Browsing by Author "Kolak, Ufuk"

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Antioxidant and Anticholinesterase Constituents of Salvia Poculata
(Tubitak Scientific & Technological Research Council Turkey, 2009) Kolak, Ufuk; Hacibekiroglu, Isil; Ozturk, Mehmet; Ozgokce, Fevzi; Topcu, Guelacti; Ulubelen, Ayhan
Two triterpenoids, namely 2 alpha,3 alpha-dihydroxy-24-nor-4(23), 12-oleanadien-28-oic acid (1) and ursolic acid (2); 4. avonoids, namely 5-hydroxy-7,4'-dimethoxyflavone (3), cirsimaritin (4), eupatilin (5), and salvigenin (6); a diterpenoid, namely sclareol (7); and a steroid, namely beta-sitosterol (8), were isolated from the aerial parts of Salvia poculata Nab., a Turkish endemic Salvia species. Total phenolic and flavonoid contents of the crude extract were determined as pyrocatechol and quercetin equivalents, respectively. The antioxidant activity of the crude extract and the isolated compounds (2-8) was established using beta-carotene bleaching, superoxide anion radical, and ABTS cation radical scavenging activity. In addition, the anticholinesterase activity of the crude extract and the isolated compounds (2-8) against the enzymes acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) was determined. The phytochemistry and antioxidant and anticholinesterase activities of S. poculata were investigated for the first time in this study. The crude extract of S. poculata exhibited a significant antioxidant effect as well as butyrylcholinesterase inhibitory activity. Ursolic acid (2) and cirsimaritin (4) possessed high butyrylcholinesterase inhibitory activity.
Bioguided Isolation of Secondary Metabolites From Salvia Cerino-Pruinosa Rech. F. Var. Cerino-Pruinosa
(Acg Publications, 2021) Ertas, Abdulselam; Cakirca, Hatice; Yener, Ismail; Akdeniz, Mehmet; Firat, Mehmet; Topcu, Gulacti; Kolak, Ufuk
In the current study, the ethanol extracts prepared from the aerial parts and roots of an endemic species, Salvia cerino-pruinosa Rech. f. var. cerino-pruinosa were fractionated on silica gel columns and tested for determination of their antioxidant activity using DPPH free radical and ABTS cation radical scavenging, and cupric reducing antioxidant capacity (CUPRAC) test assays. Twenty known secondary metabolites were isolated from the active antioxidant fractions; rosmarinic acid (1), chlorogenic acid (2), caffeic acid (3), 4-hydroxybenzoic acid (4), benzoic acid (5), luteolin 7-O-glucoside (6), bis-(2-ethylhexyl)benzene-1,2-dicarboxylate (7), salvianolic acid A (8), salvianolic acid B (9), 7-acetylroyleanone (10), 6,7-dehydroroyleanone (11), ferruginol (12), inuroyleanol (13), 12-hydroxy-6,7-secoabieta-8,11,13-triene-6,7-dial (14), ursolic acid (15), oleanolic acid (16), taraxasterol (17), lupenone (18), beta-sitosterol (19), and stigmasterol (20). Rosmarinic acid, which was obtained from the aerial parts, was found to be the best antioxidant compound among the isolated secondary metabolites in DPPH free radical and ABTS cation radical scavenging, and CUPRAC assays (IC50: 1.20 +/- 0.04 mu g/mL, IC50: 1.74 +/- 0.06 mu g/mL, A(0.5): 1.22 +/- 0.02 mu g/mL, respectively). Chlorogenic and caffeic acids, luteolin 7-O-glucoside, salvianolic acids A and B, and inuroyleanol exhibited also high antioxidant activity in the mentioned assays.
Determination of Essential Oil and Biological Activities of Hypericum Ternatum Poulter and H. Scabrum L. Species Collected From Different Localities: Is H. Scabrum an Alternative To Multifunctional Species St John's Wort (H. Perforatum)
(Tubitak Scientific & Technological Research Council Turkey, 2022) Akdeniz, Mehmet; Yener, Ismail; Irtegun Kandemir, Sevgi; Ozhan Kocakaya, Safak; Firat, Mehmet; Yigitkan, Serkan; Kolak, Ufuk
The importance of Hypericum L. species, being used in traditional medicine, in the scientific world is increasing day by day. Hypericum species are plants that have been used in the treatment of many diseases for a long time and have healing properties. In the current study, the essential oil compositions of Hypericum scabrum L. and H. ternatum Poulter collected from different localities in Turkey were determined by GC-MS/FID. In addition, their antioxidant, cytotoxic, and antimicrobial activities with their enzyme inhibitory potentials (cholinesterase, urease, tyrosinase, elastase, and collagenase) were investigated. Also, in vitro and in silico studies of the major components of the species have been carried out on the studied enzymes. It was determined that four H. scabrum samples mainly contained alpha-pinene (55.99%-62.80%) while three H. ternatum samples contained 2-methyloctane (9.45%-22.39%) and alpha-pinene (12.75%-33.08%). While H. scabrum essential oils possessed significant biological activity potential except for the antimicrobial activity, H. ternatum samples did not. All essential oil samples of H. scabrum exhibited a high cytotoxic effect (IC50 21.67 +/- 0.34 to 34.67 +/- 0 .45 mu g/mL) against colon cancer cell line (HT-29) and indicated higher acetyl-(Inhibiton% 83.30 +/- 1.90 to 93.08 +/- 1.04) and butyryl-cholinesterase (Inhibiton% 80.58 +/- 1.19 to 93.28 +/- 1.99) inhibitory activity than the standard compound, galantamine. Furthermore, all samples of H. scabrum showed high tyrosinase (Inhibiton% 69.00 +/- 1.64 to 95.25 +/- 1.42) and elastase (Inhibiton% 27.58 +/- 0.34 to 36.69 +/- 0.18) inhibitory effects. These biological activity results indicated that H. scabrum essential oil could be used in the cosmetic and pharmaceutical industries.
Development and Validation of a Novel Lc-ms/Ms Method for the Quantitation of 19 Fingerprint Phytochemicals in Salvia Species: a Chemometric Approach
(Oxford Univ Press inc, 2022) Yilmaz, Mustafa Abdullah; Ertas, Abdulselam; Yener, Ismail; Olmez, Ozge Tokul; Firat, Mehmet; Temel, Hamdi; Kolak, Ufuk
Being traditionally utilized mainly as appetizers and herbal teas as well as used to ease abdominal pains, colds and gastrointestinal issues, the genus Salvia L. has gained significant consideration owing to its remarkable phytochemicals and industrial importance. The present study aimed to develop and validate an LC-MS/MS method for the qualitative and quantitative investigation of 19 fingerprint phytochemicals in six endemic Salvia species. The validation parameters of the developed LC-MS/MS method were repeatability (intermediate precision), recovery (accuracy), limits of detection and quantification, linearity and uncertainty (U% at 95% confidence level (k = 2)). Reversed-phase HPLC separation and mass spectrometry parameters were optimized for each analyte. Ethanol extracts of the studied Salvia species collected in three consecutive years were screened for their fingerprint phytochemicals by using the developed and validated LC-MS/MS method. Moreover, studied Salvia species were subjected to multivariate analysis such as principal component analysis techniques to demonstrate the variabilities in phytochemical contents by years and parts of the samples. Roots, flowers, leaves, branches and whole plant of the Salvia species collected in 2015, 2016 and 2017 were used for the analyses. It was observed that the roots and branches of Salvia species were similar in terms of their salvianolic acid A, caffeic acid, and 6,7-dehydroroyleanone components. Accordingly, apigenin, rosmarinic acid, luteolin 7-O-glucoside, caffeic acid, salvianolic acid B, and 6,7-dehydroroyleanone were notable phytochemicals that were present in the studied Salvia species.
Essential Oil, Aroma, and Fatty Acid Profiles of Five Endemic Salvia Taxa From Turkey With Chemometric Analysis
(Wiley-v C H verlag Gmbh, 2022) Ertas, Abdulselam; Akdeniz, Mehmet; Yener, Ismail; Ozturk, Mehmet; Olmez, Ozge Tokul; Firat, Mehmet; Kolak, Ufuk
The essential oil, aroma, and fatty acid compositions of Salvia cerino-pruinosa var. cerino-pruinosa, S. cerino-pruinosa var. elazigensis, S. pseudeuphratica, S. rosifolia, and S. kurdica collected in 2015, 2016, and 2017 were analysed by GC-FID, GC/MS/Head Space and GC/MS. The results were evaluated chemometrically for principal component analyses and hierarchical clustering analyses using Minitab program. The main components of their essential oils have been determined as germacrene-D (41.79 % highest for these species), camphor (55.80 %), linalool (33.38 %), caryophyllene oxide (32.99 %), 1,8-cineole (26.30 %) and geraniol acetate (31.63 %), while for aroma 1,8-cineole (45.95 % highest for these species), camphor (58.54 %), D-limonene (40.83 %), linalool (27.67 %) and cis-linalool oxide (25.87 %). Oleic (72.65 % highest for these species), erucic (44.61 %), 2-palmitoleic (42.17 %) and nervonic (32.61 %) acids were determined as major components of their fatty acids. According to the PCA and HCA, the essential oil components of these Salvia taxa unaffected by the years, and accordingly, the Salvia taxa grouped among themselves.
A Gc-Ms Method Validation for Quantitative Investigation of Some Chemical Markers Insalvia Hypargeiafisch. & Ca Mey. of Turkey: Enzyme Inhibitory Potential of Ferruginol
(Wiley, 2020) Bakir, Derya; Akdeniz, Mehmet; Ertas, Abdulselam; Yilmaz, Mustafa A.; Yener, Ismail; Firat, Mehmet; Kolak, Ufuk
In the present study, a GC-MS method used for quantitative screening of 26 compounds (sclareolide, sclareol, ferruginol, cryptanol, 6,7-dehydroroyleanone, suginal, 9,10-dihydro-7,8-dimethyl-2-(1-methylethyl) phenanthren-3-ol, sugiol, inuroyleanone, 12-demethylmulticauline, 7 alpha-hydroxy-beta-sitosterol, stigmasterol, sitosterol, salvigenin, sinensetin,alpha-amyrin, lupeol, lupenone, 3-acetyl lupeol, 1 alpha,21 alpha-dihydroxy-2,3-(1 ' 1 '-dimethyl-dioxymethylene) urs-9(11),12-dien, uvaol, betulin, pyxinol, lup-(20),29-ene-2 alpha-hydroxy-3 beta-acetate, betulin 3 beta, 28 beta-diacetate, 21 alpha-hydroxy,2 alpha,3 beta-diacetoxy urs-9(11),12-dien) specific to TurkishSalviaspecies was developed and validated. According to the GC-MS analysis results,Salvia hypargeiaFisch. & C.A. Mey. roots were found to be rich in ferruginol (30787.97 mu g/g extract) and lupenone (23276.21 mu g/g extract), and leaves in lupeol (20625.92 mu g/g extract). Additionally, the essential oil and aroma contents of this species were identified by GC-MS technique. According to the LC-MS/MS results, especiallyS. hypargeialeaf extract was rich in rosmarinic acid (38035.7 mu g/g extract) and isoquercitrin (4136.91 mu g/g extract). Furthermore, anticholinesterase, antiurease, antityrosinase and antielastase inhibitory, antioxidant, cytotoxic activities of the ethanol extracts, essential oil, and major components of the species were evaluated. Antioxidant potentials of all extracts of this species were quite high in all studied antioxidant methods. Moreover, butyrylcholinesterase and elastase inhibitory capacities of ferruginol, the major component ofS. hypargeiaroots, were notable. For these reasons, this species has a high potential for food and pharmaceutical industries. Practical applications This new GC-MS method was applied toS. hypargeiaFisch. & C.A. Mey. and it indicated that this species possessed high amount of ferruginol and lupeol, and that this species could be used for their natural sources. According to the results of the activity studies (antioxidant, anticholinesterase, tyrosinase, elastase, and cytotoxic), this method was used to exhibit which compound may be responsible for the activities. This developed and validated method could be easily applied to determine major/active/toxic secondary metabolites ofSalviaspecies which are used and/or could be used in pharmaceutical, cosmetic, and food industries.
Isolation of Secondary Metabolites of Two Endemic Species: Salvia Rosifolia Sm. and Salvia Cerino-Pruinosa Rech. F. Var. Elazigensis (Lamiaceae)
(Springer, 2021) Yaris, Esra; Adsiz, Leyla Balur; Yener, Ismail; Tuncay, Eyyup; Yilmaz, Mustafa Abdullah; Akdeniz, Mehmet; Kolak, Ufuk
In the present study, activity-guided isolation and structural elucidation of antioxidant secondary metabolites of ethanol extracts prepared from the root and aerial parts of Salvia rosifolia and Salvia cerino-pruinosa var. elazigensis species was aimed. The ethanol extracts of the species were fractionated and the antioxidant capacities of the fractions were determined by DPPH-free radical and ABTS-cation radical scavenging activity, and cupric-reducing antioxidant capacity (CUPRAC) assays. Isolation studies of the fractions with high antioxidant activities were carried out. Thirty nine secondary metabolites of known structure were isolated from the active extracts. 17 of the isolated compounds are in phenolic-flavonoid structure, 4 of them are in fatty acid structure, 7 of them are in abietane type diterpene structure, 2 of which are paraquinone and 5 of which are in aromatic structure, 8 of them are in triterpene structure, 2 of which are ursane, 2 of which are oleane and 4 of which are lupane structure, and 3 of them are in steroid structure. The structures of the isolated compounds were determined by UV, IR, H-1- and C-13-NMR-(APT), HMQC-HMBC, LCMS-IT/TOF and GC-MS techniques. It was determined that phenolic compounds among the isolated compounds were more active than terpenoid compounds in all three methods.
Method Validation of 15 Phytochemicals Inhypericum Lysimachioidesvar.spathulatumby Lc-ms/Ms, and Fatty Acid, Essential Oil, and Aroma Profiles With Biological Activities
(Springer, 2020) Akdeniz, Mehmet; Yilmaz, Mustafa Abdullah; Ertas, Abdulselam; Yener, Ismail; Firat, Mehmet; Aydin, Firat; Kolak, Ufuk
The aim of the present study was to develop and validate a LC-MS/MS method for quantification of 15 phytochemicals inHypericumspecies. The developed method was fully validated in terms of repeatability (inter-day and intra-day precision), limits of detection and quantification, linearity, recovery and relative standard uncertainty. The developed and validated LC-MS/MS method was applied to determine 15 phytochemicals in the ethanol extracts ofH. lysimachioidesvar.spathulatumaerial parts (HLS-A) and roots (HLS-R). Hyperoside was found to be the major compound in HLS-A and HLS-R ethanol extracts (16,560.3 and 3561.6 mu g analyte/g extract, respectively). According to the results of GC-MS analyses,cis-13,16-docosadienoic acid (35.0%), caryophyllene oxide (24.33%) and undecane (28.21%) were determined as the major components in fatty acid, essential oil and aroma compositions ofH. lysimachioidesvar.spathulatum, respectively. HLS-A and HLS-R ethanol extracts showed moderate activity in ABTS cation radical decolorization assay. The major components (hyperoside, astragalin, and quercetin) present in HLS-A and HLS-R ethanol extracts were found to have also the highest antioxidant effect in ABTS cation radical scavenging method. The extracts, main constituents in the extracts and essential oil had no toxic-cytotoxic potential against PDF, MCF-7 and HT-29 cell lines. HLS-A ethanol extract and essential oil exhibited high butyrylcholinesterase inhibitory activity. Quercetin showed the highest inhibitory effect against acetyl- and butyryl-cholinesterase, urease and tyrosinase among the tested samples. According to biological activity studies,H. lysimachioidesvar.spathulatumand their major components might be promoted as promising sources of natural agents and used in the development of nutraceuticals, functional food ingredients and pharmaceutical industry.
Norditerpene Alkaloids From Delphinium Linearilobum and Antioxidant Activity
(Pergamon-elsevier Science Ltd, 2006) Kolak, Ufuk; Ozturk, Mehmet; Ozgokce, Fevzi; Ulubelen, Ayhan
From the roots of Delphinium linearilobum (Trautv.) N. Busch two new norditerpene alkaloids linearilobin and linearilin, and the known alkaloids lycoctonine, 14-acetyltalatizamine, browniine, cammaconine, talatizamine, and cochlearenine were isolated. Spectroscopic techniques were used for structure determination. Antioxidant activity was performed by DPPH and metal chelating activity assays. (c) 2006 Elsevier Ltd. All rights reserved.
Phytochemical and Biological Investigations on Two Nepeta Species: Nepeta Heliotropifolia and N. Congesta Subsp. Cryptantha
(Wiley, 2020) Akdeniz, Mehmet; Ertas, Abdulselam; Yener, Ismail; Firat, Mehmet; Kolak, Ufuk
In the present study, the essential oil and aroma compositions of Nepeta heliotropifolia (NH) and N. congesta subsp. cryptantha (NC) were determined by gas chromatography-mass spectrometry (GC-MS) and gas chromatography-flame ionization detector (GC/FID), and their phenolic compounds by liquid chromatography-tandem mass spectrometry (LC-MS/MS). In addition, antioxidant, cytotoxic, anticholinesterase, urease, and tyrosinase activities of essential oils obtained from NH and NC aerial parts and ethanol extracts prepared from different parts of NH and NC were investigated. The major constituent of water-distilled essential oils was found to be germacrene D (36.7% and 38.5%, respectively), and their main aroma component was eucalyptol (48.0% and 24.7%, respectively). Among the studied parts of NH and NC, their flowers extracts were found to be the richest in phenolic compounds and in which the most abundant compound was rosmarinic acid (8,909.91 and 4,317.20 mu g/g, respectively). NH and NC flower extracts exhibited also strong antioxidant activity in DPPH, ABTS, and CUPRAC assays. Among the tested samples, NH essential oil indicated the best cytotoxic effect against PDF, HT-29, and MCF-7 (IC50 52.34, 25.89, and 44.70 mu g/ml, respectively), and the highest butyrylcholinesterase (77.21 +/- 1.12% inhibition) and moderate acetylcholinesterase (41.36 +/- 0.69% inhibition) inhibitory activities. Practical applications This is the first report on the essential oil and aroma compositions, the phenolic compounds, the antioxidant with total phenolic and flavonoid contents, cytotoxic, anticholinesterase, urease, and tyrosinase activities of Nepeta heliotropifolia and N. congesta subsp. cryptantha, except for their essential oil compositions. The reported results suggested that Nepeta heliotropifolia and N. congesta subsp. cryptantha flowers being rich in rosmarinic acid and having strong antioxidant potential, and NH essential oil possessing significant cytotoxic and butyrylcholinesterase inhibitory effect could be source for nutraceutical, food, and drug industries.
Phytochemical Fingerprints and Bioactivities of Ripe Disseminules (fruit-Seeds) of Seventeen Gundelia (kenger-Kereng Dikeni) Species From Anatolia With Chemometric Approach
(Wiley-v C H verlag Gmbh, 2021) Ertas, Abdulselam; Firat, Mehmet; Yener, Ismail; Akdeniz, Mehmet; Yigitkan, Serkan; Bakir, Derya; Kolak, Ufuk
Gundelia species are known as "Kenger-kereng dikeni" in Anatolia, and their aerial parts are consumed as food. Also, roots and seeds (disseminules) of the Gundelia species are used to prepare gum and coffee. The chemical contents of ethanol and hexane extracts of disseminules of 17 Gundelia species, 13 of them are endemic, were studied using LC/MS/MS and GC/MS. Additionally, their antioxidant potential and enzyme inhibitory capacity against acetyl- and butyryl-cholinesterase, urease, and tyrosinase were determined. The unsaturated fatty acid ratios of Gundelia species were higher than their saturated fatty acid ratio. The highest sum of oleic and linoleic acid was detected in G. tournefortii var. tenuisecta (70.42 %). beta-Sitosterol, alpha-amyrin, 3-acetyllupeol were identified in 17 Gundelia species by GC/MS, while chlorogenic acid and luteolin by LC/MS/MS as major compounds. The ethanol and hexane extracts of G. siirtica, G. rosea, and G. mesopotamica indicated good cholinesterase inhibitory activity. Among all species, ethanol extract of G. colemerikensis exhibited the best activity in ABTS (IC50: 32.30 +/- 0.98 mu g/mL), DPPH (IC50: 59.91 +/- 0.89 mu g/mL), and CUPRAC (A(0.5): 57.41 +/- 1.03 mu g/mL) assays. Ethanol extract of G. colemerikensis also displayed the highest inhibitory activity against butyrylcholinesterase (51.14 +/- 0.25% at 200 mu g/mL), urease (51.71 +/- 1.75% at 200 mu g/mL), and tyrosinase (39.50 +/- 0.85% at 200 mu g/mL) enzymes. According to the chemometric analysis of fatty acids, four groups were observed. Therefore, it is suggested that G. colemerikensis can be used in the pharmaceutical, food, and cosmetic industries due to its antioxidant and enzyme inhibition properties.
Phytochemical Investigation of Leontice Leontopetalum L. Subsp Ewersmannii With Antioxidant and Anticholinesterase Activities
(Acg Publications, 2011) Kolak, Ufuk; Hacibekiroglu, Isil; Boga, Mehmet; Ozgokce, Fevzi; Unal, Murat; Choudhary, M. Iqbal; Ulubelen, Ayhan
Two known quinolizidine alkaloids, lupanine and leontiformidine, were isolated from the tubers of L. leontopetalum subsp. ewersmannii. Lupanine having the highest inhibition of lipid peroxidation at 100 mu g/mL among the tested samples indicated almost the same ABTS cation radical scavenging activity with BHT, alpha-tocopherol and (+)-catechin at the same concentration. Lupanine and the alkaloidal extract showed almost the same butyrylcholinesterase inhibitory activity with galantamine at 200 mu g/mL.