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1.
Food Res Int ; 180: 114097, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38395549

RESUMO

The defatted seeds of evening primrose (DE), a by-product of evening primrose oil extraction, are currently underutilized. This study aimed to valorize DE by examining its effects on melanogenesis and tyrosinase activity in zebrafish embryos and in vitro, and an innovative affinity-labeled molecular networking workflow was proposed for the rapid identification of tyrosinase inhibitors in DE. Our results indicated DE significantly reduced melanin content (53.3 % at 100 µg/mL) and tyrosinse activity (80.05 % for monophenolase and 70.40 % for diphenolase at 100 µg/mL). Furthermore, through the affinity-labeled molecular networking approach, 20 compounds were identified as potential tyrosinase inhibitors within DE, predominantly flavonoids and tannins characterized by catechin and galloyl substructures. Seven of these compounds were isolated and their inhibitory effects on tyrosinase were validated using functional assays. This study not only underscores the potential of DE as a rich source of natural tyrosinase inhibitors but also establishes the effectiveness of affinity-labeled molecular networking in pinpointing bioactive compounds in complex biological matrices.


Assuntos
Oenothera biennis , Animais , Oenothera biennis/química , Monofenol Mono-Oxigenase , Peixe-Zebra , Extratos Vegetais/farmacologia , Flavonoides/farmacologia
2.
Toxicol Mech Methods ; 34(5): 469-483, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38166523

RESUMO

The modulatory role of primrose oil (PO) supplementation enriched with γ-linolenic acid and D/L-alpha tocopherol acetate against a carbon tetrachloride (CCl4)-induced liver damage model was assessed in this study. Twenty male Albino rats were divided into four groups. The control group received corn oil orally. The PO group received 10 mg/kg P O orally. The CCl4 group received 2 mL/kg CCl4 orally and PO/CCl4 group; received PO and 2 mL/kg CCl4 orally. The relative liver weight was recorded. Serum liver enzymes, hepatic malondialdehyde (MDA), hepatic reduced glutathione (GSH) and the expression of hepatic tumor necrosis factor-alpha (TNF-α), interleukin 1 beta (IL-1ß), and interleukin 6 (IL-6) were assessed. The binding affinities of γ-linolenic acid and D/L-alpha tocopherol constituents with IL-1ß, IL-6 and TNF-α were investigated using molecular docking simulations. Histopathological and electron microscopic examinations of the liver were performed. The results indicated that CCl4 elevated serum liver enzyme and hepatic MDA levels, whereas GSH levels were diminished. The upregulation of IL-1ß, IL-6, and TNF-α gene expressions were induced by CCl4 treatment. The PO/CCl4-treated group showed amelioration of hepatic injury biomarkers and oxidative stress. Restoration of histopathological and ultrastructural alterations while downregulations the gene expressions of TNF-α, IL1-ß and IL-6 were observed. In conclusion, evening primrose oil enriched with γ-linolenic acid and D/L-alpha tocopherol acetate elicited a potential amelioration of CCl4-induced hepatic toxicity.


Assuntos
Doença Hepática Induzida por Substâncias e Drogas , Fígado , Oenothera biennis , Óleos de Plantas , Ácido gama-Linolênico , Animais , Masculino , Doença Hepática Induzida por Substâncias e Drogas/prevenção & controle , Doença Hepática Induzida por Substâncias e Drogas/patologia , Doença Hepática Induzida por Substâncias e Drogas/metabolismo , Doença Hepática Induzida por Substâncias e Drogas/tratamento farmacológico , Óleos de Plantas/farmacologia , Óleos de Plantas/química , Fígado/efeitos dos fármacos , Fígado/metabolismo , Fígado/patologia , Fígado/ultraestrutura , Ácido gama-Linolênico/farmacologia , Oenothera biennis/química , Interleucina-1beta/metabolismo , Fator de Necrose Tumoral alfa/metabolismo , Fator de Necrose Tumoral alfa/genética , Estresse Oxidativo/efeitos dos fármacos , Simulação de Acoplamento Molecular , Tetracloreto de Carbono/toxicidade , Interleucina-6/metabolismo , Ratos , Ácidos Linoleicos/farmacologia , Antioxidantes/farmacologia , Ratos Wistar , Transdução de Sinais/efeitos dos fármacos , Modelos Animais de Doenças
3.
Molecules ; 27(8)2022 Apr 07.
Artigo em Inglês | MEDLINE | ID: mdl-35458590

RESUMO

BACKGROUND: Despite advancements in cancer treatment, breast cancer (BC) is still one of the leading causes of death among women. The majority of anti-breast-cancer medications induce serious side effects and multidrug resistance. Although several natural compounds, such as evening primrose oil (EPO), have been shown to have anticancer properties when used alone, their combination with the anticancer medicine tamoxifen (TAM) has yet to be investigated. The present study aimed to investigate the anticancer efficacy of EPO, alone or in combination with TAM, in the BC cell lines MCF-7 and MDA-MB-231, as well as to elucidate the mechanism of action. METHODS: The MTT assay was used to investigate the cytotoxic effect of EPO on the two cell lines, and we discovered an acceptable IC50 that was comparable to TAM. The ELISA, qRT-PCR, flow cytometry and colorimetric techniques were used. RESULTS: The combination of EPO and TAM suppressed the VEGF level, VEGF gene expression and Cyclin D1 signaling pathways, arrested the cell cycle, and induced the apoptotic signaling pathways by increasing the Bax/Bcl-2 ratio and caspase 3 activity; this revealed significant anti-tumor activity. CONCLUSIONS: The most significant finding of this study was the confirmation of the anticancer activity of the natural product EPO, which potentiated the activity of the anticancer drug TAM against MCF-7 and MDA-MB-231 BC cell lines through the induction of apoptosis, inhibiting angiogenesis and halting cell proliferation.


Assuntos
Antineoplásicos , Neoplasias da Mama , Oenothera biennis , Óleos de Plantas , Tamoxifeno , Ácido gama-Linolênico , Inibidores da Angiogênese , Antineoplásicos/farmacologia , Antineoplásicos/uso terapêutico , Apoptose , Neoplasias da Mama/tratamento farmacológico , Neoplasias da Mama/metabolismo , Ciclo Celular , Linhagem Celular Tumoral , Proliferação de Células , Feminino , Humanos , Ácidos Linoleicos , Células MCF-7 , Masculino , Oenothera biennis/química , Óleos de Plantas/farmacologia , Óleos de Plantas/uso terapêutico , Tamoxifeno/farmacologia , Tamoxifeno/uso terapêutico , Fator A de Crescimento do Endotélio Vascular/genética , Fator A de Crescimento do Endotélio Vascular/farmacologia , Ácido gama-Linolênico/farmacologia , Ácido gama-Linolênico/uso terapêutico
4.
Arch Physiol Biochem ; 128(6): 1539-1547, 2022 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-32594769

RESUMO

The effect of evening primrose oil on adiponectin level and some biochemical parameters in model of fructose-induced metabolic syndrome were investigated. The rats were divided into 4 groups: control, evening primrose oil, fructose, fructose + evening primrose oil. Body weight, daily feed and water consumptions and systolic blood pressures of animals were measured. At the end of trial, blood samples were taken, livers were excised and histopathological examination was performed. Glucose, uric acid, triglyceride, T.cholesterol, LDL, HDL, VLDL, ALT, AST, ALP, LDH, adiponectin, insulin, IL-6, TNF-α, TAC, and TOS levels were analysed. Some analysed parameters and systolic blood pressure of fructose + evening primrose oil group decreased significantly compared to fructose group and adiponectin, TAC, and HDL levels were significantly increased. As conclusion, evening primrose oil can be considered as antioxidant agent by reducing oxidative stress, increasing adiponectin levels and insulin sensitivity, anti-inflammatory properties, exhibiting anti-atherogenic effect by regulating dyslipidemia and systolic blood pressure.


Assuntos
Insulinas , Síndrome Metabólica , Oenothera biennis , Ratos , Animais , Oenothera biennis/química , Adiponectina , Frutose/efeitos adversos , Síndrome Metabólica/induzido quimicamente , Síndrome Metabólica/tratamento farmacológico , Fator de Necrose Tumoral alfa , Antioxidantes , Ácido Úrico , LDL-Colesterol , Interleucina-6 , Triglicerídeos , Glucose , Água
5.
Int J Mol Sci ; 22(16)2021 Aug 19.
Artigo em Inglês | MEDLINE | ID: mdl-34445654

RESUMO

Rigid polyurethane/polyisocyanurate (RPU/PIR) foam formulations were modified by evening primrose (Oenothera biennis) oil cake as a bio-filler in the amount of 5 to 50 wt.%. The obtained foams were tested in terms of processing parameters, cellular structure (SEM analysis), physico-mechanical properties (apparent density, compressive strength, brittleness, accelerated aging tests), thermal insulation properties (thermal conductivity coefficient, closed cells content, absorbability and water absorption), flammability, smoke emission, and thermal properties. The obtained results showed that the amount of bio-filler had a significant influence on the morphology of the modified foams. Thorough mixing of the polyurethane premix allowed better homogenization of the bio-filler in the polyurethane matrix, resulting in a regular cellular structure. This resulted in an improvement in the physico-mechanical and thermal insulation properties as well as a reduction in the flammability of the obtained materials. This research provided important information on the management of the waste product from the edible oil industry and the production process of fire-safe RPU/PIR foams with improved performance properties. Due to these beneficial effects, it was found that the use of evening primrose oil cake as a bio-filler for RPU/PIR foams opens a new way of waste management to obtain new "green" materials.


Assuntos
Ácidos Linoleicos/química , Oenothera biennis/química , Óleos de Plantas/química , Polímeros/química , Poliuretanos/química , Triazinas/química , Resíduos/análise , Ácido gama-Linolênico/química
6.
Molecules ; 26(2)2021 Jan 07.
Artigo em Inglês | MEDLINE | ID: mdl-33430409

RESUMO

Toward the standardization of common evening primrose (Oenothera biennis) sprout extract (OBS-E), we aimed to obtain indicator compounds and use a validated method. HPLC-UVD allowed simultaneous quantification of the indicator compounds quercetin-3-O-glucuronide and ellagic acid. The method was validated in terms of specificity, linearity, precision, accuracy, and limit of detection/limit of quantification (LOD/LOQ). High specificity and linearity was demonstrated, with correlation coefficients of 1.0000 for quercetin-3-O-glucuronide and 0.9998 for ellagic acid. The LOD/LOQ values were 0.486/1.472 µg/mL for quercetin-3-O-glucuronide and 1.003/3.039 µg/mL for ellagic acid. Intra-day and inter-day variability tests produced relative standard deviation for each compound of <2%, a generally accepted precision criterion. High recovery rate were also obtained, indicating accuracy validation. The OBS-E prepared using various concentrations of ethanol were then analyzed. The 50% ethanol extract had highest content of quercetin-3-O-glucuronide, whereas the 70% ethanol extract possessed the lowest. However, the ellagic acid content was highest in the 70% ethanol extract and lowest in the 90% ethanol extract. Thus, quercetin-3-O-glucuronide and ellagic acid can be used industrially as indicator compounds for O. biennis sprout products, and our validated method can be used to establish indicator compounds for other natural products.


Assuntos
Ácido Elágico/química , Oenothera biennis/química , Quercetina/análogos & derivados , Cromatografia Líquida de Alta Pressão , Estrutura Molecular , Extratos Vegetais/química , Quercetina/química , Análise Espectral
7.
Food Chem ; 334: 127613, 2021 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-32711281

RESUMO

The optimization of ultrasound-assisted alkaline extraction and enzymatic deamidation by protein-glutaminase (PG) on evening primrose seed cake (EPSC) protein and its effect on structure (amino acid composition, secondary structure and electrophoresis pattern) and techno-functional properties (water-holding and oil-binding capacities, solubility, emulsifying and foaming properties) of EPSC protein were evaluated. The optimum conditions of the both processes were measured using response surface methodology (RSM). The maximum yield (26.4%) and protein content (86.1%) were reached at the optimized extraction conditions. Optimal conditions of PG deamidation based on reaching a high degree of deamidation (DD) with a simultaneously low degree of hydrolysis (DH). Under these conditions, DD and DH were 39.40 and 2.11%, respectively. Ultrasound-assisted alkaline extraction and enzymatic deamidation by PG have great potential to produce edible EPSC protein with modified techno-functional characteristics that can be used for several aims in the food and pharmaceutical applications.


Assuntos
Fracionamento Químico/métodos , Oenothera biennis/química , Proteínas de Vegetais Comestíveis/química , Amidas/química , Aminoácidos/análise , Emulsificantes/química , Glutaminase/química , Hidrólise , Extratos Vegetais/química , Óleos de Plantas/química , Proteínas de Vegetais Comestíveis/isolamento & purificação , Estrutura Secundária de Proteína , Solubilidade , Ultrassom
8.
Biol Pharm Bull ; 43(11): 1767-1775, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-33132322

RESUMO

Endotoxin is an unintentional contaminant that has numerous activities and can affect various biological experiments using cells. In this study, we measured the endotoxin activity of samples from a plant extract library (PEL) and determined their degrees of contamination. Endotoxin was detected in approx. 48% (n = 139) and approx. 4% (n = 5) of field-collected and crude drug samples, respectively, and in concentrations >5.0 EU/mL in some samples. The concentrations of endotoxin that affect cells in vitro vary depending on the target cell type. Although the degree of contamination varied in the present study, it was considered to have little effect on the cell experiments. More than 150 PEL samples had problems with reaction courses or recovery rates of Limulus amoebocyte lysate (LAL) tests. In the LAL tests, using three plant extracts [Sanguisorba officinalis L. (Rosaceae), Oenothera biennis L. (Onagraceae), and Lythrum salicaria L. (Lythraceae)], the polyphenolic compounds in the plant extracts affected LAL test and their effects differed depending on the plant species. When the 16 single polyphenol compounds were added to the LAL tests, the compounds with caffeoyl and pyrogallol moieties were found to affect the LAL reaction course and recovery rate. Furthermore, none of the compounds had any effects at concentrations of 1 µM. Because the plant extracts contained analogs of various polyphenolic compounds, they were presumed to actually act synergistically. Our findings demonstrated that attention must be paid to the recovery rate and reaction process of LAL tests with samples containing polyphenolic compounds.


Assuntos
Contaminação de Medicamentos/prevenção & controle , Endotoxinas/análise , Teste do Limulus/normas , Extratos Vegetais/química , Animais , Lythrum/química , Oenothera biennis/química , Extratos Vegetais/normas , Polifenóis/química , Sanguisorba/química
9.
Biomolecules ; 10(6)2020 05 26.
Artigo em Inglês | MEDLINE | ID: mdl-32466573

RESUMO

Oenothera biennis L. (OB), also commonly known as evening primrose, belongs to the Onagraceae family and has the best studied biological activity of all the members in the family. In therapy, the most frequently used type of extracts are from the aerial part, which are the fatty oils obtained from the seeds and have a wide range of medicinal properties. The aim of this study was to evaluate the phytochemical composition and biological activity of OB hydroalcoholic extract and to provide directions for the antimicrobial effect, antiproliferative and pro-apoptotic potential against A375 melanoma cell line, and anti-angiogenic and anti-inflammatory capacity. The main polyphenols and flavonoids identified were gallic acid, caffeic acid, epicatechin, coumaric acid, ferulic acid, rutin and rosmarinic acid. The total phenolic content was 631.496 µgGAE/mL of extract and the antioxidant activity was 7258.67 µmolTrolox/g of extract. The tested extract had a mild bacteriostatic effect on the tested bacterial strains. It was bactericidal only against Candida spp. and S. aureus. In the set of experimental conditions, the OB extract only manifested significant antiproliferative and pro-apoptotic activity against the A375 human melanoma cell line at the highest tested concentration, namely 60 µg/mL. The migration potential of A375 cells was hampered by the OB extract in a concentration-dependent manner. Furthermore, at the highest tested concentration, the OB extract altered the mitochondrial function in vitro, while reducing the angiogenic reaction, hindering compact tumor formation in the chorioallantoic membrane assay. Moreover, the OB extract elicited an anti-inflammatory effect on the experimental animal model of ear inflammation.


Assuntos
Inibidores da Angiogênese/farmacologia , Antibacterianos/farmacologia , Anti-Inflamatórios/farmacologia , Antifúngicos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Edema/tratamento farmacológico , Compostos Fitoquímicos/farmacologia , Inibidores da Angiogênese/química , Inibidores da Angiogênese/isolamento & purificação , Animais , Antibacterianos/química , Antibacterianos/isolamento & purificação , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Antifúngicos/química , Antifúngicos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Apoptose/efeitos dos fármacos , Candida/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Edema/induzido quimicamente , Feminino , Humanos , Camundongos , Camundongos Pelados , Testes de Sensibilidade Microbiana , Oenothera biennis/química , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Relação Estrutura-Atividade , Acetato de Tetradecanoilforbol , Células Tumorais Cultivadas
10.
Pak J Pharm Sci ; 33(4): 1473-1481, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-33583777

RESUMO

Oenothera biennis L. is a perennial herb distributed across America, Asia, and Europe. The pharmacological effect of Oenothera biennis L. stem is poorly understood. We demonstrated that lipopolysaccharide (LPS)-induced the high production of inflammatory mediators nitric oxide (NO) and prostaglandin E2 (PGE2) and the pro-inflammatory cytokines tumor necrosis factor (TNF)-α, interleukin (IL)-6 and IL-1ß in peritoneal macrophages (PMs) were significantly inhibited by the crude extract The inflammation related signaling extra cellular signal-regulated ERK, P38 of MAPK and NF-kappaB (NF-κB) activated by LPS dramatically inhibited. In conclusion, our results suggested that the stems of Oenothera biennis L. possess a high anti-inflammatory property, thus, can be used in the industrial production of medicinal products as the raw material in the future.


Assuntos
Inflamação/tratamento farmacológico , Proteínas Quinases Ativadas por Mitógeno/metabolismo , NF-kappa B/metabolismo , Oenothera biennis/química , Extratos Vegetais/farmacologia , Caules de Planta/química , Transdução de Sinais/efeitos dos fármacos , Animais , Anti-Inflamatórios/farmacologia , Ciclo-Oxigenase 2/metabolismo , Citocinas/metabolismo , Dinoprostona/metabolismo , Inflamação/induzido quimicamente , Mediadores da Inflamação/metabolismo , Interleucina-1beta/metabolismo , Interleucina-6/metabolismo , Lipopolissacarídeos/farmacologia , Macrófagos Peritoneais/efeitos dos fármacos , Macrófagos Peritoneais/metabolismo , Camundongos , Camundongos Endogâmicos C57BL , Óxido Nítrico/metabolismo , Óxido Nítrico Sintase Tipo II/metabolismo , Fator de Necrose Tumoral alfa/metabolismo
11.
J Med Life ; 12(3): 284-289, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31666832

RESUMO

Hysterosalpingography is one of the essential diagnostic methods for examining women who have difficulty becoming pregnant. This procedure is somehow invasive and is associated with numerous complications such as allergic sensitivity, pain, abdominal cramps and shock. Therefore, this study aimed to investigate the effect of evening primrose on cervical length and pain during and after hysterosalpingography. In this double-blind clinical trial, 66 candidates for hysterosalpingography were randomly divided into two groups. A group received 1000 mg of evening primrose orally for two days prior to hysterosalpingography, while the control group received a placebo drug similar in size to evening primrose three days prior to hysterosalpingography. The pain level was recorded based on the Visual Analogue Scale (VAS), during tenaculum placement but also immediately and four hours after hysterosalpingography. Finally, the data were analyzed using SPSS (version 20). There was a significant difference between the two groups in terms of pain during insertion of speculum and injection of the contrast medium (p <0.05). Less pain was reported in the evening primrose group compared to placebo. There was no significant difference between the two groups in terms of the length and diameter of the cervix (p <0.05). Given the fact that it is a medicinal plant with no complications and can reduce pain during speculum insertion and during contrast medium injection, evening primrose seems to be a good drug for managing pain during hysterosalpingography.


Assuntos
Colo do Útero/patologia , Histerossalpingografia/efeitos adversos , Oenothera biennis/química , Dor/tratamento farmacológico , Dor/etiologia , Extratos Vegetais/farmacologia , Adulto , Dilatação , Método Duplo-Cego , Feminino , Humanos , Medição da Dor , Placebos , Gravidez , Adulto Jovem
12.
J Oleo Sci ; 68(8): 719-728, 2019 Aug 01.
Artigo em Inglês | MEDLINE | ID: mdl-31292343

RESUMO

This work focused on physicochemical property assaying, fatty acid composition, triacylglycerol (TAG) profiles, and unsaponifiable matters composition of the Chinese evening primrose oil. The cold press oil possessed very low acid value and peroxide value, and relatively high iodine value. Fatty acid composition results indicated that this oil was especially high in linoleic acid and linolenic acid. Characterization of TAG composition was achieved by a two-dimensional HPLC coupling of nonaqueous reverse-phase and silver ion HPLC with atmospheric pressure chemical ionization MS method. There was a total of 38 TAGs including 27 regioisomers which had been determined. Unsaponifiable matters composition results revealed that this oil possessed a number of phytosterols, in which ß-sitosterol and stigmasterol were most predominant.


Assuntos
Ácidos Graxos/análise , Ácidos Linoleicos/análise , Oenothera biennis/química , Fitosteróis/análise , Óleos de Plantas/análise , Triglicerídeos/análise , Ácido gama-Linolênico/análise , Cromatografia Líquida de Alta Pressão , Espectrometria de Massas , Sementes/química
13.
Molecules ; 24(15)2019 Jul 25.
Artigo em Inglês | MEDLINE | ID: mdl-31349647

RESUMO

Aldose reductase (AR) is a drug target for therapies to treat complications caused by diabetes mellitus, and the development of effective AR inhibitors (ARIs) of natural origin is considered to be an attractive option for reducing these complications. In this research, the rat lens AR (RLAR) inhibitory activity of evening primrose (Oenothera biennis) seeds was investigated for the first time. In our results, the 50% (v/v) methanol extract of evening primrose seeds exhibits excellent RLAR inhibitory activity (IC50 value of 7.53 µg/mL). Moreover, after enrichment of its bioactive components, the ARIs are more likely to be present in the ethyl acetate fraction of 50% (v/v) methanol extract (EME) of evening primrose seeds, which exhibits superior RLAR inhibitory activity (IC50 value of 3.08 µg/mL). Finally, gallic acid (1), procyanidin B3 (2), catechin (3), and methyl gallate (4) were identified as the major ARIs from the EME by affinity-based ultrafiltration-high-performance liquid chromatography and were isolated by high speed countercurrent chromatography, with gallic acid (11.46 µmol/L) and catechin (14.78 µmol/L) being the more potent inhibitors of the four ARIs identified. The results demonstrated that evening primrose seeds may be a potent ingredient of ARIs.


Assuntos
Aldeído Redutase/química , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Oenothera biennis/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Sementes/química , Animais , Fracionamento Químico , Cromatografia Líquida de Alta Pressão , Avaliação Pré-Clínica de Medicamentos , Ativação Enzimática , Inibidores Enzimáticos/isolamento & purificação , Cristalino/enzimologia , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/isolamento & purificação , Ratos
14.
Food Chem ; 275: 69-76, 2019 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-30724250

RESUMO

Seeds and sprouts are of considerable interest due to their numerous pro-health benefits. The aim of this study was to investigate the effect of germination on the mineral composition (performed by flame absorption atomic spectroscopy), total phenolic content, antioxidant activity, as well as phenolic profiles (before and after alkaline hydrolysis by high-performance liquid chromatography) of chia, golden flax, evening primrose, phacelia and fenugreek seeds. Generally, significant (p < 0.05) changes in the individual minerals composition of the seeds, improvement of their antioxidant properties, as well as increase in levels of individual phenolic compounds was found after seeds germination. Alkaline hydrolysis allowed to release free forms of phenolics and to confirm (chromatographically) their significantly higher amounts when compared to the nonhydrolyzed fraction. Gallic, protocatechuic, caffeic, p-coumaric, ferulic and sinapic acids, as well as quercetin and kaempferol were identified in analyzed seeds and sprouts. Sprouts exhibited better nutritional values than their un-germinated forms.


Assuntos
Antioxidantes/farmacologia , Linho/química , Oenothera biennis/química , Fenóis/análise , Trigonella/química , Antioxidantes/química , Cromatografia Líquida de Alta Pressão , Germinação , Hydrophyllaceae/química , Minerais/análise , Salvia/química , Sementes/química , Sementes/crescimento & desenvolvimento
15.
J Chem Ecol ; 45(1): 86-94, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30511298

RESUMO

Phenolics have a role in defenses against herbivores, but the defensive functions of specific groups of phenolics are still poorly understood. For example, ellagitannins (a type of hydrolyzable tannin) are predicted to decrease insect herbivore performance, but the effect of different types of ellagitannins on generalist and specialist herbivores has rarely been assessed. Here, we test the effects of the dominant oligomeric ellagitannins of Oenothera biennis and other Onagraceae on herbivore performance. We fed artificial diets containing between 1 and 100 mg/g of polyphenol fractions comprised of varying amounts and compositions of dimeric oenothein B, the trimeric oenothein A and larger oligomers, to one generalist (Spodoptera exigua) and one specialist (Schinia florida) insect herbivore species. We compared the effects of these ellagitannin fractions on herbivore performance to the effects of artificial diet containing total phenolic extracts from O. biennis, which contained these ellagitannins as well as many additional phenolic metabolites including flavonoid glycosides and caffeic acid derivatives. Both the ellagitannin fractions and O. biennis phenolic extracts had strong negative effects on S. exigua and S. florida performance, with stronger effects on the generalist herbivore. Differences between the effects of the various ellagitannin fractions were small and depended on insect life stage. The defensive effects of these ellagitannins were large, with lethal concentrations as low as 0.1% of the diet. These results highlight the important defensive function of ellagitannins against specialist and generalist herbivores and the need to characterize the effects of these understudied phenolics.


Assuntos
Herbivoria , Taninos Hidrolisáveis/metabolismo , Mariposas/fisiologia , Onagraceae/fisiologia , Animais , Taninos Hidrolisáveis/análise , Oenothera biennis/química , Oenothera biennis/fisiologia , Onagraceae/química , Spodoptera/fisiologia
16.
Phytochem Anal ; 29(3): 275-283, 2018 May.
Artigo em Inglês | MEDLINE | ID: mdl-29280218

RESUMO

INTRODUCTION: Aroma is important in night-flowering species, as visually they can not be observed well. Thus, the analysis of the volatiles of evening-primrose is of great interest in biological fields and therapy. Furthermore, the analysis of volatiles demands rapid and simple procedure, because volatiles decompose. OBJECTIVE: The aim of this study is to show the rapid monitoring of the volatiles of evening-primrose according to the flowering or closing by fast gas chromatography/surface acoustic wave GC/SAW. Moreover, calibration according to the sensor temperature of the GC/SAW was performed, achieving a high reproducibility and excellent sensitivity. METHODOLOGY: GC/SAW is an effective analytical method that provides on-line measurements without pretreatment of sample. Headspace solid-phase micro-extraction coupled to gas chromatography mass spectrometry (HS-SPME-GC-MS) and dynamic headspace trapping and extraction with GC-MS were employed to confirm the identification of the volatiles of evening-primrose compared to GC/SAW. RESULTS: Linalool was found to be the dominant component, comprising 96.4-25.2% of the total amount, according to the opening or closing. Interestingly, the amount of indole also varied according to the opening or closing (3.0-0.0%) such as linalool. Also, while the sensitivity increased with the reduction in the sensor temperature of the GC/SAW, the reproducibility showed a tendency to decrease. CONCLUSION: The results showed that flower opening is related to the volatiles emission, which is pharmacological and plant defensive. GC/SAW can be a useful analytical method for the rapid monitoring of volatiles of evening-primrose according to the opening or closing as it provides second unit analysis, as well as simple, and aroma pattern recognition. Copyright © 2017 John Wiley & Sons, Ltd.


Assuntos
Acústica , Flores/química , Cromatografia Gasosa-Espectrometria de Massas/métodos , Odorantes , Oenothera biennis/química , Compostos Orgânicos Voláteis/análise , Monoterpenos Acíclicos , Calibragem , Limite de Detecção , Monoterpenos/análise , Padrões de Referência , Reprodutibilidade dos Testes , Microextração em Fase Sólida
17.
J Pharm Pharmacol ; 69(9): 1230-1243, 2017 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-28555835

RESUMO

BACKGROUND: Oenothera biennis L., commonly known as evening primrose, harbours the flavonoids, steroids, tannins, fatty acids and terpenoids responsible for a diverse range of biological activity, such as antitumour, anti-arthritic and anti-inflammatory effects. In addition to the previous reports from aerial parts of this plant, studies related to antiproliferative or antimicrobial activity from the roots are warranted. OBJECTIVE: To investigate antiproliferative and antimicrobial activity of compounds/mixture (1-8) isolated and characterized from the roots of O. biennis L. A possible mechanism of antiproliferative activity was also studied by targeting ornithine decarboxylase (ODC) and cathepsin D (CATD). STUDY DESIGN: Antiproliferative efficacy of the compounds/mixture was examined in selected cancer cell lines along with their probable mechanism of action. The antimicrobial activity was also studied against selected microbes (bacteria and fungi). METHODS: Antiproliferative potential was evaluated by MTT assay against selected cell lines. The mechanism of action was studied spectrophotometrically by targeting ODC and CATD using both an in-vitro and an in-silico approach. The antimicrobial efficiency was analysed using the disc diffusion and broth dilution methods. KEY FINDINGS: Oenotheralanosterol B (3) and the mixture of oenotheralanosterol A and oenotheralanosterol B (4) exhibited antiproliferative activity against breast, hepatic, prostate and leukaemia cancer cell lines as well as in mouse macrophages (IC50 8.35-49.69 µg/ml). Oenotheralanosterol B (3) and the mixture of oenotheralanosterol A and oenotheralanosterol B (4) displayed a strong molecular interaction with succinate dehydrogenase (binding energy -6.23 and -6.84 kcal/mol and Ki 27.03 and 9.6 µm, respectively). Oenotheralanosterol A (1), oenotheralanosterol B (3) and mixture of oenotheralanosterol A and oenotheralanosterol B (4) potently inhibited the ODC activity with IC50 ranging from 4.65 ± 0.35 to 19.06 ± 4.16 µg/ml and also showed a strong interaction with ODC (BE -4.17 to -4.46 kcal/mol). Oenotheralanosterol A (1), cetoleilyl diglucoside (2), oenotheralanosterol B (3), dihydroxyprenylxanthone acetylated (6) and dihydroxyprenylxanthone (7) inhibited CATD activity (IC50 3.95 ± 0.49 to 24.35 ± 2.89 µg/ml). The in-silico molecular interaction analysis of compounds with CATD revealed the non-specific interaction. A moderate antimicrobial activity was observed against selected microbes with a growth inhibition ranging from 6 to 14 mm and minimum inhibitory concentration between 125 and 500 µg/ml. Oenotheralanosterol B (3) and dihydroxyprenylxanthone acetylated (6) exhibited better antimicrobial activity with an MIC range from 62.50 to 500 µg/ml. CONCLUSION: Oenotheralanosterol B (3) exhibited stronger antiproliferative and antimicrobial potential with respect to the other compounds tested, whereas oenotheralanosterol A (1) was a potent inhibitor of ODC and CATD. Hence, it is suggested that these in-vitro findings could be studied further in vivo for biological activity, safety evaluation and derivatization to enhance potency and efficacy.


Assuntos
Anti-Infecciosos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Oenothera biennis/química , Extratos Vegetais/farmacologia , Animais , Anti-Infecciosos/administração & dosagem , Anti-Infecciosos/isolamento & purificação , Antineoplásicos Fitogênicos/administração & dosagem , Antineoplásicos Fitogênicos/isolamento & purificação , Catepsina D/metabolismo , Linhagem Celular Tumoral , Simulação por Computador , Relação Dose-Resposta a Droga , Humanos , Concentração Inibidora 50 , Testes de Sensibilidade Microbiana , Neoplasias/tratamento farmacológico , Neoplasias/patologia , Ornitina Descarboxilase/metabolismo , Extratos Vegetais/administração & dosagem , Raízes de Plantas
18.
Clin Rheumatol ; 35(8): 1909-1915, 2016 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-26758438

RESUMO

Rheumatoid arthritis is a chronic inflammatory disease. Reactive oxygen species have been considered as aggravating factors for autoimmune diseases. Fatty acids had been linked in reduction of various diseases by augment of their antioxidant potential and antiinflammatory mechanisms. The aim of this study was to assess the oxidative status in patients with rheumatoid arthritis who used concentrated fish oil only or concentrated fish oil in combination with evening primrose oil in a period of 3 months. Subjects were divided into three groups. The group I consists of patients who had been taking only their regular rheumatologic therapy; group II, patients who had been taking concentrated fish oil; and group III, patients who had been taking concentrated fish oil and evening primrose oil. Peripheral blood samples were used for all the assays. We assessed the following oxidative stress markers: index of lipid peroxidation (thiobarbituric acid-reactive substances (TBARS)), hydrogen peroxide (H2O2), superoxide anion radical (O2 (-)), nitric oxide (NO), superoxide dismutase activity (SOD), catalase activity (CAT), and glutathione levels (GSH) in erythrocytes. There were no statistically significant changes for any of the oxidative stress parameters in group I. In group II, levels of TBARS, NO2 (-), and GSH were increased, while levels of H2O2 decreased. Increased values of TBARS, NO2 (-), and SOD were found in group III. Our findings indicate that intakes of fish oil and evening primrose oil may be of importance in mitigation of inflammation, disease activity, and oxidative stress biomarkers, through increased activities of antioxidant enzymes.


Assuntos
Antioxidantes/uso terapêutico , Artrite Reumatoide/tratamento farmacológico , Óleos de Peixe/administração & dosagem , Oenothera biennis/química , Estresse Oxidativo/efeitos dos fármacos , Óleos de Plantas/administração & dosagem , Idoso , Biomarcadores/metabolismo , Suplementos Nutricionais , Feminino , Humanos , Peróxido de Hidrogênio/metabolismo , Peroxidação de Lipídeos , Pessoa de Meia-Idade , Óxido Nítrico/metabolismo , Pós-Menopausa , Substâncias Reativas com Ácido Tiobarbitúrico/metabolismo
19.
Zhong Yao Cai ; 38(6): 1290-4, 2015 Jun.
Artigo em Chinês | MEDLINE | ID: mdl-26762071

RESUMO

OBJECTIVE: To study the preparation of Oenothera biennis oil solid lipid nanoparticles and its quality evaluation. METHODS: The solid lipid nanoparticles were prepared by microemulsion technique. The optimum condition was performed based on the orthogonal design to examine the entrapment efficiency, the mean diameter of the particles and so on. RESULTS: The optimal preparation of Oenothera biennis oil solid lipid nanoparticles was as follows: Oenothera biennis dosage 300 mg, glycerol monostearate-Oenothera biennis (2: 3), Oenothera biennis -RH/40/PEG-400 (1: 2), RH-40/PEG-400 (1: 2). The resulting nanoparticles average encapsulation efficiency was (89.89 ± 0.71)%, the average particle size was 44.43 ± 0.08 nm, and the Zeta potential was 64.72 ± 1.24 mV. CONCLUSION: The preparation process is simple, stable and feasible.


Assuntos
Portadores de Fármacos , Lipídeos/química , Nanopartículas , Oenothera biennis/química , Ácidos Linoleicos/química , Tamanho da Partícula , Óleos de Plantas/química , Polietilenoglicóis , Ácido gama-Linolênico/química
20.
Naunyn Schmiedebergs Arch Pharmacol ; 387(11): 1069-78, 2014 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-25079872

RESUMO

Oenothera paradoxa (EP) preparations are commonly used in folk medicine to treat skin diseases, neuralgia, and gastrointestinal (GI) disorders. Several reports suggested that EP preparations exhibit potent anti-inflammatory and antioxidant activities both in vitro and in vivo. Here, we aimed to characterize the action of EP pomace polyphenol extract in mouse model of colitis. We analyzed the composition of EP pomace polyphenol extract using reversed phase HPLC system and ultra-performance liquid chromatography (UPLC) system coupled with a quadrupole-time of flight (Q-TOF) MS instrument. Then, we used a well-established animal model of 2,4,6-trinitrobenzenesulfonic acid (TNBS)-induced colitis to determine the anti-inflammatory action of EP pomace polyphenol extract. We also investigated the effect of the EP pomace polyphenol extract on pro-inflammatory (IL-1ß and TNF-α) cytokine mRNA levels and hydrogen peroxide concentration in the inflamed colon. Administration of EP pomace polyphenol extract significantly improved macroscopic and microscopic damage scores, as well as myeloperoxidase (MPO) activity in TNBS-treated mice. The anti-inflammatory effect of the extract was observed after intracolonic and oral administration and was dose-dependent. Significant reduction of tissue hydrogen peroxide level after treatment with EP pomace polyphenol extract suggests that its therapeutic effect is a result of free radical scavenging. This novel finding indicates that the application of the EP pomace polyphenol extract in patients with inflammatory bowel diseases (IBDs) may become an attractive supplementary treatment for conventional anti-inflammatory therapy.


Assuntos
Colite/tratamento farmacológico , Oenothera biennis/química , Extratos Vegetais/farmacologia , Polifenóis/farmacologia , Administração Oral , Animais , Anti-Inflamatórios/administração & dosagem , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Cromatografia Líquida de Alta Pressão , Colite/fisiopatologia , Modelos Animais de Doenças , Relação Dose-Resposta a Droga , Sequestradores de Radicais Livres/administração & dosagem , Sequestradores de Radicais Livres/isolamento & purificação , Peróxido de Hidrogênio/metabolismo , Interleucina-1beta/genética , Masculino , Espectrometria de Massas , Camundongos , Camundongos Endogâmicos C57BL , Extratos Vegetais/administração & dosagem , Polifenóis/administração & dosagem , Polifenóis/isolamento & purificação , Ácido Trinitrobenzenossulfônico/toxicidade , Fator de Necrose Tumoral alfa/genética
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