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Molecular mechanisms of silybin and 2,3-dehydrosilybin antiradical activity - role of individual hydroxyl groups

SYSNO ASEP	0328277
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Molecular mechanisms of silybin and 2,3-dehydrosilybin antiradical activity - role of individual hydroxyl groups
Title	Molekulární mechanismus antiradikálové aktivity silybinu a 2,3-dehydrosilybinu – úloha jednotlivých hydroxylových skupin
Author(s)	Gažák, Radek (MBU-M)_{RID, ORCID} Sedmera, Petr (MBU-M) Vrbacký, Marek (FGU-C)_{RID, ORCID} Vostálová, J. (CZ) Drahota, Zdeněk (FGU-C)_{RID, ORCID} Marhol, Petr (MBU-M)_RID Walterová, D. (CZ) Křen, Vladimír (MBU-M)_{RID, ORCID}
Source Title	Free Radical Biology and Medicine. - : Elsevier - ISSN 0891-5849 Roč. 46, č. 6 (2009), s. 745-758
Number of pages	14 s.
Language	eng - English
Country	US - United States
Keywords	silybin ; silymarin ; dehydrosilybin
Subject RIV	EE - Microbiology, Virology
R&D Projects	KJB400200701 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR)
	GA303/06/1261 GA ČR - Czech Science Foundation (CSF)
	GA303/08/0658 GA ČR - Czech Science Foundation (CSF)
CEZ	AV0Z50200510 - MBU-M (2005-2011)
	AV0Z50110509 - FGU-C (2005-2011)
UT WOS	000264061400006
DOI	10.1016/j.freeradbiomed.2008.11.016
Annotation	The flavonolignans silybin (1) and 2,3-dehydrosilybin (2) are important natural compounds with multiple biological activities operating at various cell levels. Many of these effects are connected with their radical-scavenging activities. The molecular mechanisms of the antioxidant activity of these compounds and even the functional groups responsible for this activity are not yet well known. Their mechanism can be inferred from the structures of the dimeric products obtained from radical-mediated reactions of selectively methylated derivatives of 1 and 2. The radical oxidation of 1 methylated at 7-OH and 2 methylated at both 3-OH and 7-OH yields C–C and C–O dimers that enable the molecular mechanism of their E-ring interaction with radicals to be elucidated and shows the importance of the 20-OH group in this respect. The pivotal role of the 3-OH group in the radical-scavenging activity of 2 was confirmed through the formation of another type of dimer from its selectively methylated derivative
Workplace	Institute of Microbiology
Contact	Eliška Spurná, eliska.spurna@biomed.cas.cz, Tel.: 241 062 231
Year of Publishing	2010

Number of the records: 1