Silybin
Silybin is a phytoestrogen and flavonoid originally found in the seeds of the milk thistle plant (Silybum). Silybin exhibits anti-diabetic, anti-inflammatory, anti-angiogenic, anticancer chemotherapeutic, and chemopreventive activities. In cellular and animal models of hepatocellular carcinoma, silybin increases expression of TRAIL and DR-5, activates caspase signaling, and decreases tumor growth and inflammatory cytokine release. In animal models of diabetes, silybin decrease Hb1Ac levels as well as serum triglycerides, cholesterol, and glucose in pancreatic β cells. Additionally, silybin inhibits IL-1β-induced pro-inflammatory cytokine expression and suppresses translocation of NF-κB in vitro. In animal models, this compound suppresses expression of HIF-1α and VEGF, decreases microvessel density, and delays UV-induced carcinogenesis.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18972455
| Cas No. |
22888-70-6 |
|---|---|
| Purity |
≥97% |
| Formula |
C25H22O10 |
| Formula Wt. |
482.44 |
| Chemical Name |
(2R,3R)-2-[(2R,3R)-2,3-Dihydro-3-(4-hydroxy-3- methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin- 6-yl]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran- 4-one AND (2R,3R)-2-[(2S,3S)-2,3-Dihydro-3-(4-hydroxy-3- methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin- 6-yl]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran- 4-one |
| IUPAC Name |
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one |
| Synonym |
Silibinin; Silybum substance E6; Silymarin I |
| Melting Point |
167°C °r 180°C(dec.) |
| Solubility |
Soluble in acetone, ethyl acetate, methanol or ethanol. Practically insoluble in water. |
| Appearance |
White to light yellow powder |
Bousserouel S, Bour G, Kauntz H, et al. Silibinin inhibits tumor growth in a murine orthotopic hepatocarcinoma model and activates the TRAIL apoptotic signaling pathway. Anticancer Res. 2012 Jul;32(7):2455-62. PMID: 22753701.
Wang Q, Liu M, Liu WW, et al. In vivo recovery effect of silibinin treatment on streptozotocin-induced diabetic mice is associated with the modulations of Sirt-1 expression and autophagy in pancreatic β-cell. J Asian Nat Prod Res. 2012;14(5):413-23. PMID: 22423887.
Au AY, Hasenwinkel JM, Frondoza CG. Silybin inhibits interleukin-1β-induced production of pro-inflammatory mediators in canine hepatocyte cultures. J Vet Pharmacol Ther. 2011 Apr;34(2):120-9. PMID: 21395602.
Gu M, Singh RP, Dhanalakshmi S, et al. Silibinin inhibits inflammatory and angiogenic attributes in photocarcinogenesis in SKH-1 hairless mice. Cancer Res. 2007 Apr 1;67(7):3483-91. PMID: 17409458.
Lee MH, Huang Z, Kim DJ, et al. Direct targeting of MEK1/2 and RSK2 by silybin induces cell-cycle arrest and inhibits melanoma cell growth. Cancer Prev Res (Phila). 2013 May;6(5):455-465. PMID: 23447564.
