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In this study, methanol, ethanol, methanol‐dichloromethane (1 : 1, v/v), acetone, ethyl acetate, diethyl ether, and chloroform extracts of lavender (Lavandula stoechas L. subsp. stoechas) were prepared by maceration, and the ursolic acid... more
In this study, methanol, ethanol, methanol‐dichloromethane (1 : 1, v/v), acetone, ethyl acetate, diethyl ether, and chloroform extracts of lavender (Lavandula stoechas L. subsp. stoechas) were prepared by maceration, and the ursolic acid contents in the extracts were determined quantitatively by HPLC analyses. The present results show that the methanol‐dichloromethane (1 : 1, v/v) solvent system is the most efficient solvent system for the extraction of ursolic acid from the plant sample with the highest yield (2.22 g/100 g plant sample). In the present study, a new practical method for the isolation of ursolic acid from polar extracts was also demonstrated for the first time. The inhibition effects of the extracts and ursolic acid were also revealed on α‐glycosidase, acetylcholinesterase, butyrylcholinesterase, and human carbonic anhydrase I and II enzymes by determining IC50 values for the first time. The extracts and ursolic acid acted as potent antidiabetic agents by strongly inhibiting the α‐glycosidase activity, whereas they were found to be very weak neuroprotective agents. In view of the present results, L. stoechas and its major metabolite, ursolic acid, can be recommended as a herbal source to control postprandial blood sugar levels and prevent diabetes by delaying the digestion of starch in food.
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A series of Schiff bases, combining 2,4-disubstituted thiazole and cyclobutane rings, and hydrazone moieties in the same molecule, was synthesized, characterized and evaluated for screening antibacterial and antifungal activities on... more
A series of Schiff bases, combining 2,4-disubstituted thiazole and cyclobutane rings, and hydrazone moieties in the same molecule, was synthesized, characterized and evaluated for screening antibacterial and antifungal activities on microorganisms, respectively, on four bacteria and Candida tropicalis. The structures of original compounds were confirmed by analytical and spectroscopic (FT-IR, (1)H NMR and (13)C NMR) methods and elemental analysis. Both the antibacterial and antifungal activities and MIC values of compounds were reported. Among the tested compounds, the most effective compound providing a MIC value of 16 microg ml(-1) are 2 against C. tropicalis and Bacillus subtilis and 3 against B. subtilis only.
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The majority of the synthesized compounds show better potency than 5-fluorouracil against human Huh-7 hepatoma cells.
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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.... more
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), β-sitosterol (2), stearic acid (3), diosgenin (4), resveratrol (5), wittifuran X (6), oxyresveratrol (7), β-sitosterol 3-O-β-D-glucopyranoside (8), diosgenin 3-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyronoside (9), oxyresveratrol 3-O-β-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.
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The genus Pimpinella is represented by 23 species in the flora of Turkey, 5 of them are endemic. Pimpinella species have carminative, expectorant, sedative, antidepressant, antiseptic, insecticidal, antiviral, antispasmodic, nematocidal,... more
The genus Pimpinella is represented by 23 species in the flora of Turkey, 5 of them are endemic. Pimpinella species have carminative, expectorant, sedative, antidepressant, antiseptic, insecticidal, antiviral, antispasmodic, nematocidal, mutagenic, analgesic, antifungal, antibacterial, diuretic, estrogenic, antimalarial, pectoral, stimulant. The essential oils from the fruits of some Pimpinella species are also valuable in perfumery and in medicine. Earlier investigations of Pimpinella resulted in the isolation of terpenoids, lipids, alkaloids, coumarins, flavonoids and phenylpropanoids. Pimpinella are reported to contain iridoids, diterpenoids, essential oils, ketosteroids and flavonoids. In this study, dried and powdered flowering stems of Pimpinella kotschyana were extracted with MeOH. Methanolic extract was dissolved in H2O and partitioned with CH2Cl2 followed by n-BuOH. Firstly, the n-BuOH phase (57g) was fractionated on a silica gel column. The subfractions were further chromatographed over silica gel, reversed phase silica gel and Sephadex LH-20 to give two new acylated flavonol glycosides together with four known flavonol glycosides: Kaempherol 3-O-α -L-2″- E-feruloyl, 3″- E-p-coumaroyl) rhamnopyranoside, kaempherol 3-O-α-L-(3″-E-feruloyl) rhamnopyranoside, kaempherol 3-O-rutinoside, quercetin-3-O-α-L-rhamnopyranoside, quercetin-3-O-rutinoside, isorhamnetin 3-O-α-L- rhamnopyranoside. The structure elucidation of the isolated compounds were done by spectroscopic methods [1D and 2D NMR spectra and MS data interpretation] and by comparison of their physical and spectroscopical data with literature values. This is the first report describing the isolation of flavonoids from the aerial parts of Pimpinella kotschyana.
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ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select... more
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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Previously we reported on the bromination of endo-7-bromonorbornene at different temperatures yielding mixtures of addition products. The structural elucidations of the formed compounds were achieved by NMR spectroscopy. Particularly, the... more
Previously we reported on the bromination of endo-7-bromonorbornene at different temperatures yielding mixtures of addition products. The structural elucidations of the formed compounds were achieved by NMR spectroscopy. Particularly, the γ-gauche effect and long-range couplings were instrumental in assigning the stereochemistry of the adducts. However, in a recent paper, Novitskiy and Kutateladze claimed that based on an applied machine learning-augmented DFT method for computational NMR that the structure of the product, (1R,2R,3S,4S,7s)-2,3,7-tribromobicyclo[2.2.1]heptane was wrong. With the aid of their computational method, they revised a number of published structures, including ours, and assigned our product the structure (1R,2S,3R,4S,7r)-2,3,7-tribromobicyclo[2.2.1]heptane. To fit their revised structure, they proposed an alternative mechanism featuring a skeletal rearrangement without the intermediacy of a carbocation. Herein, we are not only confirming the structure origin...
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Elaeagnus rhamnoides (L.) A. Nelson (synonym: Hippophae rhamnoides ) (Elaeagnaceae) is an important plant with multiple usages. The current study was laid on discovering the phytochemical profiling of E. rhamnoides leaves through... more
Elaeagnus rhamnoides (L.) A. Nelson (synonym: Hippophae rhamnoides ) (Elaeagnaceae) is an important plant with multiple usages. The current study was laid on discovering the phytochemical profiling of E. rhamnoides leaves through antihyperglycemic and antioxidant effects. The ethyl acetate (IC 50 = 46.89 ± 2.18 µg/mL) and n -butanol extracts (IC 50 = 51.33 ± 2.53 µg/mL) possessed potent inhibitory activity against α -glucosidase enzyme as compared with standard compound, acarbose (IC 50 = 4212.62 ± 130.00 µg/mL). Seven compounds were isolated, and their structure was determined by 1D- and 2D-NMR. Isorhamnetin-3- O - β - d -glucopyranosyl-7- O - α - l -rhamnopyranoside (1) , isorhamnetin-7- O - α - l -rhamnopyranoside (2) , isoquercitrin (3) , narcissin (4) , isorhamnetin-3- O - β - d -glucopyranoside (5) , arjunglucoside I (6) , and casuarinin (7) were isolated from n -butanol extract. All isolated compounds, especially arjunglucoside I (IC 50 = 1074 ± 32 µM) and casuarinin (IC 50 = 21 ± 2 µM), showed higher α -glucosidase inhibitory activity than acarbose (IC 50 = 6561 ± 207 µM). Casuarinin displayed powerful scavenging activity against to both ABTS radical with 2 ± 1 µM IC 50 value and DPPH radical with 14 ± 1 µM IC 50 value while IC 50 values of trolox and α -tocopherol were 31 ± 1 and 50 ± 1 µM against ABTS radical, and 67 ± 2 and 95 ± 3 µM against DPPH radical, respectively. Arjunglucoside I was isolated for first time from this species and Elaeagnaceae family. Preparations prepared from E. rhamnoides leaf extracts standardized via casuarinin and arjunglucoside I could be potential phytotherapeutics for diabetes mellitus. Graphic abstract
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Objective The Alchemilla genus, which belongs to the Rosaceae family, is known as Lady's mantle and is commonly used in traditional medicine. This study was designed to investigate the major metabolites isolation and gastroprotective... more
Objective The Alchemilla genus, which belongs to the Rosaceae family, is known as Lady's mantle and is commonly used in traditional medicine. This study was designed to investigate the major metabolites isolation and gastroprotective effects of Alchemilla caucasica. Materials and Methods Phytochemical studies were carried out using column chromatography on Alchemilla caucasica. The gastroprotective effect of ethanol extract of this plant was tested on indomethacin-induced gastric ulcer model in rats. In addition, superoxide dismutase (SOD), malondialdehyde (MDA), and glutathione (GSH) parameters in the stomach tissue were examined. Results Quercetin-3-O-glucuronide, apigenin, and catechin were isolated from aerial parts of Alchemilla caucasica. When macroscopic ulcer index and histopathological results were analyzed, the extract at 200 mg/kg dose was found to be most effective. All doses of extract reduced MDA level and enhanced SOD activity and GSH level. Conclusion The results of this study showed that Alchemilla caucasica has significant antiulcer activity. This effect was thought to be caused by antioxidant properties of flavonoids.
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The compounds titled 1-(2,5/3,5-difluorophenyl)-3-(2,3/2,4/2,5/3,4-dimethoxyphenyl)-2-propen-1-ones (1–8) were synthesized via Claisen-Schmidt condensation under basic condition. The chemical structure of the compounds were identified... more
The compounds titled 1-(2,5/3,5-difluorophenyl)-3-(2,3/2,4/2,5/3,4-dimethoxyphenyl)-2-propen-1-ones (1–8) were synthesized via Claisen-Schmidt condensation under basic condition. The chemical structure of the compounds were identified using several spectroscopic techniques such as 1H nuclear magnetic resonance (NMR), 13C NMR, 19F NMR, DEPT 90, DEPT 135, COSY, HMBC, and HMQC. Cytotoxic activities of the compounds were investigated towards several human tumour cell lines [gingival carcinoma (Ca9-22), oral squamous cell carcinoma derived from tongue (HSC-2)] and human normal oral cells [gingival fibroblasts (HGF), periodontal ligament fibroblasts (HPLF)]. Most of these compounds presented higher cytotoxicity than reference drug 5-fluorouracil while the compounds 7, [1-(3,5-difluorophenyl)-3-(2,5-dimethoxyphenyl)-2-propen-1-one)], and 2, [1-(2,5-difluorophenyl)-3-(2,4-dimethoxyphenyl)-2-propen-1-one], were presenting the best activity according to potency selectivity expression values. Type of cell death induced by compound 7 in both HSC-2 and Ca9-22 cells was investigated to understand mechanism of action of the compounds. The compound 7 produced cleaved products of PARP and caspase-3 were produced, suggesting the induction of apoptosis as a possible mechanism of action of the compounds characterized via activation of caspase-3 in both human oral squamous cell carcinomas.
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Research Interests: Microbiology, Chemistry, Organic Chemistry, Medicine, Drug, and 10 moreEscherichia coli, Bacteria, Staphylococcus aureus, Pseudomonas aeruginosa, Antibacterial activity, Benzimidazole, Enterococcus faecalis, Pseudomonas Aeruginosa, Pharmacology and pharmaceutical sciences, and Minimum Inhibitory Concentration
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Alzheimer's disease (AD) is characterized by progressive memory loss, deterioration of other cognitive functions, and inability to perform activities of daily living. Inhibiting the AChE enzyme causes Ach accumulation in cholinergic... more
Alzheimer's disease (AD) is characterized by progressive memory loss, deterioration of other cognitive functions, and inability to perform activities of daily living. Inhibiting the AChE enzyme causes Ach accumulation in cholinergic synapses and is expected to increase cognitive functions. Carbonic anhydrase enzymes (CAs) are ubiquitous in all living organisms. They have crucial physiological and pathological roles. CA inhibitors bind to catalytic zinc ion in the active site of CA isoenzymes and block their activity. The clinical use of CAIs had been established as antiglaucoma, anticonvulsant agents, diuretics, and anti-obesity drugs, in the management of mountain sickness, gastric and duodenal ulcers, neurological disorders, osteoporosis, and tumors. To evaluate the bioactive profile of dichloromethane extract prepared from Heptaptera triquetra root, isolation studies, AChE, and hCA I and II inhibitory activities were performed. According to isolation studies, one fatty acid, ...
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In this work, various compounds including ring 1,3,4-oxadiazole, 1,3,4- thiadiazole, 1,2,4-triazol were synthesized by cyclization of corresponding 1,4-disubstituted thiosemicarbazides from the reactions of hydrazide compounds with... more
In this work, various compounds including ring 1,3,4-oxadiazole, 1,3,4- thiadiazole, 1,2,4-triazol were synthesized by cyclization of corresponding 1,4-disubstituted thiosemicarbazides from the reactions of hydrazide compounds with alkyl/aryl isothiocyanates. Furthermore, Mannich bases were prepared by thione tautomer form of 1,2,4-triazole and acid derivatives were prepared by thiole tautomer form of 1,2,4-triazole. The solvents, and reactants used in the study were purified according to literature. In addition, the synthesized compounds were also purified because of being importance of purify for characterization of organic compounds. Then these compounds were characterized by performing of melting point, elemental analyses, X-RAY, FT-IR, 1H-NMR (400MHz), and 13CNMR( 100MHz).
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Related Article: Baris Anil, Kadri G. Ozokan, Seniz Kaban, Ertan Sahin, Cavit Kazaz|2016|Magn.Reson.Chem.|54|184|doi:10.1002/mrc.4361
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Racemic diisophorone (500 mg) was converted by Cephalosporium aphidicola and Neurospora crassa over 10 days at 25 degrees C to 8beta-hydroxydiisophorone in yields of 10% (52 mg) and 20% (103 mg), respectively. The structure was... more
Racemic diisophorone (500 mg) was converted by Cephalosporium aphidicola and Neurospora crassa over 10 days at 25 degrees C to 8beta-hydroxydiisophorone in yields of 10% (52 mg) and 20% (103 mg), respectively. The structure was established by IR, specific rotation, mass spectral, 1D and 2D-NMR studies.
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127 * ORCİD: 0000-0002-2378-1896, Department of Pharmacognosy, Faculty of Pharmacy, Atatürk University, Erzurum, Turkey ** ORCİD: 0000-0002-0735-4229, Department of Pharmacognosy, Faculty of Pharmacy, Erzincan University, Erzincan, Turkey... more
127 * ORCİD: 0000-0002-2378-1896, Department of Pharmacognosy, Faculty of Pharmacy, Atatürk University, Erzurum, Turkey ** ORCİD: 0000-0002-0735-4229, Department of Pharmacognosy, Faculty of Pharmacy, Erzincan University, Erzincan, Turkey *** ORCİD: 0000-0001-9561-8994, Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey **** ORCİD: 0000-0002-5249-0895, Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkey ***** ORCİD: 0000-0003-1069-1012, Non-wood Products Chief Engineering, Regional Directorate of Forestry, Erzurum, Turkey ****** ORCİD: 0000-0002-0857-4776, Department of Pharmacognosy, Faculty of Pharmacy, Atatürk University, Erzurum, Turkey ******* ORCİD: 0000-0003-3248-2377, Department of Pharmacognosy, Faculty of Pharmacy, Atatürk University, Erzurum, Turkey ******** ORCİD: 0000-0002-8803-8147, Department of Pharmacognosy, Faculty of Pharmacy, Atatürk University, Erzurum, Turkey ********* ORCİD: 0000-0002-5284-0744, ...
One naphthohydroquinone (mollugin) (1), 3 anthraquinones (1-hydroxy-2-methyl-9,10-anthraqinone (2), 1,3-dihydroxy-2-methoxymethyl- 9,10-anthraquinone (4) and 1,3-dihydroxy-2-carboxy-9,10-anthraquinone (7, munjistin)), b-sitosterol (3), 1... more
One naphthohydroquinone (mollugin) (1), 3 anthraquinones (1-hydroxy-2-methyl-9,10-anthraqinone (2), 1,3-dihydroxy-2-methoxymethyl- 9,10-anthraquinone (4) and 1,3-dihydroxy-2-carboxy-9,10-anthraquinone (7, munjistin)), b-sitosterol (3), 1 naphthalene glycoside (2-carbomethoxy-3-prenyl-1,4-naphtho-hydroquinone, 1,4-di-O-b -glucoside (5)) and 1 anthraquinone glycoside (lucidin-3-O-b -primeveroside (6)) were isolated from the underground parts of A. taurina subsp. caucasica. The structures of the isolates were established by MS, 1H-NMR and 13C-NMR analysis.
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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... more
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 chromatogr...
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Xanthohumol is an essential prenyl flavonoid of Humulus lupulus L. cones, and the taste of beer is due to this compound. Lately, xanthohumol has earned significant interest due to its potential anticancer, antigenotoxic, and adipogenesis... more
Xanthohumol is an essential prenyl flavonoid of Humulus lupulus L. cones, and the taste of beer is due to this compound. Lately, xanthohumol has earned significant interest due to its potential anticancer, antigenotoxic, and adipogenesis effects. In this paper, the inhibitory effects of xanthohumol on human carbonic anhydrase isozymes (hCAI and hCAII), acetylcholinesterase (AChE), and butyrylcholinesterase (BChE) were studied. Also, molecular docking studies were used to investigate ligand interaction diagrams of xanthohumol at the binding cavities of hCAI and II. Xanthohumol was isolated from hop cones by silica gel column chromatography. Carbonic anhydrase enzyme activities were determined spectrophotometrically. In addition, molecular modeling approaches were used for the hCAI and hCAII isoenzymes. Ellman’s method was used for the inhibitor activities of AChE and BChE. The KIvalues of xanthohumol were detected as 0.085 µM for hCAI, 0.049 µM for hCAII, 95.5 nM for AChE, and 124.9 ...
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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),... more
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 [β-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-rutinoside, 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, doxor...