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1.
Mar Drugs ; 19(3)2021 Mar 06.
Artigo em Inglês | MEDLINE | ID: mdl-33800819

RESUMO

Chemical investigation of the South-Pacific marine sponge Suberea clavata led to the isolation of eight new bromotyrosine metabolites named subereins 1-8 (2-9) along with twelve known co-isolated congeners. The detailed configuration determination of the first representative major compound of this family 11-epi-fistularin-3 (11R,17S) (1) is described. Their chemical characterization was achieved by HRMS and integrated 1D and 2D NMR (nuclear magnetic resonance) spectroscopic studies and extensive comparison with literature data. For the first time, a complete assignment of the absolute configurations for stereogenic centers C-11/17 of the known members (11R,17S) 11-epi-fistularin-3 (1) and 17-deoxyfistularin-3 (10) was determined by a combination of chemical modifications, Mosher's technology, and ECD spectroscopy. Consequently, the absolute configurations of all our new isolated compounds 2-9 were determined by the combination of NMR, Mosher's method, ECD comparison, and chemical modifications. Interestingly, compounds 2-7 were obtained by chemical transformation of the major compound 11-epi-fistularin-3 (1). Evaluation for acetylcholinesterase inhibition (AChE), DNA methyltransferase 1 (DNMT1) modulating activity and antifouling activities using marine bacterial strains are also presented.


Assuntos
Poríferos/metabolismo , Tirosina/análogos & derivados , Animais , Incrustação Biológica/prevenção & controle , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Inibidores da Colinesterase/farmacologia , DNA (Citosina-5-)-Metiltransferase 1/efeitos dos fármacos , DNA (Citosina-5-)-Metiltransferase 1/metabolismo , Espectroscopia de Ressonância Magnética , Oceano Pacífico , Tirosina/química , Tirosina/isolamento & purificação , Tirosina/farmacologia
2.
Molecules ; 26(7)2021 Mar 28.
Artigo em Inglês | MEDLINE | ID: mdl-33800622

RESUMO

Croton hirtus L'Hér methanol extract was studied by NMR and two different LC-DAD-MSn using electrospray (ESI) and atmospheric pressure chemical ionization (APCI) sources to obtain a quali-quantitative fingerprint. Forty different phytochemicals were identified, and twenty of them were quantified, whereas the main constituents were dihydro α ionol-O-[arabinosil(1-6) glucoside] (133 mg/g), dihydro ß ionol-O-[arabinosil(1-6) glucoside] (80 mg/g), ß-sitosterol (49 mg/g), and isorhamnetin-3-O-rutinoside (26 mg/g). C. hirtus was extracted with different solvents-namely, water, methanol, dichloromethane, and ethyl acetate-and the extracts were assayed using different in vitro tests. The methanolic extracts presented the highest 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline)-6-sulfonic acid (ABTS), and ferric reducing antioxidant power (FRAP) values. All the tested extracts exhibited inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), with a higher activity observed for dichloromethane (AChE: 5.03 and BChE: 16.41 mgGALAE/g), while the methanolic extract showed highest impact against tyrosinase (49.83 mgKAE/g). Taken together, these findings suggest C. hirtus as a novel source of bioactive phytochemicals with potential for commercial development.


Assuntos
Antioxidantes/química , Inibidores da Colinesterase/química , Croton/química , Glucosídeos/química , Compostos Fitoquímicos/química , Fitosteróis/química , Terpenos/química , Acetatos/química , Acetilcolinesterase/química , Acetilcolinesterase/metabolismo , Antioxidantes/classificação , Antioxidantes/isolamento & purificação , Benzotiazóis/antagonistas & inibidores , Benzotiazóis/química , Compostos de Bifenilo/antagonistas & inibidores , Compostos de Bifenilo/química , Butirilcolinesterase/química , Butirilcolinesterase/metabolismo , Inibidores da Colinesterase/isolamento & purificação , Croton/metabolismo , Glucosídeos/classificação , Glucosídeos/isolamento & purificação , Humanos , Metanol/química , Cloreto de Metileno/química , Compostos Fitoquímicos/classificação , Compostos Fitoquímicos/isolamento & purificação , Fitosteróis/classificação , Fitosteróis/isolamento & purificação , Picratos/antagonistas & inibidores , Picratos/química , Extratos Vegetais/química , Solventes/química , Relação Estrutura-Atividade , Ácidos Sulfônicos/antagonistas & inibidores , Ácidos Sulfônicos/química , Terpenos/classificação , Terpenos/isolamento & purificação , Água/química
3.
Molecules ; 26(5)2021 Mar 08.
Artigo em Inglês | MEDLINE | ID: mdl-33800212

RESUMO

Mushroom polysaccharides are active medicinal compounds that possess immune-modulatory and anticancer properties. Currently, the mushroom polysaccharides krestin, lentinan, and polysaccharopeptides are used as anticancer drugs. They are an unexplored source of natural products with huge potential in both the medicinal and nutraceutical industries. The northern parts of Pakistan have a rich biodiversity of mushrooms that grow during different seasons of the year. Here we selected an edible Morchella esculenta (true morels) of the Ascomycota group for polysaccharide isolation and characterization. Polysaccharopeptides and polysaccharides from this mushroom were isolated using the green chemistry, hot water treatment method. Fourier transform infrared spectroscopy revealed the sugar nature and possible beta-glucan type structure of these polysaccharides. Antioxidant assays showed that the deproteinized polysaccharides have moderate free radical scavenging activity. These isolated polysaccharides exhibited good acetylcholinesterase (AChE) and butyryl cholinesterase (BChE) inhibition activities. Therefore, these polysaccharides may be valuable for the treatment of Alzheimer's and Parkinson's diseases. Further bioassays are needed to discover the true potential of M. esculenta polysaccharides for medicinal purposes.


Assuntos
Ascomicetos/metabolismo , Polissacarídeos/química , Polissacarídeos/isolamento & purificação , Acetilcolinesterase , Agaricales/química , Antineoplásicos/farmacologia , Antioxidantes/química , Ascomicetos/efeitos dos fármacos , Inibidores da Colinesterase/isolamento & purificação , Inibidores da Colinesterase/farmacologia , Química Verde/métodos , Espectroscopia de Infravermelho com Transformada de Fourier/métodos
4.
Molecules ; 26(7)2021 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-33916300

RESUMO

Cholinesterase (ChE) inhibition is an important treatment strategy for Alzheimer's disease (AD) as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) are involved in the pathology of AD. In the current work, ChE inhibitory potential of twenty-four natural products from different chemical classes (i.e., diosgenin, hecogenin, rockogenin, smilagenin, tigogenin, astrasieversianins II and X, astragalosides I, IV, and VI, cyclocanthosides E and G, macrophyllosaponins A-D, kokusaginin, lamiide, forsythoside B, verbascoside, alyssonoside, ipolamide, methyl rosmarinate, and luteolin-7-O-glucuronide) was examined using ELISA microtiter assay. Among them, only smilagenin and kokusaginine displayed inhibitory action against AChE (IC50 = 43.29 ± 1.38 and 70.24 ± 2.87 µg/mL, respectively). BChE was inhibited by only methyl rosmarinate and kokusaginine (IC50 = 41.46 ± 2.83 and 61.40 ± 3.67 µg/mL, respectively). IC50 values for galantamine as the reference drug were 1.33 ± 0.11 µg/mL for AChE and 52.31 ± 3.04 µg/mL for BChE. Molecular docking experiments showed that the orientation of smilagenin and kokusaginine was mainly driven by the interactions with the peripheral anionic site (PAS) comprising residues of hAChE, while kokusaginine and methyl rosmarinate were able to access deeper into the active gorge in hBChE. Our data indicate that similagenin, kokusaginine, and methyl rosmarinate could be hit compounds for designing novel anti-Alzheimer agents.


Assuntos
Produtos Biológicos/química , Produtos Biológicos/farmacologia , Inibidores da Colinesterase/química , Inibidores da Colinesterase/farmacologia , Sítios de Ligação , Produtos Biológicos/isolamento & purificação , Inibidores da Colinesterase/isolamento & purificação , Furanos/química , Furanos/farmacologia , Concentração Inibidora 50 , Conformação Molecular , Simulação de Acoplamento Molecular , Simulação de Dinâmica Molecular , Estrutura Molecular , Ligação Proteica , Quinolinas/química , Quinolinas/farmacologia , Espirostanos/química , Espirostanos/farmacologia , Relação Estrutura-Atividade
5.
Molecules ; 26(5)2021 Feb 24.
Artigo em Inglês | MEDLINE | ID: mdl-33668096

RESUMO

Aizoaceae is a large succulent family characterized by many psychoactive species. Aizoon canariense L., a wild neglected plant traditionally used in gastrointestinal ailments, has been the subject of a limited number of phytochemical and biological studies. Therefore, herein, we investigated the in vitro cytotoxic, antimicrobial, and anticholinesteraseactivity of the aerial parts of A. canariense L. and analyzed the phytochemical compositions of the lipoidal and alkaloidal fractions. Petroleum ether extract showed the presence of behenic and tricosylic acid, while an in-depth investigation of the alkaloidal fraction revealed the identification of new adenine based alkaloids (1-5), which were isolated and identified for the first time from Aizoon canariense L. Their structures were elucidated based on extensive spectroscopic analyses. The alkaloidal extract showed a powerful cytotoxic effect (IC50 14-28 µg/mL), with the best effect against colon carcinoma, followed by liver and breast carcinomas. The alkaloidal extract also had a potent effect against Candida albicans and Escherichia coli, with minimum inhibitory concentrations (MIC) values of 312.5 and 625 µg/mL. The in vitro anticholinesterase activity was potent, with IC50 < 200 ng/mL for the tested extracts compared with 27.29 ± 0.49 ng/mL for tacrine.


Assuntos
Aizoaceae/química , Alcaloides/farmacologia , Antibacterianos/farmacologia , Antifúngicos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Inibidores da Colinesterase/farmacologia , Extratos Vegetais/farmacologia , Acetilcolinesterase/metabolismo , Alcaloides/química , Alcaloides/isolamento & purificação , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antifúngicos/química , Antifúngicos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Candida albicans/efeitos dos fármacos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Escherichia coli/efeitos dos fármacos , Humanos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Relação Estrutura-Atividade
6.
Ceska Slov Farm ; 69(1): 24-32, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32460507

RESUMO

Currently, nerve agents are often used in terrorist attacks or assassinations. In such cases, it is necessary to detect them quickly, accurately and easily right in the field. Detection tubes, which are small devices containing pellets with immobilized cholinesterase and detection reagents, meet these conditions. Their detection mechanism is based on a highly sensitive enzymatic Ellman reaction, when in the absence of cholinesterase inhibitors the pellets develop a visible yellow color, whereas in their presence the carriers retain the original color. The rate of reaction, its sensitivity and the distinct color transition are the key points of the research. In this experiment, double-coated pellets were prepared. The first coating contained the butyrylcholinesterase immobilized in hypromellose, while the second coating consisted of ethylcellulose and triethyl citrate. Based on the properties of such carriers, samples containing lactose dispersed in the ethylcellulose coating were also prepared, which was expected to have an effect on increasing the permeability of the coating and hence the detection rate and color intensity. In addition to selected physicochemical properties, carriers were evaluated for enzyme activity, sensitivity and color transition intensity. Samples showing the best properties were subjected to a 24-months stability test at three different temperatures and humidity.


Assuntos
Butirilcolinesterase/química , Celulose/análogos & derivados , Inibidores da Colinesterase/isolamento & purificação , Enzimas Imobilizadas/química
7.
Anal Chim Acta ; 1100: 215-224, 2020 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-31987143

RESUMO

The incompatibility of most organic solvents with acetylcholinesterase (AChE) inhibition assay normally limits pesticide extraction efficiency in sample pretreatment, which might cause false negatives in real world sample assessment. Herein, a novel method has been developed for an improved AChE inhibition assay via organic solvent extraction combined spontaneous in situ solvent evaporation on microfluidic paper-based analytical devices. Enzyme pre-immobilization procedure was spared and AChE was added to the system after sampling step until a complete in-situ solvent evaporation process was performed on chip. IC50 levels of the six investigated organophosphate and carbamate pesticides indicated a completely eliminated influence of solvents on AChE behavior with the new method. Most importantly, analytical performances were significantly improved in food sample measurements. Reduction in matrix effect was observed when acetonitrile was adopted for lettuce sample pretreatment instead of water. Studies on different pesticides suggested a remarkably decreased discrimination effect on recoveries from sample pretreatment with the new developed method. The recovery level for phoxim spiked head lettuce samples reached (107.5 ± 14.2) %, in comparison with that of (18.6 ± 1.4) % from water-based extraction. Spiked water and apple juice samples with carbaryl concentration of as low as 0.02 mg L-1 were also successfully recognized with the present method by visual detection. This is the first report on direct sampling of organic extracts for AChE inhibition assay on-chip and it might provide a new perspective for real world sample assessments involving bio-reagents.


Assuntos
Inibidores da Colinesterase/química , Contaminação de Alimentos/análise , Técnicas Analíticas Microfluídicas , Papel , Resíduos de Praguicidas/análise , Acetilcolinesterase/metabolismo , Carbamatos/análise , Carbamatos/metabolismo , Inibidores da Colinesterase/isolamento & purificação , Inibidores da Colinesterase/farmacologia , Análise de Alimentos , Sucos de Frutas e Vegetais/análise , Malus/química , Organofosfatos/análise , Organofosfatos/metabolismo , Resíduos de Praguicidas/metabolismo , Volatilização , Poluentes Químicos da Água/química
8.
J Chromatogr A ; 1616: 460774, 2020 Apr 12.
Artigo em Inglês | MEDLINE | ID: mdl-31937408

RESUMO

Bananas and plantains (Musa spp.) are used as nutritious foods, and at the same time, are a source of phytoconstituents for the pharmaceutical industry. As biological activities of especially the pulp and peel of Musa spp. have been documented, this study investigated the variation in the secondary metabolite profiles of the leaves from field, in vitro-grown and acclimatized accessions. The genetic fidelity of the diverse accessions was assessed using diversity array technology sequencing. It showed that the in vitro-grown accessions were true-to-type with the field samples. The antioxidant and anticholinesterase activities of the samples from different culture systems (field and in vitro) were evaluated by UV-spectrophotometry and compared to high-performance thin-layer chromatography-effect-directed analysis (HPTLC-EDA). The latter was applied for the first time for effect-directed profiling of the polar and medium polar sample components via different biochemical and biological assays. Compound zones showed acetyl-/butylrylcholinesterase inhibition (zones 1-4), α-/ß-glucosidase inhibition (zones 1 and 2) as well as antioxidative (zones 1-3) and antimicrobial (zone 4) activities. Structures were preliminary assigned by HPTLC-HRMS. The HPTLC was effective for bioactivity-guided characterization of the bioactive constituents in Musa spp. accessions. Accumulation of useful metabolites, especially compounds with antioxidant and anticholinesterase properties, was higher in samples from in vitro system. This validated the use of plant tissue culturing as an alternative method for large scale production of plant material and supply of bioactive constituents.


Assuntos
Técnicas de Química Analítica/métodos , Cromatografia em Camada Delgada , Espectrometria de Massas , Musa/química , Anti-Infecciosos/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Técnicas de Química Analítica/instrumentação , Inibidores da Colinesterase/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Musa/crescimento & desenvolvimento
9.
Chem Biodivers ; 17(1): e1900600, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31793197

RESUMO

Four new hetisine-type C20 -diterpenoid alkaloids, named as coreanines A-D (1-4), were isolated from the roots of Aconitum coreanum, together with thirteen known alkaloids (5-17). Their structures were elucidated by extensive spectroscopic methods including IR, HR-ESI-MS and NMR techniques. All the isolated compounds were screened for the acetylcholinesterase (AChE) inhibitory effects, and none of them showed considerable inhibitory activity.


Assuntos
Acetilcolinesterase/metabolismo , Aconitum/química , Alcaloides/farmacologia , Inibidores da Colinesterase/farmacologia , Diterpenos/farmacologia , Raízes de Plantas/química , Alcaloides/química , Alcaloides/isolamento & purificação , Animais , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Diterpenos/química , Diterpenos/isolamento & purificação , Electrophorus , Estrutura Molecular
10.
Mol Biol Rep ; 47(1): 489-495, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31659691

RESUMO

Highly prized huperzine A (Hup A), a natural alkaloid formerly isolated from the Chinese medicinal plant Huperzia serrata, has been widely used for the treatment of Alzheimer disease, inspiring us to search for endophytic fungi that produce this compound. In this study, we obtained the C17 fungus isolate from the Mexican club moss Phlegmariurus taxifolius, which produced a yield of 3.2 µg/g Hup A in mycelial dry weight, when cultured in potato dextrose broth medium. The C17 isolate was identified as belonging to the genus Fusarium with reference to the colony´s morphological characteristics and the presence of macroconidia and microconidia structures; and this was confirmed by DNA-barcoding analysis, by amplifying and sequencing the ribosomal internal transcribed spacer (rITS).


Assuntos
Alcaloides , Endófitos/química , Fusarium/química , Lycopodiaceae/microbiologia , Sesquiterpenos , Alcaloides/análise , Alcaloides/química , Alcaloides/isolamento & purificação , Inibidores da Colinesterase/análise , Inibidores da Colinesterase/isolamento & purificação , Inibidores da Colinesterase/metabolismo , DNA Fúngico/genética , Endófitos/isolamento & purificação , Fusarium/classificação , Fusarium/genética , Fusarium/isolamento & purificação , Sesquiterpenos/análise , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação
11.
J Pharm Biomed Anal ; 177: 112840, 2020 Jan 05.
Artigo em Inglês | MEDLINE | ID: mdl-31522096

RESUMO

Alzheimer's disease (AD) is the most widespread neurodegenerative disease; there are around ten million new cases of Alzheimer yearly worldwide especially in middle or low-income countries. Pistacia is a genus of flowering plants including the well-known, economically important P. chinensis Bunge, P. lentiscus L. and P. khinjuk. In this study, the metabolic profiling of Pistacia leaves extracts was achieved via UHPLC-ESI-MS analysis and GC-MS analysis employing chemometric analysis for their discrimination. In addition, the methanolic extracts of different Pistacia species were assessed for their anti-cholinesterase and anti-inflammatory activities by various in vitro assays. 37 and 30 metabolites belonging to different classes were identified by UHPLC-ESI-MS and GC-MS analyses respectively. Chemometric analysis revealed that P. lentiscus and P. khinjuk were more closely related chemically to each other. All studied Pistacia leaves extracts showed apparent anti-cholinesterase and anti-inflammatory activities, which promotes their use in the prevention and management of AD.


Assuntos
Anti-Inflamatórios/farmacologia , Inibidores da Colinesterase/farmacologia , Memória/efeitos dos fármacos , Pistacia/química , Extratos Vegetais/farmacologia , Acetilcolinesterase/metabolismo , Doença de Alzheimer/tratamento farmacológico , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Cromatografia Líquida de Alta Pressão/métodos , Ensaios Enzimáticos , Eritrócitos , Proteínas Ligadas por GPI/antagonistas & inibidores , Proteínas Ligadas por GPI/metabolismo , Cromatografia Gasosa-Espectrometria de Massas/métodos , Voluntários Saudáveis , Hemólise/efeitos dos fármacos , Humanos , Metabolômica/métodos , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Óleos Voláteis/farmacologia , Pistacia/metabolismo , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Folhas de Planta/metabolismo , Óleos Vegetais/química , Óleos Vegetais/isolamento & purificação , Óleos Vegetais/farmacologia , Espectrometria de Massas por Ionização por Electrospray/métodos
12.
Nat Prod Res ; 34(16): 2358-2362, 2020 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-30394109

RESUMO

Pulicaria undulata is used as a traditional herbal remedy in Egypt. We used gas chromatography-mass spectrometry for analysis of essential oil of this plant growing wild in Egypt and 64 compounds were identified. The oil was rich in oxygenated monoterpenes (64.0%) and aromatic derivatives (18.8%). The major components were carvacrol (46.5%), xanthoxylin (18.1%) and carvotanacetone (8.7%). The oil of the Egyptian plant showed significant differences from the oil results reported on this species derived from different accessions. Antioxidant activity was performed by FRAP, DPPH and ABTS assays, and the oil demonstrated a powerful antioxidant properties. Furthermore, cytotoxicity was assessed using MTT assay against three cell lines (A375, T98G, HCT116) and the oil showed moderate results with IC50 of 18.53, 40.64 and 22.23 µg/ml; respectively. The oil showed a good anti-acetylcholinesterase activity (IC50 = 139.2 µg/ml) using Ellman method. In conclusion, the studied oil exhibited a peculiar fingerprint and promising biological activities.


Assuntos
Antioxidantes/isolamento & purificação , Óleos Voláteis/química , Pulicaria/química , Acetilcolinesterase/efeitos dos fármacos , Antioxidantes/química , Antioxidantes/farmacologia , Asteraceae , Linhagem Celular , Inibidores da Colinesterase/isolamento & purificação , Inibidores da Colinesterase/farmacologia , Cimenos/análise , Citotoxinas/isolamento & purificação , Citotoxinas/farmacologia , Egito , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Óleos Voláteis/isolamento & purificação , Óleos Voláteis/farmacologia , Terpenos/análise
13.
Nat Prod Res ; 34(6): 816-822, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-30398365

RESUMO

The chemical constituents of Cupressus macrocarpa were investigated. A new neolignan glycoside (1) in addition to nine known compounds were isolated. The acetylcholinesterase (AChE) inhibitory activity and antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) of different fractions and isolates of C. macrocarpa were evaluated. The light petroleum fraction showed the highest activity in both assays with IC50 value of 88.79 µg/ml and 152.58 µg/ml for the AChE inhibitory activity and MRSA antibacterial activities, respectively. Weak to moderate activity were detected for the isolated compounds.


Assuntos
Antibacterianos/isolamento & purificação , Inibidores da Colinesterase/isolamento & purificação , Cupressus/química , Antibacterianos/farmacologia , Inibidores da Colinesterase/farmacologia , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Lignanas/isolamento & purificação , Lignanas/farmacologia , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Extratos Vegetais/química , Folhas de Planta/química
14.
Nat Prod Res ; 34(4): 549-552, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30445826

RESUMO

The aim of this study was to determine, for the first time, the chemical composition of Peltigera horizontalis thallus and apothecia extracts (ether, ethyl acetate, dichloromethane and acetone) by HPLC-UV and GC-MS, and evaluate activity of genotoxic, anticholinesterase, antioxidant and antibacterial potential of acetone extracts. Major constituents of thallus extracts were gyrophoric acid, and methyl gyrophorate while dominant component of apothecia extracts was tenuiorin. The predominant volatile compounds in extracts were methyl orsellinate, dodecyl acrylate, orcinol and orcinol monomethyl ether. The thallus acetone extract at concentration of 2.0 µg mL-1 gave the greatest decrease in the micronuclei frequency (22.4%) of all tested extracts. Apothecia extract showed stronger antioxidant activity as compared to thallus extract. Tested extracts at concentration of 10 mg mL-1 exhibited inhibitory effect (16.5% for thallus and 12.8% for apothecia) on pooled human serum cholinesterase. P. horizontalis acetone extracts had no activity against the tested five bacteria strains.


Assuntos
Antibacterianos/isolamento & purificação , Antioxidantes/isolamento & purificação , Ascomicetos/química , Inibidores da Colinesterase/isolamento & purificação , Antibacterianos/química , Antibacterianos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Bactérias/efeitos dos fármacos , Inibidores da Colinesterase/química , Inibidores da Colinesterase/farmacologia , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Extratos Vegetais/química , Resorcinóis/análise
15.
Nat Prod Res ; 34(3): 425-428, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30450961

RESUMO

Phytochemical investigation of Illicium micranthum led to the isolation of two new prenylated C6-C3 compounds, 12-O-methyl-2,3-dehydroillifunone C (1) and illiciminone A (2), together with three known analogues (3-5) and one known sesquiterpene lactone (6). The structures were established by extensive spectroscopic characterization and the reported data. All the isolates were evaluated for their acetylcholinesterase (AChE) inhibition activity. Compound 5 showed weak inhibitory activity (46.0%) at 50 µM concentration.


Assuntos
Illicium/química , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Lactonas/química , Lactonas/isolamento & purificação , Estrutura Molecular , Prenilação , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Análise Espectral
16.
Nat Prod Res ; 34(18): 2634-2638, 2020 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-30584784

RESUMO

In Tunisia, Pelargonium graveolens is widely consumed as a food aromatizing hydrosol. Recent studies have shown the potential of plant solvent-free extracts as food and pharmaceutical natural additives. Accordingly, in this study, we investigate the phenolic content, the volatile fractions of green P. graveolens extracts such as infusion and decoction, and we evaluate their biological activities. The total phenolic content of the infusion (27.05 mg GAE/gDM) is significantly different from that of decoction (31.2 mg GAE/gDM). The GC-MS analysis identified about twenty volatile components in both extracts. The DPPH inhibition and the ß-carotene bleaching tests of the infusion and the decoction had considerable results. Besides, infusion and decoction exhibited a relatively high anti-acetyl-cholinesterase activity and a considerable antimicrobial activity against S. aureus, among three tested pathogenic bacteria.


Assuntos
Anti-Infecciosos/isolamento & purificação , Antioxidantes/isolamento & purificação , Inibidores da Colinesterase/isolamento & purificação , Pelargonium/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química , Anti-Infecciosos/farmacologia , Antioxidantes/farmacologia , Bactérias/efeitos dos fármacos , Inibidores da Colinesterase/farmacologia , Fenóis/análise , Compostos Fitoquímicos/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Tunísia
17.
Nat Prod Res ; 34(14): 2001-2006, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-30721084

RESUMO

Two new alkaloids, fluevirines E (1) and F (2), along with six known Securinega alkaloids, were isolated from the methanol extract of the twigs and leaves of Flueggea virosa. The structures and absolute configurations of the new compounds were elucidated by means of MS, NMR, and ECD analyses. Compound 1 is a new dimeric indole alkaloid while 2 is a new securinega-type alkaloid. The in vitro cytotoxic activities of the isolated alkaloids against several human cancer cell lines and their acetylcholinesterase inhibitory activity were also evaluated.


Assuntos
Alcaloides/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Inibidores da Colinesterase/isolamento & purificação , Euphorbiaceae/química , Acetilcolinesterase/efeitos dos fármacos , Alcaloides/química , Alcaloides/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Inibidores da Colinesterase/química , Inibidores da Colinesterase/farmacologia , Humanos , Alcaloides Indólicos , Conformação Molecular , Estrutura Molecular , Folhas de Planta/química , Análise Espectral
18.
BMC Complement Altern Med ; 19(1): 296, 2019 Nov 06.
Artigo em Inglês | MEDLINE | ID: mdl-31694704

RESUMO

BACKGROUND: Bergenia ciliata is a medicinal plant used for the treatment of diarrhea, vomiting, fever, cough, diabetes, cancer, pulmonary disorders and wound healing. METHODS: In this study, Bergenia ciliata crude extract, subfractions, and isolated compounds were evaluated for their antioxidant and anticholinesterase potential. The free radical scavenging capacities of the extracts determined using DPPH and ABTS assays. The anticholinesterase potentials were determined using acetylcholine esterase and butyryl choline esterase enzymes. To determine the phytochemical composition, the extracts were subjected to HPLC analysis and silica gel column isolation. Based on HPLC fingerprinting results, the ethyl acetate fraction was found to have more bioactive compounds and was therefore subjected to silica gel column isolation. As a result, three compounds; pyrogallol, rutin, and morin were isolated in the pure state. The structures of the isolated compounds were elucidated using spectroscopic techniques like 1H-NMR, IR and UV-Visible. RESULTS: The crude extract showed maximum anticholinesterase (acetylcholinesterase = 90.22 ± 1.15% and butyrylcholinesterase = 88.22 ± 0.71%) and free radical scavenging (87.37 ± 2.45 and 83.50 ± 0.70% respectively against DPPH and ABTS radicals) potentials. The total phenolic contents (expressed as equivalent of gallic acid; mgGAE/g) were higher in ethyl acetate fraction (80.96 ± 1.74) followed by crude extract (70.65 ± 0.86) while the flavonoid contents (expressed as quercetin equivalent; mgQE/g) and were higher in crude extract (88.40 ± 1.12) followed by n-butanol fraction (60.10 ± 1.86). The isolated bioactive compounds pyrogallol, rutin, and morin were found active against ABTS and DPPH free radicals. Amongst them, pyrogallol was more active against both free radicals. Reasonable anticholinesterase activities were recorded for pyrogallol against selected enzymes. CONCLUSION: The extracts and isolated compounds showed antioxidant and acetylcholinesterase inhibitory potentials. It was concluded that this plant could be helpful in the treatment of oxidative stress and neurological disorders if used in the form of extracts.


Assuntos
Antioxidantes/química , Inibidores da Colinesterase/química , Extratos Vegetais/química , Saxifragaceae/química , Acetilcolinesterase/química , Antioxidantes/isolamento & purificação , Butirilcolinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Flavonoides/química , Flavonoides/isolamento & purificação , Fenóis/química , Fenóis/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Rizoma/química
19.
Sci Rep ; 9(1): 16152, 2019 11 06.
Artigo em Inglês | MEDLINE | ID: mdl-31695105

RESUMO

Huperzine A (HupA), a natural Lycopodium alkaloid derived from Huperzia serrata (Thunb. ex Murray) Trev. plants, is a highly active acetylcholinesterase inhibitor and a key compound used for treating Alzheimer's disease (AD). Recently, HupA has been reported in various endophytic fungi isolated from H. serrata. In the present study, 153 endophytic fungi were isolated from healthy tissues of H. serrata collected from natural populations in Lam Dong province of Central Vietnam. The endophytic fungi were identified based on morphological characteristics and Internal Transcribed Spacer sequences. Among them, 34 strains were classified into seven genera belonging to Ascomycota, including Alternaria, Fusarium, Trichoderma, Penicillium, Paecilomyces, and Phoma, and eight strains belonging to the genus Mucor (Zygomycota). The other strains remained unidentified. According to the results of thin-layer chromatography and high-performance liquid chromatography, only one of the 153 strains, Penicillium sp. LDL4.4, could produce HupA, with a yield 1.38 mg l-1 (168.9 µg g-1 dried mycelium) when cultured in potato dextrose broth, which was considerably higher than that of other reported endophytic fungi. Such a fungus is a promising candidate and alternative to presently available HupA production techniques for treating AD and preventing further memory decline.


Assuntos
Alcaloides/biossíntese , Ascomicetos/isolamento & purificação , Inibidores da Colinesterase/farmacologia , Endófitos/isolamento & purificação , Huperzia/microbiologia , Mucor/isolamento & purificação , Acetilcolinesterase/efeitos dos fármacos , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Inibidores da Colinesterase/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Cromatografia em Camada Delgada , DNA Fúngico/genética , DNA Espaçador Ribossômico/genética , Endófitos/química , Endófitos/classificação , Endófitos/crescimento & desenvolvimento , Huperzia/metabolismo , Técnicas de Tipagem Micológica , Filogenia , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Especificidade da Espécie , Vietnã
20.
Molecules ; 24(22)2019 Nov 18.
Artigo em Inglês | MEDLINE | ID: mdl-31752124

RESUMO

Alzheimer's disease (AD), a neurodegenerative disease, is the most common form of dementia. Inhibition of acetylcholinesterase (AChE) is a common strategy for the treatment of AD. In this study, aqueous, hydro-methanolic, and methanolic extracts of five potent herbal extracts were tested for their in vitro anti-AChE activity. Among all, the Tinospora cordifolia (Giloy) methanolic fraction performed better with an IC50 of 202.64 µg/mL. Of the HPLC analyzed components of T. cordifolia (methanolic extract), palmatine and berberine performed better (IC50 0.66 and 0.94 µg/mL, respectively) as compared to gallic acid and the tool compound "galantamine hydrobromide" (IC50 7.89 and 1.45 µg/mL, respectively). Mode of inhibition of palmatine and berberine was non-competitive, while the mode was competitive for the tool compound. Combinations of individual alkaloids palmatine and berberine resulted in a synergistic effect for AChE inhibition. Therefore, the AChE inhibition by the methanolic extract of T. cordifolia was probably due to the synergism of the isoquinoline alkaloids. Upon molecular docking, it was observed that palmatine and berberine preferred the peripheral anionic site (PAS) of AChE, with π-interactions to PAS residue Trp286, indicating that it may hinder the substrate binding by partially blocking the entrance of the gorge of the active site or the product release.


Assuntos
Inibidores da Colinesterase/farmacologia , Extratos Vegetais/farmacologia , Doença de Alzheimer/tratamento farmacológico , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Sinergismo Farmacológico , Humanos , Extratos Vegetais/química , Extratos Vegetais/uso terapêutico , Tinospora/química
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