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1.
Food Chem ; 302: 125347, 2020 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-31430631

RESUMO

This work aims to prolong the storage stability of polyphenols, obtained from grape pomace, using a spray drying-based microencapsulation technique. The microcapsules obtained under optimal conditions were stored at two different relative humidities (33% and 52%) during 75 days. The analyses of total phenolic content, antioxidant activity, and individual phenolic compounds were carried out every 15 days, and the most stable microcapsules were achieved with maltodextrin DE4-7 prepared by adding gum Arabic to the wall material at a ratio of 8:2. The phenolic content loss rate was found to be in a range of 0.93-5.42 % depending on phenolic compound. The decrease in the content of rutin, chlorogenic acid, epicatechin, caffeic acid, gallic acid, caftaric acid and catechin was only 0.93, 2.09, 2.13, 2.27, 2.41, 3.40 and 5.42%, respectively. These results indicate more efficient storage conditions than those of previously reported studies.


Assuntos
Cápsulas/química , Armazenamento de Alimentos , Polifenóis/química , Vitis/química , Antioxidantes/análise , Antioxidantes/química , Catequina/análise , Catequina/química , Ácido Clorogênico/análise , Ácido Clorogênico/química , Composição de Medicamentos/métodos , Goma Arábica/química , Umidade , Fenóis/análise , Fenóis/química , Extratos Vegetais/química , Polifenóis/análise , Polissacarídeos/química , Rutina/análise , Rutina/química
2.
J Agric Food Chem ; 67(40): 11108-11118, 2019 Oct 09.
Artigo em Inglês | MEDLINE | ID: mdl-31496243

RESUMO

A blood glucose level lowering effect is postulated for polyphenols (PPs), which is in part attributed to the inhibition of α-amylase. To estimate structure-effect relationships, chlorogenic acid (CA), phlorizin (PHL), epigallocatechin gallate (EGCG), epicatechin (EC), and malvidin-3-glucoside (Mlv-3-glc) were used as inhibitors in an enzyme assay, on the basis of the conversion of GalG2CNP by α-amylase. The detection of CNP was performed by UV/vis spectroscopy. The data reveal that the inhibitor strength decreases as follows: EGCG > Mlv-3-glc > EC > PHL ∼ CA. Detection of the substrate conversion by isothermal titration calorimetry supports these results. All PPs showed mixed inhibition, except for CA and EGCG wherein the competitive proportion was predominant. Investigations by saturation transfer difference NMR revealed interaction of PPs with α-amylase prevalently based on interactions with the aromatic or conjugated system. A correlation between the extent of the conjugated system and the IC50 of the PP could be found.


Assuntos
Antocianinas/química , Catequina/análogos & derivados , Catequina/química , Ácido Clorogênico/química , Inibidores Enzimáticos/química , Glucosídeos/química , alfa-Amilases Pancreáticas/antagonistas & inibidores , Florizina/química , Animais , Calorimetria , alfa-Amilases Pancreáticas/química , Suínos
3.
Chem Pharm Bull (Tokyo) ; 67(9): 1006-1014, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31474723

RESUMO

Chlorogenic acid (CGA) has been considered as one of important active components in a number of medicinal herbs. Recently our group demonstrated that caffeoyl salicylate scaffold derived from CGA can be employed for the development of novel anti-inflammatory agents. The most active compound D104 can be a very promising starting point for the further structural optimization. A series of novel caffeoyl salicylate analogs were designed, synthesized, and evaluated by preliminary biological evaluation. The obtained results showed that the two compounds B12 and B13 can not only inhibit production of nitric oxide (NO) in RAW264.7 cells induced by lipopolysaccharides (LPS) effectively, but also have high safety in in vitro cytotoxic test, which could be comparable with D104. Molecular docking study on the peroxisome proliferator-activated receptor γ (PPARγ) protein revealed that compounds B12 and B13 can follow the same binding mode with D104, and the carboxyl group of caffeoyl salicylate scaffold might play a key role in the interaction with protein target, which implied the carboxyl group should be retained in the further optimization.


Assuntos
Ácido Clorogênico/química , Óxido Nítrico/metabolismo , Ácido Salicílico/química , Células A549 , Animais , Sítios de Ligação , Sobrevivência Celular/efeitos dos fármacos , Ácido Clorogênico/farmacologia , Humanos , Lipopolissacarídeos/farmacologia , Macrófagos/citologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , PPAR gama/química , PPAR gama/metabolismo , Estrutura Terciária de Proteína , Células RAW 264.7
4.
J Agric Food Chem ; 67(35): 9934-9941, 2019 Sep 04.
Artigo em Inglês | MEDLINE | ID: mdl-31402655

RESUMO

A fluorescence microscopic method for characterizing size, quantity, and oxidation of lipid droplets (LDs) in HepG2 cells was developed. LDs were induced by palmitic (PA), oleic (OA), or linoleic acids (LA) and stained with two fluorescent probes for neutral lipids and lipid peroxides. Each fatty acid increased the number of LDs and oxidized LDs (oxLDs) and the degree of LD oxidation time dependently, as well as increased intracellular triglyceride hydroperoxides. LDs induced by LA without 2,2'-azobis(2-amidinopropane)dihydrochloride (AAPH) showed the most significant oxidation degree over PA and OA, especially in large LDs (area ≥ 3 µm2, oxLD/LD = 52.3 ± 21.7%). Under this condition, two food-derived antioxidants were evaluated, and both of them significantly improved the LD characteristics. Moreover, chlorogenic acid reduced the quantity of large LDs by 74.0-87.6% in a dose-dependent manner. The proposed method provides a new approach to evaluate the effect of dietary antioxidants on LD characteristics.


Assuntos
Antioxidantes/metabolismo , Hepatócitos/química , Hepatócitos/metabolismo , Gotículas Lipídicas/metabolismo , Microscopia de Fluorescência/métodos , Antioxidantes/química , Ácido Clorogênico/química , Ácido Clorogênico/metabolismo , Fluorescência , Células Hep G2 , Humanos , Gotículas Lipídicas/química , Oxirredução
5.
Food Chem ; 298: 125024, 2019 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-31261007

RESUMO

We investigated the allergenicity, digestibility and functional properties of whey protein isolate (WPI) after covalent conjugation with chlorogenic acid (CHA). The covalent conjugation of CHA may cause an unfolded protein structure. The WPI-CHA conjugate showed lower IgE binding capacity but higher intestinal digestibility than unmodified WPI. Furthermore, after digestion, the IgE binding capacity of ß-lactoglobulin and α-lactoalbumin was lower in the digested WPI-CHA conjugate than digested WPI. Moreover, the solubility, emulsifying activity, foaming properties and antioxidant capacity of WPI were enhanced by covalent conjugation of CHA. Covalent conjugation with CHA might reduce the allergenicity in vitro of WPI by improving the functional properties of the protein.


Assuntos
Alérgenos/imunologia , Proteínas do Soro do Leite/química , Proteínas do Soro do Leite/imunologia , Alérgenos/química , Ácido Clorogênico/química , Digestão , Emulsões/química , Lactoglobulinas/química , Solubilidade
6.
J Sci Food Agric ; 99(14): 6644-6648, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31325326

RESUMO

BACKGROUND: Apple juice is rich in polyphenolic compounds, especially in chlorogenic acid. A sour and bitter taste has been attributed to the compound. Chlorogenic acid in coffee powder was quickly hydrolysed by a p-coumaryl esterase of Rhizoctonia solani (RspCAE) at its optimal pH of 6.0. It was unknown, however, if RspCAE would also degrade chlorogenic acid under the strongly acidic conditions (pH 3.3) present in apple juice. RESULTS: Treatment of apple juice with RspCAE led to a chlorogenic acid degradation from 53.38 ± 0.94 mg L-1 to 21.02 ± 1.47 mg L-1 . Simultaneously, the caffeic acid content increased from 6.72 ± 0.69 mg L-1 to 19.33 ± 1.86 mg/L-1 . The aroma profile of the enzymatically treated sample and a control sample differed in only one volatile. Vitispirane had a higher flavour dilution factor in the treated juice. Sensory analysis showed no significant difference in the taste profile ( p < 0.05). CONCLUSION: These results demonstrated a high stability and substrate specificity of RspCAE. An increase in caffeic acid and a concurrent decrease in chlorogenic acid concentration may exert a beneficial effect on human health. © 2019 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.


Assuntos
Ácido Clorogênico/química , Esterases/química , Sucos de Frutas e Vegetais/análise , Proteínas Fúngicas/química , Malus/química , Rhizoctonia/enzimologia , Aromatizantes/química , Concentração de Íons de Hidrogênio , Hidrólise , Odorantes/análise , Especificidade por Substrato
7.
Food Chem ; 293: 550-560, 2019 Sep 30.
Artigo em Inglês | MEDLINE | ID: mdl-31151647

RESUMO

Green coffee beans are rich in polyphenol chlorogenic acids (CGAs), which are decomposed to give caffeic acid (CFA) and quinic acid (QNA) upon roasting. CGA, CFA and QNA primarily confer the bitterness, astringency and acidity to the coffee brew. Aiming at the structural and thermodynamic insights into the ß-cyclodextrin (ß-CD) encapsulation of key compounds in coffee (CGA 1, CFA 2, and QNA 3), a systematic, comprehensive study using single-crystal X-ray diffraction and DFT calculation has been undertaken. Scrutinizing the X-ray-derived inclusion structures of 1-3 reveals that the CFA moiety plays a determinant role in complexation, in agreement with the DFT-derived relative thermodynamic stabilities. The guest molecules gain stability through OH⋯O hydrogen bonding with ß-CD and are well shielded in the ß-CD wall. The three stable ß-CD inclusion complexes with coffee key compounds suggest the implications of CDs as encapsulating agents for improving bioactivities and masking bitter taste in foods.


Assuntos
Antioxidantes/química , Ácidos Cafeicos/química , Ácido Clorogênico/química , Café/química , Ácido Quínico/química , Paladar/fisiologia , beta-Ciclodextrinas/química , Química Farmacêutica , Cristalografia por Raios X , Teoria da Densidade Funcional , Ligações de Hidrogênio , Termodinâmica
8.
Chem Biodivers ; 16(8): e1900250, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31250533

RESUMO

Taraxacum kok-saghyz (TKS) is a dandelion species native to Kazakhstan, Uzbekistan and north-west China, considered as a promising alternative source of natural rubber from its roots. The aim of this study was to investigate the possible exploitation of TKS leaves, a rubber byproduct, as a source of phenolic compounds with antioxidant properties for potential applications in forage, nutraceutical and pharmacological fields. Two accessions (TKS016, TKS018) grown under Mediterranean conditions of Sardinia were evaluated at vegetative and flowering stages. The leaves of TKS018 had the highest antioxidant capacity (19.6 mmol trolox equivalent antioxidant capacity 100 g-1 ), total phenolic (106.4 g gallic acid equivalent kg-1 ), tannic phenolics (58.5 g gallic acid equivalent kg-1 ) and total flavonoid contents (22.9 g catechin equivalent kg-1 ). At both phenological stages, TKS016 showed significantly lower values than TKS018 in 1,1-diphenyl-2-picrylhydrazyl (DPPH), total phenolic and tannic phenolics. Six individual molecules were identified, namely chlorogenic, cryptochlorogenic, caffeic, sinapic, chicoric and 3,4-dimethoxycinnamic acids. Chicoric (8.53-10.68 g kg-1 DW) and chlorogenic acids (4.18-7.04 g kg-1 DW) were the most abundant. TKS leaves represent a valuable source of chicoric acid with potential application as antioxidant to be used as herbal medicine and nutrition for production of healthy food/feed.


Assuntos
Antioxidantes/química , Taraxacum/química , Ácidos Cafeicos/química , Ácido Clorogênico/química , Cromatografia Líquida de Alta Pressão , Flavonoides/química , Fenóis/análise , Fenóis/química , Folhas de Planta/química , Folhas de Planta/metabolismo , Federação Russa , Succinatos/química , Taraxacum/metabolismo
9.
Bol. latinoam. Caribe plantas med. aromát ; 18(3): 223-238, mayo 2019. ilus
Artigo em Inglês | LILACS | ID: biblio-1007927

RESUMO

Plants of the genera Werneria (Asteraceae) and Xenophyllum (genus extracted from Werneria) are used in traditional medicine of Latin America for the treatment of mountain sickness, hypertension and gastrointestinal disorders. Only a small number of species of these genera have been studied, leading to the isolation of compounds belonging to the classes of benzofurans, chromenes, acetophenones, coumarates, diterpenes and pyrrolizidine alkaloids. Some of the plant extracts and/or compounds have shown antimicrobial, anti-HIV, hypotensive and photoprotective activities.


Las plantas de los géneros Werneria (Asteraceae) y Xenophyllum (género extraido de Werneria) son usadas en la medicina tradicional de América Latina para el tratamiento del mal de montaña, hipertensión y desórdenes gastrointestinales. Solo un pequeño número de especies de estos géneros ha sido investigado, lográndose aislar compuestos que pertenecen a las clases de benzofuranos, cromenos, acetofenonas, cumaratos, diterpenos y alcaloides pirrolizidínicos. Algunos de los extractos y/o compuestos de dichas plantas han mostrado actividades antimicrobianas, anti-HIV, hipotensoras y fotoprotectoras.


Assuntos
Plantas Medicinais/química , Extratos Vegetais/uso terapêutico , Asteraceae/química , Acetofenonas/química , Terpenos/análise , Benzopiranos/química , Flavonoides/química , Ácido Clorogênico/química , Ácidos Cumáricos/química , Alcaloides/química , Doença da Altitude/tratamento farmacológico , Hipertensão/tratamento farmacológico , Medicina Tradicional
10.
Biomed Res Int ; 2019: 6769789, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31139644

RESUMO

Objective: Observe the protective effect of chlorogenic acid on dextran sulfate-induced ulcerative colitis in mice and explore the regulation of MAPK/ERK/JNK signaling pathway. Methods: Seventy C57BL/6 mice (half males and half females) were randomly divided into 7 groups, 10 in each group: control group (CON group), UC model group (UC group), and sulfasalazine-positive control group (SASP group), chlorogenic acid low dose group (CGA-L group), chlorogenic acid medium dose group (CGA-M group), chlorogenic acid high dose group (CGA-H group), and ERK inhibitor + chlorogenic acid group (E+CGA group). The effects of chlorogenic acid on UC were evaluated by colon mucosa damage index (CMDI), HE staining, immunohistochemistry, ELISA, and Western blot. The relationship between chlorogenic acid and MAPK/ERK/JNK signaling pathway was explored by adding ERK inhibitor. Results: The UC models were established successfully by drinking DSS water. Chlorogenic acid reduces DSS-induced colonic mucosal damage, inhibits DSS-induced inflammation, oxidative stress, and apoptosis in colon, and reduces ERK1/2, p -ERK, p38, p-p38, JNK, and p-JNK protein expression. ERK inhibitor U0126 reversed the protective effect of chlorogenic acid on colon tissue. Conclusion: Chlorogenic acid can alleviate DSS-induced ulcerative colitis in mice, which can significantly reduce tissue inflammation and apoptosis, and its mechanism is related to the MAPK/ERK/JNK signaling pathway.


Assuntos
Ácido Clorogênico/uso terapêutico , Colite Ulcerativa/tratamento farmacológico , Colite Ulcerativa/enzimologia , Sistema de Sinalização das MAP Quinases , Animais , Apoptose , Ácido Clorogênico/química , Ácido Clorogênico/farmacologia , Colite Ulcerativa/induzido quimicamente , Colo/patologia , Sulfato de Dextrana , Feminino , Inflamação/complicações , Inflamação/patologia , Mucosa Intestinal/patologia , Masculino , Camundongos Endogâmicos C57BL , Estresse Oxidativo/efeitos dos fármacos
11.
Artigo em Inglês | MEDLINE | ID: mdl-31078127

RESUMO

The optimization of electrolytes, kinds and concentrations, in mobile phase for multiple constituents analyzing using high-performance liquid chromatography-electrospray ionization tandem mass spectrometry (HPLC-ESI-MS) was usually compromised to ensure good LC separation of partial components. However, the compromised electrolytes could lead to ionization suppression of some of the analytes. To solve the compromise of electrolytes within various components, taking phenolic acids and iridoids as a case, we used electrolyte switch in contiguous running time segments of UPLC-ESI-MS/MS to ensure chromatographic separation of chlorogenic acid, neochlorogenic acid and cryptochlorogenic acid and improve the response of geniposide. Then the method was applied for pharmacokinetic study of the four components in rat after inhaling Reduning aerosol for the first time. The complete separation of the three chlorogenic acid isomers was achieved and the LLOQs of neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid, and geniposide were 1, 1, 3, and 0.2 ng/mL, respectively. In conclusion, we developed a sensitive and time-saving LC-MS/MS method for the quantitative analysis of chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, and geniposide in rat plasma, and this method appears to be useful for pharmacokinetic studies of Reduning aerosol. The method provided a sight to alleviate compromise of electrolytes in mobile phase for HPLC-ESI-MS in analyzing multi-components.


Assuntos
Ácido Clorogênico/sangue , Cromatografia Líquida/métodos , Medicamentos de Ervas Chinesas/administração & dosagem , Medicamentos de Ervas Chinesas/farmacocinética , Iridoides/sangue , Administração por Inalação , Aerossóis , Animais , Ácido Clorogênico/análogos & derivados , Ácido Clorogênico/química , Ácido Clorogênico/farmacocinética , Iridoides/química , Iridoides/farmacocinética , Masculino , Ratos , Ratos Sprague-Dawley , Espectrometria de Massas por Ionização por Electrospray/métodos , Espectrometria de Massas em Tandem/métodos
12.
Molecules ; 24(8)2019 Apr 24.
Artigo em Inglês | MEDLINE | ID: mdl-31022860

RESUMO

Carpesium divaricatum Sieb. & Zucc. has a long history of use as both a medicinal and a food plant. However, except for terpenoids, its chemical constituents have remained poorly investigated. The composition of hydroalcoholic extract from aerial parts of C. divaricatum was analyzed by HPLC-DAD-MSn, revealing the presence of numerous caffeic acid derivatives that were formerly unknown constituents of the plant. In all, 17 compounds, including commonly found chlorogenic acids and rarely occurring butyryl and methylbutyryl tricaffeoylhexaric acids, were tentatively identified. Fractionation of lipophilic extract from cultivated shoots led to the isolation of 12-oxo-phytodienoic acid (12-OPDA), which is a newly identified constituent of the plant. The compound, at concentrations of 0.5, 1.0, and 2.5 µM, significantly reduced IL-8, IL-1ß, TNFα, and CCL2 excretion by lipopolysaccharide (LPS)-stimulated human neutrophils. Reactive oxygen species (ROS) production induced by f-MLP was also significantly diminished in the neutrophils pretreated by 12-OPDA. The newly identified constituents of the plant seem to be partly responsible for its pharmacological activity and elevate the value of C. divaricatum as a potential functional food.


Assuntos
Asteraceae/química , Ácidos Cafeicos/química , Ácido Clorogênico/química , Ácidos Graxos Insaturados/química , Ácidos Cafeicos/isolamento & purificação , Ácidos Cafeicos/farmacologia , Quimiocina CCL2/genética , Ácido Clorogênico/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Ácidos Graxos Insaturados/isolamento & purificação , Ácidos Graxos Insaturados/farmacologia , Regulação da Expressão Gênica/efeitos dos fármacos , Humanos , Interleucina-8/genética , Lipopolissacarídeos/farmacologia , Neutrófilos/efeitos dos fármacos , Componentes Aéreos da Planta/química , Brotos de Planta/química , Espécies Reativas de Oxigênio/química , Fator de Necrose Tumoral alfa/genética
13.
Mater Sci Eng C Mater Biol Appl ; 100: 837-844, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-30948121

RESUMO

New organic-inorganic hybrid materials were synthesized by an acid catalysed sol-gel approach, using silicon alkoxide and low molecular weight polyethylene glycol (PEG400) as inorganic and organic precursor, respectively. Chlorogenic acid (CGA), an antioxidant natural phenol compound, enriched further the organic component. Hybrids synthesized, all identical in terms of their starting materials, but differing in terms of their relative proportions, were characterized by means of Fourier Transform InfraRed (FTIR) measurements, UV-Vis spectroscopy, and UHPLC-HRMS analysis. The preservation of the intrinsic chlorogenic acid ability to scavenge, in a dose-dependent manner, radical species was investigated by directly exposing the hybrids to DPPH radical and ABTS radical cation. The relative ratio of both the natural compound and PEG heavily affected the antiradical response, suggesting that chemical interactions in the established network were able, based on components' ratio, to differently mask and/or display the CGA moieties, commonly deemed relevant for antioxidant power exerting. Cell culture MTT assay was used to assess the biocompatibility of hybrid materials towards fibroblast NIH-3 T3 cells and neuroblastoma SH-SY5Y cells. Cells tested appeared differently responsive. In particular, a marked cell viability increase was observed when hybrids with low PEG amount (6%) and high CGA (15%) were directly exposed to fibroblast cells, whose mitochondrial redox activity was negatively affected by hybrid synthesized using the highest organic component rate (both PEG and CGA). Cell viability and morphology of human neuroblastoma SH-SY5Y cells were broadly compromised regardless of organic/inorganic starting materials ratio, suggesting the ability of hybrids to exert pro-oxidant effect towards tumour cells and to selectively interfere with their growth. The hybrids, able to elicit cleverly anti- or proliferative effects, were also shown to be bioactive. In fact, a biologically active hydroxyapatite layer was observed to be formed on the surface of the smart synthesized materials. This feature, which makes them a valuable bonding interface with tissues, opens new scenario aiming at further investigating the employment of natural phenol compounds in versatile sol-gel synthesis routes.


Assuntos
Materiais Biocompatíveis/síntese química , Ácido Clorogênico/química , Transição de Fase , Polietilenoglicóis/química , Animais , Materiais Biocompatíveis/química , Linhagem Celular Tumoral , Forma Celular , Sobrevivência Celular , Humanos , Camundongos , Células NIH 3T3 , Dióxido de Silício/química , Espectroscopia de Infravermelho com Transformada de Fourier , Difração de Raios X
14.
Phytochemistry ; 163: 1-10, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-30974396

RESUMO

Herein, five polyphenol oxidases (PPOs) obtained from Morus notabilis (Mn) were characterized. Chlorogenic acid was the most readily oxidized substrate by these MnPPOs, and the products derived from the oxidation of chlorogenic acid by MnPPOs were tested for antimicrobial activity. The results showed that products of the five MnPPOs exhibited good inhibitory effects against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Sclerotinia sclerotiorum, and Botrytis cinerea. Because the products of MnPPO1 exhibited the strongest antimicrobial activity, the antimicrobial mechanism of these products was explored. The results showed that the products of MnPPO1 increased cell membrane permeability and chitinase and ß-1,3-glucanase activities.


Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Catecol Oxidase/metabolismo , Ácido Clorogênico/farmacologia , Morus/química , Morus/enzimologia , Sequência de Aminoácidos , Antibacterianos/química , Antibacterianos/metabolismo , Antifúngicos/química , Antifúngicos/metabolismo , Ascomicetos/efeitos dos fármacos , Botrytis/efeitos dos fármacos , Catecol Oxidase/genética , Ácido Clorogênico/química , Ácido Clorogênico/metabolismo , Escherichia coli/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Pseudomonas aeruginosa/efeitos dos fármacos , Alinhamento de Sequência , Staphylococcus aureus/efeitos dos fármacos
15.
Pharm Res ; 36(6): 91, 2019 Apr 24.
Artigo em Inglês | MEDLINE | ID: mdl-31020429

RESUMO

BACKGROUND: The chemotherapy of cancer has been complicated by poor bioavailability, adverse side effects, high dose requirement, drug resistance and low therapeutic indices. Cancer cells have different ways to inhibit the chemotherapeutic drugs, use of dual/multiple anticancer agents may be achieve better therapeutic effects in particular for drug resistant tumors. Designing a biocompatible delivery system, dual or multiple drugs could addressing these chemotherapy drawbacks and it is the focus of many current biomedical research. METHODS: In the present study, graphene oxide-polyethylene glycol (GOPEG) nanocarrier is designed and loaded with two anticancer drugs; Protocatechuic acid (PCA) and Chlorogenic acid (CA). The designed anticancer nanocomposite was further coated with folic acid to target the cancer cells, as their surface membranes are overexpressed with folate receptors. RESULTS: The particle size distribution of the designed nanocomposite was found to be narrow, 9-40 nm. The release profiles of the loaded drugs; PCA and CA was conducted in human body simulated PBS solutions of pH 7.4 (blood pH) and pH 4.8 (intracellular lysosomal pH). Anticancer properties were evaluated against cancerous cells i.e. liver cancer, HEPG2 and human colon cancer, HT-29 cells. The cytocompatbility was assessed on normal 3T3 fibroblasts cells. CONCLUSION: The size of the final designed anticancer nanocomposite formulation, GOPEG-PCACA-FA was found to be distributed at 9-40 nm with a median of 8 nm. The in vitro release of the drugs PCA and CA was found to be of sustained manner which took more than 100 h for the release. Furthermore, the designed formulation was biocompatible with normal 3T3 cells and showed strong anticancer activity against liver and colon cancer cells.


Assuntos
Ácido Clorogênico/química , Portadores de Fármacos/química , Grafite/química , Hidroxibenzoatos/química , Nanopartículas/química , Polietilenoglicóis/química , Animais , Antineoplásicos/química , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Ácido Clorogênico/farmacologia , Liberação Controlada de Fármacos , Ácido Fólico/metabolismo , Humanos , Concentração de Íons de Hidrogênio , Hidroxibenzoatos/farmacologia , Nanocompostos/química , Tamanho da Partícula , Propriedades de Superfície
16.
J Pharm Biomed Anal ; 170: 83-88, 2019 Jun 05.
Artigo em Inglês | MEDLINE | ID: mdl-30909057

RESUMO

Flos Lonicerae Japonicae (FLJ), known as golden-and-silver honeysuckle, is a widely used Chinese herbal medicine with pharmacological activities and edibleness in China. Chlorogenic acid (CGA) and luteoloside are the quality control markers of FLJ regulated by the Chinese Pharmacopoeia (2015 edition). For rapid evaluation of the quality of FLJ, dipsticks for CGA and luteoloside detection were developed. The detection limit of the dipsticks for CGA and luteoloside, defined as the lowest concentration of the target analyte between which the test line was invisible, were 100 ng/mL and 200 ng/mL, respectively. The dipsticks were used for determination of CGA and luteoloside contents in FLJ, and the results were confirmed by high-performance liquid chromatography. The developed dipsticks, with their simplicity of use, lack of dependence on instruments and environmental friendliness, could be used to evaluate the quality of FLJ within 10 min.


Assuntos
Ácido Clorogênico/química , Glucosídeos/química , Coloide de Ouro/química , Imunoensaio/métodos , Lonicera/química , Luteolina/química , Extratos Vegetais/química , China , Cromatografia Líquida de Alta Pressão/métodos , Medicamentos de Ervas Chinesas/química , Flores/química , Controle de Qualidade
17.
Analyst ; 144(8): 2684-2695, 2019 Apr 08.
Artigo em Inglês | MEDLINE | ID: mdl-30855038

RESUMO

Herein, the CuO/ZnO@Fe3O4-carbon nanotubes (CNTs)-nanocomposite (NC), as a sorbent for magnetic dispersive micro-solid phase extraction, was developed for the determination of chlorogenic acid (CGA) in the medical extract of plants, food, and water samples in combination with high-performance liquid chromatography. The CuO/ZnO@Fe3O4-CNTs-NC was characterized by FESEM, EDS, XRD, TEM, BET, FT-IR, and VSM. Significant parameters (pH, temperature, eluent volume, vortex time, sonication time, CuO/ZnO@Fe3O4-CNTs-NC mass, and desorption time) that affected the extraction efficiency of CGA were optimized using Plackett-Burman as the screening design and the central composite design as the optimization strategy. Under the optimized conditions, the analytical parameters were obtained. The optimized method showed good linearity and a linear regression coefficient >0.9893. The enrichment factors ranged from 102.43 to 123.76 with the preconcentration factor of 60.0. The limits of detection (LOD) and the limits of quantification (LOQ) were 0.034-0.061 ng mL-1 and 0.114-0.202 ng mL-1, respectively. The method also reflected acceptable accuracy (from 94.07% to 109.7%) and the broad potential applications of CuO/ZnO@Fe3O4-CNTs-NC for the detection of CGA content in the medical extract of plants, food, and water samples.


Assuntos
Ácido Clorogênico/análise , Cobre/química , Óxido Ferroso-Férrico/química , Nanocompostos/química , Nanotubos de Carbono/química , Óxido de Zinco/química , Adsorção , Ácido Clorogênico/química , Água Potável/análise , Limite de Detecção , Magnoliopsida/química , Extratos Vegetais/análise , Microextração em Fase Sólida/métodos
18.
Food Chem ; 286: 51-63, 2019 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-30827640

RESUMO

This study presents unpublished data on the chlorogenic acid and caffeic acid content in fruits. Sixty-four fruits consumed in Brazil, most of which were produced domestically, were evaluated based on their levels of 3-caffeoylquinic acid, 4-caffeoylquinic acid, 5-caffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid and caffeic acid. The study investigated 15 fruits that have not been reported in the literature in relation to these compounds, including several native species. The highest concentration of mono-caffeoylquinic acid was observed in strawberry, cherry, bilberry, quince and mulberry, while the dicaffeoylquinic acid was present with highest concentration in kumquat, passion fruit and sweet granadilla. Regarding caffeic acid, the highest content was found in bilberry and yellow pitaya. Considering the sum of the concentrations of these compounds, quince, cherry, bilberry, mulberry and sweet granadilla were exceptional, with concentrations between 200.0 and 569.7 mg kg-1.


Assuntos
Ácidos Cafeicos/química , Ácido Clorogênico/química , Frutas/química , Brasil , Ácidos Cafeicos/análise , Ácido Clorogênico/análise , Cromatografia Líquida de Alta Pressão , Eugenia/química , Eugenia/metabolismo , Frutas/metabolismo , Análise de Componente Principal , Rosaceae/química , Rosaceae/metabolismo , Vaccinium myrtillus/química , Vaccinium myrtillus/metabolismo
19.
J Agric Food Chem ; 67(14): 4023-4030, 2019 Apr 10.
Artigo em Inglês | MEDLINE | ID: mdl-30901199

RESUMO

Protein hydrolysates, as surfactants, can scavenge radicals, but their poor distributions at the oil-water interface limit their storage stability. Therefore, we studied covalent interaction between rice protein hydrolysates and chlorogenic acid under alkaline conditions to improve the physical and oxidative stability of oil-in-water emulsions. Turbidity and particle size measurements demonstrated the formation of hydrolysates-chlorogenic acid complexes, and their covalent interaction resulted in the decrease and redshift of the fluorescence intensity. The emulsifying activity of the hydrolysates could be effectively improved after the covalent interaction with 0.025% chlorogenic acid. The modified emulsions possessed a notable physical stability according to the least changes in size (0.08 µm) and ζ-potential (3.34 mV) of the emulsion ( P > 0.05). Moreover, the covalent interaction endowed modified emulsions with high oxidative stability to effectively inhibit lipid oxidative deterioration during storage. The adsorption of hydrolysates to the emulsion interface was increased by the adequate addition of chlorogenic acid, which resulted in the oil droplet being surrounded by a thicker interfacial film. The covalent interaction between the protein hydrolysates and chlorogenic acid could be used to construct natural emulsion systems with a higher physical and oxidative stability during storage.


Assuntos
Ácido Clorogênico/química , Óleos/química , Oryza/química , Proteínas de Plantas/química , Hidrolisados de Proteína/química , Água/química , Emulsificantes/química , Emulsões/química , Oxirredução
20.
J Food Sci ; 84(4): 726-737, 2019 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30875438

RESUMO

The current study evaluated the effects of vacuum drying on the whole polyphenol profile of loquat fruit, including extractive and nonextractive polyphenols. Absorbance analysis determined that total polyphenol content and antioxidant levels were higher in loquat fruit vacuum dried at 140 °C than in loquat fruit vacuum dried at 70 °C. The results of ultra-HPLC-triple quadruple mass spectrum analysis showed that 15 phenolic acids and 17 flavonoids were found in dried loquat fruit. Multivariate integrative (MINT) sparse partial least square-discriminant analysis showed that vacuum drying affects the polyphenol profile of loquat fruit. Co-analysis of principal component analysis, partial least square-discriminant analysis, and orthometric partial least square-discriminant analysis revealed that vacuum drying mainly changed the content of chlorogenic acid, cryptochlorogenic acid, protocatechuic acid, phloretin, and hesperidin in loquat fruit. Chlorogenic acid (12.020 to 39.153 µg/g d.b. [dried base weight]), the main polyphenol in dried loquat fruit, was degraded to caffeic acid (0.028 to 2.365 µg/g d.b.) and protocatechuic acid (0.014 to 18.285 µg/g d.b.) during vacuum drying. Moreover, vacuum drying also induced the isomerization of chlorogenic acid into cryptochlorogenic acid (1.628 to 12.737 µg/g d.b.). These results might be used to develop dried loquat fruit with high levels of polyphenols and antioxidant activity. PRACTICAL APPLICATION: Interests in polyphenols of loquat fruit had increased greatly because of their possible role in health benefits. This work provided a holistic insight in the effects of vacuum drying on polyphenols profile of loquat fruit. Current results have contributed to the development of vacuum-drying method, which produced loquat fruit rich in polyphenols. Furthermore, it also suggested that multivariate analysis was a feasible method to reveal the important changes of polyphenols profile during food processing.


Assuntos
Eriobotrya/química , Frutas/química , Polifenóis/análise , Polifenóis/química , Ácido Clorogênico/análise , Ácido Clorogênico/química , Flavonoides/análise , Flavonoides/química , Conservação de Alimentos/métodos , Análise Multivariada , Vácuo
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