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1.
Food Chem ; 451: 139467, 2024 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-38678661

RESUMO

Betacyanins have garnered escalating research interest for their promising bioactivities. However, substantial challenges in purification and separation have impeded a holistic comprehension of the distinct bioactivities of individual betacyanins and their underlying mechanisms. Herein, betanin and phyllocactin monomers with purity exceeding 95% were successfully obtained from Hylocereus polyrhizus peel using a feasible protocol. These monomers were subsequently employed for comparative bioactivity assessments to uncover underlying mechanisms and illuminate structure-activity relationships. Interestingly, phyllocactin exhibited superior antioxidant activities and 36.1% stronger inhibitory activity on α-glucosidase compared to betanin. Mechanistic studies have revealed that they function as mixed-type inhibitors of α-amylase and competitive inhibitors of α-glucosidase, with interactions predominantly driven by hydrogen bonding. Notably, phyllocactin demonstrated a greater binding affinity with enzymes than betanin, thereby substantiating its heightened inhibitory activity. Overall, our results highlight novel bioactivities of betacyanin monomers and provide profound insights into the intricate interplay between structures and properties.


Assuntos
Antioxidantes , Betacianinas , Cactaceae , Hipoglicemiantes , Extratos Vegetais , Antioxidantes/química , Antioxidantes/farmacologia , Antioxidantes/isolamento & purificação , Betacianinas/química , Betacianinas/farmacologia , Betacianinas/isolamento & purificação , Hipoglicemiantes/química , Hipoglicemiantes/farmacologia , Hipoglicemiantes/isolamento & purificação , Cactaceae/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Extratos Vegetais/isolamento & purificação , alfa-Glucosidases/química , alfa-Glucosidases/metabolismo , alfa-Amilases/antagonistas & inibidores , alfa-Amilases/química , Relação Estrutura-Atividade
2.
J Agric Food Chem ; 72(13): 7464-7475, 2024 Apr 03.
Artigo em Inglês | MEDLINE | ID: mdl-38527235

RESUMO

Ferritin is a cage-like protein with modifiable outer and inner surfaces. To functionalize ferritin with preferable carrier applications, caffeic acid was first covalently bound to the soybean ferritin outer surface to fabricate a caffeic acid-ferritin complex (CFRT) by alkali treatment (pH 9.0). A decreased content of free amino acid (0.34 µmol/mg) and increased polyphenol binding equivalent (63.76 nmol/mg) indicated the formation of CFRT (ferritin/caffeic acid, 1:80). Fluorescence and infrared spectra verified the binding of caffeic acids to the ferritin structure. DSC indicated that the covalent modification enhanced the thermal stability of CFRT. Besides, CFRT maintained the typically spherical shape of ferritin (12 nm) and a hydration radius of 7.58 nm. Moreover, the bioactive colorant betanin was encapsulated in CFRT to form betanin-loaded CFRT (CFRTB), with an encapsulation rate of 15.5% (w/w). The betanin stabilities in CFRTB were significantly improved after heat, light, and Fe3+ treatments, and its red color retention was enhanced relative to the free betanin. This study delves into the modifiable ferritin application as nanocarriers of dual molecules and gives guidelines for betanin as a food colorant.


Assuntos
Betacianinas , Ferritinas , Betacianinas/química , Ferritinas/química , Ácidos Cafeicos
3.
J Agric Food Chem ; 71(41): 15017-15034, 2023 Oct 18.
Artigo em Inglês | MEDLINE | ID: mdl-37791532

RESUMO

A comprehensive oxidation mechanism was investigated for amaranthin-type betacyanins with a specific glucuronosylglucosyl moiety isolated from Atriplex hortensis 'rubra' using liquid chromatography coupled to diode array detection and electrospray ionization tandem mass spectrometry (LC-DAD-ESI-MS/MS) and LC-Quadrupole-Orbitrap-MS (LC-Q-Orbitrap-MS). By employing one-dimensional (1D) and two-dimensional (2D) NMR, this study elucidates the chemical structures of 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS)-oxidized celosianins for the first time. These findings demonstrate alternative oxidation pathways for acylated betacyanins compared to well-known betanidin, betanin, and gomphrenin pigments. Contrary to previous research, we uncover the existence of 17-decarboxy-neo- and 2,17-bidecarboxy-xanneo-derivatives as the initial oxidation products without the expected 2-decarboxy-xan forms. These oxidized compounds demonstrated potent free radical scavenging properties. Celosianin (IC50 = 23 µg/mL) displayed slightly higher antioxidant activity compared to oxidized forms, 17-decarboxy-neocelosianin (IC50 = 34 µg/mL) and 2,17-bidecarboxy-xanneocelosianin (IC50 = 29 µg/mL). The oxidized compounds showed no cytotoxic effects on H9c2 rat cardiomyoblasts (0.1-100 µg/mL). Additionally, treatment of H9c2 cells with the oxidized compounds (0.1-10 µg/mL) elevated glutathione levels and exhibited protective effects against H2O2-induced cell death. These findings have significant implications for understanding the impact of oxidation processes on the structures and biological activities of acylated betalains, providing valuable insights for future studies of the bioavailability and biological mechanism of their action in vivo.


Assuntos
Atriplex , Betacianinas , Animais , Ratos , Betacianinas/farmacologia , Betacianinas/química , Antioxidantes/farmacologia , Antioxidantes/química , Spinacia oleracea , Espectrometria de Massas em Tandem , Peróxido de Hidrogênio , Cromatografia Líquida de Alta Pressão/métodos
4.
Plant Foods Hum Nutr ; 78(3): 613-619, 2023 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-37466824

RESUMO

Betacyanin-rich extract from red beet (Beta vulgaris) was recently reported to inhibit amyloid ß (Aß) aggregation, a main pathological event in Alzheimer's disease. However, the anti-Aß aggregation effect of individual betacyanin isolates has not been reported before. This study investigated the anti-Aß aggregation activity and cytotoxicity of betacyanins from red pitahaya or red dragon fruit (Hylocereus polyrhizus). Betacyanin fraction (IC50 = 16.02 ± 1.15 µg/mL) and individual betacyanin isolates exhibited anti-Aß aggregation activity in a concentration-dependent manner using a thioflavin T fluorescence assay. The highest to lowest IC50 was in the order of betanin (426.30 ± 29.55 µM), phyllocactin (175.22 ± 1.52 µM), and hylocerenin (131.73 ± 5.58 µM), following a trend of increase in functional groups of carboxyl, hydroxyl, and/or carbonyl. Further, the betacyanin fraction of 135.78 µg/mL and below, which were concentrations with an anti-Aß aggregation effect, were validated as non-neurotoxic based on an in vitro cytotoxicity assay using human neuroblastoma (SH-SY5Y) cells. These findings highlight the potential neuroprotective activity of betacyanins for Alzheimer's disease.


Assuntos
Cactaceae , Sobrevivência Celular/efeitos dos fármacos , Cactaceae/química , Humanos , Linhagem Celular Tumoral , Neuroblastoma/patologia , Betacianinas/química , Betacianinas/farmacologia , Doença de Alzheimer/tratamento farmacológico , Peptídeos beta-Amiloides/química , Peptídeos beta-Amiloides/metabolismo
5.
Molecules ; 27(16)2022 Aug 11.
Artigo em Inglês | MEDLINE | ID: mdl-36014367

RESUMO

Betalains in bracts of Bougainvillea are of great application potential as natural food colorants and antioxidants. This study explored the color, spectra, composition, storage stability, and antioxidant properties of betalain-based Bougainvillea bracts extracts (BBEs) to verify their application value. The results showed that Bougainvillea bract color variance is due to varied contents and proportions of betacyanins (Bc) and betaxanthins (Bx). Bc or Bx alone determined hues of purple or yellow, respectively; the co-existence of Bc and Bx would produce varied hues of red. BBEs showed bright color and good antioxidant properties under a wide pH range. The pH range of 5−6 was optimal for the highest color stability, and pHs 3−8 were optimal for stronger antioxidants. Bc mainly underwent color fading during storage, while Bx easily produced dark precipitates or melanism under strong acidic (pH < 4) or alkaline conditions (pH > 8). However, Bougainvillea Bx showed 3−4 times higher antioxidant ability than Bc. Different considerations for Bc and Bx are needed for varied application purposes. The purple bracts containing only Bc would be more suitable as colorant sources, while additional Bx can bring enhancement of antioxidant ability and richness of Bougainvillea extract color.


Assuntos
Betalaínas , Nyctaginaceae , Antioxidantes/química , Antioxidantes/farmacologia , Betacianinas/química , Betalaínas/química , Betaxantinas , Cor , Nyctaginaceae/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia
6.
Appl Biochem Biotechnol ; 194(1): 71-83, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34762269

RESUMO

Ovarian carcinoma has a cure rate of 30% which makes it deadlier than any other disease. There are a number of genetic and epigenetic changes that lead to ovarian carcinoma cell transformation. Chemoprevention of cancer through application of natural compounds is the need of present generation as other methods are rigorous and have many side effects. Betanin, a compound from Beta vulgaris extract is used in present study to check its potential for inhibition of (PA-1) cancer cell proliferation. Determination of IC50 values through MTT assay was carried out, in addition measurement of mitochondrial membrane potential (MMP), effect of reactive oxygen species (ROS) generation, and induction of apoptosis in ovarian cancer cells through betanin was also observed. Results have shown betanin as a potential candidate for inhibition of ovarian cancer cell proliferation and it can be taken up as a serious compound for further studies for its application in cancer cure.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Betacianinas/farmacologia , Proliferação de Células/efeitos dos fármacos , Neoplasias Ovarianas/tratamento farmacológico , Neoplasias Ovarianas/metabolismo , Antineoplásicos Fitogênicos/química , Beta vulgaris/química , Betacianinas/química , Linhagem Celular Tumoral , Feminino , Humanos , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Espécies Reativas de Oxigênio/metabolismo
7.
J Sep Sci ; 44(23): 4222-4236, 2021 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-34586718

RESUMO

Betacyanins and their decarboxylated derivatives from fresh and dried edible leaves of Atriplex hortensis L. var. "Rubra" were fractionated for the first time by high-speed countercurrent chromatography. Pigments present in fresh leaf extract were separated in systems: ethanol - acetonitrile - n-propanol - ammonium sulphate - water (0.5:0.5:0.5:1.2:1.0, v/v/v/v/v) (tail-to-head mode) and tert-butyl methyl ether - n-butanol - acetonitrile - water with 0.7% heptafluorobutyric acid (2:2:1:5, v/v/v/v) (head-to-tail mode). The mobile phase flow rate was 2 mL/min and the retention of the stationary phase was 79.8 and 75.2%, respectively. Pigments from dried leaves were separated in a similar ion-pair system with heptafluorobutyric acid in different volume proportions 1:3:1:5 (head-to-tail mode) and the flow rate of the mobile phase 3 mL/min. The stationary phase retention was 64.0%. The application of the countercurrent chromatography for the fractionation of betacyanins from leaves of Atriplex hortensis enabled to isolate and pre-concentrate the pigments for further low- and high-resolution liquid chromatographic-tandem mass spectrometric detection. This study revealed the presence of 10 betacyanins in fresh and 16 in dried leaves of Atriplex hortensis. Two compounds were not previously identified in the whole Amaranthaceae family. Additionally, instead of (iso)amaranthin, celosianin and its epimer were dominant betacyanins in the Atriplex hortensis.


Assuntos
Atriplex/química , Betacianinas/isolamento & purificação , Folhas de Planta/química , Betacianinas/química , Distribuição Contracorrente , Estrutura Molecular
8.
Future Med Chem ; 13(9): 805-816, 2021 05.
Artigo em Inglês | MEDLINE | ID: mdl-33821685

RESUMO

Background: Fibroleukin-2 protein (FGL2) causes redevelopment of brain tumors. Inhibition of these proteins has shown to improve glioblastoma prognosis and treatment efficacy. Aim: The current study gathered recently exploited natural compounds that suppress glioblastoma proliferation in vitro, tested against FGL2 protein. Method: Twenty-five compounds were explored through a virtual screening platform. Results: Three natural compounds (betanine, hesperetin and ovatodiolide) hit the active site of FGL2. Furthermore, the influence of these compounds was also assessed using in silico gene expression, and ADMET tools showed downregulation of some genes, which caused rapid tumor development while possessing a moderate acute toxicity and pharmacokinetic profile. Conclusion: Our study presents three compounds that are good candidates for evaluation in FGL2 mutated glioblastoma animal models.


Assuntos
Antineoplásicos/química , Betacianinas/química , Diterpenos/química , Fibrinogênio/metabolismo , Glioblastoma/diagnóstico , Glioblastoma/tratamento farmacológico , Hesperidina/química , Antineoplásicos/farmacocinética , Apoptose/efeitos dos fármacos , Betacianinas/farmacocinética , Proliferação de Células/efeitos dos fármacos , Simulação por Computador , Diterpenos/farmacocinética , Ensaios de Seleção de Medicamentos Antitumorais , Fibrinogênio/genética , Regulação da Expressão Gênica , Hesperidina/farmacocinética , Humanos , Terapia de Alvo Molecular , Ligação Proteica
9.
Molecules ; 26(1)2021 Jan 02.
Artigo em Inglês | MEDLINE | ID: mdl-33401775

RESUMO

Hydrophobic curcumin in temulawak extract and hydrophilic betacyanin in red dragon fruit extract are high-value bioactive compounds with extensive applications in functional food. In this study, these extracts were encapsulated in water-in-oil-in-water (w/o/w) nanoemulsions as a delivery system using a two-step high-energy emulsification method. PGPR and Span 20 were used as lipophilic emulsifiers for the primary w/o emulsion. The most stable w/o/w formulation with the least oil phase separation of 5% v/v consisted of w/o emulsion (15% w/w) and Tween 80 (1.5% w/w) as hydrophilic emulsifier. The formulation was characterized by a 189-nm mean droplet diameter, 0.16 polydispersity index, and -32 mV zeta potential. The freeze-thaw stability may be attributed to the combination of low w/o emulsion content and high Tween 80 concentration in the outer water phase of the w/o/w nanoemulsions used in this study. The IC50 values of the nanoemulsion and the red dragon fruit extract were similar. It means that the higher concentration of curcumin in the nanoemulsions and the lower IC50 value of temulawak extract ensured sufficient antioxidant activities of the w/o/w nanoemulsions.


Assuntos
Cactaceae/química , Emulsões/química , Nanoestruturas/química , Extratos Vegetais/química , Antioxidantes/química , Betacianinas/química , Óleo de Milho/química , Curcuma/química , Curcumina/química , Sistemas de Liberação de Medicamentos , Emulsificantes/química , Congelamento , Hexoses , Interações Hidrofóbicas e Hidrofílicas , Microscopia Eletrônica de Transmissão , Polissorbatos/química , Espectroscopia de Infravermelho com Transformada de Fourier , Água/química
10.
Food Chem ; 348: 129152, 2021 Jun 30.
Artigo em Inglês | MEDLINE | ID: mdl-33515953

RESUMO

A red pigment was prepared by reaction of chlorogenic acid (CGA) with tryptophan (TRP) in air at pH 9 (37% w/w yield) and evaluated as food dye. The main component of pigment was formulated as an unusual benzochromeno[2,3-b]indole linked to a TRP unit, featuring a cyanine type chromophore (λmax 542, 546 nm, 1% extinction coefficient of the sodium salt = 244 ± 2). The chromophore showed a minimal pH dependence and proved stable for at least 3 h at 90 °C, both at pH 3.6 or 7.0, whereas red wine anthocyanins showed a substantial (30%) and betanin a complete abatement after 1 h at the acidic pHs. An intense coloring of different food matrices was obtained with the pigment at 0.01 % w/w. No toxicity was observed up to 0.2 mg/mL on hepatic and colonic cell lines. These data make this dye a promising alternative for red coloring of food.


Assuntos
Antocianinas/química , Ácido Clorogênico/química , Corantes de Alimentos/química , Triptofano/química , Antocianinas/farmacologia , Betacianinas/química , Betacianinas/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Corantes de Alimentos/farmacologia , Temperatura Alta , Humanos , Concentração de Íons de Hidrogênio , Acoplamento Oxidativo
11.
J Agric Food Chem ; 69(4): 1318-1328, 2021 Feb 03.
Artigo em Inglês | MEDLINE | ID: mdl-33480679

RESUMO

Betanin and curcumin hold promise as natural colorants and antioxidants for food purposes due to their anti-hypertensive, anti-inflammation, and anti-tumor effects. However, the thermal stability and bioavailability of betanin and curcumin still need improvement. Here, we fabricated sugar beet pectin-bovine serum albumin nanoparticles (SBNPs) with a mean particle size of 180 ± 5.2 nm through a genipin cross-linking strategy to stabilize a type of Pickering water-in-oil-in-water (W/O/W) emulsion and co-encapsulated betanin and curcumin. First, the W1/O emulsion was homogenized with gelatin (the gelling agent) in the water phase and polyglycerol polyricinoleate (a lipophilic surfactant) in the oil phase. Later, W1/O was homogenized with another water phase containing SBNPs. The microstructure of the emulsion was regulated by the particle concentration (c) and W1/O volume fraction (Φ), especially the gel-like high internal phase emulsions were formed at the Φ up to 70%. In this case, betanin was encapsulated in the internal water phase (encapsulation efficiency = 65.3%), whereas curcumin was in the medium-chain triglyceride (encapsulation efficiency = 84.1%). Meanwhile, the shelf stability of betanin and curcumin was improved. Furthermore, the stability of bioactive compounds was potentiated by an emulsion gel in simulated gastrointestinal digestion, resulting in higher bioaccessibility. The aforementioned results suggest that SBNP-stabilized Pickering W/O/W emulsions could be a potential alternative to co-encapsulate betanin and curcumin with enhancement of shelf stability and bioaccessibility.


Assuntos
Beta vulgaris/química , Betacianinas/química , Curcumina/química , Pectinas/química , Extratos Vegetais/química , Soroalbumina Bovina/química , Animais , Betacianinas/farmacologia , Disponibilidade Biológica , Bovinos , Sobrevivência Celular/efeitos dos fármacos , Curcumina/farmacologia , Digestão , Composição de Medicamentos , Emulsões/química , Humanos , Nanopartículas/química , Tamanho da Partícula
12.
Crit Rev Eukaryot Gene Expr ; 30(2): 169-189, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32558495

RESUMO

Currently, the demand for natural colorants is increasing instead of synthetic colorants for foodstuff, because they are harmless to human health. Betalain is group of compounds containing nitrogen and water soluble pigment. Betalain is classified into two main classes, betacyanin which is the condensation of betalamic acid with cyclo-DOPA and betaxanthin which is the conjugation of amino acid or amines with betalamic acid. They are used to color various foods and medicines. Betalain is different from anthocyanin because betalains contain nitrogen in their structures. It is interesting to hear that betalains and anthocyanins are individually significant but they have not seen together in the same plant. Their stability influenced by various factors such as, temperature, pH, water activity and light. In this review basic chemistry of betalains, classes, subclasses, their sources and biosynthesis, factors affecting their stability, health and food industry applications are discussed. Moreover, mentioned work signifies the potent anticancer, antioxidant and antimalarial activities of betalains, furthermore provides a help to do more scientific work on it.


Assuntos
Antimaláricos/química , Antioxidantes/química , Betalaínas/química , Corantes de Alimentos/química , Antimaláricos/metabolismo , Antimaláricos/uso terapêutico , Antioxidantes/metabolismo , Antioxidantes/uso terapêutico , Betacianinas/química , Betacianinas/metabolismo , Betalaínas/biossíntese , Betalaínas/uso terapêutico , Di-Hidroxifenilalanina/química , Di-Hidroxifenilalanina/genética , Corantes de Alimentos/uso terapêutico , Humanos , Ácidos Picolínicos/química , Ácidos Picolínicos/metabolismo , Piridinas/química
13.
Biomed Res Int ; 2020: 7579430, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32185218

RESUMO

BACKGROUND: Barbary fig (Opuntia spp), called prickly pear, is a cultivated species belonging to family Cactaceae. It produces fruits one time per year during a short season. It is largely spreading in the Mediterranean countries. The aim of the study was to investigate the physicochemical and biochemical analysis of powder of prickly pear fruit peels of three Moroccan varieties (Aakria, Derbana, and Mles). Material and Methods. Both physicochemical analysis (humidity, water activity, Brix, ash content, pH, and total titratable acidity) and biochemical analysis (total carotenoid content, betalain content, total polyphenolic content, and ascorbic acid content) were effectuated according to protocols reported within the present research work. RESULTS: Regarding the physiochemical analysis, the humidity of powder of prickly pear fruit peels ranged from 10.173 ± 0.002 to 15.27 ± 0.02%. The water activity (aw) ranged from 0.17 ± 0.002 to 0.336 ± 0.002. The values of Brix ranged from 68.67 ± 0.33 to 74.22 ± 0.51° Bx. pH values ranged from 5.41 ± 0.01 to 5.62 ± 0.01. The total titratable acidity values ranged from 0.644 ± 0.014 to 0.76 ± 0.007 g citric acid/100 g DM (dry matter). The ash content ranged from 1.02 ± 0.02 to 11.41 ± 0.03 g/100 g DM. Regarding the biochemical analysis, the total carotenoid content ranged from 5.14 ± 0.10 to 9.79 ± 0.06 mg/g of FM (Fresh matter). The total betalain content ranged from 2 ± 0.69 to 37.66 ± 2.65 mg/100 g of DM. The total polyphenolic content ranged from 1739.92 ± 13.69 to 2409.66 ± 43.65 mg gallic acid equivalent (GAE)/100 g of DM. The ascorbic content values ranged from 186.78 ± 13.23 to 294.04 ± 5.81 mg/100 g of DM. CONCLUSION: The results showed an interesting richness of the investigated powder in pigments (betacyanins, indicaxanthins, and carotenoids) and nutritional compounds including sugar, proteins, and vitamins that make this powder interesting for being used as a dye in food.


Assuntos
Corantes/química , Frutas/química , Opuntia/química , Pigmentos Biológicos/química , Antioxidantes/química , Ácido Ascórbico/química , Betacianinas/química , Carotenoides/química , Clima , Fenóis/química , Extratos Vegetais/química , Pós/química , Pyrus , Estresse Fisiológico/fisiologia
14.
Molecules ; 24(3)2019 Jan 28.
Artigo em Inglês | MEDLINE | ID: mdl-30696032

RESUMO

Betanin is the only betalain approved for use in food and pharmaceutical products as a natural red colorant. However, the antioxidant power and health-promoting properties of this pigment have been disregarded, perhaps due to the difficulty in obtaining a stable chemical compound, which impairs its absorption and metabolism evaluation. Herein, betanin was purified by semi-preparative HPLC-LC/MS and identified by LC-ESI(+)-MS/MS as the pseudomolecular ion m/z 551.16. Betanin showed significant stability up to -30 °C and mild stability at chilling temperature. The stability and antioxidant ability of this compound were assessed during a human digestion simulation and ex vivo colon fermentation. Half of the betanin amount was recovered in the small intestine digestive fluid and no traces were found after colon fermentation. Betanin high antioxidant ability was retained even after simulated small intestine digestion. Betanin, besides displaying an inherent colorant capacity, was equally effective as a natural antioxidant displaying peroxy-radical scavenger ability in pork meat. Betanin should be considered a multi-functional molecule able to confer an attractive color to frozen or refrigerated foods, but with the capacity to avoid lipid oxidation, thereby preserving food quality. Long-term supplementation by beetroot, a rich source of betanin, should be stimulated to protect organisms against oxidative stress.


Assuntos
Betacianinas/química , Aditivos Alimentares/química , Antioxidantes/química , Antioxidantes/farmacologia , Betacianinas/isolamento & purificação , Betacianinas/farmacologia , Disponibilidade Biológica , Cromatografia Líquida de Alta Pressão , Estabilidade de Medicamentos , Aditivos Alimentares/isolamento & purificação , Aditivos Alimentares/farmacologia , Absorção Gastrointestinal , Humanos , Peroxidação de Lipídeos/efeitos dos fármacos , Conservantes Farmacêuticos/química , Conservantes Farmacêuticos/farmacologia , Espectrometria de Massas por Ionização por Electrospray , Espectrometria de Massas em Tandem
15.
Mater Sci Eng C Mater Biol Appl ; 97: 833-841, 2019 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30678974

RESUMO

Betanin (BET) can reduce the side effects of potent anticancer drugs e.g. doxorubicin (DOX) on the normal tissues in co-administration with them because of the synergistic therapeutic effect and consequently the reduced required amount of anticancer agents. Despite interest in the use of BET, incomplete oral absorption and low stability of BET limit its application. Thus, in this study to overcome the restrictions of BET and providing the synergistic effect of DOX@BET, we designed a new pH-responsive nanocarrier via decoration of gelatin nanoparticles (GNPs) by (methoxy poly (ethylene glycol)-poly ((2-dimethylamino) ethyl methacrylate-co-itaconic acid) (PGNPs). DOX and BET were effectively loaded (the loading capacity of 20.5% and 16.25%, respectively) into the PGNPs and this nanoplatform exhibited the suitable small particle size (162 nm). Additionally, the triggered release ability of drugs was studied through the assessment of simulated physiological and tumor tissue environments and showed the controlled release of DOX and BET with adjusting the pH of environment. Moreover, the synergistic effect of DOX@BET loaded PGNPs decreased the cell viability amount of breast cancer cells (MCF-7) respect to the free form of DOX or BET which indicated that the developed smart nanocarrier will be a hopeful nanocarrier for cancer therapy.


Assuntos
Antineoplásicos/química , Betacianinas/química , Doxorrubicina/química , Portadores de Fármacos/química , Gelatina/química , Nanopartículas/química , Polietilenoglicóis/química , Antineoplásicos/farmacologia , Apoptose/efeitos dos fármacos , Betacianinas/farmacologia , Sobrevivência Celular/efeitos dos fármacos , Doxorrubicina/farmacologia , Sinergismo Farmacológico , Humanos , Concentração de Íons de Hidrogênio , Células MCF-7 , Microscopia de Fluorescência , Tamanho da Partícula
16.
J Agric Food Chem ; 66(48): 12815-12826, 2018 Dec 05.
Artigo em Inglês | MEDLINE | ID: mdl-30415538

RESUMO

Formation of glutathionic conjugates with quinonoid forms generated through oxidation of betanidin and gomphrenin obtained from fruits of Basella alba L. was studied by high-performance liquid chromatography coupled with triple quadrupole tandem mass spectrometry (HPLC-DAD-ESI-MS/MS) and ion-trap time-of-flight high-resolution mass spectrometry (LCMS-IT-TOF). The conjugates were studied for the aim of trapping the formed quinonoids by glutathione which would indicate a presence of specific quinonoid structures in reaction products of the pigments with 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) cation radicals. The structure of betanidin conjugate, which was formed with high efficiency, was established by NMR analysis. In the case of gomphrenin conjugate, its structure was tentatively indicated as analogous to betanidin conjugate by MS n fragmentation paths. In contrast, no detectable glutathionic conjugate of betanin quinonoid (quinone methide) was present in similar betanin reaction mixtures. As a result of additional experiments performed during oxidation of gomphrenin by ABTS cation radicals in the absence of glutathione, except for decarboxylated and dehydrogenated gomphrenin derivatives, generation of betanidin and its derivatives was observed which indicated that the subsequent dopachromic intermediate rearrangement affected hydrolysis of the glucosidic bond. This is in contrast to betanin which is not deglucosylated in the same conditions during the oxidation. The obtained results shed some light on the oxidation pathways of various glycosylated betacyanins with gomphrenin being presumably the most potent antioxidant ascertained in this group of pigments.


Assuntos
Betacianinas/química , Caryophyllales/química , Glutationa/química , Extratos Vegetais/química , Antioxidantes/química , Betalaínas/química , Cromatografia Líquida de Alta Pressão , Frutas/química , Glicosilação , Estrutura Molecular , Oxirredução , Espectrometria de Massas em Tandem
17.
Talanta ; 181: 210-216, 2018 May 01.
Artigo em Inglês | MEDLINE | ID: mdl-29426503

RESUMO

Deep eutectic solvent (DES) composed of polypropylene glycol 400 (PPG 400) and tetrabutylammonium bromide (TBAB) was combined with a series of new-type salts such as quaternary ammonium salts, amino acid and polyols to form Aqueous Biphasic Systems (ABSs). Phase-forming ability of the salts was investigated firstly. The results showed that polyols had a relatively weak power to produce phases within studied scopes. And the shorter of carbon chain length of salts, the easier to obtain phase-splitting. Then partitioning of three pigments in PPG 400/betaine-based ABSs was addressed to investigate the effect of pigments' hydrophobicity on extraction efficiency. It was found that an increase in hydrophobicity contributed to the migration of pigments in the DES-rich phase. On the other hand, with a decline in phase-forming ability of salts, the extraction efficiency of the whole systems started to go down gradually. Based on the results, selective separation experiment was conducted successfully in the PPG 400/betaine-based systems, including more than 93.00% Sudan Ⅲ in the top phase and about 80.00% sunset yellow FCF/amaranth in the bottom phase. Additionally, ABSs constructed by DES/betaine for partitioning amaranth were further utilized to explore the performances of influence factors and back extraction. It can be concluded that after the optimization above 98.00% amaranth was transferred into the top phase. And 67.98% amaranth can be transferred into the bottom phase in back-extraction experiment. At last, dynamic light scattering (DLS) and transmission electron microscope (TEM) were applied to probe into extraction mechanism. The results demonstrated that hydrophobicity played an important role in the separation process of pigments. Through combining with new-type DES, this work was devoted to introducing plentiful salts as novel compositions of ABSs and providing an eco-friendly extraction way for partitioning pigments, which boosted development of ABSs in the monitoring food safety field.


Assuntos
Corantes/química , Corantes/isolamento & purificação , Sais/química , Solventes/química , Alcanos/química , Compostos Azo/química , Compostos Azo/isolamento & purificação , Betacianinas/química , Betacianinas/isolamento & purificação , Interações Hidrofóbicas e Hidrofílicas , Microscopia Eletrônica de Transmissão , Polímeros/química , Propilenoglicóis/química , Compostos de Amônio Quaternário/química , Reprodutibilidade dos Testes
19.
Biomed Pharmacother ; 88: 1069-1079, 2017 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-28192880

RESUMO

Betanin, a chromoalkaloid of beetroot, has shown significant biological effects of antioxidants, anti-inflammatory and anticarcinogenic activities. So, we attempted to determine whether betanin (a natural pigment) would be protective against hyperglycemia in streptozotocin (STZ) - nicotinamide (NA) induced diabetic rats. Rats were injected with STZ (40mg/kgb.w.) 15 mins after the administration of NA (110mg/kgb.w.) by intraperitonially (i.p.) 30days for the induction of experimental diabetes mellitus. After 72h diabetic rats were treated with betanin orally at a doses of 10, 20 and 40mg/kg b.w., respectively in a dose dependent manner and glibenclamide (600µg/kgb.w.). The promising character of betanin against diabetic rats was evaluated by performing the various biochemical parameters and histomorphological changes in liver and pancreas. Among the three doses, 20mg/kgb.w. of betanin was able to positively regulate plasma glucose, insulin, glycosylated hemoglobin (HbA1c) and hemoglobin (Hb) levels by significantly increasing the activity of glycolytic enzyme (glucokinase and pyruvate kinase), glucose-6-phosphate dehydrogenase and significantly decreasing the activity of gluconeogenic enzymes (glucose-6-phosphatase and fructose-1,6-bisphosphatase) thereby increasing the glycogen content in the liver. We put forward that betanin could significantly restore the levels of carbohydrate metabolic key enzymes to near normal in diabetic rat. Immunohistochemical observation of pancreas revealed that betanin treated diabetic rats showed increased insulin immunoreactive ß-cells, which confirmed the biochemical findings. Taken together, present study suggests that betanin modulates the carbohydrate metabolism and has beneficial effects in glucose homeostasis.


Assuntos
Betacianinas/uso terapêutico , Metabolismo dos Carboidratos , Diabetes Mellitus Experimental/tratamento farmacológico , Diabetes Mellitus Experimental/enzimologia , Glicogênio/metabolismo , Fígado/enzimologia , Animais , Betacianinas/química , Betacianinas/farmacologia , Biomarcadores/metabolismo , Glicemia/metabolismo , Peso Corporal/efeitos dos fármacos , Metabolismo dos Carboidratos/efeitos dos fármacos , Diabetes Mellitus Experimental/sangue , Comportamento Alimentar/efeitos dos fármacos , Teste de Tolerância a Glucose , Hemoglobinas Glicadas/metabolismo , Glicólise/efeitos dos fármacos , Imuno-Histoquímica , Insulina/sangue , Lipogênese/efeitos dos fármacos , Fígado/efeitos dos fármacos , Fígado/patologia , Masculino , Modelos Biológicos , Niacinamida , Tamanho do Órgão/efeitos dos fármacos , Ratos Wistar , Estreptozocina
20.
Food Chem ; 216: 324-33, 2017 Feb 01.
Artigo em Inglês | MEDLINE | ID: mdl-27596427

RESUMO

Red beetroot (RB) powder was incorporated into starch-based bio-elastomers to obtain flexible biocomposites with tunable antioxidant properties. Starch granules within the bio-elastomers affected the release of the antioxidant molecule betanin in the RB powder. The bio-elastomers were hydrophobic and resisted dissolution in water, hence the release of betanin was due to diffusion rather than polymer matrix disintegration. Hydrophobicity was maintained even after water immersion. Released betanin demonstrated highly efficient antioxidant scavenging activity against 2,2-diphenyl-1-picrylhydrazyl free radical (DPPH) and 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS(+)). RB powder was also found to increase the Young's modulus of the bio-elastomers without compromising their elongation ability. Infrared spectral analysis indicated weak interactions through hydrogen bonding among starch granules, RB powder and PDMS polymer within the bio-elastomers. Hence, as a simple but intelligent biomaterial consisting of mainly edible starch and RB powder the present bio-elastomers can be used in active packaging for a variety of pharmaceutical, medical, and food applications.


Assuntos
Beta vulgaris/química , Betacianinas/química , Elastômeros/química , Preparações de Plantas/química , Amido/química , Antioxidantes/química , Benzotiazóis/química , Compostos de Bifenilo/química , Radicais Livres/química , Oxirredução , Picratos/química , Raízes de Plantas/química , Ácidos Sulfônicos/química
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