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1.
Chem Biodivers ; 18(10): e2000936, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34432933

RESUMO

The antioxidant and mutagenic/antimutagenic activities of the fixed oils from Nigella sativa (NSO) and Nigella damascena (NDO) seeds, obtained by cold press-extraction from the cultivar samples, were comparatively investigated for the first time. The antimutagenicity test was carried out using classical and modified Ames tests. The fatty acid composition of the fixed oils was characterized by gas chromatography-mass spectrometry (GC-MS) while the quantification of thymoquinone in the fixed oils was determined by UPC2 . The main components of the NSO and NDO were found to be linoleic acid, oleic acid, and palmitic acid. The results of the Ames test confirmed the safety of NSO and NDO from the viewpoint of mutagenicity. The results of the three antioxidant test methods were correlated with each other, indicating NDO as having a superior antioxidant activity, when compared to the NSO. Both NSO and NDO exhibited a significant protective effect against the mutagenicity induced by aflatoxin B1 in Salmonella typhimurium TA98 and TA100 strains. When microsomal metabolism was terminated after metabolic activation of the mycotoxin, a significant increase in antimutagenic activity was observed, suggesting that the degradation of aflatoxin B1 epoxides by these oils may be a possible antimutagenic mechanism. It is worthy to note that this is the first study to assess the mutagenicity of NSO and NDO according to the OECD 471 guideline and to investigate antimutagenicity of NDO in comparison to NSO against aflatoxin.

2.
Phytomedicine ; 58: 152872, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-30826527

RESUMO

BACKGROUND: Glycyrrhiza (licorice) species are rich in bioactive secondary metabolites and their roots are used traditionally for the treatment of several diseases. In recent years, secondary metabolites of licorice are gaining popularity, especially due to their significant cytotoxic and antitumor effects. However, Glycyrrhiza iconica, an endemic species to Turkey, was not investigated in terms of its anticancer secondary metabolites previously. PURPOSE: This study aimed to isolate the cytotoxic compounds from G. iconica through bioactivity-guided fractionation and to elucidate mechanisms of action of the most potent compounds. METHODS: Total MeOH extract and CHCl3, EtOAc, n-buOH and rH2O subextracts were prepared from G. iconica roots. Sequential chromatographic techniques were conducted for the isolation studies. The chemical structures of the isolates were established based on NMR and HR-MS analysis. Sulforhodamine B assay was used to evaluate the cytotoxic activity of extracts, main fractions as well as isolates against hepatocellular (Huh7), breast (MCF7) and colorectal (HCT116) cancer cell lines. The mechanisms underlying the cytotoxicity of the most active compounds in Huh7 cells were elucidated by using Hoechst staining, Fluorescence-activated cell sorting and Western blot assays. RESULTS: A new dihydrochalcone, iconichalcone (1) along with 15 known phenolic compounds were isolated from the active CHCl3, EtOAc and n-buOH subextracts. Compounds 2-5, 7-16 were found to be responsible for the in vitro cytotoxic activity of G. iconica against all tested cancer cell lines with IC50 values ranging from 2.4 to 33 µM. Amongst these compounds, licoricidin (10), dehydroglyasperin C (12), iconisoflaven (13) and 1-methoxyficifolinol (15) were found to be the most active compounds according to SRB and real time bioactivity assays and submitted to further mechanistic investigations in Huh7 cells. Compounds 10, 12, 13 and 15 caused accumulation of cells in different phases of cell cycle. Moreover, 10, 12, 13 and 15 induced apoptosis through caspase activation. Besides, 12 showed activation of p53 expression and thus G2/M arrest as well as a condensed nuclei, established very promising results. CONCLUSION: The results demonstrated that the aforementioned compounds, particularly 12 could be potential lead molecules for anticancer drug development that deserve further in vivo and clinical investigations.


Assuntos
Antioxidantes/farmacologia , Benzopiranos/farmacologia , Glycyrrhiza/química , Neoplasias Hepáticas/tratamento farmacológico , Fenóis/farmacologia , Extratos Vegetais/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Apoptose/efeitos dos fármacos , Benzopiranos/química , Benzopiranos/isolamento & purificação , Ciclo Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Humanos , Fenóis/química , Fenóis/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Raízes de Plantas/química
3.
J Ethnopharmacol ; 196: 236-241, 2017 Jan 20.
Artigo em Inglês | MEDLINE | ID: mdl-28011162

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Topical formulations such as oily extracts or ointments prepared with the flowering aerial parts of St. John's wort (Hypericum perforatum L., Hypericaceae) have been used in the management of a wide range dermatological problems including superficial wounds and burns, bruises, contusions and many others in the worldwide traditional medicines. AIM OF THE STUDY: This is the first case study reporting the beneficial effects of an oily extract of St. John's wort in the treatment of pressure sores in a intensive care unit (ICU) patient. MATERIAL AND METHODS: The oily extract of St. John's wort was applied to a volunteer patient at ICU daily for forty successive days for wound care and treatment. Healing status was monitored macroscopically by measuring the wound size and stages at certain intervals as well as histopathological evaluation of the tissue sections taken at the initial and final dates of treatment. RESULTS: Evaluation of the results obtained from the macroscopical and histopathological experimentation have shown that oily extract of St. John's wort provided significant efficacy for the treatment of pressure sore wounds. CONCLUSION: St. John's wort oily extract may be suggested as a cost-effective option for the prevention or treatment of pressure sores in ICU patients.


Assuntos
Hypericum , Fitoterapia , Extratos Vegetais/uso terapêutico , Óleos Vegetais/uso terapêutico , Lesão por Pressão/tratamento farmacológico , Idoso de 80 Anos ou mais , Humanos , Masculino , Componentes Aéreos da Planta , Lesão por Pressão/patologia , Pele/efeitos dos fármacos , Pele/patologia
4.
Fitoterapia ; 103: 289-93, 2015 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-25963162

RESUMO

A new prenylated isoflavan, iconisoflavan (1), and a new prenylated isoflav-3-ene, iconisoflaven (2) were isolated from the roots of Glycyrrhiza iconica together with four known ones namely (3S)-licoricidin (3), licorisoflavan A (4), topazolin (5) and glycycoumarin (6). The structures were elucidated on the basis of extensive spectroscopic analysis including 1D and 2D NMR as well as HR-MS. Furthermore, the absolute configurations of compounds 1, 3 and 4 were established by electronic circular dichroism (ECD). All the isolated compounds (1-6) were evaluated for their in vitro antimicrobial activities against five pathogenic bacteria and one yeast (Candida albicans) using an in vitro microdilution method. Compounds 1 and 3-5 displayed significant activity against Salmonella typhimurium ATCC 13311 with MIC values ranging from 2 to 8 µg/mL. Additionally, all compounds were screened for their in vitro free radical scavenging activities using an in vitro microdilution DPPH assay spectrofotometrically. The tested compounds exhibited IC50 values in the range of 0.18-0.56 mg/mL, suggesting an activity comparable with that of ascorbic acid (IC50: 0.07 mg/mL). To the best of our knowledge, the present study constitutes the first phytochemical and bioactivity investigation on G. iconica.


Assuntos
Anti-Infecciosos/química , Antioxidantes/química , Glycyrrhiza/química , Isoflavonas/química , Extratos Vegetais/química , Anti-Infecciosos/isolamento & purificação , Antioxidantes/isolamento & purificação , Candida albicans/efeitos dos fármacos , Flavonoides/química , Flavonoides/isolamento & purificação , Concentração Inibidora 50 , Isoflavonas/isolamento & purificação , Testes de Sensibilidade Microbiana , Estrutura Molecular , Raízes de Plantas/química , Polifenóis/química , Polifenóis/isolamento & purificação , Prenilação , Salmonella typhimurium/efeitos dos fármacos
5.
Food Chem Toxicol ; 59: 96-103, 2013 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-23764360

RESUMO

Inhibitory effect of the n-hexane, dichloromethane, ethyl acetate, and ethanol extracts from Anethum graveolens L. (dill) cultivated under organic (AG-O) and conventional (AG-C) conditions was tested against acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and tyrosinase at 200 µg mL⁻¹. Their antioxidant activity was determined using 2,2-diphenyl-1-picrylhydrazyl (DPPH), N,N-dimethyl-p-phenylendiamine (DMPD), and nitric oxide (NO) radical scavenging assays as well as ferric ion-chelation capacity, ferric-(FRAP), and phosphomolybdenum-reducing antioxidant power (PRAP). The phytochemical analyses have been performed on both of the plant samples. GC-MS analysis pointed out that α-phellandrene was the main component in both of the essential oils in varying amounts (47.75% for AG-O and 27.94% for AG-C), while oleic acid was the dominant in the fruit oils of two samples (36.39% for AG-O and 53.87% for AG-C). HPLC analysis showed that both of the extracts contained rosmarinic acid as the major phenolic acid. The extracts inhibited BChE at moderate level, while the ethanol extracts exerted remarkable NO scavenging effect. The results emphasize that cultivation conditions may have effect on bioactivity and phytochemical content on plant samples.


Assuntos
Anethum graveolens/química , Antioxidantes/farmacologia , Descoberta de Drogas , Inibidores Enzimáticos/farmacologia , Alimentos Orgânicos/análise , Óleos Voláteis/farmacologia , Extratos Vegetais/farmacologia , Acetilcolinesterase/química , Acetilcolinesterase/metabolismo , Anethum graveolens/crescimento & desenvolvimento , Anethum graveolens/metabolismo , Animais , Antioxidantes/análise , Antioxidantes/isolamento & purificação , Antioxidantes/metabolismo , Butirilcolinesterase/química , Butirilcolinesterase/metabolismo , Inibidores da Colinesterase/análise , Inibidores da Colinesterase/isolamento & purificação , Inibidores da Colinesterase/metabolismo , Inibidores da Colinesterase/farmacologia , Cinamatos/análise , Cinamatos/metabolismo , Monoterpenos Cicloexânicos , Depsídeos/análise , Depsídeos/metabolismo , Electrophorus , Inibidores Enzimáticos/análise , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/metabolismo , Proteínas de Peixes/antagonistas & inibidores , Proteínas de Peixes/metabolismo , Frutas/química , Frutas/crescimento & desenvolvimento , Frutas/metabolismo , Proteínas Fúngicas/antagonistas & inibidores , Proteínas Fúngicas/metabolismo , Cavalos , Quelantes de Ferro/análise , Quelantes de Ferro/isolamento & purificação , Quelantes de Ferro/metabolismo , Quelantes de Ferro/farmacologia , Monofenol Mono-Oxigenase/antagonistas & inibidores , Monofenol Mono-Oxigenase/metabolismo , Monoterpenos/análise , Monoterpenos/metabolismo , Óxido Nítrico/antagonistas & inibidores , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Solventes/química
6.
Nat Prod Res ; 26(1): 1-10, 2012.
Artigo em Inglês | MEDLINE | ID: mdl-21714737

RESUMO

In this study, composition of essential oil and antioxidant capacity of Centaurea drabifolia subsp. detonsa were investigated. The antioxidant capacity of the methanolic extract was evaluated by various methods including measuring the total phenolic content, total antioxidant capacity, free radical scavenging activity (DPPH assay), ß-carotene/linoleic acid bleaching assay and ferric and cupric ion reducing power assay. The composition of essential oil was identified by using gas chromatography-mass spectrometry. Totally, 41 compounds were described in the essential oil. Germacrene D (44.829%) was determined as the major compound of the essential oil. The total phenolic content, total antioxidant capacity, inhibition rate of oxidation of linoleic acid, IC(50) (in DPPH assay) and EC(50) (in reducing power) value were found to be 40.454 mg GAE/g, 100.840 mg AAE/g, 65.639%, 39.584 µg mL(-1) and 0.603 mg mL(-1), respectively. The results indicated that the extract of C. drabifolia subsp. detonsa has strong antioxidant properties and this species can be used as a natural antioxidant in food processing and pharmaceutical industries.


Assuntos
Antioxidantes/análise , Centaurea/química , Sequestradores de Radicais Livres/análise , Óleos Voláteis/química , Antioxidantes/farmacologia , Cobre/metabolismo , Sequestradores de Radicais Livres/farmacologia , Cromatografia Gasosa-Espectrometria de Massas , Ferro/metabolismo , Ácido Linoleico/metabolismo , Metanol , Oxirredução , Fenóis/análise , Turquia
7.
J Med Food ; 14(11): 1476-83, 2011 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-21663475

RESUMO

In European folk medicine, Salvia species have traditionally been used to enhance memory. In our previous study of 55 Salvia taxa, we explored significant anticholinesterase activity of cultivated S. fruticosa. In this study, we compared the inhibitory activity of dichloromethane, ethyl acetate, and ethanol extracts of 3 wild-grown samples and 1 cultivated sample of S. fruticosa against acetylcholinesterase and butyrylcholinesterase enzymes (which are associated with pathogenesis of Alzheimer's disease) by using the spectrophotometric Ellman method. Antioxidant activities were assessed by determining 2,2-diphenyl-1-picrylhydrazyl radical-scavenging activity, iron-chelating capacity, and ferric-reducing antioxidant power. The dichloromethane extract of the cultivated sample was then subjected to fractionation by using open column chromatography and medium-pressure liquid chromatography to obtain the most active fraction by activity-guided fractionation. All fractions and subfractions were tested in the same manner, and inactive subfractions were discarded. The essential oil of the cultivated sample was analyzed by gas chromatography-mass spectrometry.


Assuntos
Antioxidantes/farmacologia , Inibidores da Colinesterase/farmacologia , Colinesterases/metabolismo , Extratos Vegetais/farmacologia , Salvia officinalis/química , Acetilcolinesterase/metabolismo , Compostos de Bifenilo/metabolismo , Butirilcolinesterase/metabolismo , Fracionamento Químico/métodos , Sequestradores de Radicais Livres/metabolismo , Cromatografia Gasosa-Espectrometria de Massas , Óleos Voláteis/química , Picratos/metabolismo
8.
J Food Sci ; 76(8): M538-46, 2011 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-22417594

RESUMO

In the current study, in vitro inhibitory activity of several essential oils obtained from the cultivated plants, Foeniculum vulgare, Mentha piperita and M. spicata, Ocimum basilicum, Origanum majorana, O. onites, O. vulgare, Satureja cuneifolia, and a number of individual essential oil components of terpene and aromatic types were screened against 10 isolated strains of Klebsiella pneumoniae producing extended-spectrum beta-lactamase (ESBL) enzyme, which makes this microorganism quite resistant against the antibiotics: trimetoprime-sulfametoksazol, sulbactam-ampicilin, clavulonate-amoxicilin, ceftriaxon, cefepime, imipenem, ceftazidime, tobramicine, gentamisine, ofloxacin, and ciprofloksasin. All of the essential oils and the components exerted a remarkable inhibition ranging between 32 and 64 µg/mL against all of these strains as strong as the references (ampicilin and oflaxocin) inhibiting at 32 µg/mL. Besides, chemical compositions of the essential oils were elucidated by gas chromatography-mass spectrometry (GC-MS). The essential oils and the pure components widely found in essential oils screened herein have shown remarkable inhibition against ESBL-producing K. pneumoniae strains, which leads to the suggestion that they may be used as food preservatives for this purpose. Practical Application: The essential oils obtained from Foeniculum vulgare, Mentha piperita and M. spicata, O.cimum basilicum, Origanum majorana, O. onites, O. vulgare, and Satureja cuneifolia as well as common essential oil components have shown notable inhibitory effects against 10 isolated strains of Klebsiella pneumoniae producing extended-spectrum beta-lactamase (ESBL) enzyme and they might be used as food preservative or ingredient.


Assuntos
Klebsiella pneumoniae/efeitos dos fármacos , Klebsiella pneumoniae/enzimologia , Óleos Voláteis/metabolismo , beta-Lactamases/metabolismo , Antibacterianos/farmacologia , Cefepima , Cefalosporinas/farmacologia , Farmacorresistência Bacteriana/efeitos dos fármacos , Conservantes de Alimentos/farmacologia , Cromatografia Gasosa-Espectrometria de Massas/métodos , Imipenem/farmacologia , Klebsiella pneumoniae/isolamento & purificação , Lamiaceae/química , Mentha piperita/química , Testes de Sensibilidade Microbiana , Ocimum basilicum/química , Ofloxacino/farmacologia , Origanum/química , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Satureja/química , Inibidores de beta-Lactamases
9.
Z Naturforsch C J Biosci ; 63(7-8): 547-53, 2008.
Artigo em Inglês | MEDLINE | ID: mdl-18810999

RESUMO

We have tested acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities of nineteen essential oils obtained from cultivated plants, namely one from Anethum graveolens L. (organic fertilizer), two from Foeniculum vulgare Mill. collected at fully-mature and flowering stages (organic fertilizer), two from Melissa officinalis L. (cultivated using organic and chemical fertilizers), two from Mentha piperita L. and M. spicata L. (organic fertilizer), two from Lavandula officinalis Chaix ex Villars (cultivated using organic and chemical fertilizers), two from Ocimum basilicum L. (green and purple-leaf varieties cultivated using only organic fertilizer), four from Origanum onites L., O. vulgare L., O. munitiflorum Hausskn., and O. majorana L. (cultivated using organic fertilizer), two from Salvia sclarea L. (organic and chemical fertilizers), one from S. officinalis L. (organic fertilizer), and one from Satureja cuneifolia Ten. (organic fertilizer) by a spectrophotometric method of Ellman using ELISA microplate-reader at 1 mg/ml concentration. In addition, a number of single components widely encountered in most of the essential oils [gamma-terpinene, 4-allyl anisole, (-)-carvone, dihydrocarvone, (-)-phencone, cuminyl alcohol, cumol, 4-isopropyl benzaldehyde, trans-anethole, camphene, iso-borneol, (-)-borneol, L-bornyl acetate, 2-decanol, 2-heptanol, methyl-heptanol, farnesol, nerol, iso-pulegol, 1,8-cineole, citral, citronellal, citronellol, geraniol, linalool, alpha-pinene, beta-pinene, piperitone, iso-menthone, menthofurane, linalyl oxide, linalyl ester, geranyl ester, carvacrol, thymol, menthol, vanilline, and eugenol] was also screened for the same activity in the same manner. Almost all of the essential oils showed a very high inhibitory activity (over 80%) against both enzymes, whereas the single components were not as active as the essential oils.


Assuntos
Acetilcolinesterase/efeitos dos fármacos , Butirilcolinesterase/efeitos dos fármacos , Inibidores da Colinesterase/farmacologia , Óleos Voláteis/farmacologia , Plantas/química
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