Preparation of silybin and isosilybin sulfates by sulfotransferase from Desulfitobacterium hafniense
| Autor: | Aloysius F. Hartog, Marek Kuzma, Michael A. van der Horst, Josef Cvačka, Petr Marhol, Kateřina Purchartová, Kateřina Fuksová, Vladimír Křen, Ron Wever |
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| Přispěvatelé: | Biocatalysis (HIMS, FNWI) |
| Rok vydání: | 2013 |
| Předmět: |
Sulfotransferase
Milk Thistle biology Stereochemistry Process Chemistry and Technology Silibinin Desulfitobacterium hafniense Bioengineering biology.organism_classification Biochemistry Catalysis Silybum marianum Flavonolignans chemistry.chemical_compound Sulfation chemistry Biotransformation Organic chemistry |
| Zdroj: | Journal of Molecular Catalysis B-Enzymatic, 89, 24-27. Elsevier |
| ISSN: | 1381-1177 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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