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Silybin and silymarin – short introduction

Silybin (1, Scheme 1) is a flavonolignan contained among other components in the silymarin mixture, extracted from the seeds of milk thistle (Silybum marianum – Figure 1). Silymarin also contains its congeners, e.g., isosilybin, silychristin, silydianin, 2,3-dehydrosilybin, and taxifolin and ca 30 % of an undefined polymeric phenolic fraction (Scheme 2) [].

Scheme 1. Silybin diastereoisomers

Silybin A and Silybin B

Figure 1. (L.) Gaertn.

The has been recognized since ancient times for the treatment of various liver and gastrointestinal diseases including those associated with alcohol abuse and environmental toxin exposure []. These effects are directly related to its well known antioxidant (radical scavenging) activities [1,3]; we have recently described the [].

Other beneficial effects of silybin/silymarin include as well as hypocholestero­lemic, cardioprotective, and neuroprotective effects [,8]. For example, silybin is in in the US for the treatment of prostate adenocarcinoma []. Silybin activities are linked to numerous effects at the cellular and molecular level, such as , modulation of drug transporters (P-glycoprotein) [], and a specific action on DNA-expression via the (NF-κB) [].

Scheme 2. Silybin congeners contained in silymarin

Silybin congeners contained in silymarin

References

  1. Gažák R, Walterová D, Křen V. Silybin and silymarin – new and emerging applications in medicine. Curr Med Chem 2007;14:315–338
  2. Flora K, Hahn M, Rosen H, Benner K. Milk thistle (Silybum marianum) for the therapy of liver disease. Am J Gastroenterol 1998;93:139–143
  3. Křen V, Walterová D. Silybin and silymarin – new effects and applications. Biomed Papers 2005;149:29–41
  4. Trouillas P, Marsal P, Svobodová A, Vostálová J, Hrbáč J, Gažák R, Křen V, Lazzaroni R, Duroux J-L, Sedmera P, Walterová D. Mechanism of the antioxidant action of silybin and 2,3-dehydrosilybin flavonolignans: A joint experimental and theoretical study. J Phys Chem A 2008;112:10­54–1063
  5. Gažák R, Sedmera P, Vrbacký M, Vostálová J, Drahota Z, Marhol P, Walterová D, Křen V. Molecular mechanisms of silybin and 2,3-dehydrosilybin antiradical activity- role of individual hydroxyl groups. Free Radic Biol Med 2009;46:745–758
  6. Gažák R, Sedmera P, Marzorati M, Riva S, Křen V. Laccase-mediated dimerization of the flavonolignan Silybin. J Mol Catal B-Enzym 2008;50:87–92
  7. Gažák R, Svobodová A, Psotová J, Sedmera P, Přikrylová V, Walterová D, Křen V. Oxidised derivatives of silybin and their antiradical and antioxidant activity. Bioorg Med Chem 2004;12:5677–87
  8. Agarwal R, Agarwal C, Ichikawa H, Singh RP, Aggarwal BB. Anticancer potential of silymarin: From bench to bed side. Anticancer Res 2006;26:4457–4498
  9. Singh RP, Agarwal R. Prostate cancer chemoprevention by silibinin: bench to bedside. Mol Carcinogen 2006;45:436–442
  10. Džubák P, Hajdúch M, Gažák R, Svobodová A, Psotová J, Walterová D, Sedmera P, Křen V. New derivatives of silybin and 2,3-dehydrosilybin and their cytotoxic and P-glycoprotein modulatory activity. Bioorg Med Chem 2006;14:3793–3810

Institute of Microbiology - Czech Academy of Sciences