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1.
Bioorg Med Chem ; 47: 116372, 2021 10 01.
Artigo em Inglês | MEDLINE | ID: mdl-34454129

RESUMO

Breast cancer has the highest incidence and mortality in females, while prostate cancer has the second-highest incidence in males. Studies have shown that compounds from Brazilian green propolis have antitumor activities and can selectively inhibit the AKR1C3 enzyme, overexpressed in hormone-dependent prostate and breast tumors. Thus, in an attempt to develop new cytotoxic inhibitors against these cancers, three prenylated compounds, artepillin C, drupanin and baccharin, were isolated from green propolis to synthesize new derivatives via coupling reactions with different amino acids. All obtained derivatives were submitted to antiproliferative assays against four cancer cells (MCF-7, MDA MB-231, PC-3, and DU145) and two normal cell lines (MCF-10A and PNT-2) to evaluate their cytotoxicity. In general, the best activity was observed for compound6e, derived from drupanin, which exhibited half-maximal inhibitory concentration (IC50) of 9.6 ± 3 µM and selectivity index (SI) of 5.5 against MCF-7 cells.In silicostudies demonstrated that these derivatives present coherent docking interactions and binding modes against AKR1C3, which might represent a possible mechanism of inhibition in MCF-7 cells.


Assuntos
Aminoácidos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Cinamatos/farmacologia , Fenilpropionatos/farmacologia , Própole/química , Tricotecenos/farmacologia , Aminoácidos/análise , Aminoácidos/síntese química , Antineoplásicos Fitogênicos/análise , Antineoplásicos Fitogênicos/síntese química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Cinamatos/análise , Cinamatos/síntese química , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Fenilpropionatos/análise , Fenilpropionatos/síntese química , Própole/análise , Própole/síntese química , Própole/farmacologia , Relação Estrutura-Atividade , Tricotecenos/análise , Tricotecenos/síntese química
2.
Rapid Commun Mass Spectrom ; 34(11): e8766, 2020 Jun 15.
Artigo em Inglês | MEDLINE | ID: mdl-32108961

RESUMO

RATIONALE: TUG-891 is a potent and selective agonist of the long chain free fatty acid receptor 4. However, its metabolic profiles have not been revealed. The aim of this study was to investigate the in vitro metabolism of TUG-891 in hepatocytes. METHODS: TUG-891 at a concentration of 20 µM was incubated with rat, dog, and human hepatocytes at 37°C for 120 min. The samples were analyzed using ultra-high-performance liquid chromatography combined with electrospray ionization tandem mass spectrometry. The structures of the metabolites were proposed according to their MS/MS product ions. Furthermore, M4 and M5 were biosynthesized using human liver microsomes, and their structures were characterized using 13 C-NMR spectroscopy. RESULTS: Under the current conditions, eight metabolites were detected and structurally identified using high-resolution LC/MS and MS/MS spectra. The metabolites M4 and M5 were unambiguously confirmed to be TUG-891 alcohol and TUG-891 acid, respectively, using 13 C-NMR spectroscopy. Our results revealed that hydroxylation of methyl group at C-21 position to form TUG-891 alcohol (M5) followed by oxidation to yield TUG-891 aldehyde (M7) and carboxylic acid (M4) were the major metabolism processes. Phase II metabolism processes included glucuronidation and sulphation. CONCLUSIONS: Hydroxylation at the C-21 position was the primary metabolic site of TUG-891. This study provided an overview of the metabolic profiles of TUG-891 in hepatocytes.


Assuntos
Compostos de Bifenilo , Hepatócitos/metabolismo , Fenilpropionatos , Animais , Compostos de Bifenilo/análise , Compostos de Bifenilo/química , Compostos de Bifenilo/metabolismo , Células Cultivadas , Cromatografia Líquida de Alta Pressão/métodos , Cães , Humanos , Hidroxilação , Espectroscopia de Ressonância Magnética/métodos , Fenilpropionatos/análise , Fenilpropionatos/química , Fenilpropionatos/metabolismo , Ratos , Espectrometria de Massas em Tandem/métodos
3.
J Sep Sci ; 43(15): 2971-2980, 2020 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-32415756

RESUMO

A simple and green sodium dodecyl sulfate-synergistic microwave-assisted extraction method was developed to extract and determine the iridoids, phenylpropanoids, and lignans in Eucommiae Cortex followed by ultra-high-performance liquid chromatography with photodiode array detection. The biodegradable solution (sodium dodecyl sulfate) was used as a promising alternative to organic solvents. The response surface methodology provided the optimum extraction conditions (2 mg/mL sodium dodecyl sulfate, 1100 W microwave power, and 6 min extraction time). The recoveries of three types of components ranged from 95.0 to 105% (RSDs < 5%). The intra- and inter-day precision and accuracy were less than 3.40% and within the range of 97.1-105%, respectively. Compared with other extraction methods, this newly established method was more efficient and environmental friendly. The results demonstrated that sodium dodecyl sulfate-synergistic microwave-assisted extraction followed by ultra-high-performance liquid chromatography with photodiode array method was applicable for the simultaneous extraction and determination of these three types of compounds for quality evaluation of Eucommiae Cortex.


Assuntos
Medicamentos de Ervas Chinesas/análise , Eucommiaceae/química , Iridoides/análise , Lignanas/análise , Micro-Ondas , Fenilpropionatos/análise , Dodecilsulfato de Sódio/química , Cromatografia Líquida de Alta Pressão
4.
BMC Nephrol ; 21(1): 24, 2020 01 28.
Artigo em Inglês | MEDLINE | ID: mdl-31992232

RESUMO

BACKGROUND: Ambrisentan is a selective endothelin receptor antagonist used for the treatment of pulmonary arterial hypertension (PAH). Little is known about ambrisentan removal by hemodialysis in patients with end-stage renal disease (ESRD). CASE PRESENTATION: A 53-year-old woman with HIV/hepatitis C virus (HCV) co-infection, PAH and ESRD on regular hemodialyis was admitted in our hospital due to refractory heart failure while on treatment with bosentan (125 mg twice daily) and tadalafil (20 mg once daily) for PAH and antiretroviral treatment (cART) including darunavir/cobicistat (800/150 mg once daily). Excessive exposure to bosentan due to drug interactions between bosentan and darunavir/cobicistat was suspected. Bosentan was replaced by ambrisentan, with progressive improvement in her clinical condition. Pre- and postdialyzer cocentrations of ambrisentan in plasma were determined and hemodialysis extraction ratio for ambrisentan was 2%. CONCLUSIONS: Our results suggest that hemodialysis results in minimal ambrisentan removal, and therefore no specific ambrisentan dosage adjustment seems to be required in ESRD patients undergoing hemodialysis.


Assuntos
Anti-Hipertensivos/sangue , Anti-Hipertensivos/uso terapêutico , Hipertensão Pulmonar/tratamento farmacológico , Falência Renal Crônica/terapia , Fenilpropionatos/sangue , Fenilpropionatos/uso terapêutico , Piridazinas/sangue , Piridazinas/uso terapêutico , Anti-Hipertensivos/análise , Feminino , Infecções por HIV/complicações , Soluções para Hemodiálise/química , Hepatite C Crônica/complicações , Humanos , Hipertensão Pulmonar/complicações , Falência Renal Crônica/complicações , Pessoa de Meia-Idade , Fenilpropionatos/análise , Piridazinas/análise , Diálise Renal
5.
Biomed Chromatogr ; 33(6): e4496, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30663135

RESUMO

The purpose of this paper is to describe the glycosylation of ambrisentan (AMB) by cultures of Cunninghamella elegans ATCC 9245. AMB is an endothelin receptor antagonist, which is used to treat pulmonary arterial hypertension. Filamentous fungi are morphologically complex and may exhibit different forms depending on the species and the nature of the culture medium. A biotransformation study was conducted to investigate the ability of C. elegans to metabolize AMB. Parameters were optimized by testing on different culture media and concentrations, pH, drug concentration, static and shaking conditions. Ambrisentan's metabolite, obtained after 240 h of incubation as a result of glycosylation pathway, was separated by HPLC and determined by high-resolution mass spectrometry. The method showed linearity over 300-1000 µg mL-1 (r = 0.998). Accuracy, precision, robustness and stability studies agree with international guidelines. Results are consistent in accordance with the principles of green chemistry as the experimental conditions had a low environmental impact, and used little solvent.


Assuntos
Cunninghamella/metabolismo , Glicosídeos/análise , Glicosídeos/metabolismo , Fenilpropionatos/análise , Fenilpropionatos/metabolismo , Piridazinas/análise , Piridazinas/metabolismo , Biotransformação , Técnicas de Cultura de Células , Cromatografia Líquida de Alta Pressão , Glicosídeos/química , Espectrometria de Massas , Fenilpropionatos/química , Piridazinas/química
6.
Crit Rev Food Sci Nutr ; 58(2): 227-246, 2018 Jan 22.
Artigo em Inglês | MEDLINE | ID: mdl-27305453

RESUMO

Risk factors of type 2 diabetes mellitus (T2D) and cardiovascular disease (CVD) cluster together and are termed the metabolic syndrome. Key factors driving the metabolic syndrome are inflammation, oxidative stress, insulin resistance (IR), and obesity. IR is defined as the impairment of insulin to achieve its physiological effects, resulting in glucose and lipid metabolic dysfunction in tissues such as muscle, fat, kidney, liver, and pancreatic ß-cells. The potential of rooibos extract and its major C-glucosyl flavonoids, in particular aspalathin, a C-glucoside dihydrochalcone, as well as the phenolic precursor, Z-2-(ß-D-glucopyranosyloxy)-3-phenylpropenoic acid, to prevent the metabolic syndrome, will be highlighted. The mechanisms whereby these phenolic compounds elicit positive effects on inflammation, cellular oxidative stress and transcription factors that regulate the expression of genes involved in glucose and lipid metabolism will be discussed in terms of their potential in ameliorating features of the metabolic syndrome and the development of serious metabolic disease. An overview of the phenolic composition of rooibos and the changes during processing will provide relevant background on this herbal tea, while a discussion of the bioavailability of the major rooibos C-glucosyl flavonoids will give insight into a key aspect of the bioefficacy of rooibos.


Assuntos
Antioxidantes/uso terapêutico , Aspalathus/química , Suplementos Nutricionais , Flavonoides/uso terapêutico , Glucosídeos/uso terapêutico , Síndrome Metabólica/prevenção & controle , Fenilpropionatos/uso terapêutico , Extratos Vegetais/uso terapêutico , Animais , Anti-Inflamatórios não Esteroides/análise , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/uso terapêutico , Antioxidantes/análise , Antioxidantes/química , Bebidas/análise , Diabetes Mellitus Tipo 2/complicações , Diabetes Mellitus Tipo 2/dietoterapia , Diabetes Mellitus Tipo 2/imunologia , Etnofarmacologia , Flavonoides/análise , Flavonoides/química , Glucosídeos/análise , Glucosídeos/química , Humanos , Isomerismo , Medicinas Tradicionais Africanas , Síndrome Metabólica/complicações , Síndrome Metabólica/etiologia , Obesidade/complicações , Obesidade/dietoterapia , Obesidade/imunologia , Obesidade/fisiopatologia , Fenilpropionatos/análise , Fenilpropionatos/química , Extratos Vegetais/química , Folhas de Planta/química , Caules de Planta/química , África do Sul , Chás de Ervas/análise
7.
Anal Bioanal Chem ; 410(2): 373-389, 2018 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-29124305

RESUMO

A highly binding dummy template surface of molecularly imprinted polymers (MWNTs-MIPs) was synthesized on multi-walled carbon nanotubes surface using 2-phenylpropionic acid as dummy template, 4-vinylpyridine as the functional monomer, ethylene glycol dimethacrylate as the cross-linker, and DMF as porogen by precipitation polymerization method. MIPs were characterized by FT-IR spectroscopy, scanning electron microscope, thermo-gravimetric analysis, and nitrogen adsorption-desorption experiment. Adsorption and selectivity experiments of MIPs and non-imprinted polymers (NIPs) verified that the MIPs had a good selectivity and adsorption properties for five 2-phenylpropionic acid nonsteroidal anti-inflammatory drugs (NSAIDs). Imprinted polymer was used as a sorbent material for µSPE in current work and µSPE-DLLME method was selected for pretreatment of water samples. The µSPE-DLLME method was successfully used for the pre-concentration of five non-steroidal anti-inflammatory drugs in different environmental water samples prior to ultra-high performance liquid chromatography-tandem mass spectrometry. Efficiencies of µSPE and DLLME were thoroughly investigated and optimized in this study. The optimal results were obtained by using 3 mL of 1% formic acid-acetonitrile as elution solvent and dichloroethane and acetonitrile as extractant and disperser solvent, respectively. Limits of detection and quantification of five NSAIDs for different water matrices varied from 0.50 to 1.10 ng L-1 and 0.93 to 2.20 ng L-1, respectively. Each target analyte had a good linearity in its corresponding concentration range. Enrichment factors of target analytes ranged from 91 to 215. Recoveries of the target analytes were between 72.43 and 113.99% at the concentration levels of 0.02, 0.1, and 0.5 µg L-1. The developed method was successfully applied to extraction and analysis of NSAIDs in different water samples with satisfactory results which could help us better understand their environmental fate and risk to ecological health. Graphical abstract Dummy-surface molecularly imprinted polymers as a sorbent of micro-solid-phase extraction combined with dispersive liquid-liquid microextraction for determination of five 2-phenylpropionic acid NSAIDs in aquatic environmental samples.


Assuntos
Anti-Inflamatórios não Esteroides/análise , Microextração em Fase Líquida/métodos , Impressão Molecular/métodos , Fenilpropionatos/análise , Microextração em Fase Sólida/métodos , Poluentes Químicos da Água/análise , Adsorção , Anti-Inflamatórios não Esteroides/isolamento & purificação , Limite de Detecção , Nanotubos de Carbono/química , Fenilpropionatos/isolamento & purificação , Polímeros/química , Água/análise , Poluentes Químicos da Água/isolamento & purificação
8.
Molecules ; 23(2)2018 Jan 29.
Artigo em Inglês | MEDLINE | ID: mdl-29382158

RESUMO

Tinospora sinensis, a kind of Chinese folk medicine, has functions of harmonizing qi and blood, dredging the channels and collaterals, calming and soothing the nerves. In the present study, a method based on high-performance liquid chromatography coupled with linear ion trap-Orbitrap mass spectrometry (HPLC-LTQ-Orbitrap) was developed for the systematical characterization of the non-diterpenoid constituents which possessed remarkable biological activities in T. sinensis, like anti-tumor, anti-inflammatory, hypoglycemic activity and immunomodulatory activity. Based on the accurate mass measurement (<5 ppm), retention times and MS fragmentation ions, 60 non-diterpenoid constituents were unambiguously or tentatively characterized from T. sinensis extract, including 27 alkaloids, 23 phenylpropanoids, seven sesquiterpenoids and three other constituents. Among them, 13 compounds were tentatively identified as new compounds. Finally, three of the non-diterpenoid constituents were purified and identified, which further confirmed the validity of the results. This study demonstrated that the HPLC-LTQ-Orbitrap MSn platform was a useful and efficient analytical tool to screen and identify constituents in natural medicine.


Assuntos
Anti-Inflamatórios/análise , Antineoplásicos Fitogênicos/análise , Hipoglicemiantes/análise , Tinospora/química , Alcaloides/análise , Cromatografia Líquida de Alta Pressão , Espectrometria de Massas , Fenilpropionatos/análise , Sesquiterpenos/análise
9.
Molecules ; 23(10)2018 Sep 28.
Artigo em Inglês | MEDLINE | ID: mdl-30274204

RESUMO

Bee Bread samples from Romania and India were analysed by microscopy and High Performance Liquid Chromatography with Diode Array Detection (HPLC/DAD) and compared with pollen from the correspondent taxa. The quantification of sugars, fructose/glucose ratio, total phenolics and flavonoids was also carried out. From the results was possible to identify Brassica and Eucalyptus samples that present similar HPLC/DAD profiles with the respective ultraviolet (UV) identification of the main compounds as Kaempferol-3-O-glycosides and Hydrocinnamic acid derivatives. The Fructose/Glucose (F/G) ratio and the total amounts of phenolics and flavonoids was in line with the prevalence of the specie identified. These coincident fingerprints gave the identification of the samples, as was previously proposed for bee pollens. This paper relates for the first time the achievement on the taxon carried out previously only for bee pollens. It was reported for the first time that this phenolic profile remains unchanged in the case of floral pollen (hand collected), bee pollen and bee bread. Despite the biochemical transformation that occurs during the fermentation of bee bread, it seems that these phenolic compounds are not affected and remain unchanged. Also, variables such as soil and climate do not seem to influence these compounds for the kind of samples under study.


Assuntos
Própole/análise , Animais , Abelhas , Brassica/química , Eucalyptus/química , Fermentação , Flavonoides/análise , Frutose/análise , Glucose/análise , Índia , Quempferóis/análise , Fenóis/análise , Fenilpropionatos/análise , Pólen/química , Própole/classificação , Romênia
10.
Pak J Pharm Sci ; 31(6 (Supplementary): 2629-2633, 2018 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-30587471

RESUMO

A Simple, sensitive and accurate high-performance liquid chromatographic (HPLC) method for effective and specific analysis of Loxoprofen (LXP) in the mobilephase and human plasma was developed. Effective chromatographic separation was attained on a Mediterranean Sea C18 column (250×4.6mm, 5um) with mobilephase containing acetonitrile and 0.01 M NaH2PO4 buffer (55:45) by adjusting pH 6.5 with sodium dihydrogen phosphate buffer at a flow rate of 1ml/min. Calibration ranges from 0.1ppm to 10 ppm with a coefficient of relation value (R2=0.999) by using a linear regression method and lower limit of quantification was 0.1ppm. The current method showed inter-day and intra-day accuracy and precision within the range of ±10%. % RSD was found to be less than 5 %. Analytical recovery was more than 90% which confirmed the reliability of current method. The proposed method was found appropriate for assessment of LXP in pharmacokinetic and bioequivalence study.


Assuntos
Anti-Inflamatórios não Esteroides/análise , Anti-Inflamatórios não Esteroides/sangue , Química Farmacêutica/normas , Fenilpropionatos/análise , Fenilpropionatos/sangue , Química Farmacêutica/tendências , Cromatografia Líquida de Alta Pressão/normas , Cromatografia Líquida de Alta Pressão/tendências , Humanos , Reprodutibilidade dos Testes
11.
Crit Rev Food Sci Nutr ; 57(17): 3771-3780, 2017 Nov 22.
Artigo em Inglês | MEDLINE | ID: mdl-27015585

RESUMO

Agro-industry yields ample quantity of several byproducts with considerable importance. These byproducts are mostly under-utilized, often used as animal feed or rejected as waste; hence their true potential is not harnessed. The use of such superfluous resources is of not only economic significance but also a form of commercial recycling. Rice bran is an important byproduct of rice milling industry with a global potential of 29.3 million tons annually. It is gaining great attention of the researchers due to its nutrient-rich composition, easy availability, low cost, high antioxidant potential, and promising effects against several metabolic ailments. Bioactive components of rice bran, mainly γ-oryzanol, have been reported to possess antioxidant, anti-inflammatory, hypocholesterolemic, anti-diabetic, and anti-cancer activities. Rice bran oil contains appreciable quantities of bioactive components and has attained the status of "Heart oil" due to its cardiac-friendly chemical profile. Nutraceutics have successfully been extracted from rice bran using several extraction techniques such as solvent extraction, supercritical fluid extraction, microwave-, and ultrasonic-assisted extraction. Current paper is an attempt to highlight bioactive moieties of rice bran along with their extraction technologies and health benefits.


Assuntos
Oryza/química , Fenilpropionatos/análise , Óleo de Farelo de Arroz/análise , Ração Animal , Animais , Antioxidantes , Humanos , Valor Nutritivo
12.
Crit Rev Food Sci Nutr ; 57(5): 893-922, 2017 Mar 24.
Artigo em Inglês | MEDLINE | ID: mdl-25897468

RESUMO

Epidemiological and clinical studies suggest that the additive/synergistic effects of several bioactive compounds are responsible for the health benefits of rice. Among the leading contenders are phenolic acids, flavonoids, anthocyanins, proanthocyanidins, tocotrienols, tocopherols, λ-oryzanol, and phytic acid, which all possess strong antioxidant activities in vitro. In this review, data related to health effects of rice antioxidants using cultured cells, rodents and humans models are first summarized. The evidence is strong that consumption of rice tocotrienols translates into improved health outcomes. Current research, however, does not strongly support the health-promoting effects of rice tocopherols and phenolic acids. The crucial limitations in studies using rice flavonoids, anthocyanins, proanthocyanidins, λ-oryzanol and phytic acid appear to be the appropriateness of the substance tested (i.e., purity), and the scarcity of animal and human interventions. In a second part, rice antioxidants are reviewed with an emphasis on their composition and contents. Taking into account the bioavailability of these compounds, it is evident that a number of factors affect the antioxidant composition of rice, making it difficult to estimate dietary intake. Before harvest, factors including soil type, atmospheric CO2, chemical inputs, temperature, and degree of ripening are important. After harvest, rice is subjected to processing methods that include drying, parboiling, storage, irradiation, milling, stabilization, soaking, germination, fermentation, boiling, steaming, roasting, baking, and extrusion. Quantitative knowledge about the effects of these processes is summarized in this review. Surprisingly, a high level of agreement was found among study results, which could be useful in manipulating the growing and processing techniques of rice grains to facilitate efficient and safe consumption of antioxidant compounds.


Assuntos
Antioxidantes/análise , Oryza/química , Animais , Antocianinas/análise , Flavonoides/análise , Manipulação de Alimentos , Humanos , Hidroxibenzoatos/análise , Modelos Animais , Fenilpropionatos/análise , Proantocianidinas/análise , Tocoferóis/análise
13.
J Appl Microbiol ; 122(4): 911-920, 2017 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-28066967

RESUMO

AIMS: This study investigates the antimicrobial activity in Staphylococcus aureus isolates (methicillin-sensitive S. aureus (MSSA) and methicillin-resistant S. aureus (MRSA)) and antioxidant activity of green propolis, Baccharis dracunculifolia DC extracts and Artepillin C™. METHODS AND RESULTS: The amount of Artepillin C in different extracts was determined by high performance liquid chromatography analysis. Minimum inhibitory concentration 90 (MIC90) was determined using 40 isolates of S. aureus inoculated in Müeller-Hinton agar culture medium containing the green propolis and B. dracunculifolia DC extracts. PVEE (green propolis ethanolic extract) and BDEH (B. dracunculifolia hexanic extract) showed the greatest antimicrobial activity with MIC90 values of 246·3 and 295·5 µg ml-1 respectively. Green propolis ethanolic and hexanic extracts (PVEE and PVEH respectively) showed the greatest antioxidant activity assessed by DPPH (1,1-diphenyl-2-picryl hydrazyl radical) with IC50 values of 13·09 and 95·86 µg ml-1 respectively. CONCLUSIONS: Green propolis ethanolic displays better antimicrobial and antioxidant activities compared to other extracts. These activities may be related to the presence of Artepillin C in synergism with the other constituents of the extracts. SIGNIFICANCE AND IMPACT OF THE STUDY: In this study, the antimicrobial activity of the extracts of green propolis and B. dracunculifolia DC demonstrated in MRSA and MSSA clinical isolates indicated that they can be important tools to treat infections caused by these bacteria.


Assuntos
Antibacterianos/farmacologia , Antioxidantes/farmacologia , Baccharis/química , Fenóis/farmacologia , Fenilpropionatos/farmacologia , Própole/farmacologia , Antibacterianos/análise , Antioxidantes/análise , Fenilpropionatos/análise , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Própole/química , Staphylococcus aureus/efeitos dos fármacos
14.
Biosci Biotechnol Biochem ; 81(3): 573-580, 2017 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-27876437

RESUMO

Oryzanol contained in rice bran is a complex mixture of steryl ferulates (SFs) with many identified health benefits. Recently, SF has been shown to exist in other cereals such as wheat, rye, and corn. In this study, SFs in several wheats produced in Japan were analyzed. For instance, SF content of whole wheat grain, Yumekaori (Japan) was 15.2 ± 1.4 mg-oryzanol-equivalent/100 g grain, while that of the imported one, 1CW (Canada) was 11.4 ± 1.3 mg-oryzanol-equivalent/100 g grain. The main SF components in the examined wheats were campesteryl ferulate, campestanyl ferulate, and sitostanyl ferulate. SF distribution in whole wheat grain was investigated using 14 fractions produced by a conventional test milling machine. SF was intensively accumulated in the four bran fractions (24 - 95 mg-oryzanol-equivalent/100 g bran fraction). These results suggest that the wheat bran would be an important source of SF.


Assuntos
Ácidos Cumáricos/metabolismo , Fenilpropionatos/metabolismo , Triticum/química , Ácidos Cumáricos/análise , Fibras na Dieta/análise , Análise de Alimentos , Japão , Fenilpropionatos/análise , Sementes/química , Sementes/metabolismo , Triticum/metabolismo
15.
Clin Orthop Relat Res ; 475(5): 1356-1365, 2017 May.
Artigo em Inglês | MEDLINE | ID: mdl-27334326

RESUMO

BACKGROUND: Antioxidants added to UHMWPE to prevent in vivo oxidation are important to the long-term performance of hip and knee arthroplasty. Diffused vitamin E antioxidant polyethylene raised questions about potential in vivo elution that could cause inflammatory reactions in periprosthetic tissues and also potentially leave the implant once again prone to oxidation. Currently, there is no information on the elution, if any, of antioxidants from implant polyethylene materials in vivo. QUESTIONS/PURPOSES: (1) Do antioxidants, especially diffused vitamin E, elute from antioxidant polyethylene in vivo? (2) Can extraction of the retrieved antioxidant polyethylene (to remove absorbed species from the in vivo environment near the articular and nonarticular surfaces) improve the identification of antioxidant content? (3) Can actual antioxidant content be estimated from calculated antioxidant indices by accounting for ester content (from absorbed species) near the articular and nonarticular surfaces? METHODS: An institutional review board-approved retrieval laboratory received 39 antioxidant polyethylene hip and knee retrievals at revision from 25 surgeons with in vivo time of 0.02 to 3.6 years (median, 1.3 years). These consecutive antioxidant polyethylene retrievals, received between May 2010 and February 2016, were made from three different antioxidant highly crosslinked polyethylene materials: diffused vitamin E, blended vitamin E, and hindered phenol antioxidant pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)] propionate (here and after referred to as PBHP). Retrievals were analyzed using Fourier transform infrared (FTIR) spectroscopy. Absorbed ester index (1725-1740 cm-1 normalized to 1365-1371 cm-1), and vitamin E index (1245-1275 cm-1) and PBHP index (1125-1150 cm-1), normalized to 1850-1985 cm-1, were defined. Microtomed thin sections of PBHP and vitamin E retrievals were hexane-extracted to remove absorbed species from the in vivo environment in an effort to improve identification of antioxidant content. Paired Student's t-tests were used to compare as-retrieved articular antioxidant index with expected antioxidant index (the bulk value for blended antioxidants where constant antioxidant content is expected throughout and the extrapolated original vitamin E concentration at the articular surface based on the as-manufactured vitamin E concentration gradient). Linear regression was used for each of the retrievals to evaluate the correlation of antioxidant index to ester content with the goal of extrapolation to the antioxidant index at zero ester content. RESULTS: On average, vitamin E index at the articular surface (0.04 ± 0.03) was reduced compared with expected vitamin E index (0.09 ± 0.04; 95% confidence interval [CI] of the difference, 0.04-0.07; p < 0.001), and PBHP index at the articular surface (0.06 ± 0.02) was elevated compared with the average PBHP index from the bulk (0.03 ± 0.00; 95% CI of the difference, 0.03-0.05; p < 0.001). Extraction returned the PBHP index at the articular surface (0.03 ± 0.00) to bulk values (95% CI of the difference, -0.001 to 0.004; p = 0.326); diffused vitamin E was removed by extraction. Crossplots of vitamin E index and PBHP index with ester index showed significant (p < 0.001 for 32 of the 35 retrievals with sufficient data) linear trends (r ≥ 0.89) that allowed extrapolation of the articular surface antioxidant indices at zero absorbed ester index. CONCLUSIONS: Absorbed esters from time in vivo caused erroneous values of antioxidant index to be calculated. However, hexane extraction to remove absorbed species also removed diffused vitamin E. Correlating antioxidant indices with ester content, measured by FTIR in unextracted antioxidant retrievals, provides a nonaltered method for estimating actual articular surface vitamin E index and demonstrates that there was no measurable elution in these short-term retrievals. CLINICAL RELEVANCE: Assessing antioxidant content in retrieved polyethylene inserts is important to determine how much of the antioxidant remains in place to prevent oxidation of the polyethylene over time in vivo. Retrieval analyses reporting antioxidant content must account for absorbed species to be valid. Because standard hexane extraction removes both absorbed species and vitamin E from diffused vitamin E retrievals, the correlation method presented in this study is the recommended analysis alternative.


Assuntos
Antioxidantes/análise , Artroplastia de Quadril/instrumentação , Artroplastia do Joelho/instrumentação , Prótese de Quadril , Prótese do Joelho , Fenilpropionatos/análise , Polietilenos/química , Vitamina E/análise , Absorção Fisico-Química , Análise de Variância , Remoção de Dispositivo , Difusão , Ésteres/análise , Humanos , Modelos Lineares , Oxirredução , Desenho de Prótese , Reoperação , Reprodutibilidade dos Testes , Espectroscopia de Infravermelho com Transformada de Fourier , Propriedades de Superfície
16.
J Sci Food Agric ; 97(3): 793-801, 2017 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-27173638

RESUMO

BACKGROUND: Biofortified maize is not only a good vehicle for provitamin A carotenoids for vitamin A deficient populations in developing countries but also a source of vitamin E, tocochromanols and phenolic compounds, which have antioxidant properties. Using high-performance liquid chromatography and a total antioxidant performance assay, the present study analyzed the antioxidant variation and antioxidant activity of 36 provitamin A improved maize hybrids and one common yellow maize hybrid. RESULTS: The ranges of major carotenoids in provitamin A carotenoids biofortified maize were zeaxanthin [1.2-13.2 µg g-1 dry weight (DW)], ß-cryptoxanthin (1.3-8.8 µg g-1 DW) and ß-carotene (1.3-8.0 µg g-1 DW). The ranges of vitamin E compounds identified in provitamin A carotenoids biofortified maize were α-tocopherol (3.4-34.3 µg g-1 DW), γ-tocopherol (5.9-54.4 µg g-1 DW), α-tocotrienol (2.6-19.5 µg g-1 DW) and γ-tocotrienol (45.4 µg g-1 DW). The ranges of phenolic compounds were γ-oryzanol (0.0-0.8 mg g-1 DW), ferulic acid (0.4-3.6 mg g-1 DW) and p-coumaric acid (0.1-0.45 mg g-1 DW). There was significant correlation between α-tocopherol and cis isomers of ß-carotene (P < 0.01). Tocotrienols were correlated with α-tocopherol and γ-oryzanol (P < 0.01). CONCLUSION: Genotype was significant in determining the variation in ß-cryptoxanthin, ß-carotene, α-tocopherol and γ-tocopherol contents (P < 0.01). A genotype × environment interaction was observed for γ-tocopherol content (P < 0.01). © 2016 Society of Chemical Industry.


Assuntos
Biofortificação , Carotenoides/análise , Provitaminas/análise , Sementes/química , Vitamina A/análise , Vitamina E/análise , Zea mays/química , Altitude , Antioxidantes/análise , Antioxidantes/metabolismo , Carotenoides/biossíntese , Clima , Ácidos Cumáricos/análise , Ácidos Cumáricos/metabolismo , Produtos Agrícolas/química , Produtos Agrícolas/genética , Produtos Agrícolas/crescimento & desenvolvimento , Produtos Agrícolas/metabolismo , Cruzamentos Genéticos , Interação Gene-Ambiente , Genótipo , Humanos , México , Valor Nutritivo , Fenóis/análise , Fenóis/metabolismo , Fenilpropionatos/análise , Fenilpropionatos/metabolismo , Melhoramento Vegetal , Propionatos , Provitaminas/biossíntese , Sementes/genética , Sementes/crescimento & desenvolvimento , Sementes/metabolismo , Especificidade da Espécie , Vitamina A/metabolismo , Vitamina E/biossíntese , Zea mays/genética , Zea mays/crescimento & desenvolvimento , Zea mays/metabolismo
17.
Biochem Biophys Res Commun ; 479(4): 747-752, 2016 Oct 28.
Artigo em Inglês | MEDLINE | ID: mdl-27693794

RESUMO

Ricebran oil (RBO) is promoted as heart friendly oil because of its ability to maintain serum lipids at desirable levels. Inflammation also plays an important role on cardiovascular health. The role of minor constituents present in unsaponifiable fraction (UF) of RBO on inflammatory markers is not well understood. To evaluate this, we have taken RBO with UF (RBO-N), RBO stripped of UF (RBO-MCR) and RBO-MCR supplemented with UF from RBO (UFRBO) or Gamma-Oryzanol (γ-ORY) were added in AIN-93 diets which was then fed to Wistar rats for a period of 60 days. Groundnut oil with UF (GNO-N), UF removed GNO (GNO-MCR) and GNO-MCR supplemented with UF from RBO or γ-ORY was also used for comparison. The peritoneal macrophages from the rats were activated and pro-inflammatory mediators such as Reactive Oxygen Species (ROS), eicosanoids, cytokines, hydrolytic enzymes of lysosomal origin were monitored. The results indicated that UF of RBO and γ-ORY supplemented in the dietary oils play a significant role in reducing the secretion of pro-inflammatory mediators by macrophages. Hence γ-ORY in RBO significantly contributed to the anti-inflammatory properties of RBO.


Assuntos
Gorduras Insaturadas na Dieta/administração & dosagem , Inflamação/prevenção & controle , Fenilpropionatos/administração & dosagem , Óleos de Plantas/administração & dosagem , Animais , Citocinas/metabolismo , Eicosanoides/metabolismo , Inflamação/metabolismo , Mediadores da Inflamação/metabolismo , Lisossomos/efeitos dos fármacos , Lisossomos/enzimologia , Macrófagos Peritoneais/efeitos dos fármacos , Macrófagos Peritoneais/metabolismo , Masculino , Fenilpropionatos/análise , Fenilpropionatos/química , Óleos de Plantas/química , Ratos , Ratos Wistar , Espécies Reativas de Oxigênio/metabolismo , Óleo de Farelo de Arroz
18.
J Sep Sci ; 39(17): 3327-38, 2016 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-27390114

RESUMO

Traditional Tibetan medicine is important for discovery of drug precursors. However, knowledge of the chemical composition of traditional Tibetan medicines is very limited due to the lack of appropriate chromatographic purification methods. In the present work, Salvia prattii was taken as an example, and an off-line hydrophilic interaction liquid chromatography/reversed-phase liquid chromatography preparative method was developed for the purification of phenylpropanoids with high purity from a crude sample of Salvia prattii. Based on the separation results of four different chromatographic stationary phases, the first-dimensional preparation was performed on an XAmide preparative column with the crude sample concentration of 62.0 mg/mL, and five main fractions were obtained from the 12.4 g crude sample with a recovery of 54.8%. An XCharge C18 preparative column was applied in the second-dimensional preparation to further isolate the phenylpropanoids from the redissolved first-dimensional fractions with concentration of approximately 50.0 mg/mL. The purities of the phenylpropanoids isolated from the crude sample of Salvia prattii were higher than 98%, indicating that the method was efficient for the purification of phenylpropanoids with high purity from Salvia prattii. Additionally, this method showed great potential in the preparation of phenylpropanoids and can serve as a good example for the purification of phenylpropanoids from other plant materials.


Assuntos
Cromatografia Líquida/métodos , Cromatografia de Fase Reversa/métodos , Fenilpropionatos/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Salvia/química , Hepatite/tratamento farmacológico , Humanos , Interações Hidrofóbicas e Hidrofílicas , Fenilpropionatos/análise , Fenilpropionatos/farmacologia , Extratos Vegetais/análise , Extratos Vegetais/farmacologia
19.
Electrophoresis ; 36(19): 2442-50, 2015 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-26080944

RESUMO

In this study, a new CE method, employing a binary system of trimethyl-ß-CD (TM-ß-CD) and a chiral amino acid ester-based ionic liquid (AAIL), was developed for the chiral separation of seven 2-arylpropionic acid nonsteroidal anti-inflammatory drugs (NSAIDs). In particular, the enantioseparation of ibuprofen, ketoprofen, carprofen, indoprofen, flurbiprofen, naproxen, and fenoprofen was improved significantly by supporting the BGE with the chiral AAIL l-alanine tert butyl ester lactate (l-AlaC4 Lac). Parameters, such as concentrations of TM-ß-CD and l-AlaC4 Lac, and buffer pH, were systematically examined in order to optimize the chiral separation of each NSAID. It was observed that the addition of the AAIL into the BGE improved both resolution and efficiency significantly. After optimization of separation conditions, baseline separation (Rs >1.5) of five of the analytes was achieved in less than 11 min, while the resolution of ibuprofen and flurbiprofen was approximately 1.2. The optimized enantioseparation conditions for all analytes involve a BGE of 5 mM sodium acetate/acetic acid (pH 5.0), an applied voltage of 30 kV, and a temperature of 20°C. In addition, the results obtained by computing the %-RSD values of the EOF and the two enantiomer peaks, demonstrated excellent run-to-run, batch-to-batch, and day-to-day reproducibilities.


Assuntos
Alanina/química , Anti-Inflamatórios não Esteroides/isolamento & purificação , Eletroforese Capilar/métodos , Lactatos/química , Fenilpropionatos/isolamento & purificação , beta-Ciclodextrinas/química , Anti-Inflamatórios não Esteroides/análise , Anti-Inflamatórios não Esteroides/química , Fenilpropionatos/análise , Fenilpropionatos/química , Reprodutibilidade dos Testes , Estereoisomerismo
20.
Biosci Biotechnol Biochem ; 79(12): 2063-72, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-26222314

RESUMO

Measurements of singlet oxygen ((1)O2) quenching rates (kQ (S)) and the relative singlet oxygen absorption capacity (SOAC) values were performed for seven rice bran extracts 1-7, which contained different concentrations of antioxidants (AOs) (such as α-, ß-, γ-, and δ-tocopherols and -tocotrienols, three carotenoids (lutein, ß-carotene, and zeaxanthin), and γ-oryzanol), in ethanol at 35 °C using UV-vis spectrophotometry. The concentrations of four tocopherols and four tocotrienols, three carotenoids, and γ-oryzanol contained in the extracts were determined using HPLC-MS/MS, UV-HPLC, and UV-vis absorption spectroscopy, respectively. Furthermore, comparisons of kQ (S) (Obsd.) values observed for the above extracts 1-7 with the sum of the product {[Formula: see text] [AO-i]} of the [Formula: see text] values obtained for each AO-i and the concentration ([AO-i]) of AO-i contained in extracts 1-7 were performed. From the results, it has been ascertained that the SOAC method is applicable to general food extracts to evaluate their (1)O2-quenching activity.


Assuntos
Antioxidantes/química , Etanol/química , Oryza/química , Extratos Vegetais/química , Oxigênio Singlete/química , Espectrofotometria Ultravioleta/métodos , Absorção Fisico-Química , Antioxidantes/análise , Carotenoides/análise , Carotenoides/química , Cinética , Fenilpropionatos/análise , Fenilpropionatos/química , Soluções , Temperatura , Vitamina E/análise , Vitamina E/química
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