Article
Chemistry, Applied
Pingling Zhang, Shuang Liu, Zhengang Zhao, Lijun You, Mark D. Harrison, Zhanying Zhang
Summary: This study showed that acylation can enhance the stability and in vivo antioxidant activity of cyanidin-3-glucoside, with cyanidin-3-(6''-n-octanoyl)-glucoside exhibiting the highest thermal and photostability among the three esters.
Article
Food Science & Technology
Lei Zhao, Na Zhou, Huimin Zhang, Fei Pan, Xin Ai, Yong Wang, Shuai Hao, Chengtao Wang
Summary: The study showed that cyanidin-3-O-glucoside (C3G) and its metabolite protocatechuic acid (PCA) can protect against cytotoxic effects induced by heterocyclic aromatic amines. They work by interfering with Nrf2 signaling and apoptotic cascade pathways to minimize cell damage. Additionally, C3G exhibited stronger protective effects compared to PCA.
FOOD AND CHEMICAL TOXICOLOGY
(2021)
Review
Plant Sciences
Ponnuvel Deepa, Minji Hong, Kandhasamy Sowndhararajan, Songmun Kim
Summary: Obesity is a major health issue worldwide and is associated with various chronic diseases. Cyanidin-3-O-beta-glucoside (C3G), an anthocyanin compound, has shown potential health benefits in reducing obesity-related complications.
Article
Chemistry, Applied
Zhengwei Zhang, Jin Zhang, Liuping Fan, Paul A. Kilmartin
Summary: The study revealed that ascorbic acid, cysteine, and reduced glutathione can accelerate the degradation of cyanidin-3-O-glucoside, with thiols containing more -SH groups leading to faster degradation. Additionally, the formation of an anthocyanin-cysteine adduct was identified, shedding light on the degradation mechanism induced by antioxidants.
Article
Environmental Sciences
Pei Lv, Yumeng Tao, Nan Zhang, Yawei Yang, Xiangwei Wu, Qing X. Li, Rimao Hua
Summary: This study investigated the effect of flavonoids on the photolysis of profenofos and found that flavonoids can enhance the photolysis rate of profenofos under various light conditions. Flavonoids can also reduce the photolysis rate of profenofos in natural water and have the capacity to scavenge free radicals.
Article
Food Science & Technology
Lei Zhao, Fei Pan, Na Zhou, Huimin Zhang, Yong Wang, Shuai Hao, Chengtao Wang
Summary: This study revealed that C3G and its metabolite PCA protect against IQ-induced cytotoxicity in HepG2 cells, with C3G showing greater effectiveness. Proteomics analysis showed that C3G inhibits apoptosis by affecting related signaling pathways and targeting XIAP protein to prevent the toxicity of IQ.
FOOD AND CHEMICAL TOXICOLOGY
(2021)
Article
Biochemistry & Molecular Biology
Sarah Strassmann, Maike Passon, Andreas Schieber
Summary: This study chemically converted cyanidin compounds to their sulfates and found that both the A ring and the B ring are sulfated by human enzymes, providing insights into the metabolism of anthocyanins.
Review
Chemistry, Multidisciplinary
Oscar Zannou, Kouame F. Oussou, Ifagbemi B. Chabi, Nour M. H. Awad, Midimahu V. Aissi, Gulden Goksen, Mustafa Mortas, Fatih Oz, Charalampos Proestos, Adechola P. P. Kayode
Summary: The increasing popularity of natural dyes worldwide is a result of the criticism towards synthetic dyes. Natural pigments from herbal sources, such as cyanidin 3-O-glucoside (C3G), are of great interest due to their biological properties and health benefits. However, the instability of C3G and its low bioavailability hinder its application in the food industry. Nanoencapsulation technology using suitable nanocarriers is transforming the use of anthocyanin, including C3G, with its chemical stability and functional benefits expanding its application to the pharmaceutical and cosmetic fields. This review focuses on the various nanoencapsulation techniques employed and the chemical and biological benefits conferred to C3G.
Article
Food Science & Technology
Jiaxin Wang, Zhen Cheng, Ningxuan Gao, Ye Zhang, Mingshuang Wang, Guangyu Ren, Baoge Song, Qi Liang, Yiwen Bao, Hui Tan, Wei Chen, Bin Li, Jinlong Tian
Summary: In this study, the effect of sucrose on anthocyanins and its degradation product furfural (Ff) was investigated. It was found that Ff reacts with cyanidin-3-O-glucoside (C3G) to form three new adducts, leading to the destabilization of anthocyanins. These new adducts were less stable than C3G and further accelerated its degradation. The study also detected the formation of these adducts in sugar solutions supplemented with C3G, particularly under light storage conditions. These findings provide important insights for reducing anthocyanin loss in food processing.
FOOD RESEARCH INTERNATIONAL
(2023)
Article
Biochemistry & Molecular Biology
Hiroaki Eguchi, Haruka Matsunaga, Saki Onuma, Yuta Yoshino, Toshiyuki Matsunaga, Akira Ikari
Summary: The study found that cyanidin-3-glucoside (C3G) and cyanidin significantly reduce the protein level of CLDN2 in human lung adenocarcinoma A549 cells, suggesting a potential for preventing lung adenocarcinoma. C3G decreases CLDN2 expression by inhibiting Akt and activating p38, while also enhancing the accumulation and cytotoxicity of Doxorubicin in cell models.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Engineering, Environmental
Dacheng Yang, Yanhong Ran, Xusheng Li, Xinwei Jiang, Jiali Chen, Jianxia Sun, Lingmin Tian, Katia Teerds, Weibin Bai
Summary: The study demonstrated that C3G could mitigate the negative effects of Cd exposure on uterine epithelial cells, potentially preventing Cd-induced female reproductive toxicity. C3G exerts anti-estrogenic effects through various mechanisms to protect the uterus from the harm caused by Cd.
JOURNAL OF HAZARDOUS MATERIALS
(2022)
Article
Chemistry, Applied
Yuwan Li, Tongtong Yu, Zhiying Wang, Qin Li, Lei Rao, Liang Zhao, Yongtao Wang, Xiaojun Liao
Summary: The influence of system pH and hydrothermal processing of starch on the interaction between C3G and starch was investigated. The binding rates and amounts increased with increasing pH, and moderate hydrothermal processing enhanced the binding rates and amounts. Higher degree hydrothermal processing broke down the starch structure, releasing more starch chains and improving the contact with C3G. 65 degrees C/10 min treatment had better effects than 95 degrees C/20 min treatment. Increasing system pH and moderate hydrothermal processing showed a synergistic effect.
FOOD HYDROCOLLOIDS
(2023)
Article
Biochemistry & Molecular Biology
Sarah Strassmann, Tillman Brehmer, Maike Passon, Andreas Schieber
Summary: The study introduced a hemisynthesis method for methylated anthocyanins, successfully synthesizing cyanidin-3-O-glucoside derivatives with different degrees of methylation and identifying monomethylated derivatives. Dimethyl carbonate (DMC) was used as the methylation agent, and the influence of the catalyst DBU, temperature, and reaction time on product formation was examined. The identified conditions in this study led to a reduction in reaction time and minimized a side reaction known as carboxymethylation by using higher amounts of catalyst.
Article
Chemistry, Applied
Zhucheng Yin, Yaru Wu, Yao Chen, Xuejiao Qie, Maomao Zeng, Zhaojun Wang, Fang Qin, Jie Chen, Zhiyong He
Summary: The study found that the interaction between cyanidin-3-O-glucoside and casein or casein hydrolysates is mediated by different forces, forming hydrogen bonds or hydrophobic interactions. After binding with cyanidin-3-O-glucoside, a slight change in the secondary structure of casein/casein hydrolysates was observed, leading to the formation of larger particles. The antioxidant activity assessments showed a synergistic or antagonistic effect between casein/casein hydrolysates and cyanidin-3-O-glucoside.
Article
Agriculture, Multidisciplinary
Ruijing Liu, Yulong Jin, Boping Liu, Qing Zhang, Xusheng Li, Dongbao Cai, Lingmin Tian, Xinwei Jiang, Wenbao Zhang, Jianxia Sun, Weibin Bai
Summary: This study aimed to investigate the protective effect of cyanidin-3-O-glucoside (C3G) on bisphenol A (BPA)-induced liver lipid metabolism disorder and explore its mechanism via lipidomics analysis. The results showed that C3G supplementation significantly improved serum lipid levels and reversed the levels of hepatic lipid synthesis-related genes. Our findings suggest that C3G has a beneficial regulatory effect on BPA-induced disorders of lipid metabolism.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Chemistry, Applied
Fernando Pina, Nuno Basilio, A. J. Parola, Maria J. Melo, Joana Oliveira, Victor de Freitas
Summary: Blue was the last color to be spread in Nature by anthocyanins, and the last color to be managed by Humans in Anthropocene. It took a long time for humanity to figure out how to reproduce and use blue, but plants developed strategies like intramolecular copigmentation and metalloanthocyanins to achieve the color. Blue was absent in early cave paintings and came later than red and green in LEDs and LASERs. It was only in the late 20th century that genetic engineering created blue flowers and blue remains sought after as a natural alternative to synthetic colorants. Despite being second-rate in the West, blue is now the preferred color in many countries.
Article
Food Science & Technology
Ana Catarina Ribeiro, Sara Simoes, Rosa Perez-Gregorio, Susana Soares, Diogo Figueira, Diogo Castelo Branco, Ana Tasso, Anabela Raymundo, Nuno Mateus, Victor Freitas
Summary: This study evaluates the use of yeast protein extract (YPE) as an alternative to egg in mayonnaise. The natural ability of phenolic compounds (PCs) to enhance the emulsifying capacity of YPE was also investigated. The mayonnaise-like emulsions developed with YPE were found to have similar physical-chemical properties to commercial mayonnaise.
INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY
(2023)
Article
Agriculture, Multidisciplinary
Monica de Jesus, Carlos Guerreiro, Elsa Brandao, Nuno Mateus, Victor de Freitas, Susana Soares
Summary: The interaction between phenolic compounds and salivary proteins affects astringency perception. Green tea extract binds to oral cell models cumulatively, with increased salivary flow enhancing the binding capacity. Different salivary proteins may play different roles in the enhanced astringency perception.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Ana Fernandes, Sara Simoes, Isabel M. P. L. V. O. Ferreira, Maria Joao Alegria, Nuno Mateus, Anabela Raymundo, Victor de Freitas
Summary: This work examines the potential of Rocha do Oeste pear pomace as a sustainable and healthy food ingredient, and the enrichment with yeast protein extract to develop innovative food products. The study evaluates the chemical composition, antioxidant capacity, rheology, texture, and microstructure of pear pomace, both alone and enriched with YPE, before and after heating. The results demonstrate that pear pomace is a rich source of dietary fibers and phenolic compounds with antioxidant activity, and that YPE enrichment and thermal treatment do not significantly affect its technological properties.
Article
Biochemistry & Molecular Biology
Oscar H. Martinez-Costa, Laura Rodrigues-Miranda, Sofia M. Clemente, Antonio Jorge Parola, Nuno Basilio, Alejandro K. Samhan-Arias
Summary: Cytochrome b(5) reductase (Cb5R) is a flavoprotein that participates in redox reactions and generates superoxide anion. Previous studies have shown that different flavonoids can inhibit Cb5R. This study aims to investigate the molecular mechanism of interaction between flavonoids and Cb5R using flavylium salts as dynamic inhibitors.
Article
Biochemistry & Molecular Biology
Ana Rita Pereira, Carina Costa, Nuno Mateus, Victor de Freitas, Alirio Rodrigues, Joana Oliveira
Summary: Large amounts of vine shoots generated during vine pruning still contain compounds from the original plant, including phenolic compounds and structural compounds like cellulose, hemicellulose, and lignin. This study proposes the extraction of lignin from vine shoots for the production of nanoparticles, using ethanol/toluene and water/ethanol as solvents. The lignin nanoparticles showed excellent antioxidant properties and the extracts from biomass pretreatment also exhibited antioxidant activity. Overall, this work contributes to the integral reuse of vine shoot byproduct, promoting sustainability.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Joana N. Martins, Beatriz Raimundo, Alicia Rioboo, Yeray Folgar-Camean, Javier Montenegro, Nuno Basilio
Summary: In this study, photoswitchable calixarenes were introduced to activate the transport of cationic peptide cargos across lipid membranes. The calixarenes, equipped with a hydrophobic azobenzene arm, can recognize cationic peptide sequences at the nanomolar range. The activation of membrane peptide transport was confirmed in synthetic vesicles and living cells by using calixarene activators with the azobenzene arm in the E configuration. This method allows the modulation of transmembrane transport of peptide cargos through the Z-E photoisomerization of functionalized calixarenes using 500 nm visible light.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Biochemistry & Molecular Biology
Leonor Goncalves, Monica Jesus, Elsa Brandao, Paulo Magalhaes, Nuno Mateus, Victor de Freitas, Susana Soares
Summary: This study delved into the molecular mechanism of beer astringency and bitterness by exploring the interaction between salivary proteins and beer phenolic compounds. The results revealed that beers with higher phenolic compound content exhibit more astringency and bitterness, while changes in salivary proteins have a minimal correlation with these sensory attributes.
Article
Nutrition & Dietetics
Barbara Mota, Miguel Ramos, Sandra I. Marques, Ana Silva, Pedro A. Pereira, M. Dulce Madeira, Nuno Mateus, Armando Cardoso
Summary: High-caloric diets, especially those rich in saturated fats and sugar, have detrimental effects on the cognition and emotions of aged rats. The high-fat-high-sugar diet impairs spatial learning, memory, working memory, and increases anxiety levels in aged rats, while reducing the number of doublecortin cells and increasing the number of glial fibrillary acidic protein cells in the hippocampus. In contrast, the effects of the high-fat diet are milder, mainly impairing spatial memory and working memory, and also reducing the number of doublecortin cells in the hippocampus.
Review
Food Science & Technology
Ana Fernandes, Nuno Mateus, Victor de Freitas
Summary: In recent years, many studies have explored the relationship between polyphenol intake and the prevention of chronic diseases. Most research focuses on extractable polyphenols found in plant-derived foods, while non-extractable polyphenols, associated with dietary fibers, are often ignored. However, these non-extractable polyphenols may have longer-lasting bioactivities and are of interest in the food industry for their potential technological functionalities. Limited research has been conducted on these conjugates, and this review aims to examine their nutritional and biological effects, as well as their functional properties.
Article
Chemistry, Applied
Vania Gomes, Roberto Bermudez, Nuno Mateus, Alexandra Guedes, Jose Manuel Lorenzo, Victor de Freitas, Luis Cruz
Summary: A colorimetric pyranoflavylium-based pH-indicator with an improved formulation was developed as a smart label for food freshness testing. The indicator showed good performance in detecting spoilage of fish samples, with the yellow label turning purple as the spoilage process began. The film's photostability and pigment migration were also evaluated, and the label was found suitable for fresh meat and fish packaging.
FOOD HYDROCOLLOIDS
(2023)
Article
Chemistry, Physical
Dmitriy Moreira, Oren Regev, Nuno Basilio, Eduardo F. Marques
Summary: This study develops a delivery system based on dual light and pH responsive vesicles, which can achieve precise drug release. By adjusting the acid and base conditions and UV irradiation, the release of the drug is successfully controlled, demonstrating the potential application of vesicles as nano-carriers in acidic environments such as tumors.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Jialei Chen-Wu, Patricia Maximo, Patricia Remon, A. Jorge Parola, Nuno Basilio, Uwe Pischel
Summary: The tailored design of a light-triggered supramolecular cascade allows for the transduction of photons into chemical communication and the release of a neurotransmitter, reminiscent of crucial steps in natural vision process.
CHEMICAL COMMUNICATIONS
(2023)
Review
Chemistry, Applied
Vania Gomes, Nuno Mateus, Victor de Freitas, Joana Oliveira, Luis Cruz
Summary: This review provides an overview of the chemistry and potential applications of pyranoanthocyanins and pyranoflavylium analogous pigments. These compounds have attracted attention in various fields such as food, cosmetics, biomedical, and energy due to their physical-chemical features.
