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1.
J Agric Food Chem ; 72(20): 11629-11639, 2024 May 22.
Artigo em Inglês | MEDLINE | ID: mdl-38739462

RESUMO

Blueberries (Vaccinium section Cyanococcus) have a wealth of bioactive compounds, including anthocyanins and other antioxidants, that offer significant health benefits. Preserving these compounds and maintaining the sensory and nutritional qualities of blueberry products such as juice during cold market storage is critical to meet consumer expectations for nutritious, safe, and minimally processed food. In this study, we compared the effects of two preservation processing techniques, high-temperature short-time (HTST) and continuous flow high-pressure homogenization (CFHPH), on blueberry juice quality during storage at 4 °C. Our findings revealed that inlet temperature (Tin) of CFHPH processing at 4 °C favored anthocyanin retention, whereas Tin at 22 °C favored ascorbic acid retention. After 45 days of storage, CFHPH (300 MPa, 1.5 L/min, 4 °C) juice retained up to 54% more anthocyanins compared to control at 0 day. In contrast, HTST treatment (95 °C, 15 s) initially increased anthocyanin concentrations but led to their subsequent degradation over time, while also significantly degrading ascorbic acid. Furthermore, CFHPH (300 MPa, 4 °C) juice had significantly lower polyphenol oxidase activity (>80% less than control), contributing to the overall quality of the juice. This innovative processing technique has the potential to improve commercial blueberry juice, and help meet the rising demand for healthy and appealing food choices.


Assuntos
Antocianinas , Ácido Ascórbico , Mirtilos Azuis (Planta) , Temperatura Baixa , Armazenamento de Alimentos , Sucos de Frutas e Vegetais , Frutas , Antocianinas/química , Antocianinas/análise , Mirtilos Azuis (Planta)/química , Ácido Ascórbico/análise , Ácido Ascórbico/química , Sucos de Frutas e Vegetais/análise , Frutas/química , Pressão , Conservação de Alimentos/métodos , Conservação de Alimentos/instrumentação , Manipulação de Alimentos/métodos , Manipulação de Alimentos/instrumentação , Antioxidantes/química , Antioxidantes/análise
2.
J Oleo Sci ; 73(5): 657-664, 2024.
Artigo em Inglês | MEDLINE | ID: mdl-38692889

RESUMO

This present work investigated the influence of black rice anthocyanins as antioxidants on the oxidation stability of oil. Malonic acid, succinic acid and succinic anhydride were grafted on black rice anthocyanins through acylation method to improve their antioxidant activity in oil. The results from fourier transform infrared spectroscopy (FTIR) showed new absorption peaks near 1744 cm -1 and 1514 cm -1 , which implied that malonic acid, succinic acid and succinic anhydride grafted on the -OH of glucoside and rutinoside through esterification reaction and resulted that the polarity of these were reduced. Total content of anthocyanin (TAC) decreased to 166. 3 mg/g, 163.7 mg/g and 150.2 mg/g, respectively after modification with succinic acid, malonic acid and succinic anhydride. Compared with native anthocyanins, the acylation of black rice anthocyanins partially reduced its antioxidant activity. In addition, DPPH clearance of molecular modified anthocyanins decreased to 62.6% (San-An). As revealed in the oil stability through the determination of primary oxidation products (PV) and secondary oxidation products (p-AV), Sa-An, Ma-An and San-An showed stronger antioxidant activity in Schaal oven accelerated oxidation test during 12 days than native black rice anthocyanin in both corn oil and flaxseed oil. Molecular modified black rice anthocyanins are expected to be used as colorants, antioxidants, etc. in oil-rich food.


Assuntos
Antocianinas , Antioxidantes , Oryza , Oxirredução , Antocianinas/química , Antocianinas/farmacologia , Antioxidantes/farmacologia , Oryza/química , Acilação , Óleos de Plantas/química , Óleos de Plantas/farmacologia , Espectroscopia de Infravermelho com Transformada de Fourier
3.
Molecules ; 29(8)2024 Apr 21.
Artigo em Inglês | MEDLINE | ID: mdl-38675711

RESUMO

Although much less common than anthocyanins, 3-Deoxyanthocyanidins (3-DAs) and their glucosides can be found in cereals such as red sorghum. It is speculated that their bioavailability is higher than that of anthocyanins. Thus far, little is known regarding the therapeutic effects of 3-DAs and their O-ß-D-glucosides on cancer, including prostate cancer. Thus, we evaluated their potential to decrease cell viability, to modulate the activity of transcription factors such as NFκB, CREB, and SOX, and to regulate the expression of the gene CDH1, encoding E-Cadherin. We found that 4',7-dihydroxyflavylium chloride (P7) and the natural apigeninidin can reduce cell viability, whereas 4',7-dihydroxyflavylium chloride (P7) and 4'-hydroxy-7-O-ß-D-glucopyranosyloxyflavylium chloride (P3) increase the activities of NFkB, CREB, and SOX transcription factors, leading to the upregulation of CDH1 promoter activity in PC-3 prostate cancer cells. Thus, these compounds may contribute to the inhibition of the epithelial-to-mesenchymal transition in cancer cells and prevent the metastatic activity of more aggressive forms of androgen-resistant prostate cancer.


Assuntos
Antocianinas , Caderinas , Glucosídeos , Regiões Promotoras Genéticas , Neoplasias da Próstata , Sorghum , Humanos , Caderinas/metabolismo , Caderinas/genética , Masculino , Neoplasias da Próstata/tratamento farmacológico , Neoplasias da Próstata/metabolismo , Neoplasias da Próstata/patologia , Neoplasias da Próstata/genética , Antocianinas/farmacologia , Antocianinas/química , Sorghum/química , Glucosídeos/farmacologia , Glucosídeos/química , Células PC-3 , Sobrevivência Celular/efeitos dos fármacos , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Linhagem Celular Tumoral , Antígenos CD/metabolismo , Antígenos CD/genética , NF-kappa B/metabolismo
4.
J Agric Food Chem ; 72(17): 9703-9716, 2024 May 01.
Artigo em Inglês | MEDLINE | ID: mdl-38567751

RESUMO

Cyanidin-3-O-glucoside (C3G) is classified as an anthocyanin (ACN) and is recognized for its remarkable antioxidant properties. Yet, the inadequate physicochemical stability of C3G restricts its potential for various biological applications. Thus, in this study, carboxymethyl chitosan (CMC)-coated nanonutriosomes (NS) were synthesized as a novel carrier for encapsulating C3G (CMC-C3G-NS) to improve C3G stability. CMC-C3G-NS exhibited a diameter of less than 200 nm along with an encouraging encapsulation efficiency exceeding 90%. Notably, the formulated CMC-C3G-NS possessed better stability under various pH, ionic, and oxygen conditions, improved controlled release properties, and higher hepatocellular uptake than uncoated particles (C3G-NS), indicating a longer retention time of C3G in a physiological environment. Of utmost significance, CMC-C3G-NS demonstrated superior alleviating effects against palmitic acid (PA)-induced oxidative hepatic damage compared to C3G-NS. Our study provided promising nanocarriers with the potential to deliver hydrophilic ACNs and controlled release properties for PA-induced hepatotoxicity alleviation.


Assuntos
Antocianinas , Quitosana , Quitosana/análogos & derivados , Hepatócitos , Nanopartículas , Ácido Palmítico , Quitosana/química , Antocianinas/química , Antocianinas/administração & dosagem , Antocianinas/farmacologia , Ácido Palmítico/química , Hepatócitos/efeitos dos fármacos , Hepatócitos/metabolismo , Humanos , Nanopartículas/química , Portadores de Fármacos/química , Estresse Oxidativo/efeitos dos fármacos , Animais , Células Hep G2
5.
Int J Biol Macromol ; 266(Pt 2): 131308, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38569996

RESUMO

In this work, the acylated anthocyanin (Ca-An) was prepared by enzymatic modification of black rice anthocyanin with caffeic acid, and the binding mechanism of Ca-An to soybean protein isolate (SPI) was investigated by experiments and computer simulation to expand the potential application of anthocyanin in food industry. Multi-spectroscopic studies revealed that the stable binding of Ca-An to SPI induced the folding of protein polypeptide chain, which transformed the secondary structure of SPI trended to be flexible. The microenvironment of protein was transformed from hydrophobic to hydrophilic, while tyrosine played dominant role in quenching process. The binding sites and forces of the complexes were determined by computer simulation for further explored. The protein conformation of the 7S and 11S binding regions to Ca-An changed, and the amino acid microenvironment shifted to hydrophilic after binding. The results showed that more non-polar amino acids existed in the binding sites, while in binding process van der Waals forces and hydrogen bonding played a major role hydrophobicity played a minor role. Based on MM-PBSA analysis, the binding constants of 7S-Ca-An and 11S-Ca-An were 0.518 × 106 mol-1 and 5.437 × 10-3 mol-1, respectively. This information provides theoretical guidance for further studying the interaction between modified anthocyanins and biomacromolecules.


Assuntos
Antocianinas , Interações Hidrofóbicas e Hidrofílicas , Simulação de Dinâmica Molecular , Ligação Proteica , Proteínas de Soja , Antocianinas/química , Antocianinas/metabolismo , Proteínas de Soja/química , Proteínas de Soja/metabolismo , Sítios de Ligação , Solubilidade , Ligação de Hidrogênio
6.
Int J Biol Macromol ; 267(Pt 2): 131649, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38636751

RESUMO

The colorless ammonia gas has been a significant intermediate in the industrial sector. However, prolonged exposure to ammonia causes harmful effects to organs or even death. Herein, an environmentally friendly solid-state ammonia sensor was developed utilizing colorimetric polycaprolactone-co-polylactic acid nanofibrous membrane. Pomegranate (Punica granatum L.) peel contains anthocyanin (ACN) as a naturally occurring spectroscopic probe. A mordant (potassium aluminum sulfate) is used to immobilize the anthocyanin direct dyestuff inside nanofibers, generating mordant/anthocyanin (M/ACN) coordinated complex nanoparticles. When exposed to ammonia, the color change of anthocyanin-encapsulated polycaprolactone-co-polylactic acid nanofibrous membrane from purple to transparent was examined by absorbance spectra and CIE Lab color parameters. With a quick colorimetric shift, the polycaprolactone-co-polylactic acid fabric exhibits a detection limit of 5-150 mg/L. The absorbance spectra showed a hypsochromic shift when exposed to ammonia, displaying an absorption shift from 559 nm to 391 nm with an isosbestic point of 448 nm. Scanning electron microscopy (SEM) images revealed that the polycaprolactone-co-polylactic acid nanofibers had a diameter of 75-125 nm, whereas transmission electron microscopy (TEM) images revealed that M/ACN nanoparticles exhibited diameters of 10-20 nm.


Assuntos
Amônia , Antocianinas , Nanofibras , Poliésteres , Nanofibras/química , Poliésteres/química , Antocianinas/química , Amônia/química , Amônia/análise , Gases/química , Colorimetria
7.
Int J Mol Sci ; 25(8)2024 Apr 09.
Artigo em Inglês | MEDLINE | ID: mdl-38673738

RESUMO

The high content of bioactive compounds in Aronia melanocarpa fruit offers health benefits. In this study, the anti-atherosclerotic effect of Aronia extracts was assessed. The impact on the level of adhesion molecules and the inflammatory response of human umbilical vein endothelial cells (HUVECs) was shown in relation to the chemical composition and the stage of ripening of the fruits. Samples were collected between May (green, unripe) and October (red, overripe) on two farms in Poland, which differed in climate. The content of chlorogenic acids, anthocyanins, and carbohydrates in the extracts was determined using HPLC-DAD/RI. The surface expression of ICAM-1 and VCAM-1 in HUVECs was determined by flow cytometry. The mRNA levels of VCAM-1, ICAM-1, IL-6, and MCP-1 were assessed using the quantitative real-time PCR method. The farms' geographical location was associated with the quantity of active compounds in berries and their anti-atherosclerotic properties. Confirmed activity for green fruits was linked to their high chlorogenic acid content.


Assuntos
Aterosclerose , Frutas , Células Endoteliais da Veia Umbilical Humana , Photinia , Extratos Vegetais , Photinia/química , Humanos , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Frutas/química , Aterosclerose/tratamento farmacológico , Molécula 1 de Adesão de Célula Vascular/genética , Molécula 1 de Adesão de Célula Vascular/metabolismo , Molécula 1 de Adesão Intercelular/metabolismo , Molécula 1 de Adesão Intercelular/genética , Antocianinas/farmacologia , Antocianinas/química , Quimiocina CCL2/genética , Quimiocina CCL2/metabolismo , Ácido Clorogênico/farmacologia , Ácido Clorogênico/química , Interleucina-6/metabolismo , Interleucina-6/genética
8.
J Agric Food Chem ; 72(12): 6327-6338, 2024 Mar 27.
Artigo em Inglês | MEDLINE | ID: mdl-38484116

RESUMO

The present work aimed to characterize the phenolic and antioxidant content of the Argentinian purple maize "Moragro" cultivar. Additionally, the INFOGEST simulated in vitro digestion model was used to establish the effect of digestion on bioactive compounds. Finally, digestion samples were used to treat Caco-2 cells in the transwell model to better understand their bioavailability. Twenty-six phenolic compounds were found in purple maize cv. "Moragro", 15 nonanthocyanins and 11 anthocyanins. Several compounds were identified in maize for the first time, such as pyrogallol, citric acid, gallic acid, kaempferol 3-(6″-ferulylglucoside), and kaempferol 3-glucuronide. Anthocyanins accounted for 24.9% of total polyphenols, with the predominant anthocyanin being cyanidin-3-(6″ malonylglucoside). Catechin-(4,8)-cyanidin-3,5-diglucoside and catechin-(4,8)-cyanidin-3-malonylglucoside-5-glucoside were detected as characteristics of this American maize variety. Total polyphenol content (TPC; by the Folin-Ciocalteu method), HPLC-DAD/MSMS, and antioxidant activity [by DPPH and ferric-reducing antioxidant power (FRAP)] were evaluated throughout in vitro digestion. TPC, DPPH, and FRAP results were 2.71 mg gallic acid equivalents (GAE)/g, 24 µmol Trolox equiv/g, and 22 µmol Trolox eq/g, respectively. The in vitro digestion process did not cause significant differences in TPC. However, the antioxidant activity was significantly decreased. Moreover, the bioavailability of anthocyanins was studied, showing that a small fraction of polyphenols in their intact form was conserved at the end of digestion. Finally, a protective effect of digested maize polyphenols was observed in the Caco-2 cell viability. The results suggest that "Moragro" purple maize is a good source of bioavailable anthocyanins in the diet and an interesting source of this group of compounds for the food industry.


Assuntos
Antocianinas , Catequina , Humanos , Antocianinas/química , Zea mays/química , Antioxidantes , Células CACO-2 , Quempferóis , Cromatografia Líquida de Alta Pressão , Fenóis/química , Polifenóis/análise , Ácido Gálico , Digestão
9.
Food Chem ; 448: 139079, 2024 Aug 01.
Artigo em Inglês | MEDLINE | ID: mdl-38520989

RESUMO

Esterification of anthocyanins with saturated fatty acids have been widely investigated, while that with unsaturated fatty acids is little understood. In this study, crude extract (purity âˆ¼ 35 %) of cyanidin-3-O-glucoside (C3G) from black bean seed coat was utilized as reaction substrate, and enzymatically acylated with unsaturated fatty acid (oleic acid). Optimization of various reaction parameters finally resulted in the highest acylation rate of 54.3 %. HPLC-MS/MS and NMR analyses elucidated the structure of cyanidin-3-O-glucoside-oleic acid ester (C3G-OA) to be cyanidin-3-O-(6″-octadecene)-glucoside. Introduction of oleic acid into C3G improved the lipophilicity, antioxidant ability, and antibacterial activity. Further, the color and substance stability analyses showed that the susceptibility of C3G and C3G-OA to different thermal, peroxidative, and illuminant treatments were highly pH dependent, which suggested individual application guidelines. Moreover, C3G-OA showed lower toxicity to normal cell (QSG-7701) and better inhibitory effect on the proliferation of HepG2 cells than C3G, which indicated its potential anti-tumor bioactivity.


Assuntos
Antocianinas , Ácido Oleico , Antocianinas/química , Humanos , Ácido Oleico/química , Esterificação , Extratos Vegetais/química , Antioxidantes/química , Antioxidantes/farmacologia , Células Hep G2 , Phaseolus/química , Antibacterianos/química , Antibacterianos/farmacologia , Estrutura Molecular
10.
Food Chem ; 447: 138971, 2024 Jul 30.
Artigo em Inglês | MEDLINE | ID: mdl-38461718

RESUMO

This study introduces an innovative approach for the valorization and protection of anthocyanins from 'Benihoppe' strawberry (Fragaria × ananassa Duch.) based on acidified natural deep eutectic solvent (NADES). Choline chloride-citric acid (ChCl-CA, 1:1) was selected and acidified to enhance the valorization and protection of anthocyanins through hydrogen bond. The optimal conditions (ultrasonic power of 318 W, extraction temperature of 61 °C, liquid-to-solid ratio of 33 mL/g, ultrasonic time of 19 min), yielded the highest anthocyanins of 1428.34 µg CGE/g DW. UPLC-Triple-TOF/MS identified six anthocyanins in acidified ChCl-CA extract. Stability tests indicated that acidified ChCl-CA significantly increased storage stability of anthocyanins in high temperature and light treatments. Molecular dynamics results showed that acidified ChCl-CA system possessed a larger diffusion coefficient (0.05 m2/s), hydrogen bond number (145) and hydrogen bond lifetime (4.38 ps) with a reduced intermolecular interaction energy (-1329.74 kcal/mol), thereby efficiently valorizing and protecting anthocyanins from strawberries.


Assuntos
Antocianinas , Fragaria , Solventes/química , Antocianinas/química , Fragaria/química , Solventes Eutéticos Profundos , Extratos Vegetais/química
11.
Int J Biol Macromol ; 264(Pt 1): 130483, 2024 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-38430999

RESUMO

To investigate the efficacy of sodium alginate-konjac glucomannan (SA-KGM) films with anthocyanins (LRA) and tea polyphenols (TP) in meat, beef and grass carp were selected as representative meat products for preservation and freshness monitoring experiments at 4 °C. Concurrently, storage experiments of the films were conducted in this controlled environment. The results of the storage experiment showed that the films delayed meat spoilage by 2-4 days, nearly doubling the preservation time compared to the blank control. Additionally, the film exhibited significant capability to monitor the spoilage process of beef and grass carp. It was revealed by curve fitting analysis that there was a significant correlation between the color change of the film and the spoilage index of the meat. Throughout the storage experiment with the film, it was observed that moisture significantly influenced the microstructure and bonding situation of the films, thereby impacting their mechanical and barrier properties. However, the films were still able to maintain satisfactory physicochemical properties in general. The above findings were crucial in guiding the promotion of the film within the food preservation industry.


Assuntos
Alginatos , Lycium , Mananas , Animais , Bovinos , Alginatos/química , Antocianinas/química , Polifenóis/química , Chá/química , Embalagem de Alimentos
12.
J Agric Food Chem ; 72(11): 5491-5502, 2024 Mar 20.
Artigo em Inglês | MEDLINE | ID: mdl-38446808

RESUMO

Anthocyanins are phytonutrients with physiological activity belonging to the flavonoid family whose transport and absorption in the human body follow specific pathways. In the upper gastrointestinal tract, anthocyanins are rarely absorbed intact by active transporters, with most reaching the colon, where bacteria convert them into metabolites. There is mounting evidence that anthocyanins can be used for prevention and treatment of intestinal diseases, including inflammatory bowel disease (IBD), irritable bowel syndrome (IBS), and colorectal cancer (CRC), through the protective function on the intestinal epithelial barrier, immunomodulation, antioxidants, and gut microbiota metabolism. Dietary anthocyanins are summarized in this comprehensive review with respect to their classification and structure as well as their absorption and transport mechanisms within the gastrointestinal tract. Additionally, the review delves into the role and mechanism of anthocyanins in treating common intestinal diseases. These insights will deepen our understanding of the potential benefits of natural anthocyanins for intestinal disorders.


Assuntos
Microbioma Gastrointestinal , Doenças Inflamatórias Intestinais , Humanos , Antocianinas/química , Dieta , Doenças Inflamatórias Intestinais/tratamento farmacológico
13.
Food Res Int ; 179: 114017, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38342539

RESUMO

This study produced pH-sensing carboxymethyl cellulose (CMC) films functionalized with bioactive compounds obtained by pressurized liquid extraction (PLE) of grape peel to monitor the freshness of pork and milk. A semi-continuous PLE was conducted using hydroethanolic solution (70:30, v/v) at a flow rate of 5 mL/min, 15 MPa, and 60 °C. The films were produced by the casting technique using CMC (2.5 %, w/v), glycerol (1 %, v/v), and functionalized with 10, 30, and 50 % (v/v) grape peel extract. From the results obtained, LC-MS/MS revealed that PLE extracted twenty-seven phenolic compounds. The main phenolic compounds were kaempferol-3-glucoside (367.23 ± 25.88 µg/mL), prunin (270.23 ± 3.62 µg/mL), p-coumaric acid (236.43 ± 26.02 µg/mL), and procyanidin B1 (117.17 ± 7.29 µg/mL). The CMC films presented suitable color and mechanical properties for food packaging applications. The addition of grape peel extract promoted the pH-sensing property, showing the sensitivity of anthocyanins to pH changes. The films functionalized with grape peel extract presented good release control of bioactive compounds, making them suitable for food packaging applications. When applied to monitor the freshness of pork and milk, the films exhibited remarkable color changes associated with the pH of the food during storage. In conclusion, PLE is a sustainable approach to obtaining bioactive compounds from the grape peel, which can be applied in the formulation of pH-sensing films as a promising sustainable material to monitor food freshness during storage.


Assuntos
Carne de Porco , Carne Vermelha , Vitis , Animais , Suínos , Carboximetilcelulose Sódica/química , Carne Vermelha/análise , Leite , Antocianinas/química , Cromatografia Líquida , Concentração de Íons de Hidrogênio , Espectrometria de Massas em Tandem , Fenóis
14.
Food Res Int ; 176: 113837, 2024 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-38163689

RESUMO

Under natural physiological conditions, anthocyanins can keep bright and stable color for a long time due to the relatively stable acid-base environment of plant vacuoles and the copigmentation from various copigment substances, such as polyphenols, nucleotides, metallic ions and other substances. Therefore, the copigmentation caused by copigments is considered an effective way to stabilize anthocyanins against adverse environmental conditions. This is attributed to the covalent and noncovalent interactions between colored forms of anthocyanins (flavylium ions and quinoidal bases) and colorless or pale yellow organic molecules (copigments). These interactions are usually manifested in both hyperchromic effect and bathochromic shifts. In addition to making anthocyanins more stable, the copigmentation also could make an important contribution to the diversification of their tone. Based on the molecular structure of anthocyanins, this review focuses on the interaction mode of auxochrome groups or copigments with anthocyanins and their effects on the chemical and color stability of anthocyanins.


Assuntos
Antocianinas , Polifenóis , Antocianinas/química , Estrutura Molecular , Íons
15.
ACS Nano ; 18(3): 2290-2301, 2024 Jan 23.
Artigo em Inglês | MEDLINE | ID: mdl-38207222

RESUMO

Anthocyanins with different structures have different anti-inflammatory and anti-cancer properties. Precise structural use can improve the chemopreventive effects of anthocyanins and enhance treatment outcomes because the anthocyanin structure influences its functional sites and activities. However, owing to the available variety of anthocyanins and their complex structures, the low matching of intermolecular forces between existing adsorbents and anthocyanins limits the targeted separation of anthocyanin monomers. Short-range and efficient selective binding, which is difficult to achieve, is the current focus in the extraction field. We here developed self-assembled Fe3O4-based nano adsorbers with different surface modifications based on adsorption-pairing synergy. The electrostatic force, coordination bond, hydrogen bond, and π-π* bond together induced selective adsorption between Fe3O4 nanoparticles and anthocyanin molecules. An acid-release solution disrupted the polarity balance in the aforementioned association system, thereby promoting the controlled release of anthocyanins. Among the candidates, the effects of morphology, particle size, surface charge, and functional group on adsorption performance were analyzed. The polyacrylamide-modified magnetic Fe3O4 nanoparticles were found to be favorable for selectively extracting anthocyanin, with an adsorption capacity of 19.74 ± 0.07 mg g-1. The release percentage of cyanidin-3-O-glucoside reached up to 98.6% ± 1.4%. This study offers a scientific basis for developing feasible nanotechniques to extract anthocyanins and plant active substances.


Assuntos
Antocianinas , Nanopartículas , Antocianinas/química , Preparações de Ação Retardada , Adsorção
16.
J Sci Food Agric ; 104(2): 905-915, 2024 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-37699084

RESUMO

BACKGROUND: The aim of this study was to investigate the effects of covalent and non-covalent interactions between myofibrillar protein (MP) and cyanidin-3-O-glucoside (C3G) on protein structure, binding sites, and digestion properties. Four methods of inducing covalent cross-linking were used in the preparation of MP-C3G conjugates, including tyrosinase-catalyzed oxidation, alkaline pH shift treatment, free radical grafting, and ultrasonic treatment. A comparison was made between MP-C3G conjugates and complexes, and the analysis included sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE), C3G binding ratio, liquid chromatography-tandem mass spectrometry (LC-MS/MS), protein side-chain amino acids, circular dichroism spectroscopy, three-dimensional fluorescence, particle size, and in vitro simulated digestion. RESULTS: Covalent bonding between C3G and amino acid side chains in MP was confirmed by LC-MS/MS. In covalent bonding, tryptophan residues, free amino groups and sulfhydryl groups were all implicated. Among the 22 peptides covalently modified by C3G, 30 modification sites were identified, located in lysine, histidine, tryptophan, arginine and cysteine. In vitro simulated digestion experiments showed that the addition of C3G significantly reduced the digestibility of MP, with the covalent conjugate showing lower digestibility than the non-covalent conjugate. Moreover, the digestibility of protein decreased more during intestinal digestion, possibly because covalent cross-linking of C3G and MP further inhibited trypsin targeting sites (lysine and arginine). CONCLUSION: Covalent cross-linking of C3G with myofibrillar proteins significantly affected protein structure and reduced protein digestibility by occupying more trypsin binding sites. © 2023 Society of Chemical Industry.


Assuntos
Lisina , Triptofano , Cromatografia Líquida , Tripsina/metabolismo , Espectrometria de Massas em Tandem , Sítios de Ligação , Antocianinas/química , Glucosídeos/metabolismo , Digestão , Arginina
17.
Food Chem ; 440: 138181, 2024 May 15.
Artigo em Inglês | MEDLINE | ID: mdl-38118319

RESUMO

The objective of this study was to analyze and optimize the influence of heating time and citric acid (CA) or sucrose addition of Ardisia compressa K. extracts on phenolic compounds (TPC), monomeric anthocyanins (MAA), antioxidant activity (TAC), color density (CD), and hue tint (HT), using a full factorial design. Extractions were performed: temperature (25, 50, or 70 °C), time (15, 30, 60, or 90 min), CA (0.0 or 0.02 g), and sucrose (0.0 or 5.0 g). HPLC-DAD-ESI-MS was conducted in extracts without additives and with the addition of CA (0.02 g) or sucrose (5.0 g), at 25, 50, or 70 °C for 15 min. CA-added extracts showed maximum TPC, MAA, TAC (DDPH and ABTS assays), and CD values, with the lowest HT values. Malvidin 3-O-galactoside and myricetin-O-hexoside were the predominant anthocyanin and non-anthocyanin polyphenols. Time, temperature, and solute influenced the optimized extraction of TPC, MAA, anthocyanins, TAC, CD, and HT.


Assuntos
Ardisia , Polifenóis , Antocianinas/química , Antioxidantes/química , Ardisia/química , Temperatura , Extratos Vegetais/química
18.
Int J Biol Macromol ; 253(Pt 5): 127133, 2023 Dec 31.
Artigo em Inglês | MEDLINE | ID: mdl-37802437

RESUMO

The instability of anthocyanin to environmental stressors severely limits its applications as a natural bioactive pigment. To overcome these limitations, this proof-of-concept study utilizes the high biocompatibility of peptide molecules and the unique gel microstructure to develop innovative peptide-based gels. Characterization of the gels was conducted through AFM, SEM, rheological analysis, and CD spectrum. These analyses confirmed the fibrous mesh structure and impressive mechanical strength of the peptide-based gels. The cytotoxicity evaluation using MTT and hemolysis analysis showed high biocompatibility. Encapsulation efficiency analysis and fluorescence microscopy images demonstrated successful and efficient encapsulation of anthocyanins in all four peptide-based gels, with uniform distribution. Moreover, systematic investigations were conducted to assess the impact of peptide-based gels on the stability of natural anthocyanins under environmental stressors such as temperature, pH variations, and exposure to metal ions. Notably, the results revealed a significant enhancement in stability, including improved long-term storage and antioxidant activity. In conclusion, this study successfully developed four novel peptide-based gels that effectively protect natural anthocyanins from environmental stressors, highlighting their potential in various fields such as food and biology.


Assuntos
Antocianinas , Peptídeos , Antocianinas/farmacologia , Antocianinas/química , Peptídeos/farmacologia , Extratos Vegetais/química , Géis/química
19.
Adv Healthc Mater ; 12(25): e2300473, 2023 10.
Artigo em Inglês | MEDLINE | ID: mdl-37537383

RESUMO

Anthocyanin, a unique natural polyphenol, is abundant in plants and widely utilized in biomedicine, cosmetics, and the food industry due to its excellent antioxidant, anticancer, antiaging, antimicrobial, and anti-inflammatory properties. However, the degradation of anthocyanin in an extreme environment, such as alkali pH, high temperatures, and metal ions, limits its physiochemical stabilities and bioavailabilities. Encapsulation and combining anthocyanin with biomaterials could efficiently stabilize anthocyanin for protection. Promisingly, natural or artificially designed proteins and peptides with favorable stabilities, excellent biocapacity, and wide sources are potential candidates to stabilize anthocyanin. This review focuses on recent progress, strategies, and perspectives on protein and peptide for anthocyanin functionalization and delivery, i.e., formulation technologies, physicochemical stability enhancement, cellular uptake, bioavailabilities, and biological activities development. Interestingly, due to the simplicity and diversity of peptide structure, the interaction mechanisms between peptide and anthocyanin could be illustrated. This work sheds light on the mechanism of protein/peptide-anthocyanin nanoparticle construction and expands on potential applications of anthocyanin in nutrition and biomedicine.


Assuntos
Antocianinas , Nanopartículas , Antocianinas/farmacologia , Antocianinas/química , Peptídeos/farmacologia , Antioxidantes/química , Nanotecnologia
20.
Molecules ; 28(15)2023 Jul 29.
Artigo em Inglês | MEDLINE | ID: mdl-37570718

RESUMO

Color is a major quality trait of rosé wines due to their packaging in clear glass bottles. This color is due to the presence of phenolic pigments extracted from grapes to wines and products of reactions taking place during the wine-making process. This study focuses on changes occurring during the alcoholic fermentation of Syrah, Grenache and Cinsault musts, which were conducted at laboratory (250 mL) and pilot (100 L) scales. The color and phenolic composition of the musts and wines were analyzed using UV-visible spectrophotometry, and metabolomics fingerprints were acquired by ultra-high performance liquid chromatography-high-resolution mass spectrometry. Untargeted metabolomics data highlighted markers of fermentation stage (must or wine) and markers related to the grape variety (e.g., anthocyanins in Syrah, hydroxycinnamates and tryptophan derivatives in Grenache, norisoprenoids released during fermentation in Cinsault). Cinsault wines contained higher molecular weight compounds possibly resulting from the oxidation of phenolics, which may contribute to their high absorbance values.


Assuntos
Vitis , Vinho , Vinho/análise , Antocianinas/química , Fermentação , Cromatografia Líquida de Alta Pressão , Frutas/química , Cor , Vitis/química , Fenóis/química
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