期刊
JOURNAL OF NATURAL PRODUCTS
卷 79, 期 12, 页码 3086-3092出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.6b00750
关键词
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资金
- Czech Science Foundation [15-03037S]
- Ministry of Health of the Czech Republic [16-27317A]
- Ministry of Education, Youth and Sports of the Czech Republic [LO1220, LM2015063, LD15081]
- Institutional Concept of the Institute of Microbiology Prague [RVO61388971]
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), sily-hermin (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 mu M). 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).
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