Antioxidant, antiradical, and anticholinergic properties of cynarin purified from the Illyrian thistle (Onopordum illyricum L.)

References

• Gülçin İ. Antioxidant activity of food constituents: an overview. Arch Toxicol 2012;86:345–39
   PubMed Web of Science ®Google Scholar
• Köksal E, Gülçin İ, Öztürk Sarıkaya SB, Bursal E. On the in vitro antioxidant activity of silymarin. J Enzyme Inhib Med Chem 2009;24:395–405
   PubMed Web of Science ®Google Scholar
• Gülçin İ. Antioxidant and antiradical activities of l-carnitine. Life Sci 2006;78:803–11
   PubMed Web of Science ®Google Scholar
• Bursal E, Gülçin İ. Polyphenol contents and in vitro antioxidant activities of lyophilized aqueous extract of kiwifruit (Actinidia deliciosa). Food Res Int 2011;44:1482–9
   Web of Science ®Google Scholar
• Elmastaş M, Gülçin İ, Beydemir Ş, et al. A study on the in vitro antioxidant activity of juniper (Juniperus communis L.) seeds extracts. Anal Lett 2006;39:47–65
   Web of Science ®Google Scholar
• Gülçin İ. Antioxidant activity of eugenol – a structure and activity relationship study. J Med Food 2011;14:975–85
   PubMed Web of Science ®Google Scholar
• Gülçin İ. Antioxidant activity of caffeic acid (3,4-dihydroxycinnamic acid). Toxicology 2006;217:213–20
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Elias R, Gepdiremen A, et al. Antioxidant activity of bisbenzylisoquinoline alkaloids from Stephania rotunda: cepharanthine and fangchinoline. J Enzyme Inhib Med Chem 2010;25:44–53
   PubMed Web of Science ®Google Scholar
• Gülçin İ. In vitro prooxidant effect of caffeine. J Enzyme Inhib Med Chem 2008;23:149–52
   PubMed Web of Science ®Google Scholar
• Gülçin İ. Antioxidant activity of l-adrenaline: an activity–structure insight. Chem Biol Interact 2009;179:71–80
   PubMed Web of Science ®Google Scholar
• Montini M, Levoni P, Ongaro A, Pagani G. Controlled trial of cynarin in the treatment of the hyperlipemic syndrome observations in 60 cases. Drug Res 1975;25:1311–14
   Web of Science ®Google Scholar
• Adzet T, Camarasa JC, Laguna JC. Hepatoprotective activity of polyphenolic compounds from Cynara scolymus against CCl4 toxicity in isolated rat hepatocytes. J Nat Prod 1987;50:612–17
   PubMed Web of Science ®Google Scholar
• Raheem KS, Botting NP, Williamson G, Barron D. Total synthesis of 3,5-O-dicaffeoylquinic acid and its derivatives. Tetrahedron Lett 2011;52:7175–7
   Web of Science ®Google Scholar
• Panizzi L, Scarpati ML. Constitution of cynarine, the active principle of the artichoke. Nature 1954;174:1062
   PubMed Web of Science ®Google Scholar
• Panizzi L, Scarpati ML, Scarpati R. Isolation and constitution of the active principle of the artichoke. Gazzetta Chimica Italiana 1954;84:806–15
   Google Scholar
• Kung HF, Lee CW, Zhuang ZP, et al. Novel stilbenes as probes for amyloid plaques. J Am Chem Soc 2001;123:12740–1
   PubMed Web of Science ®Google Scholar
• Foürstl H, Kurz A. Clinical features of Alzheimer’s disease. Eur Arch Psychiatry Clin Neurosci 1999;249:288–90
   PubMed Web of Science ®Google Scholar
• Cummings JL, Doody R, Clark C. Disease-modifying therapies for Alzheimer disease: challenges to early intervention. Neurology 2007;69:1622–34
   PubMed Web of Science ®Google Scholar
• Meng FC, Mao F, Shan WJ, et al. Design, synthesis, and evaluation of indanone derivatives as acetylcholinesterase inhibitors and metal-chelating agents. Bioorg Med Chem Lett 2012;22:4462–6
   PubMed Web of Science ®Google Scholar
• Göçer H, Akıncıoğlu A, Öztaşkın N, et al. Synthesis, antioxidant and antiacetylcholinesterase activities of sulfonamide derivatives of dopamine related compounds. Arch Pharm 2013;346:783–92
   PubMed Web of Science ®Google Scholar
• Akıncıoğlu A, Nar M, Gülçin İ, Göksu S. Novel sulfamides and sulfonamides incorporating tetralin scaffold as carbonic anhydrase and acetylcholine esterase inhibitors. Arch Pharm 2014;347:68–76
   PubMed Web of Science ®Google Scholar
• Oyaizu M. Studies on product of browning reaction prepared from glucose amine. Jpn J Nutr 1986;44:307–15
   Web of Science ®Google Scholar
• Greenblatt HM, Dvir H, Silman I, Sussman JL. Acetylcholinesterase: a multifaceted target for structure-based drug design of anticholinesterase agents for the treatment of Alzheimer’s disease. J Mol Neurosci 2003;20:369–83
   PubMed Web of Science ®Google Scholar
• Gülçin İ. Comparison of in vitro antioxidant and antiradical activities of l-tyrosine and l-Dopa. Amino Acids 2007;32:431–843
   PubMed Web of Science ®Google Scholar
• Gülçin İ. Antioxidant properties of resveratrol: a structure–activity insight. Innov Food Sci Emerg 2010;1:210–18
   Web of Science ®Google Scholar
• Bursal E, Köksal E, Gülçin İ, et al. Antioxidant activity and polyphenol content of cherry stem (Cerasus avium L.) determined by LC-MS/MS. Food Res Int 2013;51:66–74
   Web of Science ®Google Scholar
• Elmastas M, Türkekul İ, Öztürk L, et al. The antioxidant activity of two wild edible mushrooms (Morchella vulgaris and Morchella esculanta). Comb Chem High Throug Scr 2006;9:443–8
   PubMed Web of Science ®Google Scholar
• Apak R, Güçlü K, Özyürek M, et al. The cupric ion reducing antioxidant capacity and polyphenolic content of some herbal teas. J Nutr Food Sci 2006;57:292–304
   Google Scholar
• Gülçin İ. Measurement of antioxidant ability of melatonin and serotonin by the DMPD and CUPRAC methods as trolox equivalent. J Enzyme Inhib Med Chem 2008;23:871–6
   PubMed Web of Science ®Google Scholar
• Dinis TCP, Madeira VMC, Almeida LM. Action of phenolic derivates (acetoaminophen, salycilate, and 5-aminosalycilate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Arch Biochem Biophys 1994;315:161–9
   PubMed Web of Science ®Google Scholar
• Ruch RJ, Cheng SJ, Klaunig JE. Prevention of cytotoxicity and inhibition of intracellular communication by antioxidant catechins isolated from Chinese green tea. Carcinogenesis 1989;10:1003–8
   PubMed Web of Science ®Google Scholar
• Zhishen J, Mengcheng T, Jianming W. The determination of flavonoid contents on mulberry and their scavenging effects on superoxide radical. Food Chem 1999;64:555–9
   Web of Science ®Google Scholar
• Gülçin İ, Gagua N, Beydemir Ş, et al. Apoptotic, antioxidant and antiradical effects of majdine and isomajdine from Vinca herbacea Waldst. and kit. J Enzyme Inhib Med Chem 2012;27:587–94
   PubMed Web of Science ®Google Scholar
• Çetinkaya Y, Göçer H, Menzek A, Gülçin İ. Synthesis and antioxidant properties of (3,4-dihydroxyphenyl)(2,3,4-trihydroxyphenyl)methanone and its derivatives. Arch Pharm 2012;345:323–34
   PubMed Web of Science ®Google Scholar
• Göçer H, Gülçin İ. Caffeic acid phenethyl ester (CAPE): correlation of structure and antioxidant properties. Int J Food Sci Nutr 2011;62:821–5
   PubMed Web of Science ®Google Scholar
• Ak T, Gülçin İ. Antioxidant and radical scavenging properties of curcumin. Chem Biol Interact 2008;174:27–37
   PubMed Web of Science ®Google Scholar
• Re R, Pellegrini N, Proteggente A, et al. Rice–Evans, antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biol Med 1999;26:1231–7
   PubMed Web of Science ®Google Scholar
• Fogliano V, Verde V, Randazzo G, Ritieni A. Method for measuring antioxidant activity and its application to monitoring the antioxidant capacity of wines. J Agric Food Chem 1999;47:1035–40
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Elias R, Gepdiremen A, Boyer L. Antioxidant activity of lignans from fringe tree (Chionanthus virginicus L.). Eur Food Res Technol 2006;223:759–67
   Web of Science ®Google Scholar
• Ellman GL, Courtney KD, Andres V, Featherston RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88–95
   PubMed Web of Science ®Google Scholar
• Aksu K, Nar M, Tanç M, et al. The synthesis of sulfamide analogues of dopamine related compounds and their carbonic anhydrase inhibitory properties. Bioorg Med Chem 2013;21:2925–31
   PubMed Web of Science ®Google Scholar
• Innocenti A, Öztürk Sarıkaya SB, Gülçin İ, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem 2010;18:2159–64
   PubMed Web of Science ®Google Scholar
• Innocenti A, Gülçin İ, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Antioxidant polyphenol natural products effectively inhibit mammalian isoforms I-XV. Bioorg Med Chem Lett 2010;20:18, 5050–3
   Google Scholar
• Çetinkaya Y, Göçer H, Gülçin İ, Menzek A. Synthesis and carbonic anhydrase isoenzymes inhibitory effects of brominated diphenylmethanone and its derivatives. Arch Pharm 2014;347:354–9
   PubMed Web of Science ®Google Scholar
• Yanishlieva NV, Marinova E, Pokorny J. Natural antioxidants from herbs and spices. Eur J Lipid Sci Technol 2006;108:776–93
   Web of Science ®Google Scholar
• Duh PD. Antioxidant activity of burdock (Arctium lappa L.): it's scavenging effect on free radical and active oxygen. J Am Oil Chem Soc 1998;75:455–61
   Web of Science ®Google Scholar
• Cakmakçi S, Topdas EF, Kalın P, et al. Antioxidant capacity and functionality of oleaster (Elaeagnus angustifolia L.) flour and crust in a new kind of fruity ice cream. Int J Food Sci Technol 2015;50:472–81
   Google Scholar
• Şerbetçi Tohma H, Gülçin İ. Antioxidant and radical scavenging activity of aerial parts and roots of Turkish liquorice (Glycyrrhiza glabra L.). Int J Food Propert 2010;13:657–61
   Web of Science ®Google Scholar
• Gülçin İ, Elmastaş M, Aboul-Enein HY. Antioxidant activity of clove oil-A powerful antioxidant source. Arab J Chem 2012;5:489–99
   Web of Science ®Google Scholar
• Min DB, Boff JM. Chemistry and reaction of singlet oxygen in foods. Comp Rev Food Sci Food Saf 2002;1:58–72
   PubMedGoogle Scholar
• Inatani R, Nakatani N, Fuwa H. Antioxidative effect of the constituents of rosemary (Rosemarinus officinalis L.) and their derivatives. Agric Biol Chem 1983;47:521–8
   Web of Science ®Google Scholar
• Balaydın HT, Gülçin İ, Menzek A, et al. Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product. J Enzyme Inhib Med Chem 2010;25:685–95
   PubMed Web of Science ®Google Scholar
• Wood LG, Gibson PG, Garg ML. A review of the methodology for assessing in vivo antioxidant capacity. J Sci Food Agric 2006;86:2057–66
   Web of Science ®Google Scholar
• Kehrer JP. The Haber-Weiss reaction and mechanisms of toxicity. Toxicology 2000;149:43–50
   PubMed Web of Science ®Google Scholar
• Talaz O, Gülçin İ, Göksu S, Saracoglu N. Antioxidant activity of 5,10-dihydroindeno[1,2-b]indoles containing substituents on dihydroindeno part. Bioorg Med Chem 2009;17:6583–9
   PubMed Web of Science ®Google Scholar
• Ramon R, Gonzalo R. Renal damage mediated by oxidative stress: a hypothesis of protective effects of red wine. Free Radical Biol Med 2002;33:409–22
   PubMed Web of Science ®Google Scholar
• Halliwell B, Murcia S, Chirico OI. Aruoma, free radicals and antioxidants in food and in vivo: what they do and how they work? Crit Rev Food Sci Nutr 1995;35:7–20
   PubMed Web of Science ®Google Scholar
• Fiorucci SB, Golebiowski J, Cabrol-Bass D, Antonczak S. DFT study of quercetin activated forms involved in antiradical, antioxidant, and prooxidant biological processes. J Agric Food Chem 2007;55:903–11
   PubMed Web of Science ®Google Scholar
• MacDonald-Wicks LK, Wood LG, Garg ML. Methodology for the determination of biological antioxidant capacity in vitro: a review. J Sci Food Agric 2006;86:2046–56
   Web of Science ®Google Scholar
• Gülçin İ, Beydemir Ş, Şat İG, Küfrevioğlu Öİ. Evaluation of antioxidant activity of cornelian cherry (Cornus mas L.). Acta Aliment Hung 2005;34:193–202
   Web of Science ®Google Scholar
• Matthäus B. Antioxidant activity of extracts obtained from residues of different oilseeds. J Agric Food Chem 2002;50:3444–52
   PubMed Web of Science ®Google Scholar
• Halliwell B. Antioxidants and human disease: a general introduction. Nutr Rev 1997;55:S44–9
   Web of Science ®Google Scholar
• Stief TW. The physiology and pharmacology of singlet oxygen. Med Hypot 2003;60:567–72
   PubMed Web of Science ®Google Scholar
• Lee J, Koo N, Min DB. Reactive oxygen species, aging, and antioxidative nutraceuticals. Comp Rev Food Sci Food Saf 2004;3:21–33
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Topal F, Oztürk Sarikaya SB, et al. Polyphenol contents and antioxidant properties of medlar (Mespilus germanica L.). Rec Nat Prod 2011;5:158–75
   Google Scholar
• Gülçin İ, Elmastaş M, Aboul-Enein HY. Determination of antioxidant and radical scavenging activity of basil (Ocimum basilicum) assayed by different methodologies. Phytother Res 2007;21:354–61
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Topal F, Çakmakçı R, et al. Pomological features, nutritional quality, polyphenol content analysis and antioxidant properties of domesticated and three wild ecotype forms of raspberries (Rubus idaeus L.). J Food Sci 2011;76:C585–93
   PubMed Web of Science ®Google Scholar
• Köksal E, Gülçin İ. Antioxidant activity of cauliflower (Brassica oleracea L.). Turk J Agric For 2008;32:65–78
   Web of Science ®Google Scholar
• Gülçin İ, Daştan A. Synthesis of dimeric phenol derivatives and determination of in vitro antioxidant and radical scavenging activities. J Enzyme Inhib Med Chem 2007;22:685–95
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Kirecci E, Akkemik E, et al. Antioxidant and antimicrobial activities of an aquatic plant: Duckweed (Lemna minor L.). Turk J Biol 2010;34:175–88
   Web of Science ®Google Scholar
• Gülçin İ, Alici HA, Cesur M. Determination of in vitro antioxidant and radical scavenging activities of propofol. Chem Pharm Bull 2005;53:281–5
   PubMed Web of Science ®Google Scholar
• Aksu K, Nar M, Tanç M, et al. The synthesis of sulfamide analogues of dopamine related compounds and their carbonic anhydrase inhibitory properties. Bioorg Med Chem 2013;21:2925–31
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Beydemir S. Phenolic compounds as antioxidants: carbonic anhydrase isoenzymes inhibitors. Mini Rev Med Chem 2013;13:408–30
   PubMed Web of Science ®Google Scholar
• Raschetti R, Albanese E, Vanacore N, Maggini M. Cholinesterase inhibitors in mild cognitive impairment: a systematic review of randomised trials. PloS Med 2007;4:1818–28
   Web of Science ®Google Scholar
• Akıncıoğlu A, Topal M, Gülçin İ, Göksu S. Novel sulfamides and sulfonamides incorporating tetralin scaffold as carbonic anhydrase and acetylcholine esterase inhibitors. Arch Pharm 2014;347:68–76
   PubMed Web of Science ®Google Scholar
• Cavalli A, Bolognesi ML, Minarini A, et al. Multi-target-directed ligands to combat neurodegenerative diseases. J Med Chem 2008;51:347–72
   Google Scholar
• Köksal E, Gülçin İ, Öztürk Sarıkaya SB, Bursal E. On the in vitro antioxidant activity of silymarine. J Enzyme Inhib Med Chem 2009;24:395–405
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Mshvildadze V, Gepdiremen A, Elias R. Screening of antioxidant and antiradical activity of monodesmosides and crude extract from Leontice smirnowii Tuber. Phytomedicine 2006;13:343–51
   PubMed Web of Science ®Google Scholar
• Gülçin İ, Daştan A. Synthesis of dimeric phenol derivatives and determination of in vitro antioxidant and radical scavenging activities. J Enzyme Inhib Med Chem 2007;22:685–95
   PubMed Web of Science ®Google Scholar
• Çoban TA, Beydemir Ş, Gülçin İ, Ekinci D. Morphine inhibits erythrocyte carbonic anhydrase in vitro and in vivo. Biol Pharm Bull 2007;30:2257–61
   PubMed Web of Science ®Google Scholar
• Şentürk M, Gülçin İ, Çiftci M, Küfrevioğlu Öİ. Dantrolene inhibits human erythrocyte glutathione reductase. Biol Pharm Bull 2008;31:2036–9
   PubMed Web of Science ®Google Scholar
• Şentürk M, Gülçin İ, Daştan A, et al. Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. Bioorg Med Chem 2009;17:3207–11
   PubMed Web of Science ®Google Scholar
• Öztürk Sarıkaya SB, Gülçin İ, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of phenolic acids. Chem Biol Drug Des 2010;75:515–20
   PubMed Web of Science ®Google Scholar
• Innocenti A, Öztürk Sarıkaya SB, Gülçin İ, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem 2010;18:2159–64
   PubMed Web of Science ®Google Scholar
• Şentürk M, Gülçin İ, Beydemir Ş, et al. In vitro inhibition of human carbonic anhydrase I and II isozymes with natural phenolic compounds. Chem Biol Drug Des 2011;77:494–9
   PubMed Web of Science ®Google Scholar
• Innocenti A, Gülçin İ, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Antioxidant polyphenol natural products effectively inhibit mammalian isoforms I-XV. Bioorg Med Chem Lett 2010;20:5050–3
   PubMed Web of Science ®Google Scholar
• Imramovsky A, Stepankova S, Vanco J, et al. Acetylcholinesterase-inhibiting activity of salicylanilide N-alkylcarbamates and their molecular docking. Molecules 2012;17:10142–58
   PubMed Web of Science ®Google Scholar
• Göçer H, Çetinkaya Y, Göksu S, et al. Carbonic anhydrase and acetylcholine esterase inhibitory effects of carbamates and sulfamoylcarbamates. J Enzyme Inhib Med Chem 2014. [Epub ahead of print]. doi:10.3109/14756366.2014.928704
   Google Scholar