Flavonolignan 2,3-dehydroderivatives: Preparation, antiradical and cytoprotective activity

Free Radical Biology and Medicine

Volumn 90, Issue , 2016, Pages 114-125

  Pyszková, Michaela ^a   Biler, Michal ^a,b   Biedermann, David ^c   Valentová, Kateřina ^c   Kuzma, Marek ^c   Vrba, Jiří ^a   Ulrichová, Jitka ^a   Sokolová, Romana ^d   Mojović, Miloš ^e   Popović Bijelić, Ana ^e   Kubala, Martin ^a   Trouillas, Patrick ^a,b   Křen, Vladimír ^c   Vacek, Jan ^a  

^a PALACKÝ UNIVERSITY   (Czech Republic)

^b Univ Limoges   (France)

^c INSTITUTE OF MICROBIOLOGY   (Czech Republic)

^d J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

^e UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

Antioxidants; Aryloxy radicals; Electron transfer; Flavonolignans; Hydrogen transfer; Oxidation

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 2,2' AZINOBIS(3 ETHYLBENZOTHIAZOLINE 6 SULFONIC ACID); 2,3 DEHYDROSILYCHRISTIN; 2,3 DEHYDROSILYDIANIN; 3,7 0 DIMETHYL 2,3 DEHYDROSILYCHRISTIN (3,7 DIME 2,3 DEHYDROSILYCHRISTIN); 3,7,15 O TRIMETHYL 2,3 DEHYDROSILYCHRISTIN (3,7,15 TRIME 2,3 DEHYDROSILYCHRISTIN); 7 O METHYLSILYCHRISTIN; ANTIOXIDANT; CYTOPROTECTIVE AGENT; FLAVONOLIGNAN; FLAVONOLIGNAN 2,3 DEHYDRODERIVATIVE; SILIBININ; SILICRISTIN; SILIDIANIN; SILYMARIN; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG;

ABTS RADICAL SCAVENGING ASSAY; ANTIOXIDANT ACTIVITY; ARTICLE; CELL PROTECTION; CHEMICAL BOND; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; DPPH RADICAL SCAVENGING ASSAY; DRUG SCREENING; DRUG SYNTHESIS; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; HEPG2 CELL LINE; HUMAN; HUMAN CELL; IN VITRO STUDY; LIPID PEROXIDATION; MOLECULAR INTERACTION; OXIDATION; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; SILYBUM MARIANUM; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMISTRY; HEP-G2 CELL LINE; MALE; RAT;

ANIMALS; ANTIOXIDANTS; CYTOPROTECTION; ELECTRON SPIN RESONANCE SPECTROSCOPY; FLAVONOLIGNANS; HEP G2 CELLS; HUMANS; MALE; RATS; SILYMARIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84948695030     PISSN: 08915849     EISSN: 18734596     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2015.11.014     Document Type: Article

References (61)

1. M. Carocho, and I.C.F.R. Ferreira A review on antioxidants, prooxidants and related controversy: natural and synthetic compounds, screening and analysis methodologies and future perspectives Food Chem. Toxicol. 51 2013 15 25
2. S. Quideau, D. Deffieux, C. Douat-Casassus, and L. Pouysegu Plant polyphenols: chemical properties, biological activities, and synthesis Angew. Chem. Int. Ed. 50 2011 586 621
3. D. Biedermann, E. Vavrikova, L. Cvak, and V. Kren Chemistry of silybin Nat. Prod. Rep. 31 2014 1138 1157
4. E. Theodosiou, K. Purchartova, H. Stamatis, F. Kolisis, and V. Kren Bioavailability of silymarin flavonolignans: drug formulations and biotransformation Phytochem. Rev. 13 2014 1 18
5. V. Kren, P. Marhol, K. Purchartova, E. Gabrielova, and M. Modriansky Biotransformation of silybin and its congeners Curr. Drug Metab. 14 2013 1009 1021
6. E. Vavrikova, J. Vacek, K. Valentova, P. Marhol, J. Ulrichova, M. Kuzma, and V. Kren Chemo-enzymatic synthesis of silybin and 2,3-dehydrosilybin dimers Molecules 19 2014 4115 4134
7. K. Purchartova, L. Engels, P. Marhol, M. Sulc, M. Kuzma, K. Slamova, L. Elling, and V. Kren Enzymatic preparation of silybin phase II metabolites: sulfation using aryl sulfotransferase from rat liver Appl. Microbiol. Biotechnol. 97 2013 10391 10398
8. J. Vrba, R. Gazak, M. Kuzma, B. Papouskova, J. Vacek, M. Weiszenstein, V. Kren, and J. Ulrichova A novel semisynthetic flavonoid 7-O-galloyltaxifolin upregulates heme oxygenase-1 in RAW264.7 cells via MAPK/Nrf2 pathway J. Med. Chem. 56 2013 856 866
9. R. Gazak, P. Sedmera, M. Vrbacky, J. Vostalova, Z. Drahota, P. Marhol, D. Walterova, and V. Kren Molecular mechanisms of silybin and 2,3-dehydrosilybin antiradical activity - role of individual hydroxyl groups Free Radic. Biol. Med. 46 2009 745 758
10. P. Kosinova, R. Gazak, J.L. Duroux, R. Lazzaroni, V. Kren, X. Assfeld, and P. Trouillas Dimerisation process of silybin-type flavonolignans: insights from theory ChemPhysChem 12 2011 1135 1142
11. P. Trouillas, P. Marsal, A. Svobodova, J. Vostalova, R. Gazak, J. Hrbac, P. Sedmera, V. Kren, R. Lazzaroni, J.L. Duroux, and D. Walterova Mechanism of the antioxidant action of silybin and 2,3-dehydrosilybin flavonolignans: a joint experimental and theoretical study J. Phys. Chem. A 112 2008 1054 1063
12. M. Zatloukalova, V. Kren, R. Gazak, M. Kubala, P. Trouillas, J. Ulrichova, and J. Vacek Electrochemical investigation of flavonolignans and study of their interactions with DNA in the presence of Cu(II) Bioelectrochemistry 82 2011 117 124
13. P. Kosina, V. Kren, R. Gebhardt, F. Grambal, J. Ulrichova, and D. Walterova Antioxidant properties of silybin glycosides Phytother. Res. 16 2002 S33 S39
14. A. Zarrelli, A. Sgambato, V. Petito, L. De Napoli, L. Previtera, and G. Di Fabio New C-23 modified of silybin and 2,3-dehydrosilybin: synthesis and preliminary evaluation of antioxidant properties Bioorg. Med. Chem. Lett. 21 2011 4389 4392
15. R. Gazak, K. Purchartova, P. Marhol, L. Zivna, P. Sedmera, K. Valentova, N. Kato, H. Matsumura, K. Kaihatsu, and V. Kren Antioxidant and antiviral activities of silybin fatty acid conjugates Eur. J. Med. Chem. 45 2010 1059 1067
16. R. Gazak, A. Svobodova, J. Psotova, P. Sedmera, V. Prikrylova, D. Walterova, and V. Kren Oxidised derivatives of silybin and their antiradical and antioxidant activity Bioorg. Med. Chem. 12 2004 5677 5687
17. Z. Varga, I. Seres, E. Nagy, L. Ujhelyi, G. Balla, J. Balla, and S. Antus Structure prerequisite for antioxidant activity of silybin in different biochemical systems in vitro Phytomedicine 13 2006 85 93
18. J. Vacek, M. Zatloukalova, T. Desmier, V. Nezhodova, J. Hrbac, M. Kubala, V. Kren, J. Ulrichova, and P. Trouillas Antioxidant, metal-binding and DNA-damaging properties of flavonolignans: a joint experimental and computational highlight based on 7-O-galloylsilybin Chem. Biol. Interact. 205 2013 173 180
19. M. Zatloukalova, T.A. Enache, V. Kren, J. Ulrichova, J. Vacek, and A.M. Oliveira-Brett Effect of 3-O-galloyl substitution on the electrochemical oxidation of quercetin and silybin galloyl esters at glassy carbon electrode Electroanalysis 25 2013 1621 1627
20. P. Dzubak, M. Hajduch, R. Gazak, A. Svobodova, J. Psotova, D. Walterova, P. Sedmera, and V. Kren New derivatives of silybin and 2,3-dehydrosilybin and their cytotoxic and P-glycoprotein modulatory activity Bioorg. Med. Chem. 14 2006 3793 3810
21. K. Krenek, P. Marhol, Z. Peikerova, V. Kren, and D. Biedermann Preparatory separation of the silymarin flavonolignans by Sephadex LH-20 gel Food Res. Int. 65 2014 115 120
22. T. Takemoto, S. Ikegawa, and K. Nomoto Studies on constituents of Silybum marianum (L.) Gaertn. I. New flavonolignans named 2,3 dehydrosilymarin and 2,3 dehydrosilychristin (Japanese) Yakugaku Zasshi - J. Pharm. Soc. Jpn. 95 1975 1017 1021
23. R. Sokolova, S. Ramesova, I. Degano, M. Hromadova, M. Gal, and J. Abka The oxidation of natural flavonoid quercetin Chem. Commun. 48 2012 3433 3435
24. J. Hrbac, and R. Kohen Biological redox activity: its importance, methods for its quantification and implication for health and disease Drug Dev. Res. 50 2000 516 527
25. Y.S. Velioglu, G. Mazza, L. Gao, and B.D. Oomah Antioxidant activity and total phenolics in selected fruits, vegetables, and grain products J. Agric. Food Chem. 46 1998 4113 4117
26. C. Deby, and G. Magotteaux Relationship between essential fatty acids and tissue antioxidant levels in mice C. R. Seances Soc. Biol. Fil. 164 1970 2675 2681
27. M. Joyeux, F. Mortier, and J. Fleurentin Screening of antiradical, antilipoperoxidant and hepatoprotective effects of nine plant extracts used in Caribbean folk medicine Phytother. Res. 9 1995 228 230
28. Y. Kim, Y. Choi, H. Ham, H.S. Jeong, and J. Lee Protective effects of oligomeric and polymeric procyanidin fractions from defatted grape seeds on tert-butyl hydroperoxide-induced oxidative damage in HepG2 cells Food Chem. 137 2013 136 141
29. J. Vacek, B. Papouskova, J. Vrba, M. Zatloukalova, V. Kren, and J. Ulrichova LC-MS metabolic study on quercetin and taxifolin galloyl esters using human hepatocytes as toxicity and biotransformation in vitro cell model J. Pharm. Biomed. Anal. 86 2013 135 142
30. M.J. Frisch, et al., Gaussian 09, Revision A.02, Wallingford, CT, 2004.
31. P. Trouillas, P. Marsal, D. Siri, R. Lazzaroni, and J.L. Duroux A DFT study of the reactivity of OH groups in quercetin and taxifolin antioxidants: the specificity of the 3-OH site Food Chem. 97 2006 679 688
32. J. Ulrichova, M. Zatloukalova, V. Kren, and J. Vacek Study of electrooxidation mechanisms and antioxidant properties of flavonols and flavonolignans Planta Med. 77 2011 1269 (PA1229)
33. V. Kren, R. Gazak, K. Purchartova, P. Marhol, D. Biedermann, and P. Sedmera Chemoenzymatic preparative separation of silybins A and B J. Mol. Catal. B: Enzym. 61 2009 247 251
34. H. Liu, Q. Yuan, C.F. Li, and T.X. Huang Isolation and purification of silychristin, silydianin and taxifolin in the co-products of the silybin refined process from the silymarin by high-speed counter-current chromatography Process Biochem. 45 2010 799 804
35. D. Huang, O.U. Boxin, and R.L. Prior The chemistry behind antioxidant capacity assays J. Agric. Food Chem. 53 2005 1841 1856
36. K.P. Anthony, and M.A. Saleh Free radical scavenging and antioxidant activities of silymarin components Antioxidants 2 2013 398 407
37. P. Gavezzotti, E. Vavrikova, K. Valentova, G. Fronza, T. Kudanga, M. Kuzma, S. Riva, D. Biedermann, and V. Kren Enzymatic oxidative dimerization of silymarin flavonolignans J. Mol. Catal. B - Enzym. 109 2014 24 30
38. J. Psotova, S. Chlopcikova, F. Grambal, V. Simanek, and J. Ulrichova Influence of silymarin and its flavonolignans on doxorubicin-iron induced lipid peroxidation in rat heart microsomes and mitochondria in comparison with quercetin Phytother. Res. 16 2002 S63 S67
39. F. Sersen, T. Vencel, and J. Annus Silymarin and its components scavenge phenylglyoxylic ketyl radicals Fitoterapia 77 2006 525 529
40. P. Kosinova, K. Berka, M. Wykes, M. Otyepka, and P. Trouillas Positioning of antioxidant quercetin and its metabolites in lipid bilayer membranes: implication for their lipid-peroxidation inhibition J. Phys. Chem. B 116 2012 1309 1318
41. H.S. El-Desoky, and M.M. Ghoneim Stripping voltammetric determination of silymarin in formulations and human blood utilizing bare and modified carbon paste electrodes Talanta 84 2011 223 234
42. E. Van Wenum, R. Jurczakowski, and G. Litwinienko Media effects on the mechanism of antioxidant action of silybin and 2,3-dehydrosilybin: role of the enol group J. Org. Chem. 78 2013 9102 9112
43. S.-H. Wu, F.-H. Nie, Q.-Z. Chen, and J.-J. Sun Highly sensitive detection of silybin based on adsorptive stripping analysis at single-side heated screen-printed carbon electrodes modified with multi-walled carbon nanotubes with direct current heating Anal. Chim. Acta 687 2011 43 49
44. M. Meloun, D. Burkonova, T. Syrovy, and A. Vrana Thermodynamic dissociation constants of silychristin, silybin, silydianin and mycophenolate by the regression analysis of spectrophotometric data Anal. Chim. Acta 486 2003 125 141
45. A.M.O. Brett, and M.E. Ghica Electrochemical oxidation of quercetin Electroanalysis 15 2003 1745 1750
46. N. Cotelle, J.L. Bernier, J.P. Catteau, J. Pommery, J.C. Wallet, and E.M. Gaydou Antioxidant properties of hydroxy-flavones Free Rad. Biol. Med. 20 1996 35 43
47. J.A. Kuhnle, J.J. Windle, and A.C. Waiss Jr. Electron paramagnetic resonance spectra of flavonoid anion-radicals J. Chem. Soc. B 1969 613 616
48. R. Gazak, D. Walterova, and V. Kren Silybin and silymarin - new and emerging applications in medicine Curr. Med. Chem. 14 2007 315 338
49. G. Fabre, I. Bayach, K. Berka, M. Paloncyova, M. Starok, C. Rossi, J.L. Duroux, M. Otyepka, and P. Trouillas Synergism of antioxidant action of vitamins E, C and quercetin is related to formation of molecular associations in biomembranes Chem. Commun. 51 2015 7713 7716
50. F. Di Meo, V. Lemaur, J. Cornil, R. Lazzaroni, J.L. Duroux, Y. Olivier, and P. Trouillas Free radical scavenging by natural polyphenols: atom versus electron transfer J. Phys. Chem. A 117 2013 2082 2092
51. J. Jezek, M. Jaburek, R. Gazak, V. Kren, P. Jezek, and M. Modriansky Effect of flavonolignans derived from silybin on mitochondrial production of reactive oxygen species Biochim. Biophys. Acta - Bioenerg. 1797 2010 60
52. P. Jancova, E. Anzenbacherova, B. Papouskova, K. Lemr, P. Luzna, A. Veinlichova, P. Anzenbacher, and V. Simanek Silybin is metabolized by cytochrome P450 2C8 in vitro Drug Metab. Dispos. 35 2007 2035 2039
53. K. Valentova, A. Vidlar, M. Zatloukalova, M. Stuchlik, J. Vacek, V. Simanek, and J. Ulrichova Biosafety and antioxidant effects of a beverage containing silymarin and arginine. A pilot, human intervention cross-over trial Food Chem. Toxicol. 56 2013 178 183
54. R. Gazak, K. Valentova, K. Fuksova, P. Marhol, M. Kuzma, M.A. Medina, I. Oborna, J. Ulrichova, and V. Kren Synthesis and antiangiogenic activity of new silybin galloyl esters J. Med. Chem. 54 2011 7397 7407
55. M. Novotna, R. Gazak, D. Biedermann, F. Di Meo, P. Marhol, M. Kuzma, L. Bednarova, K. Fuksova, P. Trouillas, and V. Kren Cis-trans isomerization of silybins A and B Beilstein J. Org. Chem. 10 2014 1047 1063
56. P. Marhol, P. Bednar, P. Kolarova, R. Vecera, J. Ulrichova, E. Tesarova, E. Vavrikova, M. Kuzma, and V. Kren Pharmacokinetics of pure silybin diastereoisomers and identification of their metabolites in rat plasma J. Funct. Foods 14 2015 570 580
57. D. Prochazkova, I. Bousova, and N. Wilhelmova Antioxidant and prooxidant properties of flavonoids Fitoterapia 82 2011 513 523
58. W. Bal, J. Christodoulou, P.J. Sadler, and A. Tucker Multi-metal binding site of serum albumin J. Inorg. Biochem. 70 1998 33 39
59. M. Roche, P. Rondeau, N.R. Singh, E. Tarnus, and E. Bourdon The antioxidant properties of serum albumin FEBS Lett. 582 2008 1783 1787
60. C. Smith, B. Halliwell, and O.I. Aruoma Protection by albumin against the prooxidant actions of phenolic dietary-components Food Chem. Toxicol. 30 1992 483 489
61. N. Dixit, S. Baboota, K. Kohli, S. Ahmad, and J. Ali Silymarin: a review of pharmacological aspects and bioavailability enhancement approaches Indian J. Pharmacol. 39 2007 172 179