کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
70017 48806 2013 4 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Preparation of silybin and isosilybin sulfates by sulfotransferase from Desulfitobacterium hafniense
موضوعات مرتبط
مهندسی و علوم پایه مهندسی شیمی کاتالیزور
پیش نمایش صفحه اول مقاله
Preparation of silybin and isosilybin sulfates by sulfotransferase from Desulfitobacterium hafniense
چکیده انگلیسی

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.

Figure optionsDownload as PowerPoint slideHighlights
► Optically pure stereomers of silybin and isosilybin were sulfated.
► Arylsulfotransferase from Desulfitobacterium hafniense was applied as a biocatalyst.
► The respective 20-O-sulfates were obtained and characterized by MS and NMR.
► Products will be used as authentic reference material in metabolic studies.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Molecular Catalysis B: Enzymatic - Volume 89, May 2013, Pages 24–27
نویسندگان
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