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1.
Food Chem ; 335: 127505, 2021 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-32739823

RESUMO

Dysregulation of glucose homeostasis result in hyperglycemia and pigmented rice, unique combination of high quality starch and phenolics has the potential in regulating it. In this study, pigmented rice was characterized in terms of nutraceutical starch (NS) and phenolic content. Further the effect of rice phenolics on carbolytic enzyme inhibition, glucose uptake, hepatic glucose homeostasis and anti-glycation ability was analyzed in vitro. The most relevant effect on enzyme inhibition (α-amylase: IC50-42.34 µg/mL; α-glucosidase: IC50:63.89 µg/mL), basal uptake of glucose (>39.5%) and anti-glycation ability (92%) was found in red rice (RR), than black rice (BR). The role of RR phenolics in regulating glucose homeostasis was deciphered using hepatic cell line system, which found up-regulation of glucose transporter 2 (GLUT2) and glycogen synthase 2 (GYS2); while expression of gluconeogenic genes were found down regulated. To our knowledge this study is the first report validating the role of starch-phenolic quality towards anti-hyperglycemic effect of RR.


Assuntos
Glucose/metabolismo , Homeostase , Hiperglicemia/metabolismo , Fígado/metabolismo , Oryza/química , Proantocianidinas/análise , Amido/análise , Transporte Biológico/efeitos dos fármacos , Suplementos Nutricionais/análise , Inibidores de Glicosídeo Hidrolases/farmacologia , Homeostase/efeitos dos fármacos , Fígado/efeitos dos fármacos , Fenol/análise , Fenol/farmacologia , alfa-Amilases/antagonistas & inibidores
2.
Sci Rep ; 10(1): 6361, 2020 04 14.
Artigo em Inglês | MEDLINE | ID: mdl-32286485

RESUMO

Olive oil intake has been linked with a lower incidence of breast cancer. Hypoxic microenvironment in solid tumors, such as breast cancer, is known to play a crucial role in cancer progression and in the failure of anticancer treatments. HIF-1 is the foremost effector in hypoxic response, and given that hydroxytyrosol (HT) is one of the main bioactive compounds in olive oil, in this study we deepen into its modulatory role on HIF-1. Our results in MCF-7 breast cancer cells demonstrate that HT decreases HIF-1α protein, probably by downregulating oxidative stress and by inhibiting the PI3K/Akt/mTOR pathway. Strikingly, the expression of HIF-1 target genes does not show a parallel decrease. Particularly, adrenomedullin and vascular endothelial growth factor are up-regulated by high concentrations of HT even in HIF-1α silenced cells, pointing to HIF-1-independent mechanisms of regulation. In fact, we show, by in silico modelling and transcriptional analysis, that high doses of HT may act as an agonist of the aryl hydrocarbon receptor favoring the induction of these angiogenic genes. In conclusion, we suggest that the effect of HT in a hypoxic environment is largely affected by its concentration and involves both HIF-1 dependent and independent mechanisms.


Assuntos
Neoplasias da Mama/tratamento farmacológico , Subunidade alfa do Fator 1 Induzível por Hipóxia/genética , Azeite de Oliva/farmacologia , Fenol/farmacologia , Álcool Feniletílico/análogos & derivados , Neoplasias da Mama/genética , Feminino , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Humanos , Células MCF-7 , Azeite de Oliva/química , Fenol/química , Álcool Feniletílico/metabolismo , Álcool Feniletílico/farmacologia , Fosfatidilinositol 3-Quinases/genética , Proteínas Proto-Oncogênicas c-akt/genética , Transdução de Sinais/efeitos dos fármacos , Serina-Treonina Quinases TOR/genética
3.
J Nanobiotechnology ; 18(1): 55, 2020 Mar 30.
Artigo em Inglês | MEDLINE | ID: mdl-32228604

RESUMO

BACKGROUND: Psoriasis is a malignant skin disease characterized as keratinocyte hyperproliferation and aberrant differentiation. Our previous work reported that a bibenzyl compound, erianin, has a potent inhibitory effect on keratinocyte proliferation. To improve its poor water-solubility, increase anti- proliferation activity, and enhance the skin delivery, erianin loaded dendritic mesoporous silica nanospheres (E/DMSNs) were employed. RESULTS: In this work, DMSNs with pore size of 3.5 nm (DMSN1) and 4.6 nm (DMSN2) were fabricated and E/DMSNs showed pore-size-dependent, significantly stronger anti-proliferative and pro-apoptotic effect than free erianin on human immortalized keratinocyte (HaCaT) cells, resulting from higher cellular uptake efficiency. In addition, compared to free erianin, treatment with E/DMSNs was more effective in reducing mitochondrial membrane potential and increasing cytoplasmic calcium levels, which were accompanied by regulation of mitochondria and endoplasmic reticulum stress (ERS) pathway. Porcine skin was utilized in the ex vivo accumulation and permeation studies, and the results indicated higher drug retention and less drug penetration in the skin when administered as the E/DMSNs-loaded hydrogel compared to the erianin-loaded hydrogel. Conlusions This work not only illustrated the further mechanisms of erianin in anti-proliferation of HaCaT cells but also offer a strategy to enhance the efficiency of erianin and the capacity of skin delivery through the DMSNs drug delivery systems.


Assuntos
Apoptose/efeitos dos fármacos , Bibenzilas/farmacologia , Nanosferas/química , Fenol/farmacologia , Dióxido de Silício/farmacologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular , Portadores de Fármacos/farmacologia , Sistemas de Liberação de Medicamentos , Humanos , Queratinócitos/efeitos dos fármacos , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Pele/efeitos dos fármacos , Neoplasias Cutâneas/tratamento farmacológico , Solubilidade
4.
J Biotechnol ; 310: 40-48, 2020 Feb 20.
Artigo em Inglês | MEDLINE | ID: mdl-32001255

RESUMO

The relevant microorganims driving efficiency changes in anaerobic digestion of phenol remains uncertain. In this study correlations were established between microbial population and the process performance in an anaerobic sequencing batch reactor (ASBR) treating increasing concentrations of phenol (from 120 to 1200 mg L-1). Sludge samples were taken at different operational stages and microbial community dynamics was analyzed by 16S rRNA sequencing. In addition, bamA gene was quantified in order to evaluate the dynamics of anaerobic aromatic degraders. The microbial community was dominated by Anaerolineae, Bacteroidia, Clostridia, and Methanobacteria classes. Correlation analysis between bamA gene copy number and phenol concentration were highly significant, suggesting that the increase of aromatic degraders targeted by bamA assay was due to an increase in the amount of phenol degraded over time. The incremental phenol concentration affected hydrogenotrophic archaea triggering a linear decrease of Methanobacterium and the growth of Methanobrevibacter. The best performance in the reactor was at 800 mg L-1 of phenol. At this stage, the highest relative abundances of Syntrophorhabdus, Chloroflexus, Smithella, Methanolinea and Methanosaeta were observed and correlated positively with initial degradation rate, suggesting that these microorganisms are relevant players to maintain a good performance in the ASBR.


Assuntos
Bactérias , Proteínas da Membrana Bacteriana Externa , Reatores Biológicos , Fenol , Anaerobiose/efeitos dos fármacos , Bactérias/genética , Bactérias/crescimento & desenvolvimento , Proteínas da Membrana Bacteriana Externa/genética , Proteínas da Membrana Bacteriana Externa/metabolismo , Relação Dose-Resposta a Droga , Fenol/metabolismo , Fenol/farmacologia
5.
Am J Chin Med ; 48(1): 183-200, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-31903779

RESUMO

Oral squamous cell carcinoma (OSCC) is a leading cause of cancer-related deaths worldwide. It has a very poor prognosis with over a 5-year survival rate of only 50%. Thus, it is important to identify effective therapeutic interventions against oral cancer. Apoptosis and autophagy have reported genetically regulated in physiology and diseases, which close relationship. Many natural compound study objects anticancer effect have been studied between apoptosis and autophagy relationship. The present study was designed to evaluate the effect of erianin on human oral cancer cell proliferation. Results of the study revealed that treatment with erianin significantly reduced the viability of different OSCC cell lines. Erianin exerted its cytotoxic effect by inducing cell cycle arrest and caspase-dependent apoptotic pathways. Both intrinsic and extrinsic pathways were found to be involved in erianin-mediated cell death. In addition, treatment with erianin also increased autophagy in OSCC cells. With further analysis, it was found that erianin induced both apoptosis and autophagy by regulating MAPK signaling pathways. Taken together, our study indicates that erianin plays an important role in reducing oral cancer cell viability, and thus, can be considered as a potential anticancer agent.


Assuntos
Apoptose/efeitos dos fármacos , Autofagia/efeitos dos fármacos , Bibenzilas/farmacologia , Carcinoma de Células Escamosas/patologia , Neoplasias Bucais/tratamento farmacológico , Fenol/farmacologia , Carcinoma de Células Escamosas/tratamento farmacológico , Pontos de Checagem do Ciclo Celular , Linhagem Celular Tumoral , Humanos , Estrutura Molecular
6.
Chem Biodivers ; 17(1): e1900394, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31618522

RESUMO

We aimed in the present study to investigate the chemical composition, the antioxidant capacities as well as the in vitro fermentation properties of Salvia officinalis leaves aqueous extract (SOLAE) grown in four regions of northwestern Tunisia. Our data firstly indicated a spatial variation (P<0.05) in condensed tannins, total lipids, polyphenols and flavonoids contents. The HPLC-PDA-ESI-MS/MS-LC/HR-ESI-MS technique allowed to the identification of 13 phenolic compounds and showed that protocatechuic acid is the major constituent of the plant leaves grown in Tabarka, Ain Draham and Testour. The SOLAE of the plant grown in Tabarka presents the most potent scavenging activity against DPPH radical and had the highest percentage of inhibition. More importantly, we found in the present study that the digestibility of dry matter and in vitro fermentation showed a significant variation between the regions and the animal species. Also, we showed a very positive correlation between antioxidant properties and phenolic compounds contents. In conclusion, we suggest that SOLAE had potential beneficial effects owing in part to its antioxidant and ROS scavenging activities. Therefore, S. officinalis can be proposed as an additive food for animals' nutrition and health.


Assuntos
Antioxidantes/farmacologia , Compostos de Bifenilo/antagonistas & inibidores , Fermentação , Compostos Fitoquímicos/farmacologia , Picratos/antagonistas & inibidores , Salvia officinalis/metabolismo , Animais , Antioxidantes/análise , Antioxidantes/metabolismo , Compostos de Bifenilo/metabolismo , Cromatografia Líquida de Alta Pressão , Avaliação Pré-Clínica de Medicamentos , Cabras , Hidroxibenzoatos/análise , Hidroxibenzoatos/metabolismo , Hidroxibenzoatos/farmacologia , Espectrometria de Massas , Fenol/análise , Fenol/metabolismo , Fenol/farmacologia , Compostos Fitoquímicos/análise , Compostos Fitoquímicos/metabolismo , Picratos/metabolismo , Folhas de Planta/química , Folhas de Planta/metabolismo , Salvia officinalis/química , Salvia officinalis/crescimento & desenvolvimento , Ovinos , Tunísia
7.
Chemosphere ; 243: 125382, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31775099

RESUMO

As a highly toxic pollutant, phenol is typically present in some high-strength nitrogenous wastewater. In this study, a synthetic coking wastewater with 400 mg L-1 ammonia-nitrogen and 50-250 mg L-1 phenol was treated. Results showed that simultaneous carbon oxidation, partial nitritation, denitritation and anammox (SCONDA) was successfully achieved by step-wise phenol addition. At 200 mg L-1 phenol, 99.8% phenol, 97.5% COD and 89.8% nitrogen could be together removed. However, further increase in phenol concentration caused significant deterioration of the short-terms nitrogen removal efficiency. High-throughput sequencing revealed remarkable evolution in microbial biodiversity, community composition, especially functional species at different phenol concentrations. When the phenol addition was increased from 200 to 250 mg L-1, the relative abundance of Candidatus Kuenenia as predominant anammox species decreased by 87.1%, while phenol-degrading bacteria was increasingly abundant. Furthermore, the removal mechanism of phenol and nitrogen was elucidated by the collaboration among different key functional microbial consortia.


Assuntos
Consórcios Microbianos , Nitrogênio/isolamento & purificação , Fenol/farmacologia , Fenóis/isolamento & purificação , Águas Residuárias/microbiologia , Purificação da Água/métodos , Amônia/química , Reatores Biológicos/microbiologia , Carbono/química , Coque , Nitrogênio/química , Oxirredução
8.
J Chem Ecol ; 46(2): 150-162, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31872313

RESUMO

The botanical source of Brazilian green propolis (BGP) is Baccharis dracunculifolia DC, which interacts not only with Apis mellifera, but also with galling insects. In the last decade, because of green propolis´ important biologic activities, the international demand for BGP overcame the production capacity, consequently, new approaches are required to increase this production. Hence, the understanding of the chemical ecology interactions of B. dracunculifolia with galls and bees in field conditions may provide insights to increase BGP's production. A "bee pasture" experiment aiming to better understand this plant-insect interaction was therefore performed. For that, 48 B. dracunculifolia individuals, being 24 females and 24 males, were cultivated and investigated for the following parameters: (1) phenolic and volatile compounds in both B. dracunculifolia leaves and green propolis, (2) environmental variables, (3) visiting rate by bees, (4) time of resin collection, and (5) number of galls. Regression analyses by independent linear mixed-effect models were run to correlate phenolic and volatile compounds concentration with the environmental and field variables. Significant differences in chemical profile and field variables were observed between male and female plants. Male plants showed higher infestation by galling insects while female plants showed higher number of visiting bees, time of resin collection and terpenes concentration, contributing to the differences observed in the field. The obtained results suggest that increasing the percentage of female B. dracunculifolia plants in the field may attract more bees and therefore enhance propolis production.


Assuntos
Baccharis/química , Abelhas/fisiologia , Própole/química , Animais , Baccharis/metabolismo , Comportamento Animal/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Feminino , Masculino , Espectrometria de Massas , Fenol/análise , Fenol/química , Fenol/farmacologia , Folhas de Planta/química , Folhas de Planta/metabolismo , Tumores de Planta/parasitologia , Própole/análise , Própole/farmacologia , Compostos Orgânicos Voláteis/análise , Compostos Orgânicos Voláteis/química , Compostos Orgânicos Voláteis/farmacologia
9.
Aging (Albany NY) ; 11(22): 10284-10300, 2019 11 20.
Artigo em Inglês | MEDLINE | ID: mdl-31754081

RESUMO

In this study, erianin was found to reduce the viability of cancer cells, inhibit their proliferation and migration, induce G2/M phase arrest, enhance cancer cell apoptosis, promote an increase in levels of intracellular reactive oxygen species and a decrease in mitochondrial membrane potential, and regulate the expression levels of anti- and pro-apoptosis-related proteins in HepG2 and SMMC-7721 cells. Erianin inhibited tumor growth in HepG2- and SMMC-7721-xenograft tumor nude mouse models, reduced the expression levels of anti-apoptosis proteins and enhanced the expression levels of pro-apoptosis proteins in tumor tissues. Erianin inhibited tumor growth in immunosuppressed BALB/c mice bearing heterotopic tumors. Among 111 types of cytokines detected in proteome profiling of tumor tissues, erianin substantially influenced levels of 38 types of cytokines in HepG2-xenografted tumors and of 15 types of cytokines in SMMC-7721-xenografted tumors, most of which are related to immune functions. Erianin strongly affected the serum levels of cytokines, and regulated the activation of nuclear factor-kappa B (NF-κB), and the expression levels of nuclear factor erythroid 2-related factor 2 (Nrf2) and its downstream proteins in spleen. The anti-liver cancer properties of erianin were found to be related mostly to its modulation of oxidative stress-mediated mitochondrial apoptosis and immune response.


Assuntos
Anticarcinógenos/farmacologia , Apoptose/efeitos dos fármacos , Bibenzilas/farmacologia , Neoplasias Hepáticas/imunologia , Neoplasias Hepáticas/patologia , Estresse Oxidativo/efeitos dos fármacos , Fenol/farmacologia , Animais , Humanos , Camundongos , Camundongos Endogâmicos BALB C , Camundongos Nus , Ensaios Antitumorais Modelo de Xenoenxerto
10.
Sci Rep ; 9(1): 15585, 2019 10 30.
Artigo em Inglês | MEDLINE | ID: mdl-31666589

RESUMO

Dipeptidyl peptidase IV (DPP IV) is a surface glycoprotein that can degrade glucagon like pepetide-1 (GLP-1) by decreasing blood sugar. Herbal medicines for diabetic therapy are widely used with acceptable efficacy but unsatisfied in advances. DPP IV was chosen as a template to employ molecular docking via Discovery Studio to search for natural phenolic compounds whether they have the inhibitory function of DPP IV. Then, docking candidates were validated and further performed signal pathway via Caco-2, C2C12, and AR42J cells. Lastly, a diet-induced diabetes in mice were applied to examine the efficacy and toxicity of hit natural phenolic products in long-term use (in vivo). After screening, curcumin, syringic acid, and resveratrol were found in high affinity with DPP IV enzymes. In enzymatic tests, curcumin and resveratrol showed potential inhibition of DPP IV. In vitro assays, curcumin inhibited of DPP IV activity in Caco-2 cells and ERK phosphorylation in C2C12 cells. Additionally, curcumin attenuated blood sugar in S961-treated C57BL/6 mice and in diet-induced diabetic ICR mice and long-term regulate HbA1c in diabetic mice. Curcumin targeted to DPP IV for reducing blood glucose, it possesses potential and alternative substitution of synthetic clinical drugs for the medication of diabetes.


Assuntos
Dipeptidil Peptidase 4/metabolismo , Inibidores da Dipeptidil Peptidase IV/farmacologia , Hipoglicemiantes/farmacologia , Fenol/farmacologia , Animais , Células CACO-2 , Proteínas Quinases Dependentes de AMP Cíclico/metabolismo , Dipeptidil Peptidase 4/biossíntese , Dipeptidil Peptidase 4/química , Inibidores da Dipeptidil Peptidase IV/metabolismo , MAP Quinases Reguladas por Sinal Extracelular/metabolismo , Humanos , Hipoglicemiantes/metabolismo , Masculino , Camundongos , Simulação de Acoplamento Molecular , Fenol/metabolismo , Fosforilação/efeitos dos fármacos , Conformação Proteica
11.
Mar Drugs ; 17(11)2019 Oct 24.
Artigo em Inglês | MEDLINE | ID: mdl-31653083

RESUMO

Three new prenylated phenol derivatives, terreprenphenols A-C (1-3), along with four known related compounds (4-7), were isolated from Aspergillus terreus EN-539, an endophytic fungus obtained from the marine red alga Laurencia okamurai. The structures of these compounds were established by extensive analysis of 1D/2D NMR data, mass spectrometric data, and optical rotation (OR). The corresponding relationship between absolute configuration and optical rotation for known compounds anodendroic acid (4) and asperterreusine C (5) was ambiguous in literature, and their absolute configurations were therefore discussed and confirmed for the first time by time-dependent density functional (TDDFT) ECD and OR calculations. Compounds 1-7 inhibited some common aquatic bacteria with MIC values ranging from 2 to 64 µg/mL.


Assuntos
Benzofuranos/química , Fenol/química , Fenóis/química , Antibacterianos/farmacologia , Aspergillus/química , Bactérias/efeitos dos fármacos , Benzofuranos/farmacologia , Laurencia , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Fenol/farmacologia , Fenóis/farmacologia
12.
J Food Biochem ; 43(9): e12963, 2019 09.
Artigo em Inglês | MEDLINE | ID: mdl-31489655

RESUMO

The aqueous extract of Trifolium repens (TR) leaves was analyzed for the phenolic profile using reversed phase HPLC-DAD and administered to mice against acetaminophen-induced hepatoxicity. Twenty-four phenolic compounds were identified and quantified. The highest amounts present were of kaempferol-3-(caffeoyldiglucoside)-7-glucoside (983.7 µg/ml), followed by p-coumaroyl-4-glucoside (905.6 µg/ml) and daidzein-O-sulfate (808.3 µg/ml). The aqueous extract was administered to mice along with acetaminophen at different doses. Acetaminophen was found to significantly alter body weight, serum biochemistry, and hematological indices of mice, which were ameliorated by the co-administration of aqueous extract. Liver histopathological studies revealed that acetaminophen significantly induced toxicity, while TR aqueous extract provides curative functions. Lipid peroxidation and total reduced glutathione in the liver were also normalized by the aqueous extract of TR. The aqueous extract of TR was rich in important phenolic compounds, which can be used as a source of beneficial bioactive compounds with hepato-protective function. PRACTICAL APPLICATIONS: Acetaminophen has been widely used as antipyretic and analgesic. However, the major complication reported is hepatotoxicity. Synthetic or conventional drugs used for hepatic diseases or against hepatotoxicity are insufficient and causes severe side effects. For this purpose, traditional medicinal plants or nutraceuticals are used to decrease in the side effects of different hepatotoxic medicine are demanding. Food and neutraceuticals are rich in important polyphenolic compounds which are the best antioxidants. This study was aimed to evaluate the phenolic composition of aqueous extract of Trifolium repens and its potential protective action against the acetaminophen-induced toxicity in mice. This study showed for the first time that the aqueous extract of TR was protective against the hepatotoxicity induced by acetaminophen.


Assuntos
Acetaminofen/toxicidade , Doença Hepática Induzida por Substâncias e Drogas/prevenção & controle , Fenol/farmacologia , Extratos Vegetais/farmacologia , Trifolium/química , Analgésicos não Narcóticos/toxicidade , Animais , Glutationa , Peroxidação de Lipídeos/efeitos dos fármacos , Fígado/efeitos dos fármacos , Fígado/metabolismo , Masculino , Camundongos , Extratos Vegetais/química
13.
J Orthop Surg (Hong Kong) ; 27(3): 2309499019861031, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31315494

RESUMO

PURPOSE: The aim of this study is to report the clinical and radiological outcomes following surgical treatment of chondroblastoma by means of an extended intralesional curettage using high-speed burr, with phenol as a local adjuvant which is followed by the implantation of synthetic bone graft, aiming to lower the recurrence rate of this tumor. PATIENTS AND METHODS: This retrospective study included 20 patients with chondroblastoma lesions during the period between 2000 and 2015. RESULTS: Fifteen males and five females were followed up for a mean of 63.35 (26-144) months with average age at the time of presentation was 20.8 (range: 12-32) years. Nineteen patients (95%) were complaining of pain at the time of presentation, and the lesion was discovered accidently in one patient. The mean operative time was 138.5 min (75-250). At the most recent follow-up, all patients had regained full physical function without pain at the operation site. CONCLUSION: The aggressive treatment of chondroblastoma by an extended intralesional curettage using high-speed burr with phenol as a local adjuvant seems effective in lowering the incidence of local recurrence and secondary more aggressive surgeries. Implantation of the bone defects that result from curettage with the synthetic bone substitutes is a good alternative due to rapid restoration of the mechanical strength with good remodeling.


Assuntos
Neoplasias Ósseas/cirurgia , Transplante Ósseo/métodos , Condroblastoma/cirurgia , Curetagem/métodos , Fenol/farmacologia , Adolescente , Adulto , Anti-Infecciosos Locais/farmacologia , Criança , Feminino , Humanos , Masculino , Radiografia , Estudos Retrospectivos , Resultado do Tratamento , Adulto Jovem
14.
Comb Chem High Throughput Screen ; 22(5): 307-316, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31267866

RESUMO

AIM AND OBJECTIVE: To study the structural difference, optimization, molecular docking and development of new benzoyl amino phenoxy phenol derivatives as anti-prostate cancer agents. MATERIALS AND METHODS: Strategies towards the identification of novel benzoyl amino phenoxy phenol (BAPP), molecular docking was performed with the designed Androgen Receptor (AR) blockers. Pharmacophore-based studies revealed that the nitro- or cyano-substituted anilide groups have influenced the activity profiles of non-steroidal AR antagonists, followed by the molecular docking studies with five AR receptors. Molecular docking studies were carried out using Maestro from Schrödinger. Absorption, Distribution, Metabolism, and Excretion (ADME) properties of the BAPP derivatives were evaluated for the predictive bioavailability/drug-likeness. These studies supported vital information for designing new anti-prostate cancer agents. RESULTS AND DISCUSSION: There are 125 compounds were screened and best fit compounds (12 entries) were well-synthesized in good to excellent yields and anticancer activities were evaluated. The compounds, 6i showed the highest activities of this series (14.65 ± 1.35 µM). CONCLUSION: The present approach is simple and efficient for the synthesis of BAPP derivatives and the observed IC50 values of BAPPs were in good agreement with the glide scores obtained from the molecular docking. We, further, intend to carry out in vitro and in vivo AR binding studies for the active compounds.


Assuntos
Antagonistas de Receptores de Andrógenos/química , Antineoplásicos/química , Simulação de Acoplamento Molecular , Fenol/farmacologia , Simulação por Computador , Desenho de Fármacos , Humanos , Masculino , Fenol/síntese química , Neoplasias da Próstata/tratamento farmacológico
15.
BMC Complement Altern Med ; 19(1): 146, 2019 Jun 21.
Artigo em Inglês | MEDLINE | ID: mdl-31227024

RESUMO

BACKGROUND: There is increasing interest in the pharmaceutical and food industries to substitute synthetic chemicals with naturally occurring compounds possessing bioactive properties. Plants are valuable sources of bioactive compounds. The present study investigates the chemical composition and antioxidant, antimicrobial, and anticancer activities of ethanolic extracts (EEs) and essential oils (EOs) from two species in the Lamiaceae family, Ocimum basilicum L. and Thymus algeriensis Boiss. & Reut., cultivated in the Algerian Saharan Atlas. METHODS: The total flavonoid contents of the plants' ethanolic extracts were determined by the aluminium chloride method, while the total phenols were determined using the Folin-Ciocalteu method. Essential oils were obtained by hydrodistillation of the aerial parts of the plants and were analysed by GC-MS. The free radical-scavenging ability and antioxidant potential of the plants' EEs and EOs were probed using the 2, 2-diphenyl-picrylhydrazyl radical-scavenging, ABTS radical-scavenging, ferric-reducing power and phosphomolybdenum assays. The antimicrobial activities were evaluated against several pathogens characteristic of gram-negative bacteria (three species), gram-positive bacteria (three species) and fungi (two species). The microdilution method was used to estimate the minimum inhibitory concentrations (MICs). The oils' anticancer potential against several cancer types was also studied using the MTT assay and reported as the toxic doses that resulted in a 50% reduction in cancer cell growth (LD50). RESULTS: Phenolic compounds in the EEs from both plants were analysed by HPLC and demonstrated a rich flavonoid content. Chemical analysis of the essential oil from Ocimum basilicum revealed 26 unique compounds, with linalool (52.1%) and linalyl acetate (19.1%) as the major compounds. A total of 29 compounds were identified in the essential oil from Thymus algeriensis, with α-terpinyl acetate (47.4%), neryl acetate (9.6%), and α-pinene (6.8%) as the major compounds. The ethanolic extracts and essential oils from both plants exhibited moderate antioxidant activities and moderate to weak antimicrobial activities. Furthermore, anticancer activities against the examined human cancer cell lines were associated with only the EOs from both plants, with LD50 values ranging between 300 and 1000 µg/mL. CONCLUSION: The results suggest that the bioactive compounds found in the ethanolic extracts and essential oils from Ocimum basilicum and Thymus algeriensis, with diverse antioxidant, antimicrobial and anticancer activities, may have beneficial applications in nutraceutical and pharmaceutical technologies.


Assuntos
Ocimum basilicum/química , Óleos Voláteis/química , Óleos Vegetais/química , Thymus (Planta)/química , Argélia , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Antineoplásicos/química , Antineoplásicos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Bactérias/efeitos dos fármacos , Bactérias/crescimento & desenvolvimento , Linhagem Celular Tumoral , Sobrevivência Celular , Cromatografia Líquida de Alta Pressão , Fungos/efeitos dos fármacos , Fungos/crescimento & desenvolvimento , Humanos , Fenol/química , Fenol/farmacologia , Óleos Vegetais/farmacologia
16.
Biomed Res Int ; 2019: 9165648, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31240229

RESUMO

Inflammation is a consequence of an array of biological reactions that occur in response to pain sensation, local injury, and cell damage. A large number of studies have demonstrated that quercetin and other flavonoids show anti-inflammatory effects; thus, in the present work, we evaluated a triazine-phenol derivative (TP derivative) compound as a possible drug candidate with anti-inflammatory activity. This compound was studied as a possible anti-inflammatory drug using synthesis and characterization by Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), and mass spectrometry (MS). The derivative of melamine was evaluated for its antioxidant activity and exhibited good DPPH and FRAP antioxidant activity. Additionally, we evaluated the putative effect of the molecule on the COX-2 enzyme through molecular dynamic simulation (MDS), and the result suggested that the TP derivative is a potential anti-inflammatory agent that can interact with the COX-2 enzyme because of the high number of protein-ligand interactions observed with MDS. Finally, the study of theoretical physicochemical properties, the observation of low toxicity (hemolysis assay), and the evaluation of oral bioavailability of the TP derivative showed that it is a possible anti-inflammatory drug candidate.


Assuntos
Anti-Inflamatórios/farmacologia , Antioxidantes/análise , Antioxidantes/química , Triazinas/análise , Triazinas/química , Compostos de Bifenilo , Simulação por Computador , Ciclo-Oxigenase 2/química , Eritrócitos , Flavonoides/farmacologia , Hemólise , Técnicas In Vitro , Inflamação , Ligantes , Simulação de Acoplamento Molecular , Fenol/farmacologia , Picratos , Quercetina/farmacologia
17.
Molecules ; 24(10)2019 May 15.
Artigo em Inglês | MEDLINE | ID: mdl-31096694

RESUMO

In this study, we evaluated antioxidant, antihyperuricemic, and herbicidal activities of essential oils (EOs) from Piper cubeba Bojer and Piper nigrum L.; two pepper species widely distributed in tropics, and examined their chemical compositions. Dried berries of P. cubeba and P. nigrum were hydro-distilled to yield essential oil (EO) of 1.23 and 1.11% dry weight, respectively. In the antioxidant assay, the radical scavenging capacities of P. cubeba EO against DPPH and ABTS free radicals were 28.69 and 24.13% greater than P. nigrum, respectively. In the antihyperuricemic activity, P. cubeba EO also exhibited stronger inhibitory effects on xanthine oxidase (IC50 = 54.87 µg/mL) than P. nigrum EO (IC50 = 77.11 µg/mL). In the herbicidal activity, P. cubeba EO showed greater inhibition on germination and growth of Bidens pilosa and Echinochloa crus-galli than P. nigrum EO. Besides, P. cubeba EO decreased 15.98-73.00% of photosynthesis pigments of B. pilosa and E. crus-galli, while electrolyte leakages, lipid peroxidations, prolines, phenolics, and flavonoids contents were increased 10.82-80.82% at 1.93 mg/mL dose. Gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) analyses revealed that P. nigrum and P. cubeba EOs principally possessed complex mixtures of monoterpenes and sesquiterpenes. Terpinen-4-ol (42.41%), α-copaene (20.04%), and γ-elemene (17.68%) were the major components of P. cubeba EO, whereas ß-caryophyllene (51.12%) and ß-thujene (20.58%) were the dominant components of P. nigrum EO. Findings of this study suggest both P. cubeba and P. nigrum EOs were potential to treat antioxidative stress and antihyperuricemic related diseases. In addition, the EOs of the two plants may be useful to control B. pilosa and E. crus-galli, the two invasive and problematic weeds in agriculture practice.


Assuntos
Óleos Voláteis/química , Óleos Voláteis/farmacologia , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Piper nigrum/química , Piper/química , Antioxidantes/química , Antioxidantes/farmacologia , Relação Dose-Resposta a Droga , Flavonoides/química , Flavonoides/farmacologia , Peroxidação de Lipídeos/efeitos dos fármacos , Fenol/química , Fenol/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Prolina/química , Prolina/farmacologia , Xantina Oxidase/antagonistas & inibidores , Xantina Oxidase/química
18.
Molecules ; 24(5)2019 Mar 06.
Artigo em Inglês | MEDLINE | ID: mdl-30845642

RESUMO

Endopleura uchi (Huber) Cuatrec (Humiriaceae), known as uxi or uxi-amarelo in Brazil, is an endemic tree of the Amazon forest. In traditional medicine, its stem bark is used to treat a variety of health disorders, including cancer, diabetes, arthritis, uterine inflammation, and gynecological infections. According to HPLC analysis, the main constituent of the bark extract is the polyphenol bergenin. In the current study, we demonstrate by in vitro and in vivo experiments the antioxidant potential of a water extract from the stem bark of E. uchi. When tested in the model organism Caenorhabditis elegans, the extract enhanced stress resistance via the DAF-16/FOXO pathway. Additionally, the extract promoted an increase in the lifespan of the worms independent from caloric restriction. It also attenuated the age-related muscle function decline and formation of polyQ40 plaques, as a model for Huntington's disease. Thus, these data support anti-aging and anti-oxidant properties of E. uchi, which has not yet been described. More studies are needed to assess the real benefits of E. uchi bark for human health and its toxicological profile.


Assuntos
Benzopiranos/farmacologia , Caenorhabditis elegans/efeitos dos fármacos , Longevidade/efeitos dos fármacos , Feófitas/química , Casca de Planta/química , Animais , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Antioxidantes/farmacologia , Proteínas de Caenorhabditis elegans/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão/métodos , Regulação da Expressão Gênica , Humanos , Doença de Huntington/metabolismo , Proteínas de Insetos/efeitos dos fármacos , Estresse Oxidativo/efeitos dos fármacos , Fenol/química , Fenol/farmacologia , Extratos Vegetais/farmacologia , Transdução de Sinais
19.
Bioprocess Biosyst Eng ; 42(7): 1105-1114, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-30911818

RESUMO

Nitrate and phenol often co-occur in wastewater because of the complex industrial and agricultural processes, while the impacts of phenol on autotrophic denitrification remain unclear. Here, a sulfur and hydrogen-oxidizing autotrophic denitrification reactor was established, and the effects of different concentrations of phenol on the nitrate removal performance, kinetics, microbial communities, and functional genes were investigated. Increasing concentrations of phenol significantly decreased the denitrification efficiency in the reactor. The kinetic data indicate the limitation of nitrate diffusion may be one of reasons. Increasing phenol concentrations declined the activities of nitrate and nitrite reductases and induced the production of reactive oxygen species (ROS) and the release of lactate dehydrogenase (LDH), suggesting potential toxicity to the denitrifying consortium. Denitrifying gene nirK was most sensitive to phenol stresses in the reactor. In addition, Thauera was the predominant genus in system with and without phenol, Bacillus was enriched under high phenol concentrations.


Assuntos
Processos Autotróficos/efeitos dos fármacos , Bacillus/crescimento & desenvolvimento , Desnitrificação/efeitos dos fármacos , Microbiota/efeitos dos fármacos , Fenol/farmacologia , Thauera/crescimento & desenvolvimento , Reatores Biológicos , Cinética , Águas Residuárias/microbiologia
20.
Crit Rev Eukaryot Gene Expr ; 29(6): 529-537, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-32422008

RESUMO

Resveratrol has several therapeutic effects and is a nutraceutical. It was shown to imitate caloric restriction effects, exert anti-inflammatory and antioxidative effects, and affect the development and progression of many diseases through several mechanisms. While there is a wealth of evidence in vitro and in vivo that resveratrol could be a promising therapeutic agent, its potential must be confirmed by preclinical studies and clinical trials. We analyzed the current available preclinical and clinical data on resveratrol's pharmacological action. The bulk of resveratrol's preclinical studies and clinical trials focused on cancer, neurological disorders, cardiovascular diseases, diabetes, nonalcoholic fatty liver disease (NAFLD), and obesity. The latest preclinical studies and clinical trials reported that resveratrol was well tolerated and beneficially influenced biomarkers of disease for neurological disorders, cardiovascular diseases, and diabetes. Nevertheless, in certain types of cancers and in NAFLD, resveratrol had unclear and sometimes even detrimental effects. The major obstacle posed in most preclinical studies and clinical trials was the low bioavailability of resveratrol. This work thus provides useful guidelines for future preclinical and clinical resveratrol study planning and design.


Assuntos
Fenol/farmacologia , Fenol/uso terapêutico , Resveratrol/farmacologia , Resveratrol/uso terapêutico , Animais , Antioxidantes/farmacologia , Antioxidantes/uso terapêutico , Humanos , Neoplasias/tratamento farmacológico , Hepatopatia Gordurosa não Alcoólica/tratamento farmacológico , Obesidade/tratamento farmacológico
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