Effects of organic acids on color intensification, thermodynamics, and copigmentation interactions with anthocyanins

•Copigmentation effect of KSA and tannic acid was optimal with a molar ratio of 1:150.•Phenolic acid was stronger copigment than dicarboxylic acid through π-π interaction.•Acylation groups in KSA weakened copigmentation effect due to steric hindrance.•Quantum mechanical calculation proved the bindin...

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Veröffentlicht in:Food chemistry 2022-12, Vol.396, p.133691-133691, Article 133691
Hauptverfasser: Lv, Xiaorui, Li, Liling, Lu, Xiaomin, Wang, Wenxiu, Sun, Jianfeng, Liu, Yaqiong, Mu, Jianlou, Ma, Qianyun, Wang, Jie
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container_title Food chemistry
container_volume 396
creator Lv, Xiaorui
Li, Liling
Lu, Xiaomin
Wang, Wenxiu
Sun, Jianfeng
Liu, Yaqiong
Mu, Jianlou
Ma, Qianyun
Wang, Jie
description •Copigmentation effect of KSA and tannic acid was optimal with a molar ratio of 1:150.•Phenolic acid was stronger copigment than dicarboxylic acid through π-π interaction.•Acylation groups in KSA weakened copigmentation effect due to steric hindrance.•Quantum mechanical calculation proved the binding ability with Fer was MCG > Cy-G > Dp-G. Anthocyanins are attractive alternatives to synthetic colorants, but their low stability impedes practical applications. Intermolecular copigmentation can enhance both color intensity and stability. Herein, the copigmentation interactions of Kyoho grape skin anthocyanins (KSA) or cyanidin-3-O-glucoside (Cy-G) with organic acids were investigated. Color enhancement was evaluated at different acid molar ratios and treatment temperatures. The optimal copigmentation effects were observed for KSA/tannic acid (1:150) and Cy-G/tannic acid (1:100). Based on enthalpy variation, KSA/ferulic acid and Cy-G/ferulic acid exhibited the highest stability. The distinct color differences observed in the presence of different acids were attributed to structural effects. The influence of ferulic acid on various anthocyanins was also evaluated using theoretical approaches. Owing to steric hindrance, the acyl groups in KSA affected the spatial conformation, hydrogen bonding, and van der Waals interactions of the complexes. Further, hydroxyl groups decreased complex stability. These findings contribute to furthering the understanding of copigmentation effects.
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Anthocyanins are attractive alternatives to synthetic colorants, but their low stability impedes practical applications. Intermolecular copigmentation can enhance both color intensity and stability. Herein, the copigmentation interactions of Kyoho grape skin anthocyanins (KSA) or cyanidin-3-O-glucoside (Cy-G) with organic acids were investigated. Color enhancement was evaluated at different acid molar ratios and treatment temperatures. The optimal copigmentation effects were observed for KSA/tannic acid (1:150) and Cy-G/tannic acid (1:100). Based on enthalpy variation, KSA/ferulic acid and Cy-G/ferulic acid exhibited the highest stability. The distinct color differences observed in the presence of different acids were attributed to structural effects. The influence of ferulic acid on various anthocyanins was also evaluated using theoretical approaches. Owing to steric hindrance, the acyl groups in KSA affected the spatial conformation, hydrogen bonding, and van der Waals interactions of the complexes. Further, hydroxyl groups decreased complex stability. These findings contribute to furthering the understanding of copigmentation effects.</description><identifier>ISSN: 0308-8146</identifier><identifier>EISSN: 1873-7072</identifier><identifier>DOI: 10.1016/j.foodchem.2022.133691</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Acylated anthocyanin ; Copigmentation ; Organic acid ; Quantum mechanics calculation</subject><ispartof>Food chemistry, 2022-12, Vol.396, p.133691-133691, Article 133691</ispartof><rights>2022 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c345t-503f1d53d07d6f5913f1bd21956366c7b652e593787a933c92aa95f15dbb8f5b3</citedby><cites>FETCH-LOGICAL-c345t-503f1d53d07d6f5913f1bd21956366c7b652e593787a933c92aa95f15dbb8f5b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0308814622016533$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids></links><search><creatorcontrib>Lv, Xiaorui</creatorcontrib><creatorcontrib>Li, Liling</creatorcontrib><creatorcontrib>Lu, Xiaomin</creatorcontrib><creatorcontrib>Wang, Wenxiu</creatorcontrib><creatorcontrib>Sun, Jianfeng</creatorcontrib><creatorcontrib>Liu, Yaqiong</creatorcontrib><creatorcontrib>Mu, Jianlou</creatorcontrib><creatorcontrib>Ma, Qianyun</creatorcontrib><creatorcontrib>Wang, Jie</creatorcontrib><title>Effects of organic acids on color intensification, thermodynamics, and copigmentation interactions with anthocyanins</title><title>Food chemistry</title><description>•Copigmentation effect of KSA and tannic acid was optimal with a molar ratio of 1:150.•Phenolic acid was stronger copigment than dicarboxylic acid through π-π interaction.•Acylation groups in KSA weakened copigmentation effect due to steric hindrance.•Quantum mechanical calculation proved the binding ability with Fer was MCG &gt; Cy-G &gt; Dp-G. Anthocyanins are attractive alternatives to synthetic colorants, but their low stability impedes practical applications. Intermolecular copigmentation can enhance both color intensity and stability. Herein, the copigmentation interactions of Kyoho grape skin anthocyanins (KSA) or cyanidin-3-O-glucoside (Cy-G) with organic acids were investigated. Color enhancement was evaluated at different acid molar ratios and treatment temperatures. The optimal copigmentation effects were observed for KSA/tannic acid (1:150) and Cy-G/tannic acid (1:100). Based on enthalpy variation, KSA/ferulic acid and Cy-G/ferulic acid exhibited the highest stability. The distinct color differences observed in the presence of different acids were attributed to structural effects. The influence of ferulic acid on various anthocyanins was also evaluated using theoretical approaches. 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Anthocyanins are attractive alternatives to synthetic colorants, but their low stability impedes practical applications. Intermolecular copigmentation can enhance both color intensity and stability. Herein, the copigmentation interactions of Kyoho grape skin anthocyanins (KSA) or cyanidin-3-O-glucoside (Cy-G) with organic acids were investigated. Color enhancement was evaluated at different acid molar ratios and treatment temperatures. The optimal copigmentation effects were observed for KSA/tannic acid (1:150) and Cy-G/tannic acid (1:100). Based on enthalpy variation, KSA/ferulic acid and Cy-G/ferulic acid exhibited the highest stability. The distinct color differences observed in the presence of different acids were attributed to structural effects. The influence of ferulic acid on various anthocyanins was also evaluated using theoretical approaches. 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subjects Acylated anthocyanin
Copigmentation
Organic acid
Quantum mechanics calculation
title Effects of organic acids on color intensification, thermodynamics, and copigmentation interactions with anthocyanins
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