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Phenol-pyranoanthocyanins, a structurally modified type of anthocyanin, has higher stability than anthocyanins. However, their conversion occurs slowly. Therefore, it is crucial to improve the conversion efficiency and production of pyranoanthocyanins. In this study, cranberry anthocyanin (CRAN) was fermented using two Lactobacillus strains along with caffeic acid to form cranberry-derived pyranoanthocyanins (PY-CRAN). PY-CRAN was characterized and identified. The physicochemical properties, antioxidant activity, and tyrosinase inhibitory capacity of PY-CRAN were assessed. The results showed that phenol-pyranoanthocyanins can be rapidly produced through fermentative transformation using Lactiplantibacillus plantarum and Lacticaseibacillus paracasei. Lacticaseibacillus paracasei exhibits a higher propensity for producing phenol-pyranoanthocyanins. PY-CRAN exhibits high stability under light and various pH conditions. Moreover, they possess excellent antioxidant properties and the ability to inhibit tyrosinase. These results suggest that fermentative biotransformation conducted by Lactobacillus is an ideal method for producing cranberry pyranoanthocyanins. The resulting anthocyanins have potential as antioxidant and whitening agents, making them promising bioactive ingredients.
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Ulcerative colitis is a public health issue with a rising worldwide incidence. It has been found that current medications for treating UC may cause varying degrees of damage to male fertility. Our previous study demonstrated that cyanidin-3-O-glucoside (C3G) treatment could effectively restore reproductive damage in a mouse model of DSS induced colitis. However, the underlying mechanism of C3G alleviates UC induced male reproductive disorders remain scarce. The aim of this study is to discover the molecular mechanisms of C3G on the amelioration of UC stimulated reproductive disorders. The targeted genes toward UC-induced reproductive injury upon C3G treatments were explored by transcriptomic analysis. Hematological analysis, histopathological examination, and real time transcription-polymerase chain reaction (RT-PCR) analysis were applied for conjoined identification. Results showed that C3G may effectively target for reducing pro-inflammatory cytokine IL-6 in testis through cytokine-cytokine receptor interaction pathway. Transcriptome sequencing found that a series of genetic pathways involved in the protective effects of C3G on male reproduction were identified by gene ontology and Kyoto Encyclopedia of Genes and Genomes (KEGG) pathway enrichment analysis. Further results presented that C3G could effectively restore mRNA expression levels of Ly6a and Col1a1, closely linked with UC induced male reproductive damage pathways. Sufficient results implied that Ly6a and Col1a1 may be treated as the promising therapeutic targets for the mechanism of C3G in treating UC induced reproductive impairment. C3G administration might be an effective dietary supplementation strategy for male reproduction improvement.
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Antocianinas , Citocinas , Glucosídeos , Transcriptoma , Masculino , Animais , Antocianinas/farmacologia , Glucosídeos/farmacologia , Camundongos , Citocinas/metabolismo , Citocinas/genética , Testículo/efeitos dos fármacos , Testículo/metabolismo , Testículo/patologia , Colite Ulcerativa/tratamento farmacológico , Colite Ulcerativa/induzido quimicamente , Colite Ulcerativa/metabolismo , Interleucina-6/metabolismo , Interleucina-6/genética , Perfilação da Expressão Gênica , Modelos Animais de Doenças , Infertilidade Masculina/tratamento farmacológico , Reprodução/efeitos dos fármacosRESUMO
Anthocyanins are common natural pigments with a variety of physiological activities. Traditional perspectives attribute their molecular mechanism to noncovalent interactions influencing signaling pathways. However, this ignores the nature of its benzopyrylium skeleton, which readily reacts with the electron-rich groups of proteins. Here, we modified cyanidin-3-O-glucoside (C3G) via activity-based protein profiling technology by our previous synthesis route and prepared the covalent binding probe (C3G-Probe) and the noncovalent photoaffinity probe (C3G-Diazirine). The properties of C3G's covalent binding to proteins were also discovered by comparing the labeling of the two probes to the whole HepG2 cell proteome. We further explored its target proteins and enriched pathways in HepG2 and HeLa cells. Western blot analysis further confirmed the covalent binding of C3G to four target proteins: insulin-degrading enzyme, metal cation symporter ZIP14, spermatid perinuclear RNA-binding protein, and Cystatin-B. Pathway analysis showed that covalent targets of C3G were concentrated in metabolic pathways and several ribonucleoprotein complexes that were also coenriched. The results of this study provide new insights into the interaction of the naturally active molecule C3G with proteins.
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Antocianinas , Glucosídeos , Antocianinas/química , Antocianinas/metabolismo , Humanos , Glucosídeos/química , Glucosídeos/metabolismo , Células Hep G2 , Células HeLa , Ligação Proteica , Proteínas/química , Proteínas/metabolismoRESUMO
This study aimed to investigate the problem of color instability in mulberry juice, examine the effect of mannoprotein (MP) dosage on improving the stability of anthocyanins in mulberry juice, and explore the molecular binding mechanism between them. As the mass ratio of anthocyanins to MP of 1.07 × 10-3: 1-1.65 × 10-3: 1, the retention rates of anthocyanins in mulberry juice and simulated system were significantly improved in the photostability experiment, with the highest increase of 128.89 % and 24.11 %, respectively. In the thermal stability experiment, it increased by 7.96 % and 18.49 %, respectively. The synergistic effect of combining MP with anthocyanins has been demonstrated to greatly enhance their antioxidant capacity, as measured by ABTS, FRAP, and potassium ferricyanide reduction method. Furthermore, MP stabilized more anthocyanins to reach the intestine in simulated in vitro digestion. MP and cyanidin-3-glucoside (C3G) interacted with each other through hydrogen bonding and hydrophobic interactions. Specific amino acid residues involved of MP in binding process were identified as threonine (THR), isoleucine (ILE) and arginine (ARG). The identification of the effective mass concentration ratio range and binding sites of MP and anthocyanins provided valuable insights for the application of MP in mulberry juice.
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Antocianinas , Sucos de Frutas e Vegetais , Morus , Morus/química , Antocianinas/química , Sucos de Frutas e Vegetais/análise , Antioxidantes/químicaRESUMO
The chemical synthesis of anthocyanins, especially delphinidin-3-O-glucoside and petunidin-3-O-glucoside, is preferable due to the challenges associated with their extraction and purification. However, the reported methods for the synthesis are scarce and intricate. Our research focused on exploring a one-step ester-to-ketone process and optimizing the ring formation reaction, simplifying and improving the overall synthesis strategy. Through these attempts, we were able to achieve higher production yields of delphinidin-3-O-glucoside and petunidin-3-O-glucoside. According to the results of DPPH, ABTS, and FRAP, the antioxidant activity of anthocyanins was increased with the number of B ring hydroxyl substituent. Additionally, both delphinidin-3-O-glucoside and petunidin-3-O-glucoside exhibited no cytotoxicity effects, highlighting their potential for safe application in various fields.
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Antocianinas , Antioxidantes , Glucosídeos , Antocianinas/química , Antocianinas/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Antioxidantes/síntese química , Glucosídeos/química , Glucosídeos/farmacologia , Glucosídeos/síntese química , HumanosRESUMO
Anthocyanins (ACNs) are secondary metabolites found in plants. Due to their impressive biological activities, ACNs have gained significant popularity and extensive application within the food, pharmaceutical, and nutraceutical industries. A derivative of ACNs: pyranoanthocyanins (PACNs) possesses more stable properties and interesting biological activities. However, conventional methods for the production of ACNs, including chemical synthesis and plant extraction, involve organic solvents. Microbial synthesis of ACNs from renewable biomass, such as amino acids or flavonoids, is considered a sustainable and environmentally friendly method for large-scale production of ACNs. Recently, the construction of microbial cell factories (MCFs) for the efficient biosynthesis of ACNs and PACNs has attracted much attention. In this review, we summarize the cases of microbial synthesis of ACNs, and analyze the bottlenecks in reconstructing the metabolic pathways for synthesizing PACNs in microorganisms. Consequently, there is an urgent need to investigate the mechanisms behind the development of MCFs for PACNs synthesis. Such research also holds significant promise for advancing the production of food pigments. Meanwhile, we propose potential solutions to the bottleneck problem based on metabolic engineering and enzyme engineering. Finally, the development prospects of natural food and biotechnology are discussed.
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The high prevalence of metabolic syndrome is threatening the health of populations all over the world. Contemporary work demonstrates that high leptin concentration is directly related to the development of metabolic syndrome such as obesity, fatty liver diseases, type 2 diabetes mellitus and cardiovascular diseases. Anthocyanins are a widespread group of dietary polyphenols, which can ameliorate chronic diseases related to metabolic syndrome. In addition, anthocyanins can regulate the leptin pathway in chronic metabolic diseases, however the potential mechanism between anthocyanin and leptin is complex and elusive. In this review paper, we have evaluated the bioactivity of anthocyanins on the mediation of leptin level and the upstream and downstream pathways in chronic metabolic diseases. Anthocyanins could regulate the hypertrophy of adipose tissue, and the expression of leptin level via mediating TNF-α, C/EBP, PPAR, CREB and SREBP-1. Anthocyanins promoted the leptin sensitivity by increasing the level of leptin receptor, phosphorylation of JAK2/STAT3, PI3K/AKT, and additionally ameliorated metabolic disorder related outcome, including oxidative stress, inflammation, lipid accumulation, insulin resistance and the balance of gut microbiota. However, direct evidence of anthocyanins treatment on leptin signal transduction is still limited which calls for future molecular binding and gene regulation test.
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Marine anti-fouling coatings represent an efficient approach to prevent and control the marine biofouling. However, a significant amount of antifouling agent is added to improve the static antifouling performance of the coatings, which leads to an issue whereby static antifouling performance conflicts with eco-friendly traits. Herein, this work reports an in situ reduction synthesis of silver nanoparticles (AgNPs) within polymers to produce composite coatings, aiming to solve the aforementioned issue. Firstly, urushiol-based benzoxazine monomers were synthesized by the Mannich reaction, using an eco-friendly natural product urushiol and n-octylamine and paraformaldehyde as the reactants. Additionally, AgNPs were obtained through the employment of free radicals formed by phenolic hydroxyl groups in the urushiol-based benzoxazine monomers, achieved by the in situ reduction of silver nitrate in benzoxazine. Then, the urushiol-based benzoxazine/AgNPs composite coatings were prepared by the thermosetting method. AgNPs exhibit broad-spectrum and highly efficient antimicrobial properties, with a low risk to human health and a minimal environmental impact. The composite coating containing a small amount of AgNPs (≤1 wt%) exhibits effective inhibition against various types of bacteria and marine microalgae in static immersion, thereby displaying outstanding antifouling properties. This organic polymer and inorganic nanoparticle composite marine antifouling coating, with its simple preparation method and eco-friendliness, presents an effective solution to the conflict between static antifouling effectiveness and environmental sustainability in marine antifouling coatings.
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Anthocyanins are the primary functional pigments in the diet. However, anthocyanins exhibit instability during digestion, coupled with limited bioavailability. Microencapsulation offers anthocyanins a sheltered environment, enhancing their stability and bioactivity. Fructooligosaccharides (FOS) and whey protein (WP) commonly serve as wall materials in microencapsulation and represent a significant source of probiotic functionality. Our prior research successfully established a robust microencapsulation system for anthocyanins utilizing FOS and WP. This study investigates the antioxidative capacity, stability during in vitro digestion, modulation on gut microbiota, and short-chain fatty acids (SCFAs) production of black soybean skin anthocyanins microencapsulated with FOS and WP (anthocyanin-loaded microencapsule particles, ALM). The results demonstrate that ALM exhibits a superior antioxidant capacity compared to free anthocyanins (ANCs) and cyanidin-3-glucoside (C3G). During simulated digestion, ALM exhibits enhanced anthocyanin retention compared with ANC in both gastric and intestinal phases. In comparison with ANC and even non-loaded microcapsules (NLM), in vitro fermentation demonstrates that ALM exhibits the highest gas production and lowered pH, indicating excellent fermentation activity. Furthermore, in comparison with ANC or NLM, ALM exerts a positive influence on the diversity and composition of gut microbiota, with potentially beneficial genera such as Faecalibacterium and Akkermansia exhibiting higher relative abundance. Moreover, ALM stimulates the production of SCFAs, particularly acetic and propionic acids. In conclusion, microencapsulation of anthocyanins with FOS-WP enhances their antioxidative capacity and stability during in vitro digestion. Simultaneously, this microencapsulation illustrates a positive regulatory effect on the intestinal microbiota community and SCFA production, conferring potential health benefits.
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Antioxidantes , Microbioma Gastrointestinal , Oligossacarídeos , Antocianinas , Proteínas do Soro do LeiteRESUMO
Immune functional decline and remodeling accompany aging and frailty. It is still largely unknown how changes in the immune cellular composition differentiate healthy individuals from those become frail at a relatively early age. Our aim in this exploratory study was to investigate immunological changes from newborn to frailty, and the association between health statute and various immune cell subtypes. The participants analyzed in this study covered human cord blood cells and peripheral blood cells collected from young adults, healthy and frail old individuals. A total of 30 immune cell subsets was performed by flow cytometry based on the surface markers of immune cells. Furthermore, frailty was investigated for its relations with various leukocyte subpopulations. Frail individuals exhibited a higher CD4/CD8 ratio, a higher proportion of CD4+ central memory T (TCM) cells, CD8+ effector memory T cells, CD27- switched memory B (CD27-BSM) cells, CD27+ switched memory B cells, age-associated B cells (ABCs) and CD38-CD24- B cells, and a lower proportion of naïve CD8 + T cells and progenitor B cells. The Frailty index score was found to be associated with naïve T cells, CD4/CD8 ratio, ABCs, CD27-BSM cells, and CD4+ TCM cells. Our findings conducted a relatively comprehensive and extensive atlas of age- and frailty-related changes in peripheral leukocyte subpopulations from newborn to frailty. The immune phenotypes identified in this study can contribute to a deeper understanding of immunosenescence in frailty and may provide a rationale for future interventions and diagnosis.
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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.
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Celulases , Glucosídeos , Glucosídeos/química , Antocianinas/química , Simulação de Acoplamento Molecular , Glicosídeo HidrolasesRESUMO
Anthocyanins, one of the important water-soluble pigments, are sensitive to environmental factors, which limits the application of anthocyanins in food field. In order to overcome this limitation, double Pickering emulsions stabilized by ß-cyclodextrin were developed. The optimum preparation conditions of the emulsions were determined firstly and the performance and structure of emulsions were investigated. Results showed that the optimum preparation conditions of emulsions were the ratio of (W1/O): W2 = 6:4 and 4 % ß-cyclodextrin concentration. Optical microscope and confocal laser scanning microscope results confirmed that ß-cyclodextrin adsorbed onto the surface of droplets forming stable double Pickering emulsions structure. In vitro gastrointestinal digestion experiments proved that double Pickering emulsions played a controlled-release effect in the small intestine. Rheological analysis proved that the emulsions exhibited elastic properties and demonstrated shear thinning behavior. The emulsions showed excellent stability under centrifugation and thermal conditions. These findings will promote anthocyanins' application in daily diet.
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Antocianinas , Alimentos , Emulsões/química , Tamanho da PartículaRESUMO
BACKGROUND: Diminished ovarian reserve has a serious impact on female reproduction with an increasing incidence every year. An important cause of this is oxidative stress. Rubi fructus, a traditional medicinal and edible plant, has shown therapeutic effects against gynecological diseases. Vanillic acid, isoquercitrin, kaempferol-3-O-rutinoside, kaempferol-3-O-sophoroside, oleanolic acid, tormentic acid, tiliroside, and ellagic acid are the major bioactive components in R. fructus. However, studies involved in the effectiveness and mechanism of these components in oxidative stress-induced ovarian dysfunction are scarce. RESULTS: In this study, the protective mechanisms of the bioactive components were evaluated in human ovarian granulosa cells. Isoquercitrin was significantly superior to other bioactive components in relieving damage in human ovarian granulosa cells induced by 2,2-azobis (2-methylpropionamidine) dihydrochloride, considering enhanced cell viability, reduced reactive oxygen species accumulation, and improved mitochondrial membrane potential level. Isoquercitrin protected human ovarian granulosa cells from oxidative stress by regulating the enzyme activity of glutathione peroxidase, inhibiting cell apoptosis, improving the expression of genes related to oxidative stress, and ameliorating heme oxygenase 1 protein expression. CONCLUSION: Isoquercitrin, a bioactive component in R. fructus, has a significant protective effect on oxidative damage induced by 2,2-azobis (2-methylpropionamidine) dihydrochloride in human ovarian granulosa cells, providing evidence for its potential application in protecting ovarian function. © 2024 Society of Chemical Industry.
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Antioxidantes , Estresse Oxidativo , Feminino , Humanos , Antioxidantes/metabolismo , Espécies Reativas de Oxigênio/metabolismo , Células da Granulosa/metabolismo , ApoptoseRESUMO
Aloe-emodin (AE) is a natural compound with photodynamic properties. The aim of this study was to investigate the inhibitory effect of AE-mediated photodynamic inactivation (PDI) on Staphylococcus aureus (S. aureus). The bacteriostatic efficiency under different photodynamic conditions and photosensitizing mechanism was studied in detail. The results showed that AE-mediated PDI exhibited a typical concentration and time-dependent characteristics. In terms of bactericidal mechanism, disruption of membrane integrity and increase of cell membrane permeability was observed. Type II reaction was assumed as the main photochemical reaction involved in AE-mediated PDI as evidenced by the action of different ROS quenching agents. Furthermore, AE-mediated PDI decreased the bacterial survival in freshly squeezed apple juice and maintained its quality. The combination of blue light and AE enlarged the application of AE as an effective natural photosensitizer suitable for a food system.
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Aloe , Antraquinonas , Emodina , Fotoquimioterapia , Fármacos Fotossensibilizantes/farmacologia , Fármacos Fotossensibilizantes/química , Fotoquimioterapia/métodos , Staphylococcus aureus , Emodina/farmacologiaRESUMO
Foodborne contaminants refer to substances that are present in food and threaten food safety. Due to the progress in detection technology and the rising concerns regarding public health, there has been a surge in research focusing on the dangers posed by foodborne contaminants. These studies aim to explore and implement strategies that are both safe and efficient in mitigating the associated risks. Anthocyanins, a class of flavonoids, are abundantly present in various plant species, such as blueberries, grapes, purple sweet potatoes, cherries, mulberries, and others. Numerous epidemiological and nutritional intervention studies have provided evidence indicating that the consumption of anthocyanins through dietary intake offers a range of protective effects against the detrimental impact of foodborne contaminants. The present study aims to differentiate between two distinct subclasses of foodborne contaminants: those that are generated during the processing of food and those that originate from the surrounding environment. Furthermore, the impact of anthocyanins on foodborne contaminants was also summarized based on a review of articles published within the last 10 years. However, further investigation is warranted regarding the mechanism by which anthocyanins target foodborne contaminants, as well as the potential impact of individual variations in response. Additionally, it is important to note that there is currently a dearth of clinical research examining the efficacy of anthocyanins as an intervention for mitigating the effects of foodborne pollutants. Thus, by exploring the detoxification effect and mechanism of anthocyanins on foodborne pollutants, this review thereby provides evidence, supporting the utilization of anthocyanin-rich diets as a means to mitigate the detrimental effects of foodborne contaminants.
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Antocianinas , Poluentes Ambientais , Antocianinas/farmacologia , Dieta , Inocuidade dos Alimentos , FrutasRESUMO
Pyranoanthocyanin (PACN) is a class of anthocyanin (ACN)-derived pigments found in aged red wines, which has certain advantages over the prototype ACN in terms of stability, and biological activity. However, the efficiency and yield of PACNs in the natural fermentation system are low. This article summarizes five frequently employed physical processing techniques that can accelerate the formation of PACN. From a mechanistic standpoint, these techniques can produce large amounts of active substances, further promoting the extracellular release of phenolics and the formation of some cofactors and PACNs' pyran rings. Precursor substances and environmental factors affecting PACN yields are also pointed out. It mainly included the parent ring substitution in ACNs, the type and quantity of glycosides, the electron donating ability and concentration of cofactors, etc. Thus, this article aims to provide an overview of the advancements in processing techniques, thereby facilitating their wider utilization in the food and beverage industry.
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Vinho , Vinho/análise , Antocianinas/análise , Fermentação , FenóisRESUMO
Androgenetic alopecia (AGA), one of the most common forms of hair loss, lacks satisfactory treatment methods in modern society. This study employed an experimental design combining in vitro and in vivo approaches to explore the effects of Cyanidin-3-O-glucoside (C3G) and Carboxypyranocyanidin-3-O-glucoside (Vitisin A) on AGA. In human dermal papilla cells (HDPCs), both anthocyanins demonstrated inhibitory effects on androgen receptors, significantly reduced dihydrotestosterone (DHT) induced apoptosis of HDPCs, and regulated the secretion of Fibroblast growth factor 7 and Transforming growth factor beta 1. In vitro transdermal experiment revealed that both C3G and Vitisin A could penetrate mice skin, aided by the application of cream. Furthermore, in vivo experiments with mice indicated that application of C3G or Vitisin A cream effectively improved hair follicles miniaturization, regression, and apoptosis caused by DHT. The repression of Wnt10b and ß-catenin expression induced by DHT was prevented by C3G and Vitisin A in both cell and mouse model. Consequently, these findings suggest that C3G and Vitisin A could be considered as alternative methods for alleviating AGA.
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Antagonistas de Androgênios , Antocianinas , Humanos , Animais , Camundongos , Antocianinas/farmacologia , Antocianinas/uso terapêutico , Antagonistas de Androgênios/farmacologia , Alopecia/tratamento farmacológico , Alopecia/metabolismo , Di-Hidrotestosterona/farmacologia , Apoptose , Glucosídeos/farmacologia , Glucosídeos/uso terapêuticoRESUMO
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.
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Antocianinas , Glucosídeos , Antocianinas/análise , Glucosídeos/química , Disponibilidade Biológica , Digestão , Manipulação de AlimentosRESUMO
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.
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Antocianinas , Glicosídeo Hidrolases , Antocianinas/química , Fermentação , Simulação de Acoplamento Molecular , GlucosídeosRESUMO
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.