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1.
Prep Biochem Biotechnol ; 54(7): 872-881, 2024 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-38174655

RESUMO

Ginger (Zingiber officinale Roscoe, Zingeberaceae) is a medicinal plant widely used as food, spice, or flavoring agent worldwide. 6-Shogaol is a compound of prime interest in exhibiting anti-inflammatory, antioxidant and chemopreventive effects. The objective of the study is to investigate the effect of microwave-assisted drying (MAD) followed by microwave-assisted extraction (MAE) so as to produce 6-Shogaol enriched Ginger with improved therapeutic benefits. Various drying techniques viz. shade drying, tray drying, microwave-assisted drying and osmotic dehydration as a pretreatment were used for drying Ginger rhizomes. The dried rhizomes were extracted by conventional solvent extraction and microwave-assisted extraction techniques and tested for content of 6-Shogaol using the newly developed HPLC method whereas total flavonoid and polyphenol content were determined using the UV spectrophotometric method. Subjecting the microwave dried Ginger to microwave-assisted extraction for 45 min at constant power level of 284 W resulted in a significant rise in the extractability of 6-Shogaol (1.660 ± 0.018), total polyphenols (855.46 ± 5.33) and flavonoids (617.97 ± 6.40) compared to the conventional method of extraction. The proposed Ginger processing method of microwave drying followed by microwave extraction outperforms traditional methods in terms of speed, convenience, and performance thus can be scaled up to industrial levels.


Assuntos
Catecóis , Dessecação , Micro-Ondas , Extratos Vegetais , Zingiber officinale , Zingiber officinale/química , Catecóis/isolamento & purificação , Catecóis/química , Dessecação/métodos , Cromatografia Líquida de Alta Pressão/métodos , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Flavonoides/isolamento & purificação , Flavonoides/análise , Flavonoides/química , Rizoma/química , Polifenóis/isolamento & purificação , Polifenóis/análise
2.
Mar Drugs ; 20(2)2022 Feb 10.
Artigo em Inglês | MEDLINE | ID: mdl-35200662

RESUMO

In this study, we investigated the anti-allergic effects of 3,4-dihydroxybenzaldehyde (DHB) isolated from the marine red alga, Polysiphonia morrowii, in mouse bone-marrow-derived cultured mast cells (BMCMCs) and passive cutaneous anaphylaxis (PCA) in anti-dinitrophenyl (DNP) immunoglobulin E (IgE)-sensitized mice. DHB inhibited IgE/bovine serum albumin (BSA)-induced BMCMCs degranulation by reducing the release of ß-hexosaminidase without inducing cytotoxicity. Further, DHB dose-dependently decreased the IgE binding and high-affinity IgE receptor (FcεRI) expression and FcεRI-IgE binding on the surface of BMCMCs. Moreover, DHB suppressed the secretion and/or the expression of the allergic cytokines, interleukin (IL)-4, IL-5, IL-6, IL-13, and tumor necrosis factor (TNF)-α, and the chemokine, thymus activation-regulated chemokine (TARC), by regulating the phosphorylation of IκBα and the translocation of cytoplasmic NF-κB into the nucleus. Furthermore, DHB attenuated the passive cutaneous anaphylactic (PCA) reaction reducing the exuded Evans blue amount in the mouse ear stimulated by IgE/BSA. These results suggest that DHB is a potential therapeutic candidate for the prevention and treatment of type I allergic disorders.


Assuntos
Antialérgicos/farmacologia , Benzaldeídos/farmacologia , Catecóis/farmacologia , Mastócitos/efeitos dos fármacos , Rodófitas/metabolismo , Animais , Antialérgicos/administração & dosagem , Antialérgicos/isolamento & purificação , Benzaldeídos/administração & dosagem , Benzaldeídos/isolamento & purificação , Catecóis/administração & dosagem , Catecóis/isolamento & purificação , Células Cultivadas , Citocinas/imunologia , Modelos Animais de Doenças , Relação Dose-Resposta a Droga , Imunoglobulina E/imunologia , Masculino , Mastócitos/imunologia , Camundongos , Camundongos Endogâmicos BALB C , Camundongos Endogâmicos C57BL , Anafilaxia Cutânea Passiva/efeitos dos fármacos , Anafilaxia Cutânea Passiva/imunologia , Soroalbumina Bovina/imunologia
3.
Molecules ; 26(15)2021 Jul 30.
Artigo em Inglês | MEDLINE | ID: mdl-34361791

RESUMO

As a key enzyme regulating postprandial blood glucose, α-Glucosidase is considered to be an effective target for the treatment of diabetes mellitus. In this study, a simple, rapid, and effective method for enzyme inhibitors screening assay was established based on α-glucosidase catalyzes reactions in a personal glucose meter (PGM). α-glucosidase catalyzes the hydrolysis of maltose to produce glucose, which triggers the reduction of ferricyanide (K3[Fe(CN)6]) to ferrocyanide (K4[Fe(CN)6]) and generates the PGM detectable signals. When the α-glucosidase inhibitor (such as acarbose) is added, the yield of glucose and the readout of PGM decreased accordingly. This method can achieve the direct determination of α-glucosidase activity by the PGM as simple as the blood glucose tests. Under the optimal experimental conditions, the developed method was applied to evaluate the inhibitory activity of thirty-four small-molecule compounds and eighteen medicinal plants extracts on α-glucosidase. The results exhibit that lithospermic acid (52.5 ± 3.0%) and protocatechualdehyde (36.8 ± 2.8%) have higher inhibitory activity than that of positive control acarbose (31.5 ± 2.5%) at the same final concentration of 5.0 mM. Besides, the lemon extract has a good inhibitory effect on α-glucosidase with a percentage of inhibition of 43.3 ± 3.5%. Finally, the binding sites and modes of four active small-molecule compounds to α-glucosidase were investigated by molecular docking analysis. These results indicate that the PGM method is feasible to screening inhibitors from natural products with simple and rapid operations.


Assuntos
Benzaldeídos/farmacologia , Benzofuranos/farmacologia , Glicemia/análise , Catecóis/farmacologia , Depsídeos/farmacologia , Diabetes Mellitus Tipo 2/diagnóstico , Inibidores de Glicosídeo Hidrolases/farmacologia , Monitorização Ambulatorial/métodos , alfa-Glucosidases/sangue , Acarbose/química , Acarbose/farmacologia , Benzaldeídos/química , Benzaldeídos/isolamento & purificação , Benzofuranos/química , Benzofuranos/isolamento & purificação , Sítios de Ligação , Técnicas Biossensoriais/instrumentação , Catecóis/química , Catecóis/isolamento & purificação , Depsídeos/química , Depsídeos/isolamento & purificação , Diabetes Mellitus Tipo 2/sangue , Diabetes Mellitus Tipo 2/tratamento farmacológico , Inibidores de Glicosídeo Hidrolases/química , Humanos , Hidrólise , Cinética , Maltose/metabolismo , Simulação de Acoplamento Molecular , Monitorização Ambulatorial/instrumentação , Extratos Vegetais/química , Plantas Medicinais , Ligação Proteica , Conformação Proteica em alfa-Hélice , Conformação Proteica em Folha beta , Domínios e Motivos de Interação entre Proteínas , Bibliotecas de Moléculas Pequenas/química , Bibliotecas de Moléculas Pequenas/farmacologia , Termodinâmica , Dispositivos Eletrônicos Vestíveis , alfa-Glucosidases/química
4.
Molecules ; 26(13)2021 Jun 23.
Artigo em Inglês | MEDLINE | ID: mdl-34201712

RESUMO

Alnus sibirica (AS) is distributed in Korea, Japan, China, and Russia and has reported anti-oxidant, anti-inflammatory, and reducing activities on atopic dermatitis-like skin lesions, along with other beneficial health properties. In the present study, we tried to prove the cancer-preventive activity against prostate cancer. The extracted and isolated compounds, oregonin (1), hirsutenone (2), and hirsutanonol (3), which were isolated from AS, were tested for anti-proliferative activity. To do this, we used the MTT assay; NF-κB inhibitory activity, using Western blotting; apoptosis-inducing activity using flow cytometry; DNA methylation activity, using methylation-specific polymerase chain reaction in androgen-dependent (LNCaP) and androgen-independent (PC-3) prostate cancer cell lines. The compounds (1-3) showed potent anti-proliferative activity against both prostate cancer cell lines. Hirsutenone (2) exhibited the strongest NF-κB inhibitory and apoptosis-inducing activities compared with oregonin (1) and hirsutanonol (3). DNA methylation activity, which was assessed for hirsutenone (2), revealed a concentration-dependent enhancement of the unmethylated DNA content and a reduction in the methylated DNA content in both PC-3 and LNCaP cells. Overall, these findings suggest that hirsutenone (2), when isolated from AS, may be a potential agent for preventing the development or progression of prostate cancer.


Assuntos
Alnus/química , Apoptose/efeitos dos fármacos , Catecóis/farmacologia , Proliferação de Células/efeitos dos fármacos , Desmetilação do DNA/efeitos dos fármacos , Diarileptanoides/farmacologia , Glutationa S-Transferase pi/metabolismo , Neoplasias da Próstata/prevenção & controle , Androgênios/farmacologia , Catecóis/química , Catecóis/isolamento & purificação , Linhagem Celular Tumoral , Diarileptanoides/química , Diarileptanoides/isolamento & purificação , Citometria de Fluxo , Humanos , Masculino , NF-kappa B/metabolismo , Neoplasias da Próstata/tratamento farmacológico , Neoplasias da Próstata/metabolismo
5.
Sci Rep ; 11(1): 14870, 2021 07 21.
Artigo em Inglês | MEDLINE | ID: mdl-34290338

RESUMO

This study aimed to investigate microwave-assisted extraction (MAE) of dried ginger and to develop a rice-based edible film incorporating ginger extract. The optimal MAE conditions of 400 W microwave power and an extraction time of 1 min were determined using a 32 full factorial design. The optimized extract showed total phenolic compounds (TPC, 198.2 ± 0.7 mg gallic acid equivalent/g), antioxidant activity measured by DPPH (91.4 ± 0.6% inhibition), ABTS (106.4 ± 3.1 mg Trolox/g), and FRAP (304.6 ± 5.5 mg Trolox/g), and bioactive compounds including 6-gingerol (71.5 ± 3.6 mg/g), 6-shogaol (12.5 ± 1.0 mg/g), paradol (23.1 ± 1.1 mg/g), and zingerone (5.0 ± 0.3 mg/g). Crude extract of dried ginger showed antimicrobial activity against Streptococcus mutans DMST 18777, with a minimum inhibitory concentration and minimum bactericidal concentration of 0.5 and 31.2 mg/mL, respectively. The rice-based edible film incorporating 3.2% (w/v) ginger extract tested against S. mutans DMST 18777 had a mean zone of inhibition of 12.7 ± 0.1 mm. Four main phenolic compounds, 6-gingerol, 6-shogaol, paradol, and zingerone, and six volatile compounds, α-curcumene, α-zingiberene, γ-muurolene, α-farnesene, ß-bisabolene, and ß-sesquiphellandrene, were found in rice film fortified with crude ginger extract.


Assuntos
Catecóis/farmacologia , Filmes Comestíveis , Álcoois Graxos/farmacologia , Guaiacol/análogos & derivados , Micro-Ondas , Oryza/química , Extratos Vegetais/farmacologia , Extração em Fase Sólida/métodos , Streptococcus mutans/efeitos dos fármacos , Zingiber officinale/química , Catecóis/isolamento & purificação , Farmacorresistência Bacteriana , Álcoois Graxos/isolamento & purificação , Guaiacol/isolamento & purificação , Guaiacol/farmacologia , Extratos Vegetais/isolamento & purificação , Tailândia
6.
J Nat Prod ; 84(7): 2053-2058, 2021 07 23.
Artigo em Inglês | MEDLINE | ID: mdl-34197704

RESUMO

Sparticols A (1) and B (2), two catechol-bearing naphthalenedioxy derivatives, were isolated from the submerged culture of the Spanish broom inhabiting Dothideomycetes fungus, Sparticola junci. The structures of 1 and 2 were established by NMR spectroscopic analysis and high-resolution mass spectrometry. The 8S absolute configuration of their ß-hydroxy functionalities was determined by ECD-TDDFT. Both compounds exhibited inhibitory activity against Staphylococcus aureus with an MIC value of 66.6 µg/mL. Polyketides 1 and/or 2 may be associated with pathways cascading to seco-spirodioxynapthalene derivatives.


Assuntos
Antibacterianos/farmacologia , Ascomicetos/química , Catecóis/farmacologia , Policetídeos/farmacologia , Antibacterianos/isolamento & purificação , Catecóis/isolamento & purificação , Testes de Sensibilidade Microbiana , Estrutura Molecular , Policetídeos/isolamento & purificação , Staphylococcus aureus/efeitos dos fármacos , Relação Estrutura-Atividade
7.
J Oleo Sci ; 70(5): 607-613, 2021 May 01.
Artigo em Inglês | MEDLINE | ID: mdl-33840664

RESUMO

The oil recovery from Alyanak apricot kernel was 36.65% in control (unroasted) and increased to 43.77% in microwave-roasted kernels. The total phenolic contents in extracts from apricot kernel were between 0.06 (oven-roasted) and 0.20 mg GAE/100 g (microwave-roasted) while the antioxidant activity varied between 2.55 (oven-roasted) and 19.34% (microwave-roasted). Gallic acid, 3,4-dihydroxybenzoic acid, (+)-catechin and 1,2-dihydroxybenzene were detected as the key phenolic constituents in apricot kernels. Gallic acid contents varied between 0.53 (control) and 1.10 mg/100 g (microwave-roasted) and 3,4-dihydroxybenzoic acid contents were between 0.10 (control) and 0.35 mg/100 g (microwave-roasted). Among apricot oil fatty acids, palmitic acid contents ranged from 4.38 (oven-roasted) to 4.76% (microwave-roasted); oleic acid contents were between 65.73% (oven-roasted) and 66.15% (control) and linoleic acid contents varied between 26.55 (control) and 27.12% (oven-roasted).


Assuntos
Antioxidantes/análise , Catequina/isolamento & purificação , Catecóis/isolamento & purificação , Ácido Gálico/isolamento & purificação , Hidroxibenzoatos/isolamento & purificação , Ácidos Linoleicos/isolamento & purificação , Micro-Ondas , Ácido Oleico/isolamento & purificação , Óleos de Plantas/análise , Óleos de Plantas/isolamento & purificação , Prunus armeniaca/química , Sementes/química
8.
Yakugaku Zasshi ; 141(1): 67-79, 2021.
Artigo em Japonês | MEDLINE | ID: mdl-33390450

RESUMO

In the 1980s, the authors developed the enzyme immunoassay (EIA) system for mouse nerve growth factor (NGF) to clarify its important physiological roles. Our EIA system was a new and powerful tool for measurement of extremely low levels of NGF in vitro and in vivo, and it contributed to investigation into the regulatory mechanism of NGF synthesis. After that, we demonstrated that the compounds with a low molecular weight, such as 4-methylcatechol, which elicit stimulatory activity toward NGF synthesis, were useful and practical for therapeutic purposes; as NGF has potent activity on neuronal degeneration in both the central nervous system (CNS) and the peripheral nervous system. Since 2008, we have been searching for and isolating neuroprotective component(s) from citrus peels. As a result, our study revealed that 1) 3,5,6,7,8,3',4'-heptamethoxyflavone (HMF) has neuroprotective ability in the CNS by inducing brain-derived neurotrophic factor (BDNF) and by suppressing inflammation; 2) auraptene (AUR) also has neuroprotective ability in the CNS by suppressing inflammation and by probably inducing neurotrophic factor(s). As the content of AUR in the peels of Kawachi Bankan is exceptionally high, 1) we found this peel powder to exert neuroprotective effects in the brain of various pathological model mice; 2) some of the AUR transited from the peel to the juice during the squeezing process to obtain the juice. Therefore, K. Bankan juice, which is enriched in AUR by adding peel paste to the raw juice, was shown to be practical for suppression of cognitive dysfunction of aged healthy volunteers.


Assuntos
Catecóis/farmacologia , Citrus/química , Cumarínicos/farmacologia , Descoberta de Drogas , Fator de Crescimento Neural/biossíntese , Fator de Crescimento Neural/fisiologia , Fármacos Neuroprotetores/isolamento & purificação , Fármacos Neuroprotetores/farmacologia , Animais , Catecóis/isolamento & purificação , Disfunção Cognitiva/tratamento farmacológico , Cumarínicos/administração & dosagem , Cumarínicos/isolamento & purificação , Modelos Animais de Doenças , Feminino , Humanos , Técnicas Imunoenzimáticas , Masculino , Camundongos , Fitoterapia , Ratos
9.
Nutrients ; 12(10)2020 Oct 19.
Artigo em Inglês | MEDLINE | ID: mdl-33086593

RESUMO

The beneficial effects of ginger polyphenols have been extensively reported. However, their metabolic characteristics and health effects on gut microbiota are poor understood. The purpose of this study was to investigate the digestion stability of ginger polyphenols and their prebiotic effects on gut microbiota by simulating digestion and fermentation in vitro. Following simulated digestion in vitro, 85% of the polyphenols were still detectable, and the main polyphenol constituents identified in ginger extract are 6-, 8-, and 10-gingerols and 6-shogaol in the digestive fluids. After batch fermentation, the changes in microbial populations were measured by 16S rRNA gene Illumina MiSeq sequencing. In mixed-culture fermentation with fecal inoculate, digested ginger extract (GE) significantly modulated the fecal microbiota structure and promoted the growth of some beneficial bacterial populations, such as Bifidobacterium and Enterococcus. Furthermore, incubation with GE could elevate the levels of short-chain fatty acids (SCFAs) accompanied by a decrease in the pH value. Additionally, the quantitative PCR results showed that 6-gingerol (6G), as the main polyphenol in GE, increased the abundance of Bifidobacterium significantly. Therefore, 6G is expected to be a potential prebiotic that improves human health by promoting gut health.


Assuntos
Catecóis/farmacologia , Digestão/fisiologia , Álcoois Graxos/farmacologia , Fezes/microbiologia , Fermentação/efeitos dos fármacos , Microbioma Gastrointestinal/efeitos dos fármacos , Polifenóis/farmacologia , Prebióticos , Zingiber officinale/química , Bifidobacterium/crescimento & desenvolvimento , Catecóis/isolamento & purificação , Enterococcus/crescimento & desenvolvimento , Ácidos Graxos Voláteis/metabolismo , Álcoois Graxos/isolamento & purificação , Humanos , Concentração de Íons de Hidrogênio , Técnicas In Vitro , Polifenóis/isolamento & purificação
10.
Mar Drugs ; 18(9)2020 Sep 17.
Artigo em Inglês | MEDLINE | ID: mdl-32957565

RESUMO

Gut microbiota has a critical role in metabolic diseases, including type 2 diabetes mellitus (T2DM). 3-bromo-4,5-bis(2,3-dibromo-4,5-dihydroxybenzyl)-1,2-benzenediol (BDB) is a natural bromophenol isolated from marine red alga Rhodomela confervoides. Our latest research showed that BDB could alleviate T2DM in diabetic BKS db mice. To find out whether BDB modulates the composition of the gut microbiota during T2DM treatment, 24 BKS db diabetic mice were randomly grouped to receive BDB (n = 6), metformin (n = 6), or the vehicle (n = 6) for 7 weeks in a blinded manner. Non-diabetic BKS mice (n = 6) were used as normal control. Diabetic mice treated with BDB or metformin demonstrated significant reductions in fasting blood glucose (FBG) levels compared with the vehicle-treated mice in the 7th week. Pyrosequencing of the V3-V4 regions of the 16S rRNA gene revealed the changes of gut microbiota in response to BDB treatment. The result demonstrated short-chain acid (SCFA) producing bacteria Lachnospiraceae and Bacteroides were found to be significantly more abundant in the BDB and metformin treated group than the vehicle-treatment diabetic group. Remarkably, at the genus levels, Akkermansia elevated significantly in the BDB-treatment group. Metagenomic results indicated that BDB may alleviate the metabolic disorder of diabetic mice by promoting propanoate metabolism and inhibiting starch and sucrose metabolism, amino sugar and nucleotide sugar metabolism. In conclusion, our study suggests that the anti-diabetic effect of BDB is closely related to the modulating structure of gut microbiota and the improvement of functional metabolism genes of intestinal microorganisms.


Assuntos
Bactérias/efeitos dos fármacos , Compostos Benzidrílicos/farmacologia , Glicemia/efeitos dos fármacos , Catecóis/farmacologia , Diabetes Mellitus Tipo 2/tratamento farmacológico , Microbioma Gastrointestinal/efeitos dos fármacos , Hipoglicemiantes/farmacologia , Metagenômica , Ribotipagem , Animais , Bactérias/genética , Bactérias/crescimento & desenvolvimento , Bactérias/metabolismo , Compostos Benzidrílicos/isolamento & purificação , Biomarcadores/sangue , Glicemia/metabolismo , Catecóis/isolamento & purificação , Diabetes Mellitus Tipo 2/sangue , Diabetes Mellitus Tipo 2/microbiologia , Modelos Animais de Doenças , Microbioma Gastrointestinal/genética , Sequenciamento de Nucleotídeos em Larga Escala , Hipoglicemiantes/isolamento & purificação , Masculino , Camundongos Endogâmicos C57BL , Rodófitas/química
11.
Drug Des Devel Ther ; 14: 2977-2985, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32801638

RESUMO

BACKGROUND: Streptococcus sanguinis is Gram-positive bacteria that contribute to caries. Many antibacterial agents are resistant against bacteria so that the discovery of new antibacterial agents is a crucial issue. Mechanism of antibacterial agents by disrupting cell wall bacteria is a promising target to be developed. One of the enzymes contributing to the cell wall is MurA enzyme. MurA is an enzyme catalyzing the first step of peptidoglycan biosynthesis in the cell wall formation. Inhibiting MurA is an effective and efficient way to kill the bacteria. Source of bioactive compounds including the antibacterial agent can be found in natural product such as herbal plant. Piper betle L. was reported to contain active antibacterial compounds. However, there is no more information on the antibacterial activity and molecular mechanism of P. betle's compound against S. sanguinis. PURPOSE: The study aims to identify antibacterial constituents of P. betle L. and evaluate their activities through two different methods including in vitro and in silico analysis. MATERIALS AND METHODS: The antibacterial agent was purified by bioactivity-guided isolation with combination chromatography methods and the chemical structure was determined by spectroscopic methods. The in vitro antibacterial activity was evaluated by disc diffusion and dilution methods while the in silico study of a compound binds on the MurA was determined using PyRx program. RESULTS: The antibacterial compound identified as allylpyrocatechol showed inhibitory activity against S. sanguinis with an inhibition zone of 11.85 mm at 1%, together with MIC and MBC values of 39.1 and 78.1 µg/mL, respectively. Prediction for molecular inhibition mechanism of allylpyrocatechols against the MurA presented two allylpyrocatechol derivatives showing binding activity of -5.4, stronger than fosfomycin as a reference with the binding activity of -4.6. CONCLUSION: Two allylpyrocatechol derivatives were predicted to have a good potency as a novel natural antibacterial agent against S. sanguinis through blocking MurA activity that causes disruption of bacterial cell wall.


Assuntos
Alquil e Aril Transferases/antagonistas & inibidores , Antibacterianos/farmacologia , Catecóis/farmacologia , Inibidores Enzimáticos/farmacologia , Extratos Vegetais/farmacologia , Streptococcus sanguis/efeitos dos fármacos , Alquil e Aril Transferases/metabolismo , Antibacterianos/química , Antibacterianos/isolamento & purificação , Catecóis/química , Catecóis/isolamento & purificação , Relação Dose-Resposta a Droga , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Testes de Sensibilidade Microbiana , Estrutura Molecular , Piper betle/química , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Streptococcus sanguis/enzimologia , Relação Estrutura-Atividade
12.
Chem Pharm Bull (Tokyo) ; 68(8): 784-790, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32741921

RESUMO

Malaria disease remains a serious worldwide health problem. In South-East Asia, one of the malaria infection "hot-spots," medicinal plants such as Piper betle have traditionally been used for the treatment of malaria, and allylpyrocatechol (1), a constituent of P. betle, has been shown to exhibit anti-malarial activities. In this study, we verified that 1 showed in vivo anti-malarial activity through not only intraperitoneal (i.p.) but also peroral (p.o.) administration. Additionally, some analogs of 1 were synthesized and the structure-activity relationship was analyzed to disclose the crucial sub-structures for the potent activity.


Assuntos
Antimaláricos/química , Catecóis/química , Piper betle/química , Animais , Antimaláricos/isolamento & purificação , Antimaláricos/farmacologia , Antimaláricos/uso terapêutico , Catecóis/isolamento & purificação , Catecóis/farmacologia , Catecóis/uso terapêutico , Modelos Animais de Doenças , Malária/tratamento farmacológico , Malária/parasitologia , Camundongos , Testes de Sensibilidade Parasitária , Piper betle/metabolismo , Extratos Vegetais/química , Folhas de Planta/química , Folhas de Planta/metabolismo , Plasmodium berghei/efeitos dos fármacos , Relação Estrutura-Atividade
13.
J Recept Signal Transduct Res ; 40(4): 324-338, 2020 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-32223496

RESUMO

Toll-like receptor 4 (TLR4) pathway is one of the major pathways that mediate the inflammation in human body. There are different anti-inflammatory drugs available in the market which specifically act on different signaling proteins of TLR4 pathway but they do have few side effects and other limitations for intended use in human body. In this study, Curcumin and its different analogs have been analyzed as the inhibitors of signaling proteins, i.e. Cycloxygenase-2 (COX-2), inhibitor of kappaß kinase (IKK) and TANK binding kinase-1 (TBK-1) of TLR4 pathway using different computational tools. Initially, three compounds were selected for respective target based on free binding energy among which different compounds were reported to have better binding affinity than commercially available drug (control). Upon continuous computational exploration with induced fit docking (IFD), 6-Gingerol, Yakuchinone A and Yakuchinone B were identified as the best inhibitors of COX-2, IKK, and TBK-1 respectively. Then their drug-like potentialities were analyzed in different experiments where they were also predicted to perform well. Hopefully, this study will uphold the efforts of researchers to identify anti-inflammatory drugs from natural sources.


Assuntos
Química Computacional , Curcumina/química , Inflamação/tratamento farmacológico , Receptor 4 Toll-Like/química , Catecóis/química , Catecóis/isolamento & purificação , Catecóis/uso terapêutico , Curcumina/análogos & derivados , Curcumina/isolamento & purificação , Curcumina/uso terapêutico , Ciclo-Oxigenase 2/genética , Diarileptanoides/química , Diarileptanoides/isolamento & purificação , Diarileptanoides/uso terapêutico , Álcoois Graxos/química , Álcoois Graxos/isolamento & purificação , Álcoois Graxos/uso terapêutico , Guaiacol/análogos & derivados , Guaiacol/química , Guaiacol/isolamento & purificação , Guaiacol/uso terapêutico , Humanos , Quinase I-kappa B/genética , Inflamação/genética , Lipopolissacarídeos/química , NF-kappa B/antagonistas & inibidores , NF-kappa B/genética , Preparações Farmacêuticas/química , Proteínas Serina-Treonina Quinases/genética , Transdução de Sinais/efeitos dos fármacos , Receptor 4 Toll-Like/antagonistas & inibidores , Receptor 4 Toll-Like/genética
14.
Biomolecules ; 10(2)2020 02 22.
Artigo em Inglês | MEDLINE | ID: mdl-32098310

RESUMO

Gingerols from the rhizome of fresh ginger (Zingiber officinale) were obtained by a simple extraction, followed by purification. The gingerols extract was composed of 6-gingerol (54%), 8-gingerol (20%), and 10-gingerol (26%). It was included into γ-cyclodextrin by classic co-dissolution procedures. Solid-state characterisation of γ-cyclodextrin·gingerols shows that this inclusion compound features 1:1 host-to-guest stoichiometry and that it is a microcrystalline powder with a crystalline cell that belongs to the tetragonal space group 4212, having the host molecules stacked in infinite channels where the gingerols are accommodated. In chimico studies with ABTS•+ scavenging, NO• scavenging, ß-carotene peroxidation, and 5-LOX inhibition show that γ-cyclodextrin is a suitable carrier for gingerols, because it does not alter their reactivity towards these substances. Yogurt was tested as a matrix for the incorporation of gingerols and γ-cyclodextrin·gingerols into foodstuff. The colour of the fortified yogurt suffered little alterations. In the case of yogurt with the inclusion compound, γ-cyclodextrin·gingerols, as fortificant, these alterations were not perceptible to the naked eye. Moreover, yogurt with γ-cyclodextrin·gingerols showed a good antioxidant activity, thus being suitable for use in nutraceutical applications.


Assuntos
Catecóis/química , Álcoois Graxos/química , gama-Ciclodextrinas/isolamento & purificação , Antioxidantes/metabolismo , Catecóis/isolamento & purificação , Suplementos Nutricionais , Álcoois Graxos/isolamento & purificação , Zingiber officinale/química , Extratos Vegetais/química , Rizoma/química , Rizoma/efeitos dos fármacos , Iogurte , gama-Ciclodextrinas/análise , gama-Ciclodextrinas/metabolismo
15.
Anticancer Agents Med Chem ; 20(9): 1129-1139, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-31994470

RESUMO

BACKGROUND: 6-Gingerol (6G) and 6-Shogaol (6S) are the main active components of ginger. 6-Gingerol is known for its anti-metastatic and anti-invasive pharmacological activities on cancer cells, besides, 6-Shogaol also inhibits breast cancer cell invasion. OBJECTIVE: In this study, radioiodination (131I) of 6G and 6S was aimed. Additionally, it is aimed to monitor their incorporation behavior on breast cancer cell lines. METHODS: 6-Gingerol was isolated from the fresh ginger-roots extract, additionally, dehydrated to obtain 6-Shogaol. 6G and 6S were radioiodinated using iodogen method. Quality control studies of radioiodinated ginger compounds (6G and 6S) were performed by thin layer radio-chromatography. In vitro studies of radioiodinated ginger compounds on MCF-7 and MDA-MB-231 cells were performed with incorporation assays. RESULTS: 6-Gingerol and 6-Shogaol were radioiodinated (131I-6G and 131I-6S) in high yields over 95%. 131I-6S demonstrated higher incorporation values than 131I-6G on MDA-MB-231 cells. Incorporation behavior of 131I-6G and 131I-6S was similar to MCF-7 cells. CONCLUSION: It has been observed that ginger compounds were radioiodinated successfully and 131I-6S have a noteworthy incorporation on MDA-MB-231 cells which is a known breast carcinoma cell line with highly invasive characteristics.


Assuntos
Neoplasias da Mama/diagnóstico por imagem , Catecóis/química , Álcoois Graxos/química , Zingiber officinale/química , Catecóis/isolamento & purificação , Cromatografia em Camada Fina , Álcoois Graxos/isolamento & purificação , Feminino , Humanos , Radioisótopos do Iodo , Estrutura Molecular , Células Tumorais Cultivadas
16.
J Pharm Biomed Anal ; 177: 112820, 2020 Jan 05.
Artigo em Inglês | MEDLINE | ID: mdl-31476432

RESUMO

Ginger, the rhizome of Zingiber officinale Roscoe is of great importance in the traditional medicine for the treatment of various diseases. More than 400 constituents have been reported in the plant, the most important ones being the gingerol and shogaol derivatives. Positive effects of ginger extracts and isolated [6]-gingerol have been proved in animal models of anxiety, Alzheimer's disease, Parkinson's disease and epilepsy. Taken in consideration these promising positive effects of ginger and its constituents in the central nervous system, the isolation of gingerol and shogaol derivatives ([6]-gingerol (1), [8]-gingerol (2), [10]-gingerol (3), [6]-shogaol (4), [10]-shogaol (5), 1-dehydro-[6]-gingerdione (6), 1-dehydro-[10]-gingerdione (7)) and investigation of their transcellular passive diffusion across the blood-brain barrier (BBB) were carried out. For this purpose, a Parallel Artificial Membrane Permeability Assay for the Blood-Brain Barrier (PAMPA-BBB) was chosen that had previously been validated for natural compounds. Based on our results, [6]-gingerol, [8]-gingerol and [6]-shogaol were found to be able to penetrate the BBB via passive diffusion, suggesting them to contribute to the positive effects of ginger extracts in the central nervous system.


Assuntos
Barreira Hematoencefálica/metabolismo , Catecóis/farmacologia , Catecóis/farmacocinética , Álcoois Graxos/farmacocinética , Extratos Vegetais/farmacocinética , Zingiber officinale/química , Animais , Barreira Hematoencefálica/química , Catecóis/química , Catecóis/isolamento & purificação , Cromatografia Líquida de Alta Pressão/métodos , Difusão , Álcoois Graxos/química , Álcoois Graxos/isolamento & purificação , Lipídeos/química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas/métodos , Membranas Artificiais , Permeabilidade , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Raízes de Plantas/química , Suínos
17.
J Ethnopharmacol ; 249: 112396, 2020 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-31743763

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: In silico data revealed that the active compound of ginger (Zingiber officinale Roscoe), 6-shogaol, has strong affinity toward transient receptor potential vanilloid-1 (TRPV-1). TRPV-1 is expressed in nervous tissue and pancreatic ß-cells. Prolonged induction of TRPV-1 is related to the expression of N-methyl-D-aspartate receptor subunit 2B (NMDAR2B). However, there are no data on TRPV-1 and NMDAR2B expressions in nervous tissue after 6-shogaol or ginger extract treatment nor pancreatic islet morphology and insulin expression in mice model of painful diabetic neuropathy (PDN). AIM OF THE STUDY: This study aimed to investigate the mechanism of action of ginger extract and its compound, 6-shogaol, on pancreatic islets as well as on expressions of TRPV-1 and NMDAR2B in the spinal cord of streptozotocin (STZ)-induced mice model of PDN. MATERIALS AND METHODS: Sixty-four 5-6 weeks old male-Balb/C mice were induced with 110 mg/kgBW STZ i.p., while eight mice were used as control group. Mice with blood glucose level ≥200 mg/d, that suffered hyperalgesia and allodynia were classified as PDN mice. Hot plate and von Frey filament tests were performed once a week until termination. At day 28 after considered as PDN, ginger extracts, 6-shogaol or gabapentin as control treatment were given once daily for 21 days until day 49, except for the diabetic control group. Upon termination, mice' pancreas were fixed, processed as paraffin sections and stained with hematoxylin eosin. Total volume of pancreatic islets was estimated using Cavalieri methods. Immunohistochemistry on pancreatic sections were performed to observe insulin expression. mRNA was extracted from lumbar segments of the spinal cord, followed by cDNA preparation and quantitative Real-Time Polymerase Chain Reaction (qRT-PCR) to measure the expressions of TRPV1 and NMDAR2B. The mean differences between groups were analyzed using one-way analysis of variance (ANOVA) with p < 0.05 considered statistically significant. RESULTS: Ginger extracts and 6-shogaol alleviated hyperalgesia and allodynia. The groups that received ginger extract 400 mg/kgBW or 6-shogaol 15 mg/kgBW had significantly lower TRPV1 and NMDAR2B expressions in the spinal cord compared to the diabetic control group (p < 0.001; p < 0.05). However, no differences in volume of pancreatic islets (p > 0.05) nor insulin expression were observed in all PDN groups. CONCLUSION: Ginger extracts and its compound, 6-shogaol, reduced pain symptoms in PDN via its effect on decreasing TRPV1 and NMDAR2B expressions in the spinal cord, with very limited effect on pancreatic islets.


Assuntos
Catecóis/farmacologia , Neuropatias Diabéticas/tratamento farmacológico , Extratos Vegetais/farmacologia , Medula Espinal/efeitos dos fármacos , Zingiber officinale/química , Animais , Catecóis/isolamento & purificação , Diabetes Mellitus Experimental/tratamento farmacológico , Neuropatias Diabéticas/patologia , Hiperalgesia/tratamento farmacológico , Insulina/metabolismo , Ilhotas Pancreáticas/efeitos dos fármacos , Ilhotas Pancreáticas/metabolismo , Masculino , Camundongos , Camundongos Endogâmicos BALB C , Receptores de N-Metil-D-Aspartato/metabolismo , Medula Espinal/metabolismo , Estreptozocina , Canais de Cátion TRPV/metabolismo
18.
Ecotoxicol Environ Saf ; 184: 109619, 2019 Nov 30.
Artigo em Inglês | MEDLINE | ID: mdl-31493586

RESUMO

A versatile electrochemical sensor based on titanium carbide (Ti3C2) and multi-walled carbon nanotubes (MWCNTs) nanocomposite was constructed to detection catechol (CT) and hydroquinone (HQ). To prepare this novel nanocomposite, a self-assembled process was conducted by blending two-dimensional (2D) hierarchical Ti3C2 and MWCNTs under ultrasonic-assisted. X-ray diffraction (XRD), High resolution transmission electron microscopy (HR-TEM) and Scanning electron microscopy (SEM) methods as well as electrochemical technique, such as Electrochemical impedance spectroscopy (EIS), Cyclic voltammetry (CV) and Differential pulse voltammetry (DPV) were performed to characterize the Ti3C2-MWCNTs nanocomposite and illuminate the electrochemical oxidation process. Under the optimum conditions, wide linear range from 2 µM to 150 µM for both HQ and CT and low detection limit of 6.6 nM for HQ and 3.9 nM (S/N = 3) for CT have been achieved. Impressively, the sensor possesses superior selectivity, ultra-stability, and good repeatability, which was successfully applied for detecting CT and HQ in real industrial waste water sample with recovery of 96.9%-104.7% and 93.1%-109.9% for HQ and CT, respectively. Hence, Ti3C2 nanosheeets were proved to be a promising platform to construct electrochemical oxidation sensor in environmental analyses and phenolic isomers detection.


Assuntos
Catecóis/isolamento & purificação , Hidroquinonas/isolamento & purificação , Nanotubos de Carbono/química , Titânio/química , Poluentes Químicos da Água/isolamento & purificação , Técnicas Eletroquímicas , Eletrodos , Limite de Detecção , Nanocompostos/química , Reprodutibilidade dos Testes
19.
Sci Rep ; 9(1): 12276, 2019 08 22.
Artigo em Inglês | MEDLINE | ID: mdl-31439949

RESUMO

Allylpyrocatechol (APC) was isolated from betel leaf and its possible role in L-thyroxin (L-T4)-induced thyrotoxic rats was evaluated. The disease condition, thyrotoxicosis was confirmed by higher levels of thyroid hormones and low thyrotropin (TSH) in serum. Increased hepatic activities of 5'-mono-deiodinase(5'D1), glucose-6-phospatase (G-6-Pase); serum concentrations of alanine transaminase (ALT), aspartate aminotransferase (AST), lactate dehydrogenase(LDH) and tumour necrosis factor-alpha(TNF-α) were observed in thyrotoxic rats. Hepatic lipid peroxidation(LPO) was also increased and the endogenous antioxidants were depleted in these rats. In western blot analysis thyroid peroxidase expression was found to be reduced, whereas thyrotropin receptor(TSHR) expression was enhanced in thyroid gland of these animals. On the other hand, APC treatment in thyrotoxic rats decreased the levels of serum thyroid hormones, ALT, AST, TNF-α and LDH, as well as hepatic 5' D1 and G-6-Pase activities. However, it increased the serum TSH levels. APC also reduced the hepatic LPO and increased the cellular antioxidants in thyrotoxic rats. However, expression of TSHR was inhibited and TPO was increased by APC. The test compound also improved histological features in both liver and thyroid. Present report appears to be the first one that indicates the positive role of APC in ameliorating T4-induced thyrotoxicosis.


Assuntos
Catecóis , Iodeto Peroxidase/metabolismo , Fígado/metabolismo , Piper/química , Folhas de Planta/química , Receptores da Tireotropina/metabolismo , Tireotoxicose , Animais , Catecóis/química , Catecóis/isolamento & purificação , Catecóis/farmacologia , Feminino , Fígado/patologia , Ratos , Ratos Wistar , Tireotoxicose/induzido quimicamente , Tireotoxicose/tratamento farmacológico , Tireotoxicose/metabolismo , Tireotoxicose/patologia
20.
J Antibiot (Tokyo) ; 72(8): 634-639, 2019 08.
Artigo em Inglês | MEDLINE | ID: mdl-31118481

RESUMO

A new catecholate-containing siderophore, labrenzbactin (1), was isolated from the fermentation broth of a coral-associated bacterium Labrenzia sp. The structure and absolute configuration of 1 was determined by spectroscopic methods and Marfey's analysis. Overall, 1 showed antimicrobial activity against Ralstonia solanacearum SUPP1541 and Micrococcus luteus ATCC9341 with MIC values of 25 and 50 µg ml-1, respectively, and cytotoxicity against P388 murine leukemia cells with an IC50 of 13 µM.


Assuntos
Alphaproteobacteria/química , Antozoários/microbiologia , Antibacterianos/isolamento & purificação , Catecóis/isolamento & purificação , Oxazóis/isolamento & purificação , Sideróforos/isolamento & purificação , Alphaproteobacteria/isolamento & purificação , Animais , Antibacterianos/farmacologia , Antibióticos Antineoplásicos/isolamento & purificação , Antibióticos Antineoplásicos/farmacologia , Catecóis/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Fermentação , Leucemia P388/tratamento farmacológico , Camundongos , Testes de Sensibilidade Microbiana , Micrococcus luteus/efeitos dos fármacos , Estrutura Molecular , Oxazóis/farmacologia , Ralstonia/efeitos dos fármacos , Sideróforos/farmacologia
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