Enzymatic oxidative dimerization of silymarin flavonolignans

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388971%3A_____%2F14%3A00435748" target="_blank" >RIV/61388971:_____/14:00435748 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.molcatb.2014.07.012" target="_blank" >http://dx.doi.org/10.1016/j.molcatb.2014.07.012</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.molcatb.2014.07.012" target="_blank" >10.1016/j.molcatb.2014.07.012</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Enzymatic oxidative dimerization of silymarin flavonolignans

Popis výsledku v původním jazyce

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 dimersexhibited 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

Název v anglickém jazyce

Enzymatic oxidative dimerization of silymarin flavonolignans

Popis výsledku anglicky

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 dimersexhibited 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

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CE - Biochemie

OECD FORD obor

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Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2014

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Molecular Catalysis B-Enzymatic

ISSN

1381-1177

e-ISSN

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Svazek periodika

109

Číslo periodika v rámci svazku

NOV 2014

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

6

Strana od-do

24-30

Kód UT WoS článku

000343854100004

EID výsledku v databázi Scopus

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