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1.
Phytochem Anal ; 2020 Jun 03.
Artigo em Inglês | MEDLINE | ID: mdl-32488908

RESUMO

INTRODUCTION: Rumex (Polygonaceae) species are widely grown worldwide and their main compounds are anthranoids, tannins, naphthalenes and flavonoids. Matrix metalloproteinase (MMP) enzymes that cause the breakdown of the extracellular matrix and harmful ultraviolet (UV) rays are two important causes of skin ageing. Although there have been many studies on anthraquinones, there are not many studies on their anti-ageing effects. OBJECTIVE: The aim of this study was to determine the anti-ageing effects of pure compounds isolated from Rumex crispus L. by measuring their MMP inhibitory and sunscreen activities. METHODOLOGY: Molecular docking studies on anthranoid, flavonoid, tannin and naphthalene skeletons with MMP enzymes were applied for the first time. Various chromatographic methods were used for isolation studies. The structure elucidation was performed by spectroscopic [UV, infrared (IR), electrospray ionisation mass spectrometry (ESI-MS), nuclear magnetic resonance (NMR)] methods. To determine the anti-ageing capacity of compounds, MMP-1, MMP-8, MMP-13 enzyme inhibitory effects and sun protection factors (SPFs) were investigated for the first time. RESULTS: Molecular docking results showed that skeletons had low binding energy to the target and were likely to inhibit MMP enzymes. Then, eight anthraquinones and a naphthalene glycoside were isolated from the underground parts of Rumex crispus L. According to the results, MMP inhibitory effects of compounds were found to be high. In vitro and molecular docking study results confirmed each other. All anthraquinones showed high sun protection and emodin showed highest UV capability with SPF of 30.59. CONCLUSION: This study shows that anthraquinones may be evaluated as new potential MMP inhibitors, sun protective and anti-ageing agents.

2.
Bioorg Chem ; 100: 103884, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-32388430

RESUMO

Starting from the compound (3,4-dimethoxyphenyl)(2-(3,4-dimethoxyphenyl)cyclopent-1-en-1-yl)methanone (4), two diols and three tetrol derivatives were synthesised. Morover, from the reactions of 1,3-dimethoxybenzene and 1,4-dimethoxybenzene with adipoyl chloride, fifteen new along with nine known compounds were obtained. For the characterizations of compounds, spectroscopic methods such as NMR including DEPT, COSY, HMQC and HMBC experiments and X-ray diffraction were used. The antioxidant activities of novel synthesized seventeen molecules were investigated by analytical methods like ABTS•+ and DPPH• scavenging. Also, reducing power these molecules were investigated by Fe3+, Cu2+, and [Fe3+-(TPTZ)2]3+. Some of the molecules record powerful antioxidant profile when compared to putative standards. The inhibition effects of the phenols compounds against AChE and BChE activities were analysed. Also, these phenols were found as effective inhibitors for AChE, hCA I, hCA II, and BChE with Kis in the range of 122.95 ± 18.41-351.31 ± 69.12 nM for hCA I, 62.35 ± 9.03-363.17 ± 180.1 nM for hCA II, 134.57 ± 3.99-457.43 ± 220.10 nM for AChE, and 27.06 ± 9.12-72.98 ± 9.53 nM for BChE, respectively.

3.
Bioorg Chem ; 96: 103627, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-32058104

RESUMO

A novel series of 4-(3-(difluorophenyl)-5-(dimethoxyphenyl)-4,5-dihydropyrazol-1-yl)benzenesulfonamides 1-8 were designed since sulfonamide and pyrazoline pharmacophores draw great attention in novel drug design due to their wide range of bioactivities including acetylcholinesterase (AChE) and human carbonic anhydrase I and II (hCA I and hCA II) inhibitory potencies. Comprehensive structure elucidation of the compounds synthesized was carried out by 1H NMR, 13C NMR, 19F NMR, DEPT 90-135, 1H-1H COSY, 1H-13C HMQC, HMBC, and HRMS spectra. The chemical shifts and splitting patterns of the protons and carbons were affected by the fluorine atoms and exciting splitting patterns were also recorded for the fluorinated compounds. In vitro enzyme assays obviously showed that the novel compounds had a significant inhibitory profile against hCA I, hCA II and AChE enzymes at the nanomolar levels. Ki values were in the range of 3.30 ± 1.09-5.95 ± 2.26 nM for hCA I and 4.29 ± 0.91-7.14 ± 3.15 nM for hCA II, while Ki values for AChE were in the range of 3.28 ± 1.47-9.77 ± 1.86 nM. Many of thecompounds in this study can be considered as promising AChE and CA inhibitors.

4.
Nat Prod Res ; : 1-9, 2018 Nov 17.
Artigo em Inglês | MEDLINE | ID: mdl-30449173

RESUMO

In this study, phytochemical composition of Arnebia densiflora (AD) was determined and cytotoxic effects of the n-hexane extract and compounds isolated from this species on various cell lines were investigated. By means of serial chromatographic studies, 6 naphthoquinone derivatives were yielded, which are isovalerylalkannin, α-methyl-n-butyl alkannin, acetylalkannin, ß-acetoxy isovalerylalkannin, alkannin and a new compound: 4-hydroxy 4-methyl valeryl alkannin. Structures of the isolated compounds were elucidated using UV, IR, 1D-2D NMR, MS and CD methods. Cytotoxic effects of the extract and isolated alkannins were investigated on L929, HeLa, HEp-2 cells. AD and the isolated compounds demonstrated moderate to strong cytotoxic effects (IC50 range: 4.92-172.35 µg/ml). The results of DNA fragmentation and caspase-3 activity studies on HeLa cells exhibited that AD and the naphthoquinones isolated from it caused cytotoxicity through induction of apoptosis.

5.
Pharm Biol ; 56(1): 18-24, 2018 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-29233045

RESUMO

CONTEXT: Ferulago (Apiaceae) species have been used since ancient times for the treatment of intestinal worms, hemorrhoids, and as a tonic, digestive, aphrodisiac, or sedative, as well as in salads or as a spice due to their special odors. OBJECTIVES: This study reports the α-amylase and α-glucosidase inhibitory activities of dichloromethane extract and bioactive compounds isolated from Ferulago bracteata Boiss. & Hausskn. roots. MATERIALS AND METHODS: The isolated compounds obtained from dichloromethane extract of Ferulago bracteata roots through bioassay-guided fractionation and isolation process were evaluated for their in vitro α-amylase and α-glucosidase inhibitory activities at 5000-400 µg/mL concentrations. Compound structures were elucidated by detailed analyses (NMR and MS). RESULTS: A new coumarin, peucedanol-2'-benzoate (1), along with nine known ones, osthole (2), imperatorin (3), bergapten (4), prantschimgin (5), grandivitinol (6), suberosin (7), xanthotoxin (8), felamidin (9), umbelliferone (10), and a sterol mixture consisted of stigmasterol (11), ß-sitosterol (12) was isolated from the roots of F. bracteata. Felamidin and suberosin showed significant α-glucosidase inhibitory activity (IC50 0.42 and 0.89 mg/mL, respectively) when compared to the reference standard acarbose (IC50 4.95 mg/mL). However, none of the tested extracts were found to be active on α-amylase inhibition. DISCUSSION AND CONCLUSIONS: The present study demonstrated that among the compounds isolated from CH2Cl2 fraction of F. bracteata roots, coumarins were determined as the main chemical constituents of this fraction. This is the first report on isolation and characterization of the bioactive compounds from root extracts of F. bracteata and on their α-amylase and α-glucosidase inhibitory activities.


Assuntos
Apiaceae , Inibidores de Glicosídeo Hidrolases/farmacologia , Cloreto de Metileno/farmacologia , Extratos Vegetais/farmacologia , Raízes de Plantas , alfa-Amilases/antagonistas & inibidores , Cumarínicos/química , Cumarínicos/isolamento & purificação , Cumarínicos/farmacologia , Relação Dose-Resposta a Droga , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/farmacologia , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Cloreto de Metileno/química , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , alfa-Amilases/metabolismo , alfa-Glucosidases/metabolismo
6.
Anticancer Agents Med Chem ; 17(10): 1426-1433, 2017.
Artigo em Inglês | MEDLINE | ID: mdl-28356013

RESUMO

BACKGROUND: Although anticancer chemotherapeutics are available in markets, side effects related to the drugs in clinical use lead to researchers to investigate new drug candidates which are more safe, potent and selective than others. Chalcones are popular with their anticancer activities with the several reported mechanisms including inhibition of angiogenesis, inhibition of tubulin polymerization, and induction of apoptosis etc. OBJECTIVE: This study was focused on to synthesize of 1-(2,4/2,6-difluorophenyl)-3-(2,3/2,4/2,5/3,4- dimethoxyphenyl)-2-propen-1-ones (1-8) and investigate their cytotoxic properties with possible mechanism of action. METHOD: The compounds were synthesized by Claisen-Schmidt condensation. The chemical structures were confirmed by 1H NMR, 13C NMR, DEPT, COSY, HMQC, HMBC, 19F NMR and HRMS. In vitro cytotoxic effects of the compounds against human tumour cell lines [gingival carcinoma (Ca9-22), oral squamous cell carcinoma (HSC-2)] and human normal oral cells [gingival fibroblasts (HGF), periodontal ligament fibroblasts (HPLF)] were evaluated via MTT test. RESULTS: All compounds had higher cytotoxicity than reference compound 5-Fluorouracil (5-FU). The compounds 3-7 had higher potency selectivity expression values (PSE) than 5-FU and PSE values of the compounds were over 100. All chalcone derivatives seem good candidates for further studies according to very remarkable and high PSE values. CONCLUSION: It was clearly demonstrated that compound 7 can induce early apoptosis at a concentration of 10 µM and dose-dependent late apoptosis starting at 10 µM. Compound 7 induced cleavage of the apoptosis marker PARP. The results indicate that new chalcones reported here can promote apoptosis in human tumour cell lines.


Assuntos
Antineoplásicos/farmacologia , Chalconas/farmacologia , Receptores ErbB/antagonistas & inibidores , Inibidores de Proteínas Quinases/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/química , Apoptose/efeitos dos fármacos , Ciclo Celular/efeitos dos fármacos , Linhagem Celular , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Chalconas/síntese química , Chalconas/química , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Receptores ErbB/metabolismo , Humanos , Estrutura Molecular , Inibidores de Proteínas Quinases/síntese química , Inibidores de Proteínas Quinases/química , Relação Estrutura-Atividade
7.
J Enzyme Inhib Med Chem ; 31(sup3): 105-109, 2016.
Artigo em Inglês | MEDLINE | ID: mdl-27435293

RESUMO

A series of Mannich bases having piperidine moiety were reacted with 2-mercaptoethanol, leading to 1-aryl-3-piperidine-4-yl-1-propanone hydrochlorides. The cytotoxicity and carbonic anhydrase inhibitory activities of these new compounds were evaluated. Among the compounds, only one derivative, nitro substituent bearing EU9, showed an effective cytotoxicity, although weak tumor specificity against human oral malignant versus nonmalignant cells. The compound induced apoptosis in HSC-2 oral squamous cell carcinoma cells, but not in human gingival fibroblast. Chemical modifications of this lead are thus necessary to further investigate it as a drug candidate and to obtain compounds with a better activity profile.


Assuntos
Antineoplásicos/farmacologia , Anidrase Carbônica II/antagonistas & inibidores , Anidrase Carbônica I/antagonistas & inibidores , Inibidores da Anidrase Carbônica/farmacologia , Propano/farmacologia , Compostos de Sulfidrila/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/química , Apoptose/efeitos dos fármacos , Anidrase Carbônica I/metabolismo , Anidrase Carbônica II/metabolismo , Inibidores da Anidrase Carbônica/síntese química , Inibidores da Anidrase Carbônica/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Isoenzimas/antagonistas & inibidores , Isoenzimas/metabolismo , Estrutura Molecular , Propano/síntese química , Propano/química , Relação Estrutura-Atividade , Compostos de Sulfidrila/síntese química , Compostos de Sulfidrila/química
9.
Nat Prod Res ; 30(7): 750-4, 2016.
Artigo em Inglês | MEDLINE | ID: mdl-26207840

RESUMO

A new ß-hydroxydihydrochalcone glycoside named ziganin (1) and a new acylated flavonol glycoside named isorhamnetin-3-O-α-L-(2″,3″-di-O-trans-coumaroyl)-rhamnopyranoside) (2), along with two known flavonoid glycosides, a ß-hydroxydihydrochalcone glycoside, a hydroxybenzoic acid derivative, a trinorguaiane type sesquiterpenoid, a triterpenic saponin and a polyol were isolated from the herbs of Pimpinella rhodantha Boiss. Their structures were elucidated on the basis of spectroscopic analyses including 1D-and 2D-NMR, UV, IR, CD, ESI-MS, APCI-MS, HR-ESI-MS techniques. The isolated compounds were evaluated for their antioxidant capacity through the DPPH free-radical scavenging assay and ferrous ion-chelating power test.


Assuntos
Flavonoides/química , Glicosídeos/química , Pimpinella/química , Sesquiterpenos/química , Triterpenos/química , Antioxidantes/química , Antioxidantes/isolamento & purificação , Glicosídeos/isolamento & purificação , Estrutura Molecular , Extratos Vegetais/química , Saponinas/química , Saponinas/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Triterpenos/isolamento & purificação
10.
Chem Biodivers ; 12(11): 1756-67, 2015 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-26567953

RESUMO

Two lichen metabolites, rhizonaldehyde (1) and rhizonyl alcohol (2), were isolated from the acetone extract of Lobaria pulmonaria by chromatographic methods, and their chemical structures were determined by UV/VIS, IR, and 1D- and 2D-NMR spectroscopic methods. The gastroprotective and in vivo antioxidant activities of extracts of L. pulmonaria and its metabolites, 1 and 2, were investigated in indomethacin-induced ulcer models in rats. The gastric lesions were significantly reduced by acetone, hexane, and CHCl3 extracts, with 75.3-41.5% inhibition. Rhizonyl alcohol (2) significantly reduced the gastric lesions with an inhibition rate of 84.6-42.8%, whereas rhizonaldehyde (1) significantly increased the gastric lesions. Antioxidant parameters and myeloperoxidase activities were also evaluated in the gastric tissues of the rats. Indomethacin caused oxidative stress, which resulted in lipid peroxidation in gastric tissues by decreasing the levels of the antioxidants as compared to healthy rat tissues. In contrast to indomethacin, all extracts and rhizonyl alcohol (2) caused a significant decrease in lipid peroxidation levels and an increase in antioxidant parameters, superoxide dismutase, glutathione peroxidase, and glutathione-S-transferase, and reduced glutathione in gastric tissues. The administration of rhizonyl alcohol (2) also resulted in a decrease in gastric myeloperoxidase activity increased by indomethacin. The gastroprotective effect of rhizonyl alcohol (2) can be attributed to its antioxidant properties and its suppressing effect on neutrophil infiltration into gastric tissues.


Assuntos
Álcoois/farmacologia , Antiulcerosos/farmacologia , Antioxidantes/farmacologia , Indometacina/farmacologia , Líquens/metabolismo , Úlcera Gástrica/induzido quimicamente , Úlcera Gástrica/tratamento farmacológico , Álcoois/química , Álcoois/isolamento & purificação , Álcoois/metabolismo , Animais , Antiulcerosos/química , Antiulcerosos/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Modelos Animais de Doenças , Relação Dose-Resposta a Droga , Feminino , Líquens/química , Peroxidação de Lipídeos/efeitos dos fármacos , Estrutura Molecular , Estresse Oxidativo/efeitos dos fármacos , Ratos , Ratos Wistar , Úlcera Gástrica/metabolismo
11.
Chem Pharm Bull (Tokyo) ; 63(9): 720-5, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-26329865

RESUMO

Thymus praecox ssp. grossheimii (RONNIGER) JALAS var. grossheimii (Lamiaceae) is used as an herbal tea for cold, stomachache, cough, and infections in Turkey. There are no phytochemical studies on this species. We performed phytochemical studies and quantitative analysis of rosmarinic acid and luteolin 5-O-ß-D-glucopyranoside in the methanol extract of the plant. Several chromatographic methods were used for the isolation of major compounds. HPLC methods were applied for quantitative analysis of rosmarinic acid and luteolin 5-O-ß-D-glucopyranoside in the methanol extract. In this study, ursolic acid (1), oleanolic acid (2), methyl rosmarinate (3), ethyl rosmarinate (4), rosmarinic acid (5), luteolin 5-O-ß-D-glucopyranoside (6), and thymoquinol 2,5-O-ß-diglucopyranoside (7) were isolated from the aerial parts of the plant. The relative contents of rosmarinic acid and luteolin 5-O-ß-D-glucopyranoside in the extract were 15.2 and 57.8 mg/g of dry weight, respectively. Compounds isolated from this plant and the contents of rosmarinic acid and luteolin 5-O-ß-D-glucopyranoside provided reasonable evidence for the traditional usages of this plant.


Assuntos
Cinamatos/análise , Depsídeos/análise , Flavonas/análise , Glucosídeos/análise , Compostos Fitoquímicos/análise , Thymus (Planta)/química , Cromatografia Líquida de Alta Pressão , Conformação Molecular
12.
Nat Prod Commun ; 10(4): 595-6, 2015 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-25973485

RESUMO

Phytochemical studies of the roots and aerial parts of endemic Arnebia purpurea S. Erik & H. Sumbul resulted in the isolation and characterization of four naphthoquinones [isovalerylalkannin (1), α-methyl-n-butanoyl alkannin (2), acetylalkannin (3), and alkannin (4)], a triterpene derivative [3-O-acetyl-oleanolic acid (5)], a steroid [ß-sitosterol (6)], three flavonoid glycosides [isorhamnetin-3-O-rutinoside (7), kaempferol-3-O-rutinoside (8), kaempferol 3-O-(5"-acetyl) apiofuranoside 7-O-rhamnopyranoside (9)] and a phenolic acid [rosmarinic acid (10)]. 3-O-Acetyl-oleanolic acid, isorhamnetin-3-O-rutinoside, kaempferol-3-O-mrutinoside, and kaempferol 3-O-(5"-acetyl) apiofuranoside 7-O-rhamnopyranoside are reported from an Arnebia species for the first time. Cytotoxic activities on L929 murine fibrosarcoma cell line of the isolated compounds were investigated using MTT assay. Naphthoquinones (1-4) showed intermediate cytotoxic activity in comparison with the standard, doxorubicin.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Boraginaceae/química , Naftoquinonas/farmacologia , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Fibrossarcoma/tratamento farmacológico , Camundongos , Naftoquinonas/química , Naftoquinonas/isolamento & purificação , Componentes Aéreos da Planta/química , Raízes de Plantas/química
13.
Chem Biodivers ; 11(8): 1192-204, 2014 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-25146763

RESUMO

The dried rhizomes of Veratrum album were individually extracted with CHCl3 , acetone, and NH4 OH/benzene to test the toxic effects against the Colorado potato beetle, Leptinotarsa decemlineata, which is an important agricultural pest. Fifteen compounds in various amounts were isolated from the extracts using column and thin-layer chromatography. The chemical structures of 14 compounds were characterized as octacosan-1-ol (1), ß-sitosterol (2), stearic acid (3), diosgenin (4), resveratrol (5), wittifuran X (6), oxyresveratrol (7), ß-sitosterol 3-O-ß-D-glucopyranoside (8), diosgenin 3-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyronoside (9), oxyresveratrol 3-O-ß-D-glucopyranoside (10), jervine (11), pseudojervine (13), 5,6-dihydro-1-hydroxyjervine (14), and saccharose (15) using UV, IR, MS, (1) H- and (13)C-NMR, and 2D-NMR spectroscopic methods. However, the chemical structure of 12, an oligosaccharide, has not fully been elucidated. Compounds 4, 6, 9, and 10 were isolated from V. album rhizomes for the first time in the current study. The toxic effects of three extracts (acetone, CHCl3 , and NH4 OH/benzene) and six metabolites, 2, 2+4, 5, 7, 8, and 11, were evaluated against the Colorado potato beetle. The assay revealed that all three extracts, and compounds 7, 8, and 11 exhibited potent toxic effects against this pest. This is the first report on the evaluation of the toxic effects of the extracts and secondary metabolites of V. album rhizomes against L. decemlineata. Based on these results, it can be concluded that the extracts can be used as natural insecticides.


Assuntos
Besouros/efeitos dos fármacos , Inseticidas/química , Inseticidas/farmacologia , Veratrum/química , Animais , Cromatografia em Camada Delgada , Inseticidas/isolamento & purificação , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Rizoma/química , Veratrum/metabolismo
14.
Dalton Trans ; 43(16): 6148-64, 2014 Apr 28.
Artigo em Inglês | MEDLINE | ID: mdl-24589530

RESUMO

Novel multifunctional hydroxyphenylimino ligands (L1, L2 and L3) were synthesized by the condensation of 2-aminophenol, 3-aminophenol and 4-aminophenol with usnic acid, a lichen metabolite. The synthesized ligands and their Cu(II), Co(II), Ni(II) and Mn(II) complexes were characterized using FT-IR, UV-Vis, (1)H-NMR, (13)C-NMR, 1D- and 2D NMR (DEPT, COSY, HMQC and HMBC), LC-MS and TGA. In addition, the metal complexes of the novel ligands were prepared with high yields using Cu(II), Co(II), Ni(II) and Mn(II) salts and were characterized using the FT-MIR/FAR, UV-Vis, elemental analysis, ICP-OES and TG/DTA techniques. The ligands and their complexes were tested against ten important pathogen microorganisms using the disc diffusion method and the metal complexes of the ligands were more active against all of the microorganisms tested with a broad spectrum than the ligands exhibiting 11­32 mm inhibition zones. On the other hand, a broad spectrum of the strongest antimicrobial activity was determined for the Mn(II) and Cu(II) complexes of the hydroxyphenylimino ligand with usnic acid (L3). In addition, the antimutagenic activities of all of the ligands and their metal complexes were determined using the Ames-Salmonella and E. coli WP2 microbial assay systems and they showed varied and strong antimutagenic effects. In general, it has been found that the Co and Mn complexes of the ligands possess potent antimutagenic activity. In view of these results, it can be concluded that some metal complexes can be used as antimicrobial and anticancer agents.


Assuntos
Anti-Infecciosos , Antimutagênicos , Benzofuranos , Complexos de Coordenação , Metais Pesados , Aminofenóis/química , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Antimutagênicos/química , Antimutagênicos/farmacologia , Bactérias/efeitos dos fármacos , Bactérias/genética , Benzofuranos/química , Benzofuranos/farmacologia , Complexos de Coordenação/química , Complexos de Coordenação/farmacologia , Ligantes , Metais Pesados/química , Metais Pesados/farmacologia , Mutagênicos/toxicidade , Usnea , Leveduras/efeitos dos fármacos
15.
Nat Prod Commun ; 7(2): 187-90, 2012 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-22474951

RESUMO

From the aerial parts of Salvia trichoclada Bentham and S. verticillata L. one new and two known phenolic acids, 3-(3',4'-dihydroxyphenyl)-2-hydroxymethyl propionic acid (1), 3-(3',4'-dihydroxyphenyl) lactic acid (2), and rosmarinic acid (3); two flavonoids, apigenin 4'-methyl ether 7-O-glucuronide (4), and luteolin 7-O-beta glucuronide (5); two lupan type triterpene aglycones, lupeol (6), and 30-hydroxylup-20 (29)-en-3-on (7); an oleanane-type triterpene acid, oleanolic acid (8); and an ursan-type triterpene acid, ursolic acid (9) were isolated. The structures of the compounds were elucidated by spectroscopic analysis. Different extracts of the plants were examined for their free radical scavenging activities by DPPH (2,2-Diphenyl-1-picrylhydrazyl) assay. Some of the polar extracts showed high free radical scavenging activity.


Assuntos
Depuradores de Radicais Livres/química , Salvia/química , Compostos de Bifenilo/química , Estrutura Molecular , Picratos/química , Componentes Aéreos da Planta/química , Salvia/classificação
16.
Org Biomol Chem ; 9(22): 7887-96, 2011 Oct 26.
Artigo em Inglês | MEDLINE | ID: mdl-21969183

RESUMO

A series of sulfoxides were sulfoximinated using oxidative addition of 3-aminoquinazolinones by lead tetraacetate in the presence of hexamethyldisilazane. They were applied for the first time in catalytic enantioselective addition to aromatic aldehydes with a product enantiopurity (ee) of 92% in the case of 2-methoxybenzaldehyde.

17.
Arzneimittelforschung ; 61(6): 366-71, 2011.
Artigo em Inglês | MEDLINE | ID: mdl-21827048

RESUMO

1-Aryl-3-dimethylamino-1-propanone hydrochlorides type mono Mannich bases, D series, and corresponding hydrazone derivatives, K series, were synthesized and their cytotoxicity was tested against Jurkat cells (transformed human T-lymphocytes). The aryl part was changed as phenyl in D1 and K1, 4-methylphenyl in D2 and K2, 4-methoxyphenyl in D3 and K3, 4-hydroxyphenyl in D4 and K4, 4-chlorophenyl in D5 and K5, 3-methoxyphenyl in D6 and K6, 4-fluorophenyl in D7 and K7, 4-bromophenyl in D8 and K8, 3-hydroxyphenyl in D9 and K9, and 2-acetylthiophene in D10 and K10. Of the compounds synthesized, K2, K3, K5, K6, K7, K8, K9, and K10 are reported for the first time. Cytotoxic activities of the D and K series were compared with each other to see alterations in bioactivity depending on the chemical structures in Jurkat cells. Cytotoxicities of the compounds synthesized were also compared with the reference compound, 5-fluorouracil (CAS 148-82-3). Mono Mannich bases, D1 (3.60 times), D2 (4.45 times), D3 (2.46 times), D4 (3.52 times), D5 (5.18 times), D6 (3.20 times), D7 (3.23 times), D8 (3.95 times), D9 (3.36 times) and D10 (3.99 times) had 2.46-5.18 times higher cytotoxic potency than the reference compound 5-fluorouracil against Jurkat cells, while hydrazones K1 (4.92 times), K2 (4.65 times), K3 (6.04 times), K4 (6.34 times), K5 (4.67 times), K6 (5.12 times), K7 (5.39 times), K8 (8.31 times), K9 (4.65 times) and K10 (8.65 times) had 4.65-8.65 times higher cytotoxic potency than the reference compound 5-fluorouracil against the same cell line. On the other hand, hydrazone compounds K1 (1.37 times), K3 (2.46 times), K4 (1.80 times), K6 (1.60 times), K7 (1.67 times), K8 (2.11 times), K9 (1.38 times), and K10 (2.17 times) had 1.37-2.46 times higher cytotoxic potency than their corresponding mono Mannich bases. The results of this study suggest that hydrazones were better compounds compared with the corresponding mono Mannich bases in terms of cytotoxicity, and they may serve as model compounds to develop new cytotoxic agents for further studies.


Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Dimetilaminas/síntese química , Dimetilaminas/farmacologia , Bases de Mannich , Antimetabólitos Antineoplásicos/farmacologia , Fluoruracila/farmacologia , Humanos , Hidrazonas/síntese química , Hidrazonas/farmacologia , Indicadores e Reagentes , Células Jurkat , Espectroscopia de Ressonância Magnética , Relação Estrutura-Atividade
18.
Molecules ; 16(6): 4660-71, 2011 Jun 03.
Artigo em Inglês | MEDLINE | ID: mdl-21642940

RESUMO

The development of resistance to current antifungal therapeutics drives the search for new effective agents. The fact that several acetophenone-derived Mannich bases had shown remarkable antifungal activities in our previous studies led us to design and synthesize some acetophenone-derived Mannich bases, 1-8 and 2-acetylthiophene-derived Mannich base 9, 1-aryl-2-dimethylaminomethyl-2-propen-1-one hydrochloride, to evaluate their antifungal activities. The designed chemical structures have α,ß-unsaturated ketone moieties, which are responsible for the bioactivities of the Mannich bases. The aryl part was C6H5(1); 4-CH3C6H4 (2); 4-CH3OC6H4 (3); 4-ClC6H4 (4); 4-FC6H4 (5); 4-BrC6H4 (6); 4-HOC6H4 (7); 4-NO2C6H4 (8); and C4H3S(2-yl) (9). In this study the designed compounds were synthesized by the conventional heating method and also by the microwave irradiation method to compare these methods in terms of reaction times and yields to find an optimum synthetic method, which can be applied for the synthesis of Mannich bases in further studies. Since there are limited number of studies reporting the synthesis of Mannich bases by microwave irradiation, this study may also contribute to the general literature on Mannich bases. Compound 7 was reported for the first time. Antifungal activities of all compounds and synthesis of the compounds by microwave irradiation were also reported for the first time by this study. Fungi (15 species) were used for antifungal activity test. Amphotericin B was tested as an antifungal reference compound. In conclusion, compounds 1-6, and 9, which had more potent (2-16 times) antifungal activity than the reference compound amphotericin B against some fungi, can be model compounds for further studies to develop new antifungal agents. In addition, microwave irradiation can be considered to reduce reaction period, while the conventional method can still be considered to obtain compounds with higher reaction yields in the synthesis of new Mannich bases.


Assuntos
Antifúngicos/síntese química , Antifúngicos/farmacologia , Fungos/efeitos dos fármacos , Antifúngicos/química , Bases de Mannich/síntese química , Bases de Mannich/química , Bases de Mannich/farmacologia , Micro-Ondas
19.
Arch Pharm (Weinheim) ; 344(5): 333-9, 2011 May.
Artigo em Inglês | MEDLINE | ID: mdl-21319206

RESUMO

A series of 1-aryl-3-isopropylamino-1-propanone hydrochlorides 1 and a related heterocyclic analog 2 as candidate antineoplastic agents were prepared and the rationale for designing these compounds is presented. A specific objective in this study is the discovery of novel compounds possessing growth-inhibiting properties of hepatoma cells. The compounds in series 1 and 2 were prepared and their structures established unequivocally. X-ray crystallography of two representative compounds 1d and 1g were achieved. Over half of the compounds are more potent than 5-fluorouracil which is an established drug used in treating liver cancers. QSAR evaluations and molecular modeling studies were undertaken with a view to detecting some physicochemical parameters which govern cytotoxic potencies. A number of guidelines for amplification of the project have been formulated.


Assuntos
Acetona/análogos & derivados , Acetona/química , Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Desenho de Fármacos , Propilaminas/síntese química , Propilaminas/farmacologia , Antineoplásicos/química , Carcinoma Hepatocelular , Linhagem Celular Tumoral , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Fluoruracila/farmacologia , Humanos , Neoplasias Hepáticas , Modelos Moleculares , Propilaminas/química , Relação Quantitativa Estrutura-Atividade
20.
Molecules ; 15(4): 2593-9, 2010 Apr 12.
Artigo em Inglês | MEDLINE | ID: mdl-20428066

RESUMO

Sonchus erzincanicus (Asteraceae) is an endemic species in Turkey, where six Sonchus species grow. In this study, a phytochemical study was performed on the aerial parts of the plant. The study describes the isolation and structure elucidation of five flavonoids and two a-ionone glycosides from S. erzincanicus. The compounds were isolated using several and repeated chromatographic techniques from ethyl acetate and aqueous phases that were partitioned from a methanol extract obtained from the plant. 5,7,3',4'-Tetrahydroxy-3-methoxyflavone (1) and quercetin 3-O-beta-D-glucoside (2) were isolated from the ethyl acetate phase, while corchoionoside C 6'-O-sulfate (3), corchoionoside C (4), luteolin 7-O-glucuronide (5) and luteolin 7-O-beta-D-glucoside (6), apigenin 7-O-glucuronide (7) were isolated from the aqueous phase. Corchoionoside C 6'-O-sulfate (3), isolated for the first time from a natural source, was a new compound. The structures of the compounds were elucidated by means of 1H-NMR, 13C-NMR, 2D-NMR (COSY, HMQC, HMBC) and ESI-MS.


Assuntos
Glucosídeos/química , Norisoprenoides/química , Sonchus/química , Ésteres do Ácido Sulfúrico/química , Flavonoides/química , Flavonoides/isolamento & purificação , Glucosídeos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Norisoprenoides/isolamento & purificação , Espectrometria de Massas por Ionização por Electrospray , Ésteres do Ácido Sulfúrico/isolamento & purificação
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