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1.
Chem Biodivers ; 21(2): e202301753, 2024 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-38156418

RESUMEN

In current study antioxidant, antidiabetic, antimicrobial, anticholinesterase, and human carbonic anhydrase I, and II (hCA I and II) isoenzymes inhibition activities of Astrodaucus orientalis different parts were investigated. Achetylcholinesterse (AChE) and butyrylcholinesterse (BChE) inhibitory activities of octyl acetate were determined via molecular docking. Quantitative assessment of specific secondary metabolites was conducted using LC-MS/MS. An examination of chemical composition of essential oils was carried out by GC-MS/MS. A thorough exploration of plant's anatomical characteristics was undertaken. The highest phenolics level and DPPH antioxidant capacity were seen in root and fruit. Fruit essential oil demonstrated the highest AChE inhibition (44.13±3.61 %), while root dichloromethane sub-extract had the best inhibition towards BChE (86.13±2.58 %). Cytosolic hCA I, and II isoenzymes were influentially inhibited by root oil with 1.974 and 2.207 µM IC50 values, respectively. The most effective extracts were found to be root all extract/sub-extracts (except water) against C. tropicalis and C. krusei strains with MIC value 160>µg/mL. Sabinene (29.4 %), α-pinene (20.2 %); octyl acetate (54.3 %); myrcene (28.0 %); octyl octanoate (71.3 %) were found principal components of aerial parts, roots, flowers, and fruits, respectively. Flower essential oil, fruit dicloromethane and ethyl acetate exhibited potent α-glucosidase inhibitory activity with 900, 40, and 937 µg/mL IC50 values, respectively.


Asunto(s)
Acetatos , Enfermedad de Alzheimer , Diabetes Mellitus , Aceites Volátiles , Humanos , Antioxidantes/farmacología , Antioxidantes/química , Simulación del Acoplamiento Molecular , Cromatografía Liquida , Espectrometría de Masas en Tándem , Enfermedad de Alzheimer/tratamiento farmacológico , Isoenzimas , Fitoquímicos/farmacología , Aceites Volátiles/farmacología , Aceites Volátiles/química , Extractos Vegetales/farmacología , Extractos Vegetales/química
2.
J Biomol Struct Dyn ; 41(2): 445-456, 2023 02.
Artículo en Inglés | MEDLINE | ID: mdl-34822320

RESUMEN

The present ethnobotanical study unravelled the phenolic reservoir (UHPLC-MS/TQ-MS) and pharmacological activity (antioxidant and enzyme inhibitory activities) of an endemic plant, Achillea pseudoaleppica Hub.-Mor. (Asteraceae). The effective antioxidant properties of ethanol and water extracts of A. pseudoaleppica leaves were determined by using six different in vitro bioanalytical methods including three reducing antioxidant methods and three radical scavenging antioxidant methods. In the other step of the study, the enzyme inhibitory effects of water and ethanol extracts of A. pseudoaleppica were determined against acetylcholinesterase (AChE), butyrylcholinesterase (BChE), α-amylase, and α-glucosidase enzymes. The ethanol extract was found to have effective inhibition potential for all four respected enzymes. The IC50 values of A. pseudoaleppica extract against AChE, BChE, α-amylase, and α-glucosidase enzymes were found to be 2.67 mg/mL, 4.55 mg/mL, 16.51 mg/mL, and 12.37 mg/mL, respectively. Also, UHPLC-MS/TQ-MS analyses revealed quinic acid as the most abundant phenolic compound of the water extract (31.12 ± 1.65 µg/mg) and ethanol extract (11.75 ± 0.82 µg/mg). In addition, the molecular docking interaction of the most abundant phenolic compound of A. pseudoaleppica (quinic acid) with AChE, BChE, α-amylase, and α-glucosidase target enzymes were evaluated using Chimera and AutoDock Vina softwares. In conclusion, the rich phenolic content and the potent antioxidant and enzyme inhibitory properties of A. pseudoaleppica extracts may support the widespread ethnobotanical use of the plant application.Communicated by Ramaswamy H. Sarma.


Asunto(s)
Achillea , Antioxidantes , Antioxidantes/farmacología , Butirilcolinesterasa , Acetilcolinesterasa , alfa-Glucosidasas , Simulación del Acoplamiento Molecular , Ácido Quínico , Extractos Vegetales/farmacología , Etanol , alfa-Amilasas , Agua
3.
Molecules ; 27(20)2022 Oct 14.
Artículo en Inglés | MEDLINE | ID: mdl-36296499

RESUMEN

Studies have shown an inverse correlation among age-related illnesses like coronary heart disease and cancer and intake of fruit and vegetable. Given the probable health benefits of natural antioxidants from plants, research on them has increased. Dactylorhiza osmanica is consumed as a food and traditional medicine plant in some regions of Turkey, so evaluation of the biological ability of this species is important. In this study, the amount of phenolic content (LC-HRMS), antioxidant activities and enzyme inhibitory properties of an endemic plant, D. osmanica, were investigated. The antioxidant capacities of an ethanol extract of D. osmanica aerial parts (EDOA) and roots (EDOR) were evaluated with various antioxidant methods. Additionally, the enzyme inhibitory effects of EDOA and EDOR were examined against acetylcholinesterase (AChE), α-glycosidase, and α-amylase enzymes, which are associated with common and global Alzheimer's disease and diabetes mellitus. The IC50 values of EDOA against the enzymes were found to be 1.809, 1.098, and 0.726 mg/mL, respectively; and the IC50 values of EDOR against the enzymes were found to be 2.466, 0.442, and 0.415 mg/mL, respectively. Additionally, LC-HRMS analyses revealed p-Coumaric acid as the most plentiful phenolic in both EDOA (541.49 mg/g) and EDOR (559.22 mg/g). Furthermore, the molecular docking interaction of p-coumaric acid, quercitrin, and vanillic acid, which are the most plentiful phenolic compounds in the extracts, with AChE, α-glucosidase, and α-amylase, were evaluated using AutoDock Vina software. The rich phenolic content and the effective antioxidant ability and enzyme inhibition potentials of EDOA and EDOR may support the plant's widespread food and traditional medicinal uses.


Asunto(s)
Antioxidantes , alfa-Glucosidasas , Antioxidantes/farmacología , Antioxidantes/química , Simulación del Acoplamiento Molecular , alfa-Glucosidasas/química , Acetilcolinesterasa , Ácido Vanílico , Extractos Vegetales/farmacología , Extractos Vegetales/química , Fitoquímicos/farmacología , alfa-Amilasas , Fenoles/farmacología , Etanol
4.
Chem Biodivers ; 19(3): e202100775, 2022 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-35015378

RESUMEN

In the present work, antioxidant and antidiabetic potentials of mountain mint [Cyclotrichium leu-cotrichum (Stapf ex Rech. Fil.) Leblebici] was the first time appraised. In this sense, methanol (MECL) and water (WECL) extracts were obtained from aerial parts of mountain mint (Cyclotrichium leucotrichum) and studied for their antioxidant ability by several bioanalytical assays. Also, their inhibition profiles were realized toward several metabolic enzymes connected to some diseases, including butyrylcholinesterase (BChE), α-glycosidase, acetylcholinesterase (AChE), and α-amylase enzymes. Additionally, their phenolic contents were determined by putative chromatographic method of LC/MS/MS. Consequently, nineteen phenolic molecules were identified in MECL and fifteen phenolic molecules were found in WECL. Also, antioxidant effects of both extracts were studied using by the methods of 1,1-diphenyl-2-picryl-hydrazyl (DPPH⋅), 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS.+ ) and N,N-dimethyl-p-phenylenediamine (DMPD.+ ) scavenging activities, ferric (Fe3+ ) and cupric (Cu2+ ) ions and Fe3+ -2,4,6-tri(2-pyridyl)-s-triazine (TPTZ) reducing capacities. MECL and WECL were found as powerful DPPH⋅ (IC50 : 23.74 and 28.85 µg/mL), ABTS.+ (IC50 : 12.53 and 14.05 µg/mL) and DMPD.+ scavenging effects (IC50 : 43.52 and 54.80 µg/mL). Also, both extracts demonstrated the effective inhibition on AChE (IC50 : 69.31 and 115.51 µg/mL), BChE (IC50 : 57.75 and 86.62 µg/mL), α-glycosidase (IC50 : 36.47 and 62.94 µg/mL) and α-amylase (IC50 : 1.01 and 3.43 µg/mL). This study will be useful for future studies to determine the antioxidant properties and enzyme inhibition profile of food, medical and industrially important plants.


Asunto(s)
Antioxidantes , Mentha , Acetilcolinesterasa/química , Antioxidantes/química , Butirilcolinesterasa/química , Antagonistas Colinérgicos , Hipoglucemiantes/farmacología , Extractos Vegetales/química , Polifenoles/farmacología , Espectrometría de Masas en Tándem
5.
Molecules ; 26(9)2021 Apr 23.
Artículo en Inglés | MEDLINE | ID: mdl-33922645

RESUMEN

Kinkor (Ferulago stellata) is Turkish medicinal plant species and used in folk medicine against some diseases. As far as we know, the data are not available on the biological activities and chemical composition of this medicinal plant. In this study, the phytochemical composition; some metabolic enzyme inhibition; and antidiabetic, anticholinergic, and antioxidant activities of this plant were assessed. In order to evaluate the antioxidant activity of evaporated ethanolic extract (EEFS) and lyophilized water extract (WEFS) of kinkor (Ferulago stellata), some putative antioxidant methods such as DPPH· scavenging activity, ABTS•+ scavenging activity, ferric ions (Fe3+) reduction method, cupric ions (Cu2+) reducing capacity, and ferrous ions (Fe2+)-binding activities were separately performed. Furthermore, ascorbic acid, BHT, and α-tocopherol were used as the standard compounds. Additionally, the main phenolic compounds that are responsible for antioxidant abilities of ethanol and water extracts of kinkor (Ferulago stellata) were determined by liquid chromatography-high-resolution mass spectrometry (LC-HRMS). Ethanol and water extracts of kinkor (Ferulago stellata) demonstrated effective antioxidant abilities when compared to standards. Moreover, ethanol extract of kinkor (Ferulago stellata) demonstrated IC50 values of 1.772 µg/mL against acetylcholinesterase (AChE), 33.56 ± 2.96 µg/mL against α-glycosidase, and 0.639 µg/mL against α-amylase enzyme respectively.


Asunto(s)
Antioxidantes/química , Apiaceae/química , Antagonistas Colinérgicos/química , Cromatografía Liquida/métodos , Hipoglucemiantes/química , Componentes Aéreos de las Plantas/química , Plantas Medicinales/química , alfa-Amilasas/metabolismo
6.
Bioorg Chem ; 103: 104171, 2020 10.
Artículo en Inglés | MEDLINE | ID: mdl-32891857

RESUMEN

Sulfur-containing pyrroles (1-3), tris(2-pyridyl)phosphine(selenide) sulfide (4-5) and 4-benzyl-6-(thiophen-2-yl)pyrimidin-2-amine (6) were synthesized and characterized by elemental analysis, IR and NMR spectra. In this study, the synthesized compounds of nitrogen, phosphorus, selenium and sulfur-containing heterocyclic compounds (1-6) were evaluated against the human erythrocyte carbonic anhydrase I, and II isoenzymes, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glycosidase enzymes. The synthesized heterocyclic compounds showed IC50 values in range of 33.32-60.79 nM against hCA I, and 37.05-66.64 nM against hCA II closely associated with various physiological and pathological processes. On the other hand, IC50 values were found in range of 13.13-22.21 nM against AChE, 0.54-31.22 nM against BChE, and 13.51-26.55 nM against α-glycosidase as a hydrolytic enzyme. As a result, nitrogen, phosphorus, selenium and sulfur-containing heterocyclic compounds (1-6) demonstrated potent inhibition profiles against indicated metabolic enzymes. Therefore, we believe that these results may contribute to the development of new drugs particularly in the treatment of some global disorders including glaucoma, Alzheimer's disease and diabetes.


Asunto(s)
Acetilcolinesterasa/química , Butirilcolinesterasa/química , Inhibidores de Glicósido Hidrolasas/química , Compuestos Heterocíclicos/síntesis química , Nitrógeno/química , Fósforo/química , Selenio/química , Compuestos Heterocíclicos/química , Humanos , Relación Estructura-Actividad
7.
Z Naturforsch C J Biosci ; 75(11-12): 459-466, 2020 Nov 26.
Artículo en Inglés | MEDLINE | ID: mdl-32598328

RESUMEN

The aim of this study was to investigate the effects of extracts and pure Artemisia dracunculus L. (tarragon) metabolites on the antimonoamine oxidase and anticholinesterase activities. The compounds were characterized as stigmasterol (1), herniarin (2), (2E,4E)-1-(piperidin-1-yl)undeca-2,4-diene-8,10-diyn-1-one (3), (2E,4E)-N-isobutylundeca-2,4-dien-8,10-diynamide (4), 3,4-dehydroherniarin (5) and skimmin (6) by 1H-NMR, 13C-NMR, 1D and 2D NMR methods. The compounds 5 and 6 were isolated from tarragon for the first time. The extracts and pure compounds have inhibitory effects on the human monoamine oxidase (hMAO) A and B enzymes, whereas they did not exhibit any anticholinesterase activities. Among the tarragon compounds, only 2 and 6 compounds showed the inhibitory effects against hMAO A (IC50 = 51.76 and 73.47 µM, respectively) and hMAO B (IC50 = 0.84 and 1.63 mM, respectively). In the study, herniarin content in the extracts was also analysed by high-performance liquid chromatography and it was found that there was a relationship between the inhibition effects of the extracts and their herniarin content.


Asunto(s)
Artemisia/química , Cumarinas/farmacología , Monoaminooxidasa/efectos de los fármacos , Umbeliferonas/farmacología , Inhibidores Enzimáticos/farmacología , Humanos , Inhibidores de la Monoaminooxidasa/farmacología
8.
Chem Biodivers ; 16(10): e1900341, 2019 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-31465610

RESUMEN

The aim of this work was to investigate the enzyme inhibition, antioxidant activity, and phenolic compounds of Lecokia cretica (Lam.) DC. Acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glycosidase enzymes were strongly inhibited by the L. cretica extracts. IC50 values for the three enzymes were found as 3.21 mg/mL, 2.1 mg/mL, and 2.07 mg/mL, respectively. Antioxidant activities were examined in both aqueous and ethanol (EtOH) extracts using CUPRAC, FRAP, and DPPH method. Also, the phenolic compounds of the endemic plant were identified and quantified by using HPLC/MS/MS. According to the results, the extracts have remarkable antioxidant activities. The most abundant phenolic acids of L. cretica in EtOH extract were determined as quinic acid (12.76 mg/kg of crude extract), chlorogenic acid (3.39 mg/kg), and malic acid (2.38 mg/kg).


Asunto(s)
Antioxidantes/farmacología , Antagonistas Colinérgicos/farmacología , Hipoglucemiantes/farmacología , Fenoles/farmacología , Fitoquímicos/farmacología , Extractos Vegetales/farmacología , Acetilcolinesterasa/metabolismo , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Apiaceae/química , Butirilcolinesterasa/metabolismo , Antagonistas Colinérgicos/química , Antagonistas Colinérgicos/aislamiento & purificación , Inhibidores de la Colinesterasa/química , Inhibidores de la Colinesterasa/aislamiento & purificación , Inhibidores de la Colinesterasa/farmacología , Relación Dosis-Respuesta a Droga , Inhibidores de Glicósido Hidrolasas/química , Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Inhibidores de Glicósido Hidrolasas/farmacología , Glicósido Hidrolasas/metabolismo , Hipoglucemiantes/química , Hipoglucemiantes/aislamiento & purificación , Fenoles/química , Fenoles/aislamiento & purificación , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Relación Estructura-Actividad
9.
J Food Biochem ; 43(3): e12776, 2019 03.
Artículo en Inglés | MEDLINE | ID: mdl-31353544

RESUMEN

Many taxa of Salvia genus have been used in herbal beverages, food flavoring, cosmetics, and pharmaceutical industry. In this paper, chemical compounds of Salvia eriophora (S. eriophora) leaves were determined by LC-MS/MS (Liquid Chromatography tandem Mass Spectrometry). Salvigenin (158.64 ± 10.8 mg/kg), fumaric acid (123.09 ± 8.54 mg/kg), and quercetagetin-3.6-dimethylether (37.85 ± 7.09 mg/kg) were detected as major compounds in the ethanol extract, whereas fumaric acid (555.96 ± 38.56 mg/kg), caffeic acid (103.62 ± 20.51 mg/kg), and epicatechin (83.19 ± 8.43 mg/kg) were detected as major compounds in the water extract. Furthermore, enzyme inhibition of S. eriophora against acetylcholinesterase (AChE), α-amylase (AM), butyrylcholinesterase (BChE), and α-glycosidase (AG) enzymes were detected. AChE, BChE, AG, and AM enzymes were very strongly inhibited by S. eriophora water extract (WES) and S. eriophora methanol extract (MES). Additionally, antioxidant potential of S. eriophora was determined by in vitro analytical methods. IC50 values of WES and MES were performed for radicals. PRACTICAL APPLICATIONS: Metabolic enzymes have crucial functions on living systems due to inhibition or activation of them mainly attributed with some health disorders. AChE, BChE, AM, and AG enzymes have important roles on carbohydrate metabolism or cholinergic pathways. The relation between enzyme inhibition effect and phenolic compounds or antioxidant activity need to be confirmed. Thus, many studies tested to clarify this relation for pure samples or plant extracts. To the best of our knowledge, this is the first report about inhibition effects of Salvia eriophora extracts against AChE, BChE, AM, and AG enzymes as well as their phenolic contents and antioxidant activities.


Asunto(s)
Antioxidantes/química , Inhibidores de la Colinesterasa/química , Glicósido Hidrolasas/antagonistas & inhibidores , Fitoquímicos/química , Extractos Vegetales/química , Salvia/química , alfa-Amilasas/antagonistas & inhibidores , Acetilcolinesterasa/química , Butirilcolinesterasa/química , Glicósido Hidrolasas/química , Cinética , alfa-Amilasas/química
10.
J Food Biochem ; 43(7): e12908, 2019 07.
Artículo en Inglés | MEDLINE | ID: mdl-31353687

RESUMEN

The phenolic contents and antioxidant, anticancer, antidiabetic, and anticholinergic potentials of four endemic Gysophila taxa (G. pallida, G. arrosti, G. tuberculosa, and G. eriocalyx) were investigated. The HPLC analysis showed that methanol extracts of all the tested species were richer in phenolics than water extracts. 3,4-dihydroxybenzoic acid, p-hydroxybenzoic acid, vanillin, syringic acid, and p-coumaric acid were detected in all extracts. In parallel to the phenolic contents, methanol extracts displayed comparatively higher antioxidant activity than water extracts. Additionally, all extracts exhibited dose-dependent antiproliferative activity on the cancer cell lines with lower IC50 values changing from 0.170 to 1.805 mg/ml. Moreover, the extracts impressively inhibited the acetylcholinesterase (0.63-26.04), butyrylcholinesterase (3.66-10.73), and α-glycosidase (98.52-235.55) enzymes with very low IC50 (mg/ml) values. Together, the present results indicate that Gysophila taxa have various biological activities together with higher phenolic contents. Hence, these species hold good potential for use in the pharmaceutical industry. PRACTICAL APPLICATIONS: Gypsophila taxa having numerous biological activities have been used for different purpose in folk medicine as well as their use in the food industry. The obtained results of the current study indicated that the extracts of Gypsophila taxa are rich in phenolics and flavonoids with powerful antioxidant and antiproliferative activity against different type of cancer cell lines. In addition, the extracts obtained from these taxa showed notable antidiabetic and anticholinergics effects. Gypsophila taxa could be used as a natural material to develop anticancer, antidiabetic, and anticholinergic drugs.


Asunto(s)
Antioxidantes/farmacología , Caryophyllaceae/química , Antagonistas Colinérgicos/farmacología , Flavonoides/farmacología , Hipoglucemiantes/farmacología , Fenoles/farmacología , Fitoquímicos/farmacología , Antioxidantes/análisis , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Antagonistas Colinérgicos/análisis , Flavonoides/análisis , Humanos , Hipoglucemiantes/análisis , Fenoles/análisis , Fitoquímicos/química , Componentes Aéreos de las Plantas/química
11.
Biotechnol Appl Biochem ; 66(5): 781-786, 2019 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-31135076

RESUMEN

Aldose reductase (AR), α-amylase, and α-glycosidase are vital enzymes to prevent diabetic complications. Here, AR was purified from sheep kidney using elementary methods with 111.11-purification fold and with 0.85% purification yield. The interactions between some phenolic compounds and the AR, α-glycosidase, and α-amylase enzyme were determined. It was found that phenolic compounds exhibit potential inhibitor properties for these enzymes. For α-amylase, studied phenolic compounds showed IC50 values in the range of 601.56-2,067.78 nM. For α-glycosidase, Ki values were found in the range of 169.25 ± 27.22-572.88 ± 106.76 nM. For AR, Ki values in the range of 8.48 ± 0.56-43.26 ± 7.63 µM. However, genistein showed the best inhibition effect toward AR and α-glycosidase, but delphinidin chloride exhibited the best inhibition effect against α-amylase enzyme. We determined that all compounds showed noncompetitive inhibition effect against AR and α-glycosidase. Also, studied phenolic compounds may be useful in the prevention or treatment of diabetic complications.


Asunto(s)
Aldehído Reductasa/antagonistas & inhibidores , Inhibidores Enzimáticos/farmacología , Glicósido Hidrolasas/antagonistas & inhibidores , Hipoglucemiantes/farmacología , Fenoles/farmacología , alfa-Amilasas/antagonistas & inhibidores , Aldehído Reductasa/aislamiento & purificación , Aldehído Reductasa/metabolismo , Animales , Suplementos Dietéticos , Relación Dosis-Respuesta a Droga , Inhibidores Enzimáticos/química , Glicósido Hidrolasas/aislamiento & purificación , Glicósido Hidrolasas/metabolismo , Hipoglucemiantes/administración & dosificación , Hipoglucemiantes/química , Riñón/efectos de los fármacos , Riñón/enzimología , Estructura Molecular , Fenoles/administración & dosificación , Fenoles/química , Ovinos , alfa-Amilasas/aislamiento & purificación , alfa-Amilasas/metabolismo
12.
Bioorg Chem ; 82: 393-404, 2019 02.
Artículo en Inglés | MEDLINE | ID: mdl-30428418

RESUMEN

In this study, a series of novel bis-thiomethylcyclohexanone compounds (3a-3j) were synthesized by the addition of thio-Michael to the bis-chalcones under mild reaction conditions. The bis-thiomethylcyclohexanone derivatives (bis-sulfides) were characterized by 1H NMR, 13C NMR, FTIR and elemental analysis techniques. Furthermore, the molecular and crystal structures of 3h, 3i and 3j compounds were determined by single crystal X-ray diffraction studies. In this study, X-ray crystallography provided an alternative and often-complementary means for elucidating functional groups at the enzyme inhibitory site. Acetylcholinesterase (AChE) is a member of the hydrolase protein super family and has a significant role in acetylcholine-mediated neurotransmission. Here, we report the synthesis and determining of novel bis-thiomethylcyclohexanone compounds based hybrid scaffold of AChE inhibitors. The newly synthesized bis-thiomethylcyclohexanone compounds showed Ki values of in range of 39.14-183.23 nM against human carbonic anhydrase I isoenzyme (hCA I), 46.03-194.02 nM against human carbonic anhydrase II isoenzyme (hCA II), 4.55-32.64 nM against AChE and 12.77-37.38 nM against butyrylcholinesterase (BChE). As a result, novel bis-thiomethylcyclohexanone compounds can have promising anti Alzheimer drug potential and record novel hCA I, and hCA II enzymes inhibitor.


Asunto(s)
Inhibidores de Anhidrasa Carbónica/química , Inhibidores de la Colinesterasa/química , Ciclohexanonas/química , Sulfuros/química , Acetazolamida/química , Acetilcolinesterasa/química , Butirilcolinesterasa/química , Anhidrasa Carbónica I/antagonistas & inhibidores , Anhidrasa Carbónica II/antagonistas & inhibidores , Inhibidores de Anhidrasa Carbónica/síntesis química , Inhibidores de la Colinesterasa/síntesis química , Cristalografía por Rayos X , Ciclohexanonas/síntesis química , Humanos , Cinética , Estructura Molecular , Sulfuros/síntesis química , Tacrina/química
13.
Methods Mol Biol ; 1208: 233-46, 2015.
Artículo en Inglés | MEDLINE | ID: mdl-25323511

RESUMEN

If we look at the multitude of varied and interesting reaction that constitute biochemistry and bioorganic chemistry, it is possible to classify a great many as either oxidation or reduction reactions. The reducing agent transfers electrons to another substance and is thus it oxidized. And, because it gives electrons, it is also called an electron donor. Electron donors can also form charge transfer complexes with electron acceptors. Reductants in biochemistry are very diverse. For example ferric ions (Fe(3+)) are good reducing agents. Also, different bioanalytical reduction methods are available such as Fe(3+)-ferrous ions (Fe(2+)) reduction method, ferric reducing antioxidant power reducing assay. In this section, Fe(3+)-Fe(2+) transformation will be discussed. Recently there has been growing interest in research into the role of plant-derived antioxidants in food and human health. The beneficial influence of many foodstuffs and beverages including fruits, vegetables, tea, coffee, and cacao on human health has been recently recognized to originate from their antioxidant activity. For this purpose, the most commonly method used in vitro determination of reducing capacity of pure food constituents or plant extracts is Fe(3+) reducing ability. This commonly used reducing power method is reviewed and presented in this study. Also, the general chemistry underlying this assay was clarified. Hence, this overview provides a basis and rationale for developing standardized antioxidant capacity methods for the food, nutraceutical, and dietary supplement industries. In addition, the most important advantages of this method were detected and highlighted. The chemical principles of these methods are outlined and critically discussed. The chemical principles of methods of Fe(3+)-Fe(2+) transformation assay are outlined and critically discussed.


Asunto(s)
Antioxidantes/análisis , Bioensayo/métodos , Hierro/química , Electrones , Humanos , Oxidación-Reducción , Extractos Vegetales/química , Protones , Especies de Nitrógeno Reactivo/química , Especies Reactivas de Oxígeno/química
14.
Arch Toxicol ; 86(3): 345-91, 2012 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-22102161

RESUMEN

Recently, there has been growing interest in research into the role of plant-derived antioxidants in food and human health. The beneficial influence of many foodstuffs and beverages including fruits, vegetables, tea, coffee, and cacao on human health has been recently recognized to originate from their antioxidant activity. For this purpose, the most commonly methods used in vitro determination of antioxidant capacity of food constituents are reviewed and presented. Also, the general chemistry underlying the assays in the present paper was clarified. Hence, this overview provides a basis and rationale for developing standardized antioxidant capacity methods for the food, nutraceutical, and dietary supplement industries. In addition, the most important advantages and shortcomings of each method were detected and highlighted. The chemical principles of these methods are outlined and critically discussed. The chemical principles of methods of 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulphonate) radical (ABTS(·+)) scavenging, 1,1-diphenyl-2-picrylhydrazyl (DPPH(·)) radical scavenging, Fe(3+)-Fe(2+) transformation assay, ferric reducing antioxidant power (FRAP) assay, cupric ions (Cu(2+)) reducing power assay (Cuprac), Folin-Ciocalteu reducing capacity (FCR assay), peroxyl radical scavenging, superoxide anion radical (O (2) (·-)) scavenging, hydrogen peroxide (H(2)O(2)) scavenging, hydroxyl radical (OH(·)) scavenging, singlet oxygen ((1)O(2)) quenching assay and nitric oxide radical (NO(·)) scavenging assay are outlined and critically discussed. Also, the general antioxidant aspects of main food components were discussed by a number of methods which are currently used for detection of antioxidant properties food components. This review consists of two main sections. The first section is devoted to main components in the foodstuffs and beverages. The second general section is some definitions of the main antioxidant methods commonly used for determination of antioxidant activity of components in the foodstuffs and beverages. In addition, there are given some chemical and kinetic basis and technical details of the used methods.


Asunto(s)
Antioxidantes/farmacología , Análisis de los Alimentos , Cobre/metabolismo , Compuestos Férricos/metabolismo , Flavonoides/farmacología , Depuradores de Radicales Libres/farmacología , Hidroxibenzoatos/farmacología , Especies Reactivas de Oxígeno/metabolismo , Superóxidos/metabolismo , Vitamina E/farmacología
15.
Arch Pharm (Weinheim) ; 345(4): 323-34, 2012 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-22147548

RESUMEN

(3,4-Dihydroxyphenyl)(2,3,4-trihydroxyphenyl)methanone (5) and its two derivatives with bromine were synthesized from reactions such as bromination and demethylation of (3,4-dimethoxyphenyl)(2,3,4-trimethoxyphenyl)methanone (6). The Wolf-Kishner reduction product (9) of 6 and its three derivatives with bromine were obtained. 4-(3,4-Dihydroxybenzyl)benzene-1,2,3-triol and its dibromide derivative (16) were also synthesized from 9 and the corresponding dibromide derivative. The in vitro antioxidant activities of nine new compounds synthesized in these reactions were determined by analyzing the radical scavenging activities of bromophenols for 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS), 1,1-diphenyl-2-picryl-hydrazyl (DPPH), N,N-dimethyl-p-phenylenediamine (DMPD), and the superoxide anion radical (O(2)(·-)) and examining the total reducing power through Fe(3+)-Fe(2+) transformation, FRAP and CUPRAC assays and the ferrous ions (Fe(2+)) chelating activities. Moreover, the results of these activities were compared to those of standard antioxidant compounds such as butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), α-tocopherol, and trolox. The results showed that the synthesized bromophenols had effective antioxidant power. The phenol 5 with two phenolic rings and five phenolic hydroxyl groups was the most potent antioxidant and radical scavenger. In conclusion, the new compounds are promising molecules to be used owing to their potential antioxidant properties.


Asunto(s)
Antioxidantes/síntesis química , Antioxidantes/farmacología , Benzofenonas/síntesis química , Benzofenonas/farmacología , Fenoles/síntesis química , Fenoles/farmacología , Antioxidantes/química , Benzofenonas/química , Quelantes/síntesis química , Quelantes/química , Quelantes/farmacología , Evaluación Preclínica de Medicamentos , Técnicas In Vitro , Estructura Molecular , Oxidación-Reducción/efectos de los fármacos , Fenoles/química , Relación Estructura-Actividad
16.
Eur J Pharmacol ; 668(3): 407-13, 2011 Oct 15.
Artículo en Inglés | MEDLINE | ID: mdl-21839078

RESUMEN

The objective of this study was to investigate temperature dependent effects of oral l-carnitine supplementation on exhaustive exercise induced oxidative damage in rats. 42 male Spraque Dawley rats were randomly divided into seven experimental groups. These groups were formed as three non-carnitine exercise groups, three carnitine-exercise groups and a sedentary group. l-carnitine was given intraperitoneally to the carnitine-exercise groups 1h before the exercise in 100mg/kg. Blood was collected to measure paraoxonase-1 (PON1) activity, plasma malondialdehyde (MDA), low-density lipoprotein (LDL) and cholesterol concentrations. These biomarkers were measured in venous blood samples collected before and after the rats swam in pools at different water temperatures (18°C, 28°C and 38°C). In the non-carnitine group, exercise caused a significant decrease in PON1 activity and a significant elevation in MDA concentration at 28°C compared to the sedentary group. No significant alterations were evidenced in LDL and cholesterol concentrations upon exercise. The decrease in PON1 activity became higher with increasing temperature whereas the elevation in MDA levels increased at 18°C. In the l-carnitine supplementation group, recovery in PON1 activity was observed significant at 28°C and very significant at 38°C. MDA concentration was almost the same with that of the non-carnitine group at 18 and 38°C, but it significantly decreased at 28°C. Considering the recovery in PON1 and MDA levels at 28°C, which is the temperature of the sedentary group; our results suggest that l-carnitine supplementation has a protective role on exhaustive exercise-induced oxidative stress. Findings of this study also demonstrate influences of thermal stress on these parameters during exhaustive exercise.


Asunto(s)
Carnitina/farmacología , Suplementos Dietéticos , Estrés Oxidativo/efectos de los fármacos , Condicionamiento Físico Animal/efectos adversos , Animales , Arildialquilfosfatasa/metabolismo , Colesterol/sangre , Lipoproteínas LDL/sangre , Masculino , Malondialdehído/sangre , Ratas , Ratas Sprague-Dawley
17.
Int J Food Sci Nutr ; 62(8): 821-5, 2011 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-21631390

RESUMEN

Caffeic acid phenethyl ester (CAPE), a plant polyphenolic concentrated in honeybee propolis, has been found to be biologically active in a variety of pathways. The aim of this study was to determine the antioxidant activity of CAPE using different methods such as total antioxidant activity by the thiocyanate method, 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid radicals, 1,1-diphenyl-2-picryl-hydrazyl free radicals, N,N-dimethyl-p-phenylenediamine dihydrochloride radicals and superoxide anion radicals scavenging activities, reducing power and ferrous ions (Fe(2+)) chelating activities. CAPE showed 97.9% inhibition on lipid peroxidation of linoleic acid emulsion. On the other hand, butylated hydroxyanisole, butylated hydroxytoluene, α-tocopherol and trolox indicated an inhibition of 87.3, 97.6, 75.3 and 90.3% on peroxidation in the same system, respectively.


Asunto(s)
Antioxidantes/farmacología , Ácidos Cafeicos/farmacología , Ácido Linoleico/metabolismo , Peroxidación de Lípido/efectos de los fármacos , Alcohol Feniletílico/análogos & derivados , Extractos Vegetales/farmacología , Polifenoles/farmacología , Própolis/química , Emulsiones , Alcohol Feniletílico/farmacología
18.
J Med Food ; 14(9): 975-85, 2011 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-21554120

RESUMEN

Eugenol (4-allyl-2-methoxyphenol), a major phenolic component from clove oil (Eugenia caryophyllata), has several biological activities. To estimate the capacity of eugenol to act as an antioxidant, the following were studied: 1,1-diphenyl-2-picryl-hydrazyl-, 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid)-, and N,N-dimethyl-p-phenylenediamine-scavenging activity; total antioxidant activity; and ability to reduce ferric ions and cupric ions. Eugenol inhibited 96.7% (r(2)=0.9319) lipid peroxidation of a linoleic acid emulsion at a 15-µg/mL concentration. Butylated hydroxyanisole, butylated hydroxytoluene, α-tocopherol, and Trolox(®) displayed 95.4% (r(2)=0.8482), 99.7% (r(2)=0.7798), 84.6% (r(2)=0.9272), and 95.6% (r(2)=0.8511) inhibition of peroxidation, respectively, at the 15-µg/mL concentration. According to the results of this study, eugenol had the most powerful antioxidant activity and radical-scavenging activity. This study should prompt further studies of the antioxidant properties of eugenol.


Asunto(s)
Antioxidantes/farmacología , Eugenol/farmacología , Antioxidantes/química , Aceite de Clavo/química , Eugenol/química , Conservantes de Alimentos/química , Conservantes de Alimentos/farmacología , Depuradores de Radicales Libres/química , Depuradores de Radicales Libres/farmacología , Cinética , Peróxidos Lipídicos/antagonistas & inhibidores , Peróxidos Lipídicos/química , Oxidación-Reducción , Relación Estructura-Actividad
19.
J Food Sci ; 76(4): C585-93, 2011 May.
Artículo en Inglés | MEDLINE | ID: mdl-22417339

RESUMEN

The raspberry (Rubus idaeus L.) is an economically important berry crop that contains many phenolic compounds with potential health benefits. In this study, important pomological features, including nutrient content and antioxidant properties, of a domesticated and 3 wild (Yayla, Yavuzlar, and Yedigöl) raspberry fruits were evaluated. Also, the amount of total phenolics and flavonoids in lyophilized aqueous extracts of domesticated and wild ecotypes of raspberry fruits were calculated as gallic acid equivalents (GAEs) and quercetin equivalents (QE). The highest phenolic compounds were found in wild Yayla ecotype (26.66 ± 3.26 GAE/mg extract). Whilst, the highest flavonoids were determined in wild Yedigöl ecotype (6.09 ± 1.21 QA/mg extract). The antioxidant activity of lyophilized aqueous extracts of domesticated and wild ecotypes of raspberry fruits were investigated as trolox equivalents using different in vitro assays including DPPH(•), ABTS(•+), DMPD(•+), and O(•-)(2) radical scavenging activities, H(2)O(2) scavenging activity, ferric (Fe(3+)) and cupric ions (Cu(2+)) reducing abilities, ferrous ions (Fe(2+)) chelating activity. In addition, quantitative amounts of caffeic acid, ferulic acid, syringic acid, ellagic acid, quercetin, α-tocopherol, pyrogallol, p-hydroxybenzoic acid, vanillin, p-coumaric acid, gallic acid, and ascorbic acid in lyophilized aqueous extracts of domesticated and wild ecotypes of raspberry fruits were detected by high-performance liquid chromatography and tandem mass spectrometry (LC-MS-MS). The results clearly show that p-coumaric acid is the main phenolic acid responsible for the antioxidant and radical scavenging activity of lyophilized aqueous extracts of domesticated and wild ecotypes of raspberry fruits.


Asunto(s)
Antioxidantes/análisis , Ecotipo , Frutas/química , Extractos Vegetales/análisis , Polifenoles/análisis , Rosaceae/química , Ácido Ascórbico/análisis , Benzaldehídos/análisis , Benzotiazoles/análisis , Benzotiazoles/metabolismo , Cromatografía Líquida de Alta Presión/métodos , Ácidos Cumáricos/análisis , Ácido Elágico/análisis , Ácido Gálico/análogos & derivados , Ácido Gálico/análisis , Peróxido de Hidrógeno/análisis , Peróxido de Hidrógeno/metabolismo , Hidroxibenzoatos/análisis , Extractos Vegetales/química , Propionatos , Pirogalol/análisis , Ácidos Sulfónicos/análisis , Ácidos Sulfónicos/metabolismo , Espectrometría de Masas en Tándem/métodos
20.
World J Gastroenterol ; 13(4): 607-11, 2007 Jan 28.
Artículo en Inglés | MEDLINE | ID: mdl-17278229

RESUMEN

AIM: To examine the anti-ulcerogenic and antioxidant effects of aqueous extracts of Foeniculum vulgare (FVE) on ethanol-induced gastric lesions in rats. METHODS: FVE was administered by gavage at doses of 75, 150 and 300 mg/kg, and famotidine was used at the dose of 20 mg/kg. Following a 60 min period, all the rats were given 1 mL of ethanol (80%) by gavage. One hour after the administration of ethanol, all groups were sacrificed, and the gastric ulcer index was calculated; whole blood malondialdehyde (MDA) and reduced glutathione (GSH), serum nitrate, nitrite, ascorbic acid, retinol and beta-carotene levels were measured in all the groups. RESULTS: It was found that pretreatment with FVE significantly reduced ethanol-induced gastric damage. This effect of FVE was highest and statistically significant in 300 mg/kg group compared with the control (4.18 +/- 2.81 vs 13.15 +/- 4.08, P < 0.001). Also, pretreatment with FVE significantly reduced the MDA levels, while significantly increased GSH, nitrite, nitrate, ascorbic acid, retinol and beta-carotene levels. CONCLUSION: FVE has clearly a protective effect against ethanol-induced gastric mucosal lesion, and this effect, at least in part, depends upon the reduction in lipid peroxidation and augmentation in the antioxidant activity.


Asunto(s)
Etanol/toxicidad , Foeniculum , Mucosa Gástrica/efectos de los fármacos , Fitoterapia , Extractos Vegetales/uso terapéutico , Animales , Antioxidantes/uso terapéutico , Mucosa Gástrica/metabolismo , Mucosa Gástrica/patología , Glutatión/sangre , Peroxidación de Lípido , Malondialdehído/sangre , Ratas , Ratas Sprague-Dawley , Úlcera Gástrica/prevención & control
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