Chemo-enzymatic synthesis of silybin and 2,3-dehydrosilybin dimers

Molecules

Volumn 19, Issue 4, 2014, Pages 4115-4134

  Vavríková, Eva ^a   Vacek, Jan ^b   Valentová, Katerina ^a,b   Marhol, Petr ^a   Ulrichová, Jitka ^b   Kuzma, Marek ^a   Kren, Vladimír ^a  

^a INSTITUTE OF MICROBIOLOGY   (Czech Republic)

^b PALACKÝ UNIVERSITY   (Czech Republic)

Author keywords

Antioxidant; Cytotoxicity; Dimerization; Electrochemistry; Flavonolignan; HUVEC; Microsomal lipid peroxidation; Silibinin; Silybin

Indexed keywords

2,2-DIPHENYL-1-PICRYLHYDRAZYL; BIPHENYL DERIVATIVE; DEHYDROSILYBIN; FUNGAL PROTEIN; PICRIC ACID; SCAVENGER; SILIBININ; SILYMARIN; TRIACYLGLYCEROL LIPASE;

ANIMAL; ANTAGONISTS AND INHIBITORS; BIOCATALYSIS; CELL SURVIVAL; CHEMISTRY; CYTOLOGY; DIMERIZATION; DRUG EFFECTS; FIBROBLAST; HEPG2 CELL LINE; HUMAN; KERATINOCYTE; LIPID PEROXIDATION; LIVER MICROSOME; MOUSE; OXIDATION REDUCTION REACTION; RAT; SYNTHESIS; UMBILICAL VEIN ENDOTHELIAL CELL;

ANIMALS; BIOCATALYSIS; BIPHENYL COMPOUNDS; CELL SURVIVAL; DIMERIZATION; FIBROBLASTS; FREE RADICAL SCAVENGERS; FUNGAL PROTEINS; HEP G2 CELLS; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; KERATINOCYTES; LIPASE; LIPID PEROXIDATION; MICE; MICROSOMES, LIVER; OXIDATION-REDUCTION; PICRATES; RATS; SILYMARIN;

EID: 84899505952     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules19044115     Document Type: Article

References (50)

1. Gazak, R.; Walterova, D.; Kren, V. Silybin and silymarin-New and emerging applications in medicine. Curr. Med. Chem. 2007, 14, 315-338.
2. Kren, V.; Gazak, R.; Purchartova, K.; Marhol, P.; Biedermann, D.; Sedmera, P. Chemoenzymatic preparative separation of silybins A and B. J. Mol. Catal. B: Enzymat. 2009, 61, 247-251.
3. Gazak, R.; Trouillas, P.; Biedermann, D.; Fuksova, K.; Marhol, P.; Kuzma, M.; Kren, V. Base-catalyzed oxidation of silybin and isosilybin into 2,3-dehydro derivatives. Tetrahedron Lett. 2013, 54, 315-317.
4. Huber, A.; Thongphasuk, P.; Erben, G.; Lehmann, W.D.; Tuma, S.; Stremmel, W.; Chamulitrat, W. Significantly greater antioxidant anticancer activities of 2,3-dehydrosilybin than silybin. Biochim. Biophys. Acta 2008, 1780, 837-847.
5. Thongphasuk, P.; Stremmel, W.; Chamulitrat, W. 2,3-dehydrosilybin is a better DNA topoisomerase I inhibitor than its parental silybin. Chemotherapy 2009, 55, 42-48.
6. Gazak, R.; Svobodova, A.; Psotova, J.; Sedmera, P.; Prikrylova, V.; Walterova, D.; Kren, V. Oxidised derivatives of silybin and their antiradical and antioxidant activity. Bioorg. Med. Chem. 2004, 12, 5677-5687.
7. Zatloukalova, M.; Kren, V.; Gazak, R.; Kubala, M.; Trouillas, P.; Ulrichova, J.; Vacek, J. Electrochemical investigation of flavonolignans and study of their interactions with DNA in the presence of Cu(II). Bioelectrochemistry 2011, 82, 117-124.
8. Gazak, R.; Sedmera, P.; Vrbacky, M.; Vostalova, J.; Drahota, Z.; Marhol, P.; Walterova, D.; Kren, V. Molecular mechanisms of silybin and 2,3-dehydrosilybin antiradical activity-Role of individual hydroxyl groups. Free Radic. Biol. Med. 2009, 46, 745-758.
9. Gazak, R.; Purchartova, K.; Marhol, P.; Zivna, L.; Sedmera, P.; Valentova, K.; Kato, N.; Matsumura, H.; Kaihatsu, K.; Kren, V. Antioxidant and antiviral activities of silybin fatty acid conjugates. Eur. J. Med. Chem. 2010, 45, 1059-1067.
10. Theodosiou, E.; Katsoura, M.H.; Loutrari, H.; Purchartova, K.; Kren, V.; Kolisis, F.N.; Stamatis, H. Enzymatic preparation of acylated derivatives of silybin in organic and ionic liquid media and evaluation of their antitumor proliferative activity. Biocatal. Biotrans. 2009, 27, 161-169.
11. Theodosiou, E.; Loutrari, H.; Stamatis, H.; Roussos, C.; Kolisis, F.N. Biocatalytic synthesis and antitumor activities of novel silybin acylated derivatives with dicarboxylic acids. New Biotechnol. 2011, 28, 342-348.
12. Monti, D.; Gazak, R.; Marhol, P.; Biedermann, D.; Purchartova, K.; Fedrigo, M.; Riva, S.; Kren, V. Enzymatic kinetic resolution of silybin diastereoisomers. J. Nat. Prod. 2010, 73, 613-629.
13. Chen, X.Y.; Zenger, K.; Lupp, A.; Kling, B.; Heilmann, J.; Fleck, C.; Kraus, B.; Decker, M. Tacrine-silibinin codrug shows neuro- and hepato protective effects in vitro and pro-cognitive and hepatoprotective effects in vivo. J. Med. Chem. 2012, 55, 5231-5242.
14. Zarrelli, A.; Romanucci, V.; Greca, M.D.; de Napoli, L.; Previtera, L.; di Fabio, G. New silybin scaffold for chemical diversification: Synthesis of novel 23-phosphodiester silybin conjugates. Synlett 2013, 24, 45-48.
15. Gazak, R.; Sedmera, P.; Marzorati, M.; Riva, S.; Kren, V. Laccase-mediated dimerization of the flavonolignan silybin. J. Mol. Catal. B 2008, 50, 87-92.
16. Trouillas, P.; Marsal, P.; Svobodova, A.; Vostalova, J.; Gazak, R.; Hrbac, J.; Sedmera, P.; Kren, V.; Lazzaroni, R.; Duroux, J.L.; et al. Mechanism of the antioxidant action of silybin and 2,3-dehydrosilybin flavonolignans: A joint experimental and theoretical study. J. Phys. Chem. A 2008, 112, 1054-1063.
17. Pliskova, M.; Vondracek, J.; Kren, V.; Gazak, R.; Sedmera, P.; Walterova, D.; Psotova, J.; Simanek, V.; Machala, M. Effects of silymarin flavonolignans and synthetic silybin derivatives on estrogen and aryl hydrocarbon receptor activation. Toxicology 2005, 215, 80-89.
18. Berube, G. Natural and synthetic biologically active dimeric molecules: Anticancer agents, anti-hiv agents, steroid derivatives and opioid antagonists. Curr. Med. Chem. 2006, 13, 131-154.
19. Mott, B.T.; Tripathi, A.; Siegler, M.A.; Moore, C.D.; Sullivan, D.J.; Posner, G.H. Synthesis and antimalarial efficacy of two-carbon-linked, artemisinin-derived trioxane dimers in combination with known antimalarial drugs. J. Med. Chem. 2013, 56, 2630-2641.
20. Jenett-Siems, K.; Kohler, I.; Kraft, C.; Pertz, H.H.; Kren, V.; Fiserova, A.; Kuzma, M.; Ulrichova, J.; Bienzle, U.; Eich, E. In vitro antiplasmodial activities of semisynthetic N,N'-spacer-linked oligomeric ergolines. Bioorg. Med. Chem. 2004, 12, 817-824.
21. Chan, K.F.; Zhao, Y.Z.; Burkett, B.A.; Wong, I.L.K.; Chow, L.M.C.; Chan, T.H. Flavonoid dimers as bivalent modulators for P-glycoprotein-based multidrug resistance: Synthetic apigenin homodimers linked with defined-length poly(ethylene glycol) spacers increase drug retention and enhance chemosensitivity in resistant cancer cells. J. Med. Chem. 2006, 49, 6742-6759.
22. Dolle, C.; Magrone, P.; Riva, S.; Ambrosi, M.; Fratini, E.; Peruzzi, N.; Lo Nostro, P. Symmetric and asymmetric bolaamphiphiles from ascorbic acid. J. Phys. Chem. B 2011, 115, 11638-11649.
23. Chebil, L.; Humeau, C.; Falcimaigne, A.; Engasser, J.M.; Ghoul, M. Enzymatic acylation of flavonoids. Process Biochem. 2006, 41, 2237-2251.
24. Magrone, P.; Cavallo, F.; Panzeri, W.; Passarella, D.; Riva, S. Exploiting enzymatic regioselectivity: A facile methodology for the synthesis of polyhydroxylated hybrid compounds. Org. Biomol. Chem. 2010, 8, 5583-5590.
25. Zatloukalova, M.; Enache, T.A.; Kren, V.; Ulrichova, J.; Vacek, J.; Oliveira-Brett, A.M. Effect of 3-O-galloyl substitution on the electrochemical oxidation of quercetin and silybin galloyl esters at glassy carbon electrode. Electroanalysis 2013, 25, 1621-1627.
26. Vacek, J.; Zatloukalova, M.; Desmier, T.; Nezhodova, V.; Hrbac, J.; Kubala, M.; Kren, V.; Ulrichova, J.; Trouillas, P. Antioxidant, metal-binding and DNA-damaging properties of flavonolignans: A joint experimental and computational highlight based on 7-O-galloylsilybin. Chem. Biol. Interact. 2013, 205, 173-180.
27. Valentova, K.; Vidlar, A.; Zatloukalova, M.; Stuchlik, M.; Vacek, J.; Simanek, V.; Ulrichova, J. Biosafety and antioxidant effects of a beverage containing silymarin and arginine. A pilot, human intervention cross-over trial. Food Chem. Toxicol. 2013, 56, 178-183.
28. Wang, F.; Huang, K.X.; Yang, L.X.; Gong, J.X.; Tao, Q.F.; Li, H.B.; Zhao, Y.; Zeng, S.; Wu, X.M.; Stockigt, J.; et al. Preparation of C-23 esterified silybin derivatives and evaluation of their lipid peroxidation inhibitory and DNA protective properties. Bioorg. Med. Chem. 2009, 17, 6380-6389.
29. Abourashed, E.A.; Mikell, J.R.; Khan, I.A. Bioconversion of silybin to phase I and II microbial metabolites with retained antioxidant activity. Bioorg. Med. Chem. 2012, 20, 2784-2788.
30. Zhu, L.F.; Xu, M.; Zhu, H.T.; Wang, D.; Yang, S.X.; Yang, C.R.; Zhang, Y.J. New flavan-3-ol dimer from green tea produced from camellia taliensis in the Ai-Lao Mountains of Southwest China. J. Agric. Food Chem. 2012, 60, 12170-12176.
31. Lu, Y.R.; Foo, L.Y. Antioxidant and radical scavenging activities of polyphenols from apple pomace. Food Chem. 2000, 68, 81-85.
32. Fujisawa, S.; Atsumi, T.; Ishihara, M.; Kadoma, Y. Cytotoxicity, ROS-generation activity and radical-scavenging activity of curcumin and related compounds. Anticancer Res. 2004, 24, 563-569.
33. Osman, A.M. Multiple pathways of the reaction of 2,2-diphenyl-1- picrylhydrazyl radical (DPPH center dot) with (+)-catechin: Evidence for the formation of a covalent adduct between DPPH center dot and the oxidized form of the polyphenol. Biochem. Bioph. Res. Commun. 2011, 412, 473-478.
34. Kawabata, J.; Okamoto, Y.; Kodama, A.; Makimoto, T.; Kasai, T. Oxidative dimers produced from protocatechuic and gallic esters in the DPPH radical scavenging reaction. J. Agric. Food Chem. 2002, 50, 5468-5471.
35. Yamaguchi, H.; Ishii, E.; Tashiro, K.; Miyazaki, S. Role of umbilical vein endothelial cells in hematopoiesis. Leukemia Lymphoma 1998, 31, 61-69.
36. Rasmussen, C.; Thomas-Virnig, C.; Allen-Hoffmann, B.L. Classical human epidermal keratinocyte cell culture. In Methods in Molecular Biology; Randell, S.H., Fulcher, M.L., Eds.; Humana Press: Clifton, NJ, USA, 2013; Volume 945, pp. 161-175.
37. Mersch-Sundermann, V.; Knasmuller, S.; Wu, X.-J.; Darroudi, F.; Kassie, F. Use of a human-derived liver cell line for the detection of cytoprotective, antigenotoxic and cogenotoxic agents. Toxicology 2004, 198, 329-340.
38. Pham, A.; Bortolazzo, A.; White, J.B. Rapid dimerization of quercetin through an oxidative mechanism in the presence of serum albumin decreases its ability to induce cytotoxicity in MDA-MB-231 cells. Biochem. Bioph. Res. Commun. 2012, 427, 415-420.
39. Figueiredo, P.; Elhabiri, M.; Toki, K.; Saito, N.; Dangles, O.; Brouillard, R. New aspects of anthocyanin complexation. Intramolecular copigmentation as a means for colour loss? Phytochemistry 1996, 41, 301-308.
40. Di Meo, F.; Garcia, J.C.S.; Dangles, O.; Trouillas, P. Highlights on anthocyanin pigmentation and copigmentation: A matter of flavonoid p-stacking complexation to be described by dft-d. J. Chem. Theory Comput. 2012, 8, 2034-2043.
41. Nave, F.; Bras, N.F.; Cruz, L.; Teixeira, N.; Mateus, N.; Ramos, M.J.; di Meo, F.; Trouillas, P.; Dangles, O.; de Freitas, V. Influence of a flavan-3-ol substituent on the affinity of anthocyanins (pigments) toward vinylcatechin dimers and proanthocyanidins (copigments). J. Phys. Chem. B 2012, 116, 14089-14099.
42. Velu, S.S.; di Meo, F.; Trouillas, P.; Sancho-Garcia, J.C.; Weber, J.F. Regio- and stereocontrolled synthesis of oligostilbenoids: Theoretical highlights at the supramolecular level. J. Nat. Prod. 2013, 76, 538-546.
43. Gazak, R.; Marhol, P.; Purchartova, K.; Monti, D.; Biedermann, D.; Riva, S.; Cvak, L.; Kren, V. Large-scale separation of silybin diastereoisomers using lipases. Process Biochem. 2010, 45, 1657-1663.
44. Zatloukalova, M.; Orolinova, E.; Kubala, M.; Hrbac, J.; Vacek, J. Electrochemical determination of transmembrane protein Na+/K+-ATPase and its cytoplasmic loop C45. Electroanalysis 2012, 24, 1758-1765.
45. Joyeux, M.; Mortier, F.; Fleurentin, J. Screening of antiradical, antilipoperoxidant and hepatoprotective effects of 9 plant-extracts used in caribbean folk medicine. Phytother. Res. 1995, 9, 228-230.
46. Siekevitz, P.; Sidney, P.C.; Nathan, O.K. Preparation of microsomes and submicrosomal fractions: Mammalian. In Methods in Enzymology; Academic Press: Waltham, MA, USA, 1962; Volume 5, pp. 61-68.
47. Bradford, M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 1976, 72, 248-54.
48. Council for International Organizations of Medical Sciences. International ethical guidelines for biomedical research involving human subjects. Bull. Med. Ethics 2002, 182, 17-23.
49. Gazak, R.; Valentova, K.; Fuksova, K.; Marhol, P.; Kuzma, M.; Medina, M.A.; Oborna, I.; Ulrichova, J.; Kren, V. Synthesis and antiangiogenic activity of new silybin galloyl esters. J. Med. Chem. 2011, 54, 7397-7407.
50. Atanasova, G.; Jans, R.; Zhelev, N.; Mitev, V.; Poumay, Y. Effects of the cyclin-dependent kinase inhibitor CYC202 (R-roscovitine) on the physiology of cultured human keratinocytes. Biochem. Pharmacol. 2005, 70, 824-836.