Chemical stability of carboxylpyranocyanidin-3-O-glucoside under ß-glucosidase treatment and description of their interaction.

Anthocyanins are susceptible to degradation by ß-glycosidase, resulting in color loss. This study analyzed the impact of ß-glycosidase on carboxylpyranocyanidin-3-O-glucoside (Carboxyl-pycy-3-gluc) and its precursor cyanidin-3-O-glucoside (Cy-3-gluc). Carboxyl-pycy-3-gluc exhibited enhanced stability upon treatment with ß-glucosidase. Ultraviolet-visible and circular dichroism spectroscopy revealed slight changes in the microenvironment and secondary structure of ß-glycosidase when carboxyl-pycy-3-gluc was present. The fluorescence experiment indicated that anthocyanins quench the fluorescence of ß-glycosidase through static quenching via hydrophobic interactions. Molecular docking of six types of carboxylpyranoanthocyanins and their precursors with ß-glycosidase revealed that carboxylpyranoanthocyanins exhibited lower binding affinity than their precursors, consistent with the enzyme kinetic experiment results. The incorporation carboxyl-pycy-3-gluc into Sanhua Plum Juice and Wine endowed them with vivid and stable coloration. The study illustrated that carboxyl-pycy-3-gluc exhibits low binding affinity with ß-glycosidase, thereby maintaining stability and confirming its potential as a colorant.

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

BACKGROUND: Pyranoanthocyanins are stable anthocyanin derivatives. Carboxylpyranoanthocyanin is one of the simplest pyranoanthocyanin, among which the production of carboxylpyranocyanidin-3-O-glucoside (crboxyl-pycy-3-gluc) is most feasible as a result of the abundance of its reactant, cyanidin-3-O-glucoside (Cy-3-gluc). RESULTS: In the present study, carboxyl-pycy-3-gluc was synthesized and its stability during processing and after ingestion as well as its bioavailability in vivo were comprehensively evaluated. Our results indicated that the color of carboxyl-pycy-3-gluc remained more stable compared to Cy-3-gluc when facing the large-span pH variation. The high retention of anthocyanin symbolized the superb stability under thermal processing, sulfur dioxide bleaching and ultrasonic treatment of carboxyl-pycy-3-gluc. Because of the stability under the alkaline condition, carboxyl-pycy-3-gluc is more stable after oral-gastrointestinal 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 more difficult than its precursor. CONCLUSION: The present study demonstrated the promising stability of carboxyl-pycy-3-gluc during food processing and after digestion, confirming the potential of carboxyl-pycy-3-gluc as a colorant. © 2023 Society of Chemical Industry.

Anthocyanins degradation mediated by ß-glycosidase contributes to the color loss during alcoholic fermentation in a structure-dependent manner.

Anthocyanins deteriorate during fermentation to varying degrees depending on the structure of the anthocyanin, thus affecting the sensory quality of the wine, and the degradation of anthocyanins is closely associated with the ß-glycosidase. In this study, the alcoholic fermentation systems containing cyanidin-3-O-glucoside (C3G), peonidin-3-O-glucoside (Pn3G), delphinidin-3-O-glucoside (D3G), petunidin-3-O-glucoside (Pt3G), and malvidin-3-O-glucoside (M3G) incubated for eight days. Our results indicated that the color of the systems containing different anthocyanins saw significant and dissimilar changes during fermentation, in relation to anthocyanin degradation. The five anthocyanins showed varying degradation degrees, which are relevant to theß-glycosidase produced by yeast. Enzyme kinetics and molecular docking analysis showed the affinity between anthocyanins and ß-glucosidase: C3G < M3G < Pn3G < Pt3G < D3G. This study demonstrated that ß-glycosidase had distinct effects on anthocyanins with diverse structures, resulting in different color changes in fermentation systems. It provided a potential strategy for sensory quality improvement during the fermentation of fruit wines rich in anthocyanins.

Anthocyanins Prevent AAPH-Induced Steroidogenesis Disorder in Leydig Cells by Counteracting Oxidative Stress and StAR Abnormal Expression in a Structure-Dependent Manner.

Testosterone deficiency may increase the risk of sexual dysfunction and the failure of spermatogenesis. Oxidative stress that is derived from the destruction of homeostasis, disease, and exposure to contaminants can damage the steroidogenicity process in Leydig cells, resulting in a reduction in testosterone synthesis. Anthocyanins are a group of innoxious antioxidants widely recognized in food sources, and are an ideal candidate to relieve oxidative stress-related steroidogenesis disorder. However, there is still a major gap in our knowledge of the structure-function relationship of anthocyanin on the activity mentioned above. In the present study, four anthocyanins including cyanidin-3-glucoside (Cy-3-glu), delphinidin-3-glucoside (Dp-3-glu), pelargonidin-3-glucoside (Pg-3-glu), and cyanidin-3,5-diglucoside (Cy-3,5-diglu) were applied to reverse testosterone generation after employing 2,2'-Azobis(2-amidinopropane)-dihydrochloride (AAPH) as the inducer of oxidative stress in R2C cells. The results demonstrated that all four kinds of anthocyanins can inhibit ROS generation, alleviate mitochondrial membrane potential damage, and contribute to increased testosterone. Among them, Cy-3,5-diglu with diglycoside performed best on antioxidative ability and improved cell dysfunction and upregulated the expression of the steroidogenic acute regulatory protein (StAR). The molecular docking further revealed the direct combination between anthocyanins and StAR, suggesting that anthocyanins with monosaccharide were more likely to interact with StAR than with diglycoside. Taken together, these data indicate that recipient R2C cells under oxidative stress submitted to anthocyanins exhibited improved steroidogenesis in a structure-dependent manner. Anthocyanins could be considered the ideal ingredients against oxidative stress-induced testosterone deficiency.

Modeling and application of sensory evaluation of blueberry wine based on principal component analysis.

In this study, eight different levels of commercial blueberry wines were studied to establish the comprehensive quality evaluation method of blueberry wine. Eleven physicochemical indexes (total carbohydrates (TC), total acids (TA), total esters (TE), total phenols (TP), total anthocyanins (ANT), color density (CD), tint (T), alcohol by volume (ABV), total soluble solids (TSS), Ph value, total dry extracts (TDE)) were used to establish the quality evaluation model and conduct the principal component analysis (PCA). Based on the results from PCA, the first three principal components accounted for 85.73% of the total quality variability. The consistent ranking of blueberry wines between quality evaluation model and sensory evaluation test verified the reliability of this model. In addition, ultrasonic-treated blueberry wine showed a higher score than the untreated group, which reflected the sensory quality changes of blueberry wine during ultrasonic treatment with high sensitivity. This study provides a theoretical basis for the comprehensive quality evaluation of blueberry wines and reasonable instruction for consumers' choices.

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

Hydroxyphenyl-pyranoanthocyanins (PACNs), derived from anthocyanins (ACNs) reacted with hydroxycinnamic acids, have higher practical application value because of better physicochemical stability than their precursors. However, the slow formation rate restricted their broader applications. In the present study, cyanidin-3-O-glucoside (C3G) was chosen to react with four kinds of hydroxycinnamic acids in a model solution. Changes of color and the production of hydroxyphenyl-PACNs were monitored. The formation of derivatives was time-dependent, and the orange-yellow changing trend was correlated with the formation of PACNs and the consumption of C3G. In addition, high-pressure processing (HPP) as a widely-used non-thermal processing method in the food industry was conducted to investigate its impact on hydroxyphenyl-PACNs formation. The results showed that HPP significantly improves the yield of two types of hydroxyphenyl-PACNs (C3G-4-vinylcatechol and C3G-4-vinylphenol) and the retention of total residual pigments during 56 days of storage. Therefore, HPP contributed to color-protecting and the transformation of hydroxyphenyl-PACNs.