About: Preparation of silybin phase II metabolites: Streptomyces catalyzed glucuronidation

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About: Preparation of silybin phase II metabolites: Streptomyces catalyzed glucuronidation Goto Sponge NotDistinct Permalink

An Entity of Type : http://linked.opendata.cz/ontology/domain/vavai/Vysledek, within Data Space : linked.opendata.cz associated with source document(s)

Attributes	Values
rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://dx.doi.org/10.1016/j.molcatb.2014.02.008
Description	Flavonolignan silybin is a major component of the silymarin complex isolated from seeds of the milk thistle (Silybum marianum) having strong antioxidant and hepatoprotective effects, and also anticancer, chemoprotective, dermatoprotective and hypocholesterolemic activities. Natural silybin (silibinin in pharmacological literature) is a mixture of two diastereomers: silybin A and silybin B. Their metabolism is strongly linked to Phase II biotransformations and respective conjugates are rapidly excreted in bile and urine. Conjugation reactions of both silybins are strictly stereoselective. Therefore, optically pure compounds must be used for metabolic studies. The aim of this study was to obtain the glucuronidated metabolites of both silybin A and B. Streptomyces sp. strain M52104 was found to be a highly effective tool for the preparation of silybin A-20-O-beta-glucuronide, silybin B-20-O-beta-glucuronide, silybin glucuronide and silybin B-7-O-beta-glucuronide and minor amounts of silybin A and B-5-O-beta-glucuronide. The glucuronides, which were thoroughly characterized by MS and NMR spectroscopy, can be used as invaluable authentic standards in metabolic studies of both silybin diastereomers. Flavonolignan silybin is a major component of the silymarin complex isolated from seeds of the milk thistle (Silybum marianum) having strong antioxidant and hepatoprotective effects, and also anticancer, chemoprotective, dermatoprotective and hypocholesterolemic activities. Natural silybin (silibinin in pharmacological literature) is a mixture of two diastereomers: silybin A and silybin B. Their metabolism is strongly linked to Phase II biotransformations and respective conjugates are rapidly excreted in bile and urine. Conjugation reactions of both silybins are strictly stereoselective. Therefore, optically pure compounds must be used for metabolic studies. The aim of this study was to obtain the glucuronidated metabolites of both silybin A and B. Streptomyces sp. strain M52104 was found to be a highly effective tool for the preparation of silybin A-20-O-beta-glucuronide, silybin B-20-O-beta-glucuronide, silybin glucuronide and silybin B-7-O-beta-glucuronide and minor amounts of silybin A and B-5-O-beta-glucuronide. The glucuronides, which were thoroughly characterized by MS and NMR spectroscopy, can be used as invaluable authentic standards in metabolic studies of both silybin diastereomers. (en)
Title	Preparation of silybin phase II metabolites: Streptomyces catalyzed glucuronidation Preparation of silybin phase II metabolites: Streptomyces catalyzed glucuronidation (en)
skos:prefLabel	Preparation of silybin phase II metabolites: Streptomyces catalyzed glucuronidation Preparation of silybin phase II metabolites: Streptomyces catalyzed glucuronidation (en)
skos:notation	RIV/00216208:11310/14:10289023!RIV15-MSM-11310___
http://linked.open...avai/riv/aktivita	I P S
http://linked.open...avai/riv/aktivity	I, P(GAP301/11/0662), P(LD13041), S
http://linked.open...iv/cisloPeriodika	April 2014
http://linked.open...vai/riv/dodaniDat	2015
http://linked.open...aciTvurceVysledku	Purchartová, Kateřina
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Karlova v Praze / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	39055
http://linked.open...ai/riv/idVysledku	RIV/00216208:11310/14:10289023
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Glucuronyl transferase; Glucuronidation; Silymarin; Silibinin; Silybin diastereomers (en)
http://linked.open.../riv/klicoveSlovo	Silibinin Silymarin Glucuronidation Glucuronyl transferase Silybin diastereomers
http://linked.open...odStatuVydavatele	NL - Nizozemsko
http://linked.open...ontrolniKodProRIV	[460926EE1B95]
http://linked.open...i/riv/nazevZdroje	Journal of Molecular Catalysis - B Enzymatic
http://linked.open...in/vavai/riv/obor	CE
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	6 (xsd:int)
http://linked.open...vavai/riv/projekt	Supramolecular antioxidants protecting proteins against oxidative damage Elucidation of the mechanism of flavonoid-dependent cardioprotection and changes in the bioenergetic status of the cell
http://linked.open...UplatneniVysledku	2014
http://linked.open...v/svazekPeriodika	102
http://linked.open...iv/tvurceVysledku	Křen, Vladimír Kuzma, Marek Marhol, Petr Purchartová, Kateřina Azerad, Robert Charrier, Cedric
http://linked.open...ain/vavai/riv/wos	000335872900024
issn	1381-1177
number of pages	7 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.molcatb.2014.02.008
http://localhost/t...ganizacniJednotka	11310

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