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1.
Food Chem ; 335: 127644, 2021 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-32739815

RESUMO

This study provides a robust and reproducible approach for selective extraction of rosmarinic acid (RA) using molecularly imprinted polymers (MIPs). Computational modeling and UV spectroscopic analysis were performed to optimize MIP synthesis. Consequently, six different bulk and surface imprinted polymers were generated using RA as the template. Binding performance of the imprinted polymers was evaluated using static equilibrium and complementary dynamic rebinding experiments. Despite the high selectivity of thus generated surface imprinted polymers, the corresponding bulk polymers exhibited better binding performance when serving as sorbents during solid phase extraction (SPE). An optimized molecularly imprinted solid phase extraction (MISPE) protocol was developed in respect to loaded amount of RA, composition of the loading solution, washing solvent, and elution volume. Thereby, a remarkably selective extraction of RA from real-world Rosmarinus officinalis L. extract with a recovery rate and purity of 81.96 ± 6.33% and 80.59 ± 0.30%, respectively, was achieved.


Assuntos
Cinamatos/isolamento & purificação , Depsídeos/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Rosmarinus/química , Extração em Fase Sólida/métodos , Adsorção , Cromatografia Líquida de Alta Pressão , Cinamatos/química , Depsídeos/química , Impressão Molecular , Extratos Vegetais/química , Polímeros/síntese química , Polímeros/química , Extração em Fase Sólida/instrumentação
2.
PLoS One ; 15(9): e0236081, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32960890

RESUMO

Type 2 diabetes mellitus (T2DM), one of the most common metabolic diseases, is characterized by insulin resistance and inadequate insulin secretion of ß cells. Glycogen phosphorylase (GP) is the key enzyme in glycogen breakdown, and contributes to hepatic glucose production during fasting or during insulin resistance. Pharmacological GP inhibitors are potential glucose lowering agents, which may be used in T2DM therapy. A natural product isolated from the cultured broth of the fungal strain No. 138354, called 2,3-bis(4-hydroxycinnamoyloxy)glutaric acid (FR258900), was discovered a decade ago. In vivo studies showed that FR258900 significantly reduced blood glucose levels in diabetic mice. We previously showed that GP inhibitors can potently enhance the function of ß cells. The purpose of this study was to assess whether an analogue of FR258900 can influence ß cell function. BF142 (Meso-Dimethyl 2,3-bis[(E)-3-(4-acetoxyphenyl)prop-2-enamido]butanedioate) treatment activated the glucose-stimulated insulin secretion pathway, as indicated by enhanced glycolysis, increased mitochondrial oxidation, significantly increased ATP production, and elevated calcium influx in MIN6 cells. Furthermore, BF142 induced mTORC1-specific phosphorylation of S6K, increased levels of PDX1 and insulin protein, and increased insulin secretion. Our data suggest that BF142 can influence ß cell function and can support the insulin producing ability of ß cells.


Assuntos
Cinamatos/farmacologia , Inibidores Enzimáticos/farmacologia , Glutaratos/farmacologia , Glicogênio Fosforilase/antagonistas & inibidores , Secreção de Insulina/efeitos dos fármacos , Células Secretoras de Insulina/efeitos dos fármacos , Ácido Succínico/farmacologia , Animais , Linhagem Celular Tumoral , Cinamatos/química , Inibidores Enzimáticos/química , Glucose/metabolismo , Glutaratos/química , Glicogênio Fosforilase/metabolismo , Glicólise/efeitos dos fármacos , Insulina/metabolismo , Células Secretoras de Insulina/metabolismo , Metilação , Camundongos , Ácido Succínico/química
3.
J Nat Med ; 74(4): 834-839, 2020 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-32488608

RESUMO

Caffeic acid and rosmarinic acid are common components of Labiatae plants, such as shiso (Perilla frutescens Britton var. crispa W. Deane) and Boraginaceae plants. These compounds have various pharmacological activities, such as anti-inflammatory, anti-anxiety, and anti-depressive activities, but the content of these compounds in perilla has not been studied in detail. This study investigated the caffeic acid and rosmarinic acid contents of several pure strains in genus Perilla. Perilla plants cultivated under a certain set of conditions had different caffeic acid and rosmarinic acid contents. For example, their contents were higher in P. setoyensis ("Setoegoma"), suggesting that the genetic background of the species greatly affects caffeic acid and rosmarinic acid contents. Several strains of P. frutescens var. crispa were cultivated at the Experimental Station for Medicinal Plants, Graduate School of Pharmaceutical Sciences, Kyoto University and differences in their caffeic acid and rosmarinic acid contents were also observed. The total content of anthocyanins, which are closely related to the leaf color of perilla, was measured as cyanidin-3-glucoside equivalents, and a weak positive correlation was observed between the content of rosmarinic acid, and the total content of total anthocyanins. Furthermore, the results suggest that luminosity and photon flux density of light during cultivation can affect rosmarinic acid content.


Assuntos
Ácidos Cafeicos/química , Cinamatos/química , Depsídeos/química , Perilla/química , Extratos Vegetais/química , Folhas de Planta/química
4.
Arch Biochem Biophys ; 690: 108446, 2020 09 15.
Artigo em Inglês | MEDLINE | ID: mdl-32593678

RESUMO

A simple NMR method to analyze the data obtained by NMR titration experiment of amyloid formation inhibitors against uniformly 15N-labeled amyloid-ß 1-42 peptide (Aß(1-42)) was described. By using solution nuclear magnetic resonance (NMR) measurement, the simplest method for monitoring the effects of Aß fibrilization inhibitors is the NMR chemical shift perturbation (CSP) experiment using 15N-labeled Aß(1-42). However, the flexible and dynamic nature of Aß(1-42) monomer may hamper the interpretation of CSP data. Here we introduced principal component analysis (PCA) for visualizing and analyzing NMR data of Aß(1-42) in the presence of amyloid inhibitors including high concentration osmolytes. We measured 1H-15N 2D spectra of Aß(1-42) at various temperatures as well as of Aß(1-42) with several inhibitors, and subjected all the data to PCA (PCA-HSQC). The PCA diagram succeeded in differentiating the various amyloid inhibitors, including epigallocatechin gallate (EGCg), rosmarinic acid (RA) and curcumin (CUR) from high concentration osmolytes. We hypothesized that the CSPs reflected the conformational equilibrium of intrinsically disordered Aß(1-42) induced by weak inhibitor binding rather than the specific molecular interactions.


Assuntos
Peptídeos beta-Amiloides/química , Fenóis/química , Análise de Componente Principal/métodos , Amiloide/metabolismo , Peptídeos beta-Amiloides/genética , Catequina/análogos & derivados , Catequina/química , Cinamatos/química , Curcumina/química , Depsídeos/química , Escherichia coli/genética , Humanos , Espectroscopia de Ressonância Magnética , Isótopos de Nitrogênio/química , Conformação Proteica , Temperatura , Termodinâmica
5.
J Enzyme Inhib Med Chem ; 35(1): 786-804, 2020 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-32200650

RESUMO

Rosmarinic acid, a phytochemical compound, bears diverse pharmaceutical profile. It is composed by two building blocks: caffeic acid and a salvianic acid unit. The interaction profile, responsible for the delivery of rosmarinic acid and its two substructure components by serum albumin remains unexplored. To unveil this, we established a novel low-cost and efficient method to produce salvianic acid from the parent compound. To probe the interaction profile of rosmarinic acid and its two substructure constituents with the different serum albumin binding sites we utilised fluorescence spectroscopy and competitive saturation transfer difference NMR experiments. These studies were complemented with transfer NOESY NMR experiments. The thermodynamics of the binding profile of rosmarinic acid and its substructures were addressed using isothermal titration calorimetry. In silico docking studies, driven by the experimental data, have been used to deliver further atomic details on the binding mode of rosmarinic acid and its structural components.


Assuntos
Cinamatos/química , Depsídeos/química , Soroalbumina Bovina/química , Animais , Sítios de Ligação , Calorimetria , Bovinos , Cinamatos/síntese química , Depsídeos/síntese química , Simulação de Acoplamento Molecular , Estrutura Molecular , Espectrometria de Fluorescência , Termodinâmica
6.
Artigo em Inglês | MEDLINE | ID: mdl-32168922

RESUMO

The nitrogen pollution of rivers as a global environmental problem has received great attentions in recent years. The occurrence of emerging pollutants in high-altitude rivers will inevitably affect the dissimilatory nitrate reduction processes. In this study, sediment slurry experiments combined with 15N tracer techniques were conducted to investigate the influence of pharmaceutical and personal care products (alone and in combination) on denitrification and the anaerobic ammonium oxidation (anammox) process and the resulting N2O release in the sediments of the Yarlung Zangbo River. The results showed that the denitrification rates were inhibited by sulfamethoxazole (SMX) treatments (1-100 µg L-1) and the anammox rates decreased as the SMX concentrations increased, which may be due to the inhibitory effect of this antibiotic on nitrate reducing microbes. 2-Ethylhexyl-4-methoxycinnamate (EHMC) impacted nitrogen transformation mainly though the inhibition of the anammox processes. SMX and EHMC showed a superposition effect on the denitrification processes. The expression levels of the denitrifying functional genes nirS and nosZ were decreased and N2O release was stimulated due to the presence of SMX and/or EHMC in the sediments. To the best of our knowledge, this study is the first to report the effects of EHMC and its mixtures on the dissimilatory nitrate reduction processes and N2O releases in river sediments. Our results indicated that the widespread occurrence of emerging pollutants in high-altitude rivers may disturb the nitrogen transformation processes and increase the pressure of global warming.


Assuntos
Cinamatos/química , Sedimentos Geológicos/química , Nitratos/química , Óxido Nitroso/química , Rios/química , Sulfametoxazol/química , Desnitrificação , Nitrogênio , Tibet
7.
Food Chem ; 313: 126163, 2020 May 30.
Artigo em Inglês | MEDLINE | ID: mdl-31945702

RESUMO

The copigmentation effects of polyphenol with different structures vary greatly. Therefore, the aim of this study is to investigate possible interactions in red wine model solutions between oenin and three phenolic compounds: danshensu, caffeic acid and rosmarinic acid. Our results show that the copigmentation of rosmarinic acid is the strongest among the compounds tested. The colourimetric parameters indicate that colour intensity becomes enhanced with increasing concentration of these copigments, leading to darker and more vivid bluish colours. Thermodynamic and quantum chemical investigations are performed to interpret the absorption properties in the visible range. Fluorescence spectroscopy confirms the interaction between caffeic acid and oenin, while FTIR spectroscopic results further suggest a role for hydrogen bonds in the overall process. To our knowledge, this is the first experimentally corroborated direct evidence of hydrogen bonds in copigmentation.


Assuntos
Antocianinas/química , Ácidos Cafeicos/química , Cinamatos/química , Depsídeos/química , Lactatos/química , Vinho , Cor , Espectrometria de Fluorescência , Espectroscopia de Infravermelho com Transformada de Fourier , Termodinâmica , Vinho/análise
8.
Molecules ; 25(3)2020 Jan 21.
Artigo em Inglês | MEDLINE | ID: mdl-31972970

RESUMO

For the convenient introduction of simple linear/branched alkyl groups into biologically important azaspirocyclohexadienones, a practical Fe-catalyzed decarbonylative cascade spiro-cyclization of N-aryl cinnamamides with aliphatic aldehydes to provide alkylated 1-azaspiro-cyclohexadienones was developed. Aliphatic aldehydes were oxidative decarbonylated into primary, secondary and tertiary alkyl radicals conveniently and allows for the subsequent cascade construction of dual C(sp3)-C(sp3) and C=O bonds via radical addition, spirocyclization and oxidation sequence.


Assuntos
Alquilantes/química , Compostos Aza/química , Cinamatos/química , Cicloexenos/química , Ferro/química , Compostos de Espiro/química , Aldeídos/química , Alquilação , Catálise , Ciclização
9.
Molecules ; 25(3)2020 Jan 21.
Artigo em Inglês | MEDLINE | ID: mdl-31973244

RESUMO

Tuberculosis, caused by Mycobacterium tuberculosis (Mtb), remains one of the top ten causes of death worldwide and the main cause of mortality from a single infectious agent. The upsurge of multi- and extensively-drug resistant tuberculosis cases calls for an urgent need to develop new and more effective antitubercular drugs. As the cinnamoyl scaffold is a privileged and important pharmacophore in medicinal chemistry, some studies were conducted to find novel cinnamic acid derivatives (CAD) potentially active against tuberculosis. In this context, we have engaged in the setting up of a quantitative structure-activity relationships (QSAR) strategy to: (i) derive through multiple linear regression analysis a statistically significant model to describe the antitubercular activity of CAD towards wild-type Mtb; and (ii) identify the most relevant properties with an impact on the antitubercular behavior of those derivatives. The best-found model involved only geometrical and electronic CAD related properties and was successfully challenged through strict internal and external validation procedures. The physicochemical information encoded by the identified descriptors can be used to propose specific structural modifications to design better CAD antitubercular compounds.


Assuntos
Antituberculosos/química , Antituberculosos/farmacologia , Cinamatos/química , Cinamatos/farmacologia , Relação Quantitativa Estrutura-Atividade , Modelos Lineares , Testes de Sensibilidade Microbiana , Mycobacterium tuberculosis/efeitos dos fármacos
10.
Molecules ; 25(1)2020 Jan 03.
Artigo em Inglês | MEDLINE | ID: mdl-31947799

RESUMO

Unlike its aerial parts, the underground parts of Mentha have so far been studied only marginally. By examining the polyphenolic fingerprint, the antioxidant efficacy and the mutual antioxidant behaviour of mixtures of mint rhizomes, our study presents a modest contribution to addressing this gap. Firstly, we examined the composition of the mint rhizomes: Mentha × piperita cv. 'Perpeta' (MPP), M. longifolia (ML), and M. × villosa cv. 'Snezna' (MVS). Our LC-MS-DAD analysis revealed the presence of ten compounds belonging to groups of phenolic acids and flavonoids, of which the rosmarinic acid (RA) and lithospermic were most strongly represented. Secondly, we evaluated the antioxidant activity of rhizome infusions by DPPH and ABTS and on NIH/3T3 cell lines by DCFH-DA. Thirdly, we determined, examined, and explained the mutual interactions of rhizome infusions mixtures. While most of the combinations acted additive, synergy was observed in ternary infusion mixtures. The synergic action was also detected in the combination of MPP rhizome infusion and RA in the DCFH-DA test. The combinations of mint rhizomes and rosmarinic acid displayed a high dose-reduction index. This leads to beneficial dose reduction at a given antioxidant effect level in mixtures, compared to the dose of the parts used alone. So far, the pharmaceutical and food industry has not used mint rhizomes in commercial products. Hence, our study draws attention to further applications of the Mentha rhizomes as a valuable alternative source of natural antioxidants.


Assuntos
Antioxidantes , Cinamatos , Depsídeos , Flavonoides , Hidroxibenzoatos , Mentha/química , Rizoma/química , Animais , Antioxidantes/química , Antioxidantes/farmacologia , Cinamatos/química , Cinamatos/farmacologia , Depsídeos/química , Depsídeos/farmacologia , Flavonoides/química , Flavonoides/farmacologia , Hidroxibenzoatos/química , Hidroxibenzoatos/farmacologia , Camundongos , Células NIH 3T3
11.
Biochimie ; 170: 128-139, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31945397

RESUMO

In search of the compounds that interfere with amyloid transformation of alpha-synuclein, 9 natural and synthetic cinnamic acid derivatives were studied. They are structurally similar to a half of curcumin, which has pronounced anti-aggregatory and anti-amyloid effects. We have shown that some of these derivatives prevent ovine prion protein amyloidization. Subsequently, thioflavin T binding assay showed that 3 out of 9 studied compounds effectively prevented amyloid transformation of alpha-synuclein with IC50 of 13, 50 and 251 µM. Molecular modeling approach revealed possible binding sites of the three selected ligands with alpha-synuclein fibrils, while monomeric alpha-synuclein does not bind to the ligands according to experimental results. This led us to believe that compounds may act by changing the structure of primary aggregates, preventing the formation of full-length fibrils. The inhibiting effect of the ligands on aggregation of alpha-synuclein was further confirmed by monitoring aggregation via turbidimetry, susceptibility to proteolytic cleavage, changes in beta-sheet content, and scanning ion-conductance microscopy. Studied derivatives were not cytotoxic, and, moreover, two studied compounds (ferulic and 3,4-dimethoxycinnamic acid) are found in plant sources and are natural metabolites present in human blood, so they can be promising candidate drugs for synucleinopathies, including Parkinson's disease.


Assuntos
Amiloide/química , Amiloide/metabolismo , Produtos Biológicos/metabolismo , Cinamatos/metabolismo , alfa-Sinucleína/química , alfa-Sinucleína/metabolismo , Produtos Biológicos/química , Cinamatos/química , Humanos , Simulação de Acoplamento Molecular , Conformação Proteica
12.
Food Funct ; 11(1): 722-729, 2020 Jan 29.
Artigo em Inglês | MEDLINE | ID: mdl-31912082

RESUMO

The objective of this study was to evaluate the benefits of a new extraction process, the ipowder® technology, applied to Melissa officinalis L. Compared to M. officinalis ground dry leaves, the ipowder® had a similar phytochemical fingerprint but contained twice the concentration of rosmarinic acid (by HPTLC and HPLC) and had a two-fold greater antioxidant activity (DPPH* method). In vitro digestion experiments (TIM-1 model) showed better availability of rosmarinic acid for intestinal absorption with the ipowder® than with ground dry leaves, manifested by a three-fold reduction in the quantity of ingested product needed for delivery of the same amount of rosmarinic acid into the upper gastro-intestinal tract. This study shows that the ipowder® technology preserves all the original plant compounds intact while making some active ingredients more accessible and available to exert their effects. To obtain a given effect, the amount of ipowder® extract to ingest will therefore be lower; a reduction in the daily dosage will be more convenient for the patient and will improve patient compliance with supplementation.


Assuntos
Antioxidantes/química , Cinamatos/química , Depsídeos/química , Intestinos/efeitos dos fármacos , Melissa , Extratos Vegetais/química , Estômago/efeitos dos fármacos , Antioxidantes/farmacologia , Cinamatos/farmacologia , Depsídeos/farmacologia , Composição de Medicamentos , Humanos , Técnicas In Vitro , Modelos Anatômicos , Fitoterapia , Folhas de Planta/química
13.
J Am Chem Soc ; 142(7): 3613-3625, 2020 02 19.
Artigo em Inglês | MEDLINE | ID: mdl-31984734

RESUMO

High-level quantum electronic structure calculations are used to provide a deep insight into the mechanism and stereocontrolling factors of two recently developed catalytic asymmetric Diels-Alder (DA) reactions of cinnamate esters with cyclopentadiene. The reactions employ two structurally and electronically very different in situ silylated enantiopure Lewis acid organocatalysts: i.e., binaphthyl-allyl-tetrasulfone (BALT) and imidodiphosphorimidate (IDPi). Each of these catalysts activates only specific substrates in an enantioselective fashion. Emphasis is placed on identifying and quantifying the key noncovalent interactions responsible for the selectivity of these transformations, with the final aim of aiding in the development of designing principles for catalysts with a broader scope. Our results shed light into the mechanism through which the catalyst architecture determines the selectivity of these transformations via a delicate balance of dispersion and steric interactions.


Assuntos
Cinamatos/química , Ciclopentanos/química , Ácidos de Lewis/química , Catálise , Química Computacional , Estereoisomerismo
14.
Chem Biodivers ; 17(1): e1900683, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31797569
15.
Eur J Med Chem ; 187: 111927, 2020 Feb 01.
Artigo em Inglês | MEDLINE | ID: mdl-31812035

RESUMO

Harmicines constitute novel hybrid compounds that combine two agents with reported antiplasmodial properties, namely ß-carboline harmine and a cinnamic acid derivative (CAD). Cu(I) catalyzed azide-alkyne cycloaddition was employed for the preparation of three classes of hybrid molecules: N-harmicines 6a-i, O-harmicines 7a-i and N,O-bis-harmicines 8a-g,i. In vitro antiplasmodial activities of harmicines against the erythrocytic stage of Plasmodium falciparum (chloroquine-sensitive Pf3D7 and chloroquine-resistant PfDd2 strains) and hepatic stage of P. berghei, as well as cytotoxicity against human liver hepatocellular carcinoma cell line (HepG2), were evaluated. Remarkably, most of the compounds exerted significant activities against both stages of the Plasmodium life cycle. The conjugation of various CADs to harmine resulted in the increased antiplasmodial activity relative to harmine. In general, O-harmicines 7 exhibited the highest activity against the erythrocytic stage of both P. falciparum strains, whereas N,O-bis harmicines 8 showed the most pronounced activity against P. berghei hepatic stages. For the latter compound, molecular dynamics simulations confirmed binding within the ATP binding site of PfHsp90, while the weaker binders, namely 6b and harmine, were found to be positioned away from this structural element. In addition, decomposition of the computed binding free energies into contributions from individual residues suggested guidelines for further derivatization of harmine towards more efficient compounds. Cytotoxicity screening revealed N-harmicines 6 as the least, and O-harmicines 7 as the most toxic compounds. Harmicines 6g, 8b and 6d exerted the most selective action towards Plasmodium over human cells, respectively. These results establish harmicines as hits for future optimisation and development of novel antiplasmodial agents.


Assuntos
Antimaláricos/farmacologia , Cinamatos/farmacologia , Harmina/farmacologia , Alcaloides Indólicos/farmacologia , Plasmodium berghei/efeitos dos fármacos , Plasmodium falciparum/efeitos dos fármacos , Antimaláricos/síntese química , Antimaláricos/química , Cinamatos/síntese química , Cinamatos/química , Relação Dose-Resposta a Droga , Harmina/síntese química , Harmina/química , Alcaloides Indólicos/síntese química , Alcaloides Indólicos/química , Simulação de Dinâmica Molecular , Estrutura Molecular , Testes de Sensibilidade Parasitária , Relação Estrutura-Atividade
16.
Biomed Chromatogr ; 34(3): e4773, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31813160

RESUMO

Lonicerae Japonicae Flos (LJF) is a typical herbal medicine and is used as a functional food. LJF, which has complex chemical compounds, has various biological effects. The global metabolomics, focusing on both the endogenous and exogenous metabolites, have not yet been investigated for LJF in normal healthy rats using LC-MS. In this study, plasma metabolomics was analyzed after the administration of LJF at different time intervals, and the exogenous metabolites were identified. Partial least squares discriminant analysis showed significant differences in chemical content in the dosed rats. Cholic acid, indoleacrylic acid, indolelactic acid, hippuric acid, N-acetyl-phenylalanine, and N-acetyl-serotonin significantly accumulated in the dosed rats. Lysophosphatidylethanolamine and lysophosphatidylcholine content, including plasmalogen, increased. There were 25 components of LJF, including 15 prototypes and 10 metabolites, that were identified. The 15 prototypes included phenolic acids, flavonoids, and iridoids, and their contents decreased with an increase in the administration time. Glucuronidation and sulfation of polyphenols were found for LJF. The exogenous glucuronide and sulfate metabolites-including dihydrocoumaric acid-sulfate, dihydrocaffeic acid-sulfate, dihydroferulic acid-sulfate, apigenin-glucuronide, apigenin-glucuronide-sulfate, isorhamnetin-glucuronide-sulfate, and others-were identified with a neutral loss of 176 and 80, respectively. The metabolic differences found in the study may serve as biomarkers of LJF consumption and promote the understanding of the mechanism of action of LJF.


Assuntos
Lonicera , Metaboloma/efeitos dos fármacos , Metabolômica/métodos , Extratos Vegetais , Administração Oral , Animais , Biomarcadores/sangue , Biomarcadores/química , Biomarcadores/metabolismo , Cromatografia Líquida de Alta Pressão , Cinamatos/sangue , Cinamatos/química , Cinamatos/metabolismo , Masculino , Espectrometria de Massas , Extratos Vegetais/administração & dosagem , Extratos Vegetais/metabolismo , Extratos Vegetais/farmacologia , Quercetina/sangue , Quercetina/química , Quercetina/metabolismo , Ratos , Ratos Sprague-Dawley , Reprodutibilidade dos Testes
17.
J Agric Food Chem ; 68(1): 340-350, 2020 Jan 08.
Artigo em Inglês | MEDLINE | ID: mdl-31874034

RESUMO

Folic acid, a synthetic form of folate, is a water-soluble vitamin that is essential during periods of rapid cell division and growth. However, it decomposes upon ultraviolet irradiation to form inactive photoproducts. In this study, the protective effect and mechanisms of antioxidants, including cinnamic acids, flavonoids, catechol and its derivatives, stilbenes, p-benzoquinone and its derivatives, isoprenoids, curcumin, oleic acid, and linoleic acid, against folic acid photodecomposition were investigated by using fluorescence and absorbance spectroscopy, high-performance liquid chromatography, and antioxidant assay. It was found that antioxidants could inhibit or delay the folic acid decomposition in varying degrees, among which caffeic acid was the most effective. The increase in its remarkable antioxidant efficiency and absorbance in the UVA region during irradiation contributed to its effective protection. This finding could be useful for the protection of photolabile components in food and other uses.


Assuntos
Antioxidantes/química , Ácido Fólico/química , Benzoquinonas/química , Catecóis/química , Cinamatos/química , Flavonoides/química , Fotólise/efeitos dos fármacos , Fotólise/efeitos da radiação , Estilbenos/química , Raios Ultravioleta
18.
Eur J Med Chem ; 185: 111786, 2020 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-31671308

RESUMO

In this paper, we described the synthesis and cytotoxic activities of two new series of thieno[2,3-d]pyrimidine and thieno[3,2-d] pyrimidine derivatives. Most of the synthesized compounds had significant antiproliferative activities against PC3, MDA-MB-231, A549, and HeLa cell lines in comparison to the reference drug, erlotinib. Compounds N-(4-((3,5-dichlorophenyl)amino)thieno[2,3-d]pyrimidin-6-yl)cinnamamide 8e and (E)-N-(4-((3,4-dichlorophenyl)amino)thieno[2,3-d]pyrimidin-6-yl)-3-(4-methoxyphenyl)acrylamide 8g with IC50 values of 4 nM and 33 nM, respectively, against HeLa cell line were chosen for further studies. The apoptosis induced activity and cell cycle arrest were determined and the results provided evidence that these compounds induced cell death via apoptosis and arrested cell growth in sub-G1 phase. In addition, western blot analysis manifested the promising result of suppressing the EGFR signaling pathway (p-EGFR/p-ERK1/2). The docking studies appreciated the considerable potency of compound 8e based on hydrogen and covalent binding interactions. Eventually, in silico pharmacokinetic prediction indicated the acceptable bioavailability of all final compounds.


Assuntos
Antineoplásicos/farmacologia , Cinamatos/farmacologia , Citotoxinas/farmacologia , Desenho de Fármacos , Pirimidinas/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/química , Apoptose/efeitos dos fármacos , Ciclo Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Cinamatos/síntese química , Cinamatos/química , Citotoxinas/síntese química , Citotoxinas/química , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Simulação de Acoplamento Molecular , Estrutura Molecular , Pirimidinas/síntese química , Pirimidinas/química , Relação Estrutura-Atividade
19.
Food Chem ; 309: 125796, 2020 Mar 30.
Artigo em Inglês | MEDLINE | ID: mdl-31706678

RESUMO

Interest in anthocyanins has increased remarkably in recent decades, although their wider application has been hampered by instability problems. Thus, this study aimed at developing a strategy to gain access to more stable anthocyanins via enzymatic esterification. For that purpose, three cyanidin derivatives were obtained from underutilized, but easily accessible sources, and their total anthocyanin content was quantified. The purity of cyanidins obtained ranged from 40% to 88% depending on their source. Subsequently, the critical enzymatic reaction conditions were established, and the best results were found using tert-butanol as a solvent, 20 g/L of lipase B from Candida Antarctica, and vinyl cinnamate as acyl donor at ratio 250:1 (acyl donor to anthocyanin). Finally, five new acylated anthocyanin derivatives were synthesized with improved antioxidant activity and thermostability, in comparison to the cyanidin-3-glucoside, which is an advantageous feature for industrial applications.


Assuntos
Antocianinas/metabolismo , Antioxidantes/química , Proteínas Fúngicas/metabolismo , Glucosídeos/metabolismo , Lipase/metabolismo , Acilação , Antocianinas/química , Cinamatos/química , Esterificação , Glucosídeos/química , Espectroscopia de Ressonância Magnética , Prunus domestica/química , Prunus domestica/metabolismo , Solventes/química , Temperatura
20.
J Nat Med ; 74(2): 341-352, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31848798

RESUMO

High-quality perilla leaves are defined as those having purple upper and lower surfaces and a pleasant smell. The Japanese Pharmacopoeia specifies the content of essential oils in perilla leaves but not the content of rosmarinic acid. Rosmarinic acid is a common component of Labiatae plants such as shiso (Perilla frutescens Britton var. crispa W. Deane). Rosmarinic acid has been reported to exhibit anti-inflammatory and anti-oxidant activity but the factors affecting the content of rosmarinic acid in plants remain unknown. This study describes a simple and reproducible method for quantifying rosmarinic acid. We elucidated the main causes for the different rosmarinic acid contents of plants by examining various samples of perilla using the proposed method. Significant differences in rosmarinic acid content between varieties and cultivators were observed. The rosmarinic acid content was higher in green perilla compared with red perilla, in wild species compared with cultivated species, and in plants cultivated in outdoor nurseries compared with in indoor nurseries. The proposed quantitative method was used to examine the rosmarinic acid content in a Kampo formula, Hangekobokuto, and was found to be higher in decoctions prepared using the Kouge method compared with the typical preparation method. We examined the chlorophyll and caffeic acid contents of several samples and their relationship with the rosmarinic acid content.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Cinamatos/química , Depsídeos/química , Perilla frutescens/química , Perilla/química , Extratos Vegetais/química , Folhas de Planta/química , Cinamatos/farmacologia , Depsídeos/farmacologia
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