About: Enzymatic oxidative dimerization of silymarin flavonolignans

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Dimerization of phenolic compounds can potentially enhance their biological (antioxidant) activity. We present here the selective oxidative dimerization of several flavonolignans from Silybum marianum seed extract, namely, silybin A (1a), silybin B (1b), silychristin (3), and silydianin (4) catalyzed by a laccase from Trametes versicolor. Selective benzylation of C-7 OH group of both silybins ensured the priority of the dimerization reaction, avoiding thus polymerization. C-C homodimers connected via E-rings of silybin A and B and silydianin dimers were successfully isolated after respective debenzylation. On the contrary, dimerization of 7-O-benzyl silychristin afforded a complex, inseparable mixture of the products. All isolated flavonolignan dimers exhibited significantly improved 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity compared to their monomers and, therefore, seem to be promising for further biological studies Dimerization of phenolic compounds can potentially enhance their biological (antioxidant) activity. We present here the selective oxidative dimerization of several flavonolignans from Silybum marianum seed extract, namely, silybin A (1a), silybin B (1b), silychristin (3), and silydianin (4) catalyzed by a laccase from Trametes versicolor. Selective benzylation of C-7 OH group of both silybins ensured the priority of the dimerization reaction, avoiding thus polymerization. C-C homodimers connected via E-rings of silybin A and B and silydianin dimers were successfully isolated after respective debenzylation. On the contrary, dimerization of 7-O-benzyl silychristin afforded a complex, inseparable mixture of the products. All isolated flavonolignan dimers exhibited significantly improved 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity compared to their monomers and, therefore, seem to be promising for further biological studies (en)
Title	Enzymatic oxidative dimerization of silymarin flavonolignans Enzymatic oxidative dimerization of silymarin flavonolignans (en)
skos:prefLabel	Enzymatic oxidative dimerization of silymarin flavonolignans Enzymatic oxidative dimerization of silymarin flavonolignans (en)
skos:notation	RIV/61388971:_____/14:00435748!RIV15-GA0-61388971
http://linked.open...avai/riv/aktivita	I P
http://linked.open...avai/riv/aktivity	I, P(GP14-14373P), P(LD13041)
http://linked.open...iv/cisloPeriodika	NOV 2014
http://linked.open...vai/riv/dodaniDat	2015
http://linked.open...aciTvurceVysledku	Valentová, Kateřina Kuzma, Marek Biedermann, David Vavříková, Eva Křen, Vladimír
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	Mikrobiologický ústav AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	14814
http://linked.open...ai/riv/idVysledku	RIV/61388971:_____/14:00435748
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Silybin dimers; Silydianin dimer; Silymarin (en)
http://linked.open.../riv/klicoveSlovo	Silybin dimers Silydianin dimer Silymarin
http://linked.open...odStatuVydavatele	NL - Nizozemsko
http://linked.open...ontrolniKodProRIV	[F1460638D00A]
http://linked.open...i/riv/nazevZdroje	Journal of Molecular Catalysis B-Enzymatic
http://linked.open...in/vavai/riv/obor	CE
http://linked.open...ichTvurcuVysledku	5 (xsd:int)
http://linked.open...cetTvurcuVysledku	9 (xsd:int)
http://linked.open...vavai/riv/projekt	Supramolecular antioxidants protecting proteins against oxidative damage Syntéza nových derivátů a metabolitů quercetin-3-O-glukosidu
http://linked.open...UplatneniVysledku	2014
http://linked.open...v/svazekPeriodika	109
http://linked.open...iv/tvurceVysledku	Křen, Vladimír Kuzma, Marek Riva, S. Vavříková, Eva Valentová, Kateřina Biedermann, David Fronza, G. Gavezzotti, P. Kudanga, T.
http://linked.open...ain/vavai/riv/wos	000343854100004
issn	1381-1177
number of pages	6 (xsd:int)
http://bibframe.org/vocab/doi	10.1016/j.molcatb.2014.07.012

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