0468176 - MBÚ 2017 RIV US eng J - Journal Article
Biedermann, David - Buchta, M. - Holečková, Veronika - Sedlák, David - Valentová, Kateřina - Cvačka, Josef - Bednárová, Lucie - Křenková, Alena - Kuzma, Marek - Škuta, Ctibor - Peikerová, Žaneta - Bartůněk, Petr - Křen, Vladimír
Silychristin: Skeletal Alterations and Biological Activities.
Journal of Natural Products. Roč. 79, č. 12 (2016), s. 3086-3092. ISSN 0163-3864. E-ISSN 1520-6025
R&D Projects: GA ČR(CZ) GA15-03037S; GA MZd(CZ) NV16-27317A; GA MŠMT LO1220; GA MŠMT LM2015063; GA MŠMT(CZ) LD15081
Institutional support: RVO:61388971 ; RVO:68378050 ; RVO:61388963
Keywords : Silychristin * skeletal alterations * biological activities
Subject RIV: CC - Organic Chemistry
Impact factor: 3.281, year: 2016

Silychristin is the second most abundant flavonolignan (after silybin) present in the fruits of Silybum marianum. A group of compounds containing silychristin (3) and its derivatives such as 2,3-dehydrosilychristin (4), 2,3-dehydroanhydrosilychristin (5), anhydrosilychristin (6), silyhermin (7), and isosilychristin (8) were studied. Physicochemical data of these compounds acquired at high resolution were compared. The absolute configuration of silyhermin (7) was proposed to be identical to silychristin A (3a) in ring D (10R,11S). The preparation of 2,3-dehydrosilychristin (4) was optimized. The Folin-Ciocalteau reduction and DPPH and ABTS radical scavenging assays revealed silychristin and its analogues to be powerful antioxidants, which were found to be more potent than silybin and 2,3-dehydrosilybin. Compounds 4-6 exhibited inhibition of microsomal lipoperoxidation (IC50 4-6 microM). Moreover, compounds 4-8 were found to be almost noncytotoxic for 10 human cell lines of different histogenetic origins. On the basis of these results, compounds 3-6 are likely responsible for most of the antioxidant properties of silymarin attributed traditionally to silybin (silibinin).
Permanent Link: http://hdl.handle.net/11104/0266155