Formation of hydroxyphenyl-pyranoanthocyanins derived from cyanidin-3-O-glucoside and effects of high-pressure processing on the transformation efficiency

Zeng, Yingyu; Liu, Xusheng; Yuan, Kailan; Chen, Bo; Zhang, Wenbao; Wang, Chao; Sun, Jianxia; Ramaswamy, Hosahalli S.; Bai, Weibin

doi:10.1016/j.foodchem.2022.135247

Cited by 12 publications

(5 citation statements)

References 35 publications

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“…Additionally, we established a general scheme for preparing anthocyanin by introducing a selective iodination reaction, providing a feasible applicable strategy to synthesize anthocyanin with fewer steps and costs 14 . We also confirmed that ultrasonic and ultrahigh‐pressure treatment can accelerate the formation of PACNs 5,15 . These technologies and findings make it possible to mass‐produce carboxyl‐pycy‐3‐gluc.…”

Section: Introductionsupporting

confidence: 75%

“…14 We also confirmed that ultrasonic and ultrahighpressure treatment can accelerate the formation of PACNs. 5,15 These technologies and findings make it possible to mass-produce carboxyl-pycy-3-gluc. Thus, it is necessary to comprehensively evaluate the stability of carboxyl-pycy-3-gluc during processing and after ingestion, and the bioavailability of carboxylpycy-3-gluc also deserves attention as a functional ingredient.…”

Section: Introductionmentioning

confidence: 99%

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The promising stability of carboxylpyranocyanidin‐3‐O‐glucoside during food processing and simulated digestion and its bioavailability research

Li,

Yuan,

Zhang

et al. 2023

J Sci Food Agric

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BackgroundPyranoanthocyanins are stable anthocyanin derivatives. Carboxylpyranoanthocyanin is one of the simplest pyranoanthocyanin, among which the production of carboxylpyranocyanidin‐3‐O‐glucoside (Carboxyl‐pycy‐3‐gluc) is most feasible owing to the abundance of its reactant, cyanidin‐3‐O‐glucoside (Cy‐3‐gluc).ResultsIn this study, Carboxyl‐pycy‐3‐gluc was synthesized and its stability during processing and after ingestion as well as the bioavailability in vivo were comprehensively evaluated. Our results indicated that the color of Carboxyl‐pycy‐3‐gluc remained more steady compared with Cy‐3‐gluc when facing the large‐span pH variation. The high retention of anthocyanin symbolized the superb stability under thermal processing, SO2 bleaching, and ultrasonic treatment of Carboxyl‐pycy‐3‐gluc. Due to the stability under the alkaline condition, Carboxyl‐pycy‐3‐gluc is more stable after oral‐gastro‐intestinal digestion. After in vitro gut microbiota fermentation, the retention of Carboxyl‐pycy‐3‐gluc was significantly higher than that of Cy‐3‐gluc. The larger molecular size made absorption of Carboxyl‐pycy‐3‐gluc into blood tougher than its precursor.ConclusionsThis study demonstrated the promising stability of Carboxyl‐pycy‐3‐gluc during food processing and after digestion, proving the potential of Carboxyl‐pycy‐3‐gluc as a colorant.This article is protected by copyright. All rights reserved.

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Section: Introductionsupporting

confidence: 75%

Section: Introductionmentioning

confidence: 99%

The promising stability of carboxylpyranocyanidin‐3‐O‐glucoside during food processing and simulated digestion and its bioavailability research

Li,

Yuan,

Zhang

et al. 2023

J Sci Food Agric

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“…The gradient program is described in Supplementary Table 1. Finally, C3GVP was qualitatively analyzed using a UPLC-MS/MS workstation (8045, Shimadzu Corporation, Japan), as previously described . The purity of C3GVP was verified at 280 nm by HPLC (Ultimate 3000, Thermo Scientific, USA) using a reverse C18 column (4.6 × 250 mm, 5 μm, Agela Technology, Tianjin, China) at 30 °C.…”

Section: Materials and Methodsmentioning

confidence: 99%

“…C3GVP is a novel pyranoanthocyanin generated when C3G reacts with p-coumaric acid. 4 As previously reported, 4 we first synthesized C3GVP and purified it using medium-pressure liquid chromatography. The C3GVP prepared was over 94% C3GVP was considerably water-soluble (Figure 1D).…”

Section: Intervention Of Mp In C3gvp Self-aggregationmentioning

confidence: 98%

“…Hydroxyphenyl-pyranoanthocyanins are formed when anthocyanins react with phenolic acids, such as p-coumaric acid, ferulic acid, sinapic acid, and caffeic acid, leading to the formation of alternative pigments and bioactive ingredients. 4 However, hydroxyphenyl-pyranoanthocyanins can react with quercetin, vanillic acid, and cinnamic acid to form highmolecular-mass polymeric polyphenols, which is the predominant reason for sediments in aged wine. 5 Extracted and purified hydroxyphenyl-pyranoanthocyanins are also prone to selfassociation and precipitation when dissolved in a solution containing salt ions.…”

Section: Introductionmentioning

confidence: 99%

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Interaction between a Commercial Mannoprotein and Cyanidin-3-O-glucoside-4-vinylphenol and Its Stability and Antioxidative Properties as a Novel Functional Pigment

Liu,

Li,

Zeng

et al. 2023

J. Agric. Food Chem.

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Hydroxyphenyl-pyranoanthocyanins, which are derived from anthocyanins and phenolic acids during the fermentation and aging of red wine, are prone to polymerization and precipitation, which largely limits their application and bioactivity research. In the present study, cyanidin-3-O-glucoside-4-vinylphenol (C3GVP), a hydroxyphenyl-pyranoanthocaynin, was prepared from C3G and p-coumaric acid, and mannoprotein (MP) was employed to improve its stability in various complex solvents by forming a stable anthocyanin–MP complex. We used scanning electron microscopy, ultraviolet–visible spectroscopy, Fourier-transform infrared spectroscopy, and circular dichroism spectroscopy to observe structural changes in C3GVP and MP. The results demonstrated that the intermolecular polymerization of C3GVP was mitigated and the secondary conformation of MP was changed slightly. Fluorescence spectroscopy and molecular docking indicated that C3GVP and MP interacted via hydrogen bonds and hydrophobic interactions. Importantly, the C3GVP–MP complex exhibited better thermal stability and antioxidant capacity than C3G.

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Bioactivity and application of anthocyanins in skin protection and cosmetics: an extension as a functional pigment

Li,

Liu,

et al. 2023

Phytochem Rev

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Formation of hydroxyphenyl-pyranoanthocyanins derived from cyanidin-3-O-glucoside and effects of high-pressure processing on the transformation efficiency

Cited by 12 publications

References 35 publications

The promising stability of carboxylpyranocyanidin‐3‐O‐glucoside during food processing and simulated digestion and its bioavailability research

The promising stability of carboxylpyranocyanidin‐3‐O‐glucoside during food processing and simulated digestion and its bioavailability research

Interaction between a Commercial Mannoprotein and Cyanidin-3-O-glucoside-4-vinylphenol and Its Stability and Antioxidative Properties as a Novel Functional Pigment

Bioactivity and application of anthocyanins in skin protection and cosmetics: an extension as a functional pigment

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