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1.
Food Chem ; 332: 127461, 2020 Dec 01.
Artigo em Inglês | MEDLINE | ID: mdl-32659698

RESUMO

The self-microemulsifying delivery system was fabricated by whey protein isolate (WPI), daidzein (Dai) and surfactants, the interaction of WPI, Dai and D-α-Tocopherol polyethylene glycol succinate (TPGS) was hereby studied in the absence or presence of Tween 20. The increase of surfactant concentration led to the decrease of the modulus and changes of protein interfacial conformation, which allowed the formation of a strong intermolecular network. The environment and structure of WPI and daidzein could be changed by TPGS, and the addition of Tween 20 could further enhance the interaction between the components by changing TPGS structure. With the increase of surfactants and oil phase, Ksv and Ka values of WPI-Dai increased first and then decreased. Therefore, the interaction between the components was also dependent on the WPI-surfactant ration. These findings provide a potential strategy for designing microemulsion food system based on the understanding of the interactions among individual composition of microemulsions.


Assuntos
Isoflavonas/química , Tensoativos/química , Proteínas do Soro do Leite/química , Animais , Bovinos , Emulsões/química , Polietilenoglicóis/química , Polissorbatos/química
2.
Food Chem ; 331: 127312, 2020 Nov 30.
Artigo em Inglês | MEDLINE | ID: mdl-32619907

RESUMO

Growing interest in the health benefits of soy isoflavones has led to research in the isolation of individual isoflavone species for further application. Herein, we develop a new strategy to isolate daidzein, genistein, daidzin and genistin in soybean. We investigated the impact of solvents used and the extraction time on the extracted isoflavone contents from soybean. A 30-min extraction with 65% aqueous methanol gave a total isoflavone yield of 345 mg/100 g soybean, the highest value among tested conditions. Further, we proposed a two-stage adsorption/desorption chromatography comprising macroporous resin and aluminium oxide to isolate isoflavone. First, HP-20 resin was used to separate the glucosidic and aglyconic forms of isoflavone, then individual species of isoflavone could be isolated using aluminium oxide by specific retention of 5-hydroxy isoflavone. This process achieved overall high recovery (82-97%) and purity (92-95%) of the four isoflavones, which confirms a high separating efficiency for isoflavones from soybean.


Assuntos
Óxido de Alumínio/química , Isoflavonas/isolamento & purificação , Resinas Sintéticas/química , Solventes/química , Soja/química , Isoflavonas/análise , Isoflavonas/química , Porosidade , Resinas Vegetais
3.
J Food Sci ; 85(4): 1302-1306, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-32144772

RESUMO

The effects and mechanisms of soybean isoflavone on osteoblast (OB) proliferation in vitro were investigated. Fifty female Wistar rats were randomly divided into five groups with 10 rats in each group. Rat OBs were separated and cultured. The first generation of OBs cultured for 48 hr at various concentrations of isoflavone were set as the experimental groups, the OBs exposed to estradiol (E2 ) culture were considered as positive control group. The biological characterization of OBs was investigated by phase contrast microscopy and alkaline phosphatase (ALP) histochemistry. The concentrations of interleukin (IL-1), osteoprotegerin (OPG), transforming growth factor (TGF), granulocyte-macrophage colony-stimulating factor (GM-CSF), and vascular endothelial growth factor (VEGF) in isoflavone culture solutions were determined. Proliferation rate of OBs was increased in experimental group comparing that in the blank group. ALP activity in experimental group was higher than that in blank group. No significant differences of ALP activity were observed between E2 culture group and isoflavone group at concentrations of 10-5 and 10-7 mM (P > 0.05). Furthermore, in the experimental groups at low isoflavone concentrations, the concentrations of OPG, TGF, and VEGF were increased and positively correlated with OB proliferation. However, the concentrations of IL-1, GM-CSF were decreased at higher concentration of isoflavone and were negatively correlated with OB proliferation. Soybean isoflavone could promote the growth and proliferation of rat OB, it might act as the stimulator of OPG, TGF, and VEGF pathway, and the inhibitor of IL-1, GM-CSF pathway as well.


Assuntos
Isoflavonas/farmacologia , Osteoblastos/efeitos dos fármacos , Soja/química , Fosfatase Alcalina , Animais , Células Cultivadas , Citocinas/metabolismo , Feminino , Fator Estimulador de Colônias de Granulócitos e Macrófagos , Isoflavonas/química , Osteoblastos/metabolismo , Ratos , Ratos Wistar , Soja/metabolismo , Fator A de Crescimento do Endotélio Vascular/metabolismo
4.
Chem Commun (Camb) ; 56(17): 2606-2609, 2020 Feb 27.
Artigo em Inglês | MEDLINE | ID: mdl-32016210

RESUMO

In this work we highlight two new methods for the synthesis of isoflavones through consecutive domino arylation of ortho-hydroxyarylenaminones with in situ photogenerated aryl radicals. As precursors for aryl radicals we used aryl onium reagents such as diazonium and diaryliodonium salts. Notably, the photo-Meerwein arylation by aryl diazonium tetrafluoroborates demonstrated high efficiency in terms of yields and can be considered as a method of choice for the straightforward assembly of 3-aryl-substituted chromones. Ultimately, 26 compounds were prepared in good to excellent yields using the developed synthetic protocols.


Assuntos
Aminas/química , Isoflavonas/química , Luz , Cromonas/química , Estrutura Molecular
5.
J Food Sci ; 85(3): 689-695, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-32078746

RESUMO

Sprouting is one of the processing methods to enhance bioavailability of some nutrients of agricultural products. Soybeans were germinated for 6 days and soybean (SB), soybean sprout (SBS), cotyledon of soybean sprout (CSS), and hypocotyl and root of soybean sprout (HRSS) were collected. Isoflavone profiles and in vitro antioxidant activities of 80% ethanol extracts of samples were analyzed. In addition, oxidative stability of the extract was evaluated in corn oils heated at 100 °C. The hypocotyl and root part of soybean sprout contained significantly (P < 0.05) higher content of isoflavone aglycones than the cotyledon part of soybean sprout. Diphenyl-1-picrylhydrazyl radial and 2,2'-azinobis(3-ethylbenzothiazoline-6-sul-fonic acid cation radical scavenging activities of SBS were 1.6 and 1.3 times higher than those of SB, respectively (P < 0.05), whereas those of CSS were 1.1 and 1.8 times higher than those of HRSS, respectively (P < 0.05). CSS had higher ORAC and FRAP values than others. High correlations between contents of total flavonoids and antioxidant activities were observed in all in vitro antioxidant assays. SBS, CSS, and HRSS had significantly higher oxidative stability than SB in 100 °C heated corn oil after 9 hr treatment (P < 0.05). Generally, 80% ethanol extract of CSS had high in vitro antioxidant properties whereas HRSS had high aglycone forms of isoflavones. Isoflavone aglycones may not be major ingredients providing antioxidant activities of soybean sprout. PRACTICAL APPLICATION: Soybeans are important crops for the preparation of tofu, soymilk, and protein sources. Soybean sprout prepared by germinating soybean and growing for several days is one of important food materials used as daily diet in some countries. In this study, antioxidant activities of different parts of soybean sprouts were evaluated using in vitro methods and bulk oil model systems. In addition, isoflavone profiles of soybean sprouts were determined. Enhanced antioxidant activities of soybean sprouts may help consumers choose healthier foods and extend business areas of the soybean food industry.


Assuntos
Antioxidantes/química , Isoflavonas/química , Sementes/crescimento & desenvolvimento , Soja/química , Flavonoides/química , Germinação , Oxirredução , Sementes/química , Soja/crescimento & desenvolvimento
6.
Molecules ; 25(1)2020 Jan 03.
Artigo em Inglês | MEDLINE | ID: mdl-31947859

RESUMO

Receptor activator of nuclear factor-κB ligand (RANKL) is a cytokine responsible for bone resorption. It binds its receptor RANK, which activates osteoporosis. High levels of osteoprotegerin (OPG) competitively binding RANKL limit formation of ligand-receptor complexes and enable bone mass maintenance. The new approach to prevent osteoporosis is searching for therapeutics that can bind RANKL and support OPG function. The aim of the study was to verify the hypothesis that isoflavones can form complexes with RANKL limiting binding of the cytokine to its receptor. Interactions of five isoflavones with RANKL were investigated by isothermal titration calorimetry (ITC), by in silico docking simulation and on Saos-2 cells. Daidzein and biochanin A showed the highest affinity for RANKL. Among studied isoflavones coumestrol, formononetin and biochanin A showed the highest potential for Saos-2 mineralization and were able to regulate the expression of RANKL and OPG at the mRNA levels, as well as osteogenic differentiation markers: alkaline phosphatase (ALP), collagen type 1, and Runt-related transcription factor 2 (Runx2). Comparison of the osteogenic activities of isoflavones showed that the use of physicochemical techniques such as ITC or in silico docking are good tools for the initial selection of substances showing a specific bioactivity.


Assuntos
Conservadores da Densidade Óssea , Isoflavonas , Simulação de Acoplamento Molecular , Osteogênese/efeitos dos fármacos , Osteoporose , Ligante RANK , Conservadores da Densidade Óssea/química , Conservadores da Densidade Óssea/farmacologia , Linhagem Celular Tumoral , Avaliação Pré-Clínica de Medicamentos , Humanos , Isoflavonas/química , Isoflavonas/farmacologia , Osteoporose/tratamento farmacológico , Osteoporose/metabolismo , Osteoporose/patologia , Ligante RANK/agonistas , Ligante RANK/química , Ligante RANK/metabolismo
7.
Molecules ; 25(1)2020 Jan 03.
Artigo em Inglês | MEDLINE | ID: mdl-31947862

RESUMO

The seeds of Millettia ferruginea are used in fishing, pesticides, and folk medicine in Ethiopia. Here, the anti-cancer effects of isoflavones isolated from M. ferruginea were evaluated in human ovarian cancer cells. We found that isoflavone ferrugone and 6,7-dimethoxy-3',4'-methylenedioxy-8-(3,3-dimethylallyl)isoflavone (DMI) had potent cytotoxic effects on human ovarian cancer cell A2780 and SKOV3. Ferrugone and DMI treatment increased the sub-G1 cell population in a dose-dependent manner in A2780 cells. The cytotoxic activity of ferrugone and DMI was associated with the induction of apoptosis, as shown by an increase in annexin V-positive cells. Z-VAD-fmk, a broad-spectrum caspase inhibitor, and z-DEVD-fmk, a caspase-3 inhibitor, significantly reversed both the ferrugone and DMI-induced apoptosis, suggesting that cell death stimulated by the isoflavones is mediated by caspase-3-dependent apoptosis. Additionally, ferrugone-induced apoptosis was found to be caspase-8-dependent, while DMI-induced apoptosis was caspase-9-dependent. Notably, DMI, but not ferrugone, increased the intracellular levels of reactive oxygen species (ROS), and antioxidant N-acetyl-L-cysteine (NAC) attenuated the pro-apoptotic activity of DMI. These data suggest that DMI induced apoptotic cell death through the intrinsic pathway via ROS production, while ferrugone stimulated the extrinsic pathway in human ovarian cancer cells.


Assuntos
Antineoplásicos Fitogênicos , Apoptose/efeitos dos fármacos , Isoflavonas , Millettia/química , Neoplasias Ovarianas/tratamento farmacológico , Sementes/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular , Feminino , Humanos , Isoflavonas/química , Isoflavonas/isolamento & purificação , Isoflavonas/farmacologia , Neoplasias Ovarianas/metabolismo , Neoplasias Ovarianas/patologia
8.
Food Chem ; 313: 126095, 2020 May 30.
Artigo em Inglês | MEDLINE | ID: mdl-31923873

RESUMO

Core-shell hydrogel beads were successfully produced from soybean hull polysaccharides (SHP). Using electron microscopy, the beads were found to be spherical with smooth surfaces and have tight gel network internal structures. Fourier transform infrared spectroscopy, differential scanning calorimetry, and X-ray diffraction were used to investigate the interaction between soy isoflavone and SHP in the gel beads mesh-like structure. Furthermore, the encapsulation efficiency and loading capacity of gel beads for soy isoflavone are 66.90% and 4.67%, respectively, and have the ability of pH-responsive release in vitro. Through the mathematical model of kinetics, we found that the release of soy isoflavone from gel beads showed Fickian diffusion in release media (pH 2.0 and 7.4), but showed non-Fickian diffusion at pH 4.0 and 6.8. This polymer can be extended to prepare more versatile delivery and controlled release system, appealing for food, pharmaceutical, biomedicine and cosmetics applications.


Assuntos
Hidrogéis/química , Isoflavonas/química , Polissacarídeos/química , Soja/metabolismo , Portadores de Fármacos/química , Liberação Controlada de Fármacos , Concentração de Íons de Hidrogênio , Isoflavonas/metabolismo , Cinética
9.
Molecules ; 25(1)2020 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-31906359

RESUMO

Isoflavones in soybeans are well-known phytoestrogens. Soy isoflavones present in conjugated forms are converted to aglycone forms during processing and storage. Isoflavone aglycones (IFAs) of soybeans in human diets have poor solubility in water, resulting in low bioavailability and bioactivity. Enzyme-mediated glycosylation is an efficient and environmentally friendly way to modify the physicochemical properties of soy IFAs. In this study, we determined the optimal reaction conditions for Deinococcus geothermalis amylosucrase-mediated α-1,4 glycosylation of IFA-rich soybean extract to improve the bioaccessibility of IFAs. The conversion yields of soy IFAs were in decreasing order as follows: genistein > daidzein > glycitein. An enzyme quantity of 5 U and donor:acceptor ratios of 1000:1 (glycitein) and 400:1 (daidzein and genistein) resulted in high conversion yield (average 95.7%). These optimal reaction conditions for transglycosylation can be used to obtain transglycosylated IFA-rich functional ingredients from soybeans.


Assuntos
Deinococcus/enzimologia , Glucosiltransferases/metabolismo , Isoflavonas/química , Extratos Vegetais/química , Soja/química , beta-Glucanas/química , Disponibilidade Biológica , Cromatografia Líquida de Alta Pressão , Escherichia coli/genética , Vetores Genéticos , Genisteína/química , Glucosiltransferases/genética , Glicosilação , Isoflavonas/biossíntese , Isoflavonas/isolamento & purificação , Isoflavonas/farmacocinética , Espectrometria de Massas , Fitoestrógenos/química , Extratos Vegetais/isolamento & purificação , beta-Glucanas/farmacocinética
10.
Biomed Chromatogr ; 34(4): e4774, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-31813157

RESUMO

The aim of this study was to confirm pharmacokinetic screening of multiple components in healthy Korean subjects after oral administration of Samso-eum and perform quantitation of active components in the human plasma. Thirteen potential bioactive components [puerarin (PRR), daidzin, nodakenin, ginsenoside Rb1, 18ß-glycyrrhetinic acid (18ß-GTA), 6-shogaol, naringin, glycyrrhizin, hesperidin, platycodin D, naringenin, hesperetin, and 6-gingerol] were screened based on literature. The results showed that three analytes (daidzin, naringenin, and hesperetin) were detected in trace amounts. In addition, PRR and 18ß-GTA were detected in human plasma after the oral administration of Samso-eum. In this study, a liquid chromatography-electrospray ionization-tandem mass spectrometry method was validated for the simultaneous determination of PRR and 18ß-GTA in human plasma. This was the first study to evaluate pharmacokinetics of PRR and 18ß-GTA after the usual oral dose of Samso-eum (30 g containing 102.48 mg PRR, 48.18 mg glycyrrhizin) in human subjects.


Assuntos
Cromatografia Líquida/métodos , Medicamentos de Ervas Chinesas , Ácido Glicirretínico/análogos & derivados , Isoflavonas/sangue , Espectrometria de Massas em Tandem/métodos , Administração Oral , Adulto , Medicamentos de Ervas Chinesas/administração & dosagem , Medicamentos de Ervas Chinesas/farmacocinética , Ácido Glicirretínico/sangue , Ácido Glicirretínico/química , Ácido Glicirretínico/farmacocinética , Humanos , Isoflavonas/química , Isoflavonas/farmacocinética , Limite de Detecção , Modelos Lineares , Masculino , Reprodutibilidade dos Testes , Adulto Jovem
11.
Nat Prod Res ; 34(7): 981-987, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30636441

RESUMO

A new isoflavone, milletenol A (1), along with four known flavonoids (2-5) were isolated from the seeds of Millettia pachycarpa. The structure of 1 was established by extensive spectroscopic methods while known compounds were identified by comparisons with literature data. Compound 1 and 2 showed significant anti-inflammatory activities against nitric oxide production in LPS-induced RAW264.7 macrophages. The state of CuSO4-stimulated inflammation was effectively alleviated by compound 1 in zebrafish. However, no significant cytotoxicity against human breast cancer cells was observed among all isolates.


Assuntos
Anti-Inflamatórios/isolamento & purificação , Isoflavonas/isolamento & purificação , Millettia/química , Sementes/química , Animais , Anti-Inflamatórios/farmacologia , Humanos , Isoflavonas/química , Isoflavonas/farmacologia , Lipopolissacarídeos , Macrófagos/efeitos dos fármacos , Camundongos , Óxido Nítrico/biossíntese , Células RAW 264.7 , Peixe-Zebra
12.
Nat Prod Res ; 34(5): 659-667, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30406690

RESUMO

A new isoflavonoid, excelsanone (2), was isolated from the ethyl acetate extract of Erythrina excelsa stem bark, together with three known compounds namely 6,8-diprenylgenistein (3), ß-sitosterol (1) and sitosteryl-ß-D-glucopyranoside (4). Their structures were elucidated using spectroscopic methods (HR-ESI-MS, NMR and IR) and by comparison with some literature data. The antioxidant activity of crude extracts and two isolated compounds was evaluated using free radical scavenging (DPPH) and Ferric Reducing Ability Power (FRAP) methods with catechin as standard. The results of the radical scavenging activity showed that excelsanone (2) has a moderate potential with an IC50 of 1.31 mg/ml. The cytotoxicity of compounds 2 and 3 as well as the ethyl acetate extract was evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay in two prostate cancer cell lines (DU145 and PC3). Excelsanone (2) induced a greater cytotoxicity in all tested cell lines, with a significant inhibition of DU145 cells growth in a concentration-dependent manner.


Assuntos
Antineoplásicos/isolamento & purificação , Antioxidantes/isolamento & purificação , Erythrina/química , Isoflavonas/isolamento & purificação , Neoplasias da Próstata/tratamento farmacológico , Antineoplásicos/química , Antineoplásicos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Fabaceae/química , Humanos , Isoflavonas/química , Isoflavonas/farmacologia , Masculino , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Neoplasias da Próstata/patologia
13.
Nat Prod Res ; 34(5): 613-620, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30375885

RESUMO

A new rotenoid named 12-O-methylrotenolol along with five known rotenoid and isoflavone metabolites were isolated from the seeds of Dalbergia lanceolaria subsp. paniculata, collected from Egypt. The structures of these compounds were identified by physical and spectroscopic data measurements ([α]D, UV, 1D- and 2D-NMR and MS). The methanol extract of the seeds exhibited strong antioxidant activity with IC50 value 0.7 µg/µl against DPPH radical, in respect to quercetin as antioxidant reference (IC50 1.5 µM), while the tested compounds from this extract showed weak activities with IC50 values ranged from 19.6 to 33.0 µM.


Assuntos
Antioxidantes/isolamento & purificação , Dalbergia/química , Isoflavonas/isolamento & purificação , Sementes/química , Antioxidantes/química , Compostos de Bifenilo/antagonistas & inibidores , Egito , Concentração Inibidora 50 , Isoflavonas/química , Estrutura Molecular , Picratos/antagonistas & inibidores , Extratos Vegetais/química
14.
Phytother Res ; 34(3): 649-659, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31858651

RESUMO

The limitation of doxorubicin (DOX), which is widely used for the treatment of solid tumors and hematologic malignancies, is a vital problem in clinical application. The most serious of limit factors is cardiotoxicity. Calycosin (CA), an isoflavonoid that is the major active component in Radix astragali, has been reported in many bioactivities including antitumor, anti-inflammatory, and cardioprotection. The aim of the study was to investigate the effects and mechanisms of CA on DOX-induced cardiotoxicity in vitro and in vivo. CA increased H9c2 cell viability and reduced apoptosis induced by DOX via Bcl-2, Bax, and the PI3K-Akt signaling pathway. Moreover, CA prevented DOX-induced oxidative stress in cells by decreasing the generation of reactive oxygen species. Similarly, oxidative stress was inhibited by CA through the increased activities of antioxidant enzymes such as glutathione peroxidase, catalase, and superoxide dismutase and decreased the levels of aspartate aminotransferase, lactate dehydrogenase, and malondialdehyde in vivo. Furthermore, the levels of sirtuin 1 (Sirt1)-NOD-like receptor protein 3 (NLRP3) and related proteins were ameliorated by CA in cells and in mice hearts. When H9c2 cells were treated by Ex527 (Sirt1 inhibitor), the effect of CA on expressions of NLRP3 and thioredoxin-interacting protein was suppressed. In conclusion, the results suggested that CA might be a cotreatment with DOX to ameliorate cardiotoxicity by Sirt1-NLRP3 pathway.


Assuntos
Cardiotoxicidade/tratamento farmacológico , Inflamação/tratamento farmacológico , Isoflavonas/farmacologia , Receptores de Superfície Celular/metabolismo , Transdução de Sinais/efeitos dos fármacos , Animais , Antioxidantes/metabolismo , Apoptose/efeitos dos fármacos , Linhagem Celular , Doxorrubicina/efeitos adversos , Isoflavonas/química , Masculino , Camundongos , Estresse Oxidativo/efeitos dos fármacos , Fosfatidilinositol 3-Quinases/metabolismo , Espécies Reativas de Oxigênio/metabolismo , Sirtuína 1/metabolismo
15.
Enzyme Microb Technol ; 132: 109394, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31731960

RESUMO

Microorganism selection is critical to deglycosylation in soybean fermentation for producing beneficial phytochemicals. This study investigated isoflavone bioconversion in soybean extract inoculated with Lactobacillus plantarum K2-12 and Lactobacillus curvatus JD0-31 exhibiting different enzyme activities. L. plantarum showed higher esterase (C4), esterase (C8), ß-galactosidase, α-glucosidase, ß-glucosidase, and N-acetyl-ß-glucosaminase activities. We found that isoflavone bioconversion was distinguished into isoflavone backbone structure types. Malonyl- and acetyl- types of isoflavones except for malonyl daidzin were not significantly differed their contents between lactobacilli. Deglycosylating severity was observed in malonyl genistin in both lactobacilli, resulting mass production of genistein. On the other hand, daidzein glycosides were dependable to lactobacilli, in which L. plantarum efficiently degraded malonyl daidzin and daidzin in fast time. Glycitein was most degradable among the three aglycones by fermentation. These results suggest that efficient control of isoflavone deglycosylation by Lactobacillus species should be controlled to the inoculation period and select target isoflavones.


Assuntos
Glucosídeos/química , Isoflavonas/química , Lactobacillus/enzimologia , Extratos Vegetais/química , Soja/química , Fermentação , Glicosídeos/química , Glicosilação
16.
AAPS PharmSciTech ; 21(1): 20, 2019 Dec 09.
Artigo em Inglês | MEDLINE | ID: mdl-31820224

RESUMO

Thermal extrusion (TE) 3D printing is a thermoplastic semisolid-based rapid prototyping process, which is capable of building complex structures. The aim of this study was to manufacture rapid-release puerarin tablets without solvent through TE 3D printing. Novel rapid-release tablets were fabricated with polyethylene glycol (PEG 4000) as the carrier at appropriate puerarin/PEG 4000 ratios, assessed through differential scanning calorimetry (DSC), solubility, and dissolution tests. The novel structures of 3D-printed tablets with five different values were formed by printing paths, which established a flexible way of adjusting in vitro drug release. An obvious acceleration (85% of cumulative release about 7.5 min at the soonest) was observed for the tablets with internal structural design. It was inferred that puerarin formed simple eutectic mixtures with PEG 4000 and that puerarin dispersed into the carrier based on DSC and X-Ray powder diffraction (XRD). This highlights the combined advantage of PEG as a soluble polymer with TE 3D printing and provides a suitable system for rapid puerarin release.


Assuntos
Isoflavonas/química , Impressão Tridimensional , Tecnologia Farmacêutica , Liberação Controlada de Fármacos , Polietilenoglicóis/química , Solubilidade , Comprimidos/química
17.
Molecules ; 25(1)2019 Dec 19.
Artigo em Inglês | MEDLINE | ID: mdl-31861730

RESUMO

The main aim of this study was to evaluate the volatile profile, sensory perception, and phytochemical content of bovine milk produced from cows fed on three distinct feeding systems, namely grass (GRS), grass/clover (CLV), and total mixed ration (TMR). Previous studies have identified that feed type can influence the sensory perception of milk directly via the transfer of volatile aromatic compounds, or indirectly by the transfer of non-volatile substrates that act as precursors for volatile compounds. In the present study, significant differences were observed in the phytochemical profile of the different feed and milk samples. The isoflavone formonoetin was significantly higher in CLV feed samples, but higher in raw GRS milk, while other smaller isoflavones, such as daidzein, genistein, and apigenin were highly correlated to raw CLV milk. This suggests that changes in isoflavone content and concentration in milk relate to diet, but also to metabolism in the rumen. This study also found unique potential volatile biomarkers in milk (dimethyl sulfone) related to feeding systems, or significant differences in the concentration of others (toluene, p-cresol, ethyl and methyl esters) based on feeding systems. TMR milk scored significantly higher for hay-like flavor and white color, while GRS and CLV milk scored significantly higher for a creamy color. Milk samples were easily distinguishable by their volatile profile based on feeding system, storage time, and pasteurization.


Assuntos
Ração Animal/análise , Leite/química , Compostos Fitoquímicos/análise , Compostos Orgânicos Voláteis/análise , Animais , Apigenina/química , Bovinos , Dimetil Sulfóxido/química , Feminino , Genisteína/química , Isoflavonas/química , Sulfonas/química
18.
Int J Mol Sci ; 20(21)2019 Oct 26.
Artigo em Inglês | MEDLINE | ID: mdl-31717797

RESUMO

In the present study, a series of 4-acyloxy robustic acid derivatives were synthesized and characterized for evaluation of their anti-cancer activity. The structures of these derivatives were elucidated by mass spectra (MS) nuclear magnetic resonance spectra (NMR). The single-crystal X-ray diffraction structure of one of these compounds was obtained, for further validation of the target compound structures. The anticancer activities of the target products were evaluated against human leukemic cells HL-60, human non-small cell lung carcinoma cells A-549, human hepatic carcinoma cells SMMC-7721, human hepatocellular carcinoma cells HepG2, and human cervical carcinoma cells Hela. Three compounds among them exhibited potent in-vitro cytotoxicity and excellent DNA topoisomerase I inhibitory activity, even at 0.1 mM concentrations. The most noteworthy observation was the minor toxicity of two of these compounds to normal cells, with an activity similar to the positive control in cancerous cells. A Surflex-Dock docking study was performed to investigate the topoisomerase I activity of all compounds. Of all the other compounds, the most sensitive compound was selected for further investigation of its effect on apoptosis induction and cell cycle regulation in HL-60 cells. Our results suggest that the anticancer effects of these compounds can be attributed to their pharmacological effects on topoisomerase I, cell apoptosis, and cell cycle. These findings suggest that robustic acid derivatives could be used as potential antitumor drugs.


Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Isoflavonas/química , Piranocumarinas/síntese química , Piranocumarinas/farmacologia , Células A549 , Antineoplásicos/química , Antineoplásicos/uso terapêutico , Apoptose/efeitos dos fármacos , Pontos de Checagem do Ciclo Celular/efeitos dos fármacos , Células Cultivadas , DNA Topoisomerases Tipo I/efeitos dos fármacos , Dalbergia/química , Ensaios de Seleção de Medicamentos Antitumorais , Células HL-60 , Células HeLa , Células Hep G2 , Humanos , Concentração Inibidora 50 , Isoflavonas/farmacologia , Simulação de Acoplamento Molecular , Estrutura Molecular , Piranocumarinas/química , Piranocumarinas/uso terapêutico , Inibidores da Topoisomerase I/síntese química , Inibidores da Topoisomerase I/química , Inibidores da Topoisomerase I/farmacologia
19.
Arch Pharm Res ; 42(12): 1081-1091, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31705299

RESUMO

Daidzein, one of the important isoflavones, is extensively metabolized in the human body following consumption. In particular, 6,7,4'-trihydroxyisoflavone (THIF), a major metabolite of daidzein, has been the focus of recent investigations due to its various health benefits, such as anti-cancer and anti-obesity effects. However, the protective effects of 6,7,4'-THIF have not yet been studied in models of Parkinson's disease (PD). Therefore, the present study aimed to investigate the protective activity of 6,7,4'-THIF on 6-hydroxydopamine (OHDA)-induced neurotoxicity in SH-SY5Y human neuroblastoma cells. Pretreatment of SH-SY5Y cells with 6,7,4'-THIF significantly inhibited 6-OHDA-induced neuronal cell death, lactate dehydrogenase release, and reactive oxygen species production. In addition, 6,7,4'-THIF significantly attenuated reductions in 6-OHDA-induced superoxide dismutase activity and glutathione content. Moreover, 6,7,4'-THIF attenuated alterations in Bax and Bcl-2 expression and caspase-3 activity in 6-OHDA-induced SH-SY5Y cells. Furthermore, 6,7,4'-THIF significantly reduced 6-OHDA-induced phosphorylation of c-Jun N-terminal kinase, p38 mitogen-activated protein kinase, and extracellular signal-regulated kinase 1/2. Additionally, 6,7,4'-THIF effectively prevented 6-OHDA-induced loss of tyrosine hydroxylase. Taken together, these results suggest that 6,7,4'-THIF, a major metabolite of daidzein, may be an attractive option for treating and/or preventing neurodegenerative disorders such as PD.


Assuntos
Antineoplásicos/farmacologia , Isoflavonas/metabolismo , Isoflavonas/farmacologia , Neuroblastoma/tratamento farmacológico , Neurônios/efeitos dos fármacos , Oxidopamina/antagonistas & inibidores , Antineoplásicos/química , Antineoplásicos/metabolismo , Morte Celular/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Isoflavonas/química , Estrutura Molecular , Neuroblastoma/metabolismo , Neuroblastoma/patologia , Neurônios/metabolismo , Neurônios/patologia , Estresse Oxidativo/efeitos dos fármacos , Oxidopamina/farmacologia , Doença de Parkinson/metabolismo , Doença de Parkinson/patologia , Doença de Parkinson/prevenção & controle , Células Tumorais Cultivadas
20.
Molecules ; 24(21)2019 Oct 30.
Artigo em Inglês | MEDLINE | ID: mdl-31671623

RESUMO

Biorenovation is a microbial enzyme-catalyzed structural modification of organic compounds with the potential benefits of reduced toxicity and improved biological properties relative to their precursor compounds. In this study, we synthesized a novel compound verified as formononetin 7-O-phosphate (FMP) from formononetin (FM) using microbial biotransformation. We further compared the anti-inflammatory properties of FMP to FM in lipopolysaccharide (LPS)-treated RAW264.7 macrophage cells. We observed that cell viabilities and inhibitory effects on LPS-induced nitric oxide (NO) production were greater in FMP-treated RAW 264.7 cells than in their FM-treated counterparts. In addition, FMP treatment suppressed the production of proinflammatory cytokines such as prostaglandin-E2 (PGE2), interleukin-6 (IL-6), and interleukin-1ß (IL-1ß) in a dose-dependent manner and concomitantly decreased the mRNA expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2). We also found that FMP exerted its anti-inflammatory effects through the downregulation of the extracellular signal-regulated kinase (ERK), c-Jun N-terminal kinase (JNK), and nuclear factor kappa B (NF-κB) signaling pathways. In conclusion, we generated a novel anti-inflammatory compound using biorenovation and demonstrated its efficacy in cell-based in vitro assays.


Assuntos
Anti-Inflamatórios/farmacologia , Isoflavonas/farmacologia , Lipopolissacarídeos/farmacologia , Macrófagos/metabolismo , Animais , Anti-Inflamatórios/química , Sobrevivência Celular/efeitos dos fármacos , Ciclo-Oxigenase 2/genética , Ciclo-Oxigenase 2/metabolismo , Citocinas/metabolismo , Dinoprostona/metabolismo , Mediadores da Inflamação/metabolismo , Isoflavonas/química , Sistema de Sinalização das MAP Quinases , Macrófagos/efeitos dos fármacos , Camundongos , NF-kappa B/metabolismo , Óxido Nítrico/metabolismo , Óxido Nítrico Sintase Tipo II/genética , Óxido Nítrico Sintase Tipo II/metabolismo , Células RAW 264.7 , RNA Mensageiro/genética , RNA Mensageiro/metabolismo
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