Preparation of silybin and isosilybin sulfates by sulfotransferase from Desulfitobacterium hafniense

0395307 - MBÚ 2014 RIV NL eng J - Článek v odborném periodiku
Marhol, Petr - Hartog, F. A. - van der Horst, A. M. - Wever, R. - Purchartová, Kateřina - Fuksová, Kateřina - Kuzma, Marek - Cvačka, Josef - Křen, Vladimír
Preparation of silybin and isosilybin sulfates by sulfotransferase from Desulfitobacterium hafniense.
Journal of Molecular Catalysis B-Enzymatic. Roč. 89, MAY (2013), s. 24-27. ISSN 1381-1177
Grant CEP: GA ČR(CZ) GAP301/11/0662; GA MŠMT(CZ) LD11051; GA MŠMT(CZ) ME10027
Institucionální podpora: RVO:61388971 ; RVO:61388963
Klíčová slova: Silybin * Silibinin * Isosilybin
Kód oboru RIV: CE - Biochemie
Impakt faktor: 2.745, rok: 2013

Flavonolignans silybin and isosilybin are major components of silymarin complex isolated from seeds of the milk thistle (Silybum marianum) featuring strong antioxidant and hepatoprotective effects, and also anticancer, chemoprotective, dermatoprotective and hypocholesterolemic activities. Natural silybin and isosilybin are mixtures of diastereoisomers: silybin/isosilybin A (1a, 1b) and silybin/isosilybin B (2a, 2b). The metabolism of these compounds is supposed to be strongly linked to Phase II of biotransformation and the respective conjugates are rapidly excreted in bile and urine. The aim of this study was to obtain optically pure sulfated metabolites of both silybins and isosilybins. Aryl-sulfate sulfotransferase (EC 2.8.2.22) from Desulfitobacterium hafniense was found to be a highly effective tool for the regiospecific enzymatic synthesis of silybin A-20-O-sulfate, silybin B-20-O-sulfate, isosilybin A-20-O-sulfate and isosilybin B-20-O-sulfate providing nearly quantitative yields and employing cheap p-nitrophenyl sulfate as sulfate donor. The isolated sulfated products will be used as authentic standards in metabolic studies of both silybins and isosilybins. (C) 2012 Elsevier B.V. All rights reserved
Trvalý link: http://hdl.handle.net/11104/0223378