메뉴 건너뛰기




Volumn 45, Issue 10, 2010, Pages 1657-1663

Large-scale separation of silybin diastereoisomers using lipases

Author keywords

Diastereoselectivity; Lipase; Novozym 435; Silibinin; Silybin A; Silymarin

Indexed keywords

DIASTEREO-SELECTIVITY; NOVOZYM435; SILIBININ; SILYBIN; SILYMARIN;

EID: 77956174741     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2010.06.019     Document Type: Article
Times cited : (56)

References (39)
  • 1
    • 33847265733 scopus 로고    scopus 로고
    • Silybin and silymarin-new and emerging applications in medicine
    • Gažák R., Walterová D., Křen V. Silybin and silymarin-new and emerging applications in medicine. Curr Med Chem 2007, 14:315-338.
    • (2007) Curr Med Chem , vol.14 , pp. 315-338
    • Gažák, R.1    Walterová, D.2    Křen, V.3
  • 2
    • 0028956461 scopus 로고
    • Silybum marianum (Carduus marianus)
    • Morazzoni P., Bombardelli E. Silybum marianum (Carduus marianus). Fitoterapia 1995, 66:3-42.
    • (1995) Fitoterapia , vol.66 , pp. 3-42
    • Morazzoni, P.1    Bombardelli, E.2
  • 3
    • 29344461962 scopus 로고    scopus 로고
    • Effect of silymarin and its polyphenolic fraction on cholesterol absorption in rats
    • Sobolová L., Škottová N., Večeřa R., Urbánek K. Effect of silymarin and its polyphenolic fraction on cholesterol absorption in rats. Pharmacol Res 2006, 53:104-112.
    • (2006) Pharmacol Res , vol.53 , pp. 104-112
    • Sobolová, L.1    Škottová, N.2    Večeřa, R.3    Urbánek, K.4
  • 4
    • 0017371328 scopus 로고
    • Callus- und Suspensionskulturen von Silybum marianum
    • Schrall R., Becker H. Callus- und Suspensionskulturen von Silybum marianum. Planta Med 1977, 32:27-32.
    • (1977) Planta Med , vol.32 , pp. 27-32
    • Schrall, R.1    Becker, H.2
  • 5
    • 0141566436 scopus 로고    scopus 로고
    • Molecular structure and stereochemistry of silybin A, silybin B, isosilybin A, and isosilybin B, isolated from Silybum marianum (milk thistle)
    • Lee D.Y.-W., Liu Y. Molecular structure and stereochemistry of silybin A, silybin B, isosilybin A, and isosilybin B, isolated from Silybum marianum (milk thistle). J Nat Prod 2003, 66:1171-1174.
    • (2003) J Nat Prod , vol.66 , pp. 1171-1174
    • Lee, D.Y.-W.1    Liu, Y.2
  • 6
    • 0141974905 scopus 로고    scopus 로고
    • Complete isolation and characterization of silybins and isosilybins from milk thistle (Silybum marianum)
    • Kim N.-C., Graf T.N., Sparacino C.M., Wani M.C., Wall M.E. Complete isolation and characterization of silybins and isosilybins from milk thistle (Silybum marianum). Org Biomol Chem 2003, 1:1684-1689.
    • (2003) Org Biomol Chem , vol.1 , pp. 1684-1689
    • Kim, N.-C.1    Graf, T.N.2    Sparacino, C.M.3    Wani, M.C.4    Wall, M.E.5
  • 11
    • 0032008339 scopus 로고    scopus 로고
    • Milk thistle (Silybum marianum) for the therapy of liver disease
    • Flora K., Hahn M., Rosen H., Benner K. Milk thistle (Silybum marianum) for the therapy of liver disease. Am J Gastroenterol 1998, 93:139-143.
    • (1998) Am J Gastroenterol , vol.93 , pp. 139-143
    • Flora, K.1    Hahn, M.2    Rosen, H.3    Benner, K.4
  • 12
    • 33744971866 scopus 로고    scopus 로고
    • Silybin and silymarin-new effects and applications
    • Křen V., Walterová D. Silybin and silymarin-new effects and applications. Biomed Pap 2005, 149:29-41.
    • (2005) Biomed Pap , vol.149 , pp. 29-41
    • Křen, V.1    Walterová, D.2
  • 13
    • 39649096744 scopus 로고    scopus 로고
    • Mechanism of the antioxidant action of silybin and 2,3-dehydrosilybin flavonolignans: a joint experimental and theoretical study
    • Trouillas P., Marsal P., Svobodová A., Vostálová J., Hrbáč J., Gažák R., 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.
    • (2008) J Phys Chem A , vol.112 , pp. 1054-1063
    • Trouillas, P.1    Marsal, P.2    Svobodová, A.3    Vostálová, J.4    Hrbáč, J.5    Gažák, R.6
  • 14
    • 60449093727 scopus 로고    scopus 로고
    • Molecular mechanisms of silybin and 2,3-dehydrosilybin antiradical activity-role of individual hydroxyl groups
    • Gažák R., Sedmera P., Vrbacký M., Vostálová J., Drahota Z., Marhol P., et al. Molecular mechanisms of silybin and 2,3-dehydrosilybin antiradical activity-role of individual hydroxyl groups. Free Radic Biol Med 2009, 46:745-758.
    • (2009) Free Radic Biol Med , vol.46 , pp. 745-758
    • Gažák, R.1    Sedmera, P.2    Vrbacký, M.3    Vostálová, J.4    Drahota, Z.5    Marhol, P.6
  • 18
    • 33745002041 scopus 로고    scopus 로고
    • Prostate cancer chemoprevention by silibinin: bench to bedside
    • Singh R.P., Agarwal R. Prostate cancer chemoprevention by silibinin: bench to bedside. Mol Carcinog 2006, 45:436-442.
    • (2006) Mol Carcinog , vol.45 , pp. 436-442
    • Singh, R.P.1    Agarwal, R.2
  • 19
    • 33646471119 scopus 로고    scopus 로고
    • New derivatives of silybin and 2,3-dehydrosilybin and their cytotoxic and P-glycoprotein modulatory activity
    • Džubák P., Hajdúch M., Gažák R., Svobodová A., Psotová J., Walterová D., et al. New derivatives of silybin and 2,3-dehydrosilybin and their cytotoxic and P-glycoprotein modulatory activity. Bioorg Med Chem 2006, 14:3793-3810.
    • (2006) Bioorg Med Chem , vol.14 , pp. 3793-3810
    • Džubák, P.1    Hajdúch, M.2    Gažák, R.3    Svobodová, A.4    Psotová, J.5    Walterová, D.6
  • 20
    • 20144372639 scopus 로고    scopus 로고
    • Milk thistle and prostate cancer: differential effects of pure flavonolignans from Silybum marianum on antiproliferative end points in human prostate carcinoma cells
    • Davis-Searles P.R., Nakanishi Y., Kim N.-Ch., Graf T.N., Oberlies N.H., Wani M.C., et al. Milk thistle and prostate cancer: differential effects of pure flavonolignans from Silybum marianum on antiproliferative end points in human prostate carcinoma cells. Cancer Res 2005, 65:4448-4457.
    • (2005) Cancer Res , vol.65 , pp. 4448-4457
    • Davis-Searles, P.R.1    Nakanishi, Y.2    Kim, N.-C.3    Graf, T.N.4    Oberlies, N.H.5    Wani, M.C.6
  • 21
    • 26444583841 scopus 로고    scopus 로고
    • Effects of silymarin flavonolignans and synthetic silybin derivatives on estrogen and aryl hydrocarbon receptor activation
    • Plíšková M., Vondráček J., Křen V., Gažák R., Sedmera P., Walterová D., et al. Effects of silymarin flavonolignans and synthetic silybin derivatives on estrogen and aryl hydrocarbon receptor activation. Toxicology 2005, 215:80-89.
    • (2005) Toxicology , vol.215 , pp. 80-89
    • Plíšková, M.1    Vondráček, J.2    Křen, V.3    Gažák, R.4    Sedmera, P.5    Walterová, D.6
  • 25
    • 38649113235 scopus 로고    scopus 로고
    • Preparative chromatographic purification of diastereomers of silybin and their quantification in human plasma by liquid chromatography-tandem mass spectrometry
    • Li W., Han J., Li Z.N., Li X., Zhou S., Liu C. Preparative chromatographic purification of diastereomers of silybin and their quantification in human plasma by liquid chromatography-tandem mass spectrometry. J Chromatogr B 2008, 862:51-57.
    • (2008) J Chromatogr B , vol.862 , pp. 51-57
    • Li, W.1    Han, J.2    Li, Z.N.3    Li, X.4    Zhou, S.5    Liu, C.6
  • 26
    • 36949024949 scopus 로고    scopus 로고
    • Gram-scale purification of flavonolignan diastereoisomers from Silybum marianum (milk thistle) extract in support of preclinical in vivo studies for prostate cancer chemoprevention
    • Graf T.N., Wani M.C., Agarwal R., Kroll D.J., Oberlies N.H. Gram-scale purification of flavonolignan diastereoisomers from Silybum marianum (milk thistle) extract in support of preclinical in vivo studies for prostate cancer chemoprevention. Planta Med 2007, 73:1495-1501.
    • (2007) Planta Med , vol.73 , pp. 1495-1501
    • Graf, T.N.1    Wani, M.C.2    Agarwal, R.3    Kroll, D.J.4    Oberlies, N.H.5
  • 28
    • 33846209146 scopus 로고    scopus 로고
    • Trends in lipase-catalyzed asymmetric access to enantiomerically pure/enriched compounds
    • Ghanem A. Trends in lipase-catalyzed asymmetric access to enantiomerically pure/enriched compounds. Tetrahedron 2007, 63:1721-1754.
    • (2007) Tetrahedron , vol.63 , pp. 1721-1754
    • Ghanem, A.1
  • 33
    • 20644469267 scopus 로고
    • Quantitative analyses of biochemical kinetic resolutions of enantiomers
    • Chen C.S., Fujimoto Y., Girdaukas G., Sih C.J. Quantitative analyses of biochemical kinetic resolutions of enantiomers. J Am Chem Soc 1982, 104:7294-7299.
    • (1982) J Am Chem Soc , vol.104 , pp. 7294-7299
    • Chen, C.S.1    Fujimoto, Y.2    Girdaukas, G.3    Sih, C.J.4
  • 34
  • 35
    • 68649084001 scopus 로고    scopus 로고
    • Novozym 435 displays very different selectivity compared to lipase from Candida antarctica B adsorbed on other hydrophobic supports
    • Cabrera Z., Fernandez-Lorente G., Fernandez-Lafuente R., Palomo J.M., Guisan J.M. Novozym 435 displays very different selectivity compared to lipase from Candida antarctica B adsorbed on other hydrophobic supports. J Mol Catal B: Enzym 2009, 57:171-176.
    • (2009) J Mol Catal B: Enzym , vol.57 , pp. 171-176
    • Cabrera, Z.1    Fernandez-Lorente, G.2    Fernandez-Lafuente, R.3    Palomo, J.M.4    Guisan, J.M.5
  • 36
    • 68049137644 scopus 로고    scopus 로고
    • Enzymatic preparation of acylated derivatives of silybin in organic and ionic liquid media and evaluation of their antitumor proliferative activity
    • Theodosiou E., Katsoura M.H., Loutrari H., Purchartová K., Křen V., Kolisis F.N., et al. Enzymatic preparation of acylated derivatives of silybin in organic and ionic liquid media and evaluation of their antitumor proliferative activity. Biocatal Biotransform 2009, 27:161-169.
    • (2009) Biocatal Biotransform , vol.27 , pp. 161-169
    • Theodosiou, E.1    Katsoura, M.H.2    Loutrari, H.3    Purchartová, K.4    Křen, V.5    Kolisis, F.N.6
  • 37
    • 0028855057 scopus 로고
    • Role of solvents in the control of enzyme selectivity in organic media
    • Carrea G., Ottolina G., Riva S. Role of solvents in the control of enzyme selectivity in organic media. Trends Biotechnol 1995, 13:63-70.
    • (1995) Trends Biotechnol , vol.13 , pp. 63-70
    • Carrea, G.1    Ottolina, G.2    Riva, S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.