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Title: Enzymatic oxidative dimerization of silymarin flavonolignans
Authors: Gavezzotti, P
Vavríková, E
Valentová, K
Fronzaa, G
Kudangaa, T
Kuzma, M
Rivaa, S
Biedermannb, D
Kren, V
Keywords: Silybin dimers;Silydianin dimer;Silymarin;Laccase;Trametes versicolor laccase;DPPH assay
Issue Date: 2014
Publisher: Elsevier
Abstract: 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 ofthe 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.
Appears in Collections:Appsc - Journal Articles (DHET subsidised)

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