Manuel A. ;
de Freitas, Victor .
CARBOHYDRATE POLYMERS, 2021, 255
[12]   Antioxidant properties of anthocyanins and their mechanism of action in atherosclerosis [J].
Garcia, Chelsea ;
Blesso, Christopher N. .
FREE RADICAL BIOLOGY AND MEDICINE, 2021, 172 :152-166
[13]   Study on the interaction mechanism of purple potato anthocyanins with casein and whey protein [J].
Gong, Shengxiang ;
Yang, Chengyu ;
Zhang, Jianhua ;
Yu, Ying ;
Gu, Xinzhe ;
Li, Wenhui ;
Wang, Zhengwu .
FOOD HYDROCOLLOIDS, 2021, 111
[14]   Colour implications of self-association processes of wine anthocyanins [J].
Gonzalez-Manzano, Susana ;
Santos-Buelga, Celestino ;
Duenas, Montserrat ;
Rivas-Gonzalo, Julian C. ;
Escribano-Bailon, Teresa .
EUROPEAN FOOD RESEARCH AND TECHNOLOGY, 2008, 226 (03) :483-490
[15]   Dispersion-Corrected Mean-Field Electronic Structure Methods [J].
Grimme, Stefan ;
Hansen, Andreas ;
Brandenburg, Jan Gerit ;
Bannwarth, Christoph .
CHEMICAL REVIEWS, 2016, 116 (09) :5105-5154
[16]   Anthocyanins and Their Variation in Red Wines I. Monomeric Anthocyanins and Their Color Expression [J].
He, Fei ;
Liang, Na-Na ;
Mu, Lin ;
Pan, Qiu-Hong ;
Wang, Jun ;
Reeves, Malcolm J. ;
Duan, Chang-Qing .
MOLECULES, 2012, 17 (02) :1571-1601
[17]   Revealing Noncovalent Interactions [J].
Johnson, Erin R. ;
Keinan, Shahar ;
Mori-Sanchez, Paula ;
Contreras-Garcia, Julia ;
Cohen, Aron J. ;
Yang, Weitao .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (18) :6498-6506
[18]   A comparative study of the extractive desulfurization mechanism by Cu(II) and Zn-based imidazolium ionic liquids [J].
Li, Hongping ;
Zhang, Beibei ;
Jiang, Wei ;
Zhu, Wenshuai ;
Zhang, Ming ;
Wang, Chao ;
Pang, Jingyu ;
Li, Huaming .
GREEN ENERGY & ENVIRONMENT, 2019, 4 (01) :38-48
[19]   Spectrophotometric study of the copigmentation of malvidin 3-O-glucoside with p-coumaric, vanillic and syringic acids [J].
Malaj, Naim ;
De Simone, Bruna Clara ;
Quartarolo, Angelo Domenico ;
Russo, Nino .
FOOD CHEMISTRY, 2013, 141 (04) :3614-3620
[20]   The copigmentation effect of sinapic acid on malvin: a spectroscopic investigation on colour enhancement [J].
Markovic, JMD ;
Petranovic, NA ;
Baranac, JM .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 2005, 78 (03) :223-228