Silybin

Names

[ Name ]:
Silybin

[Synonym ]:
(2R,3R)-2-[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
silibin
silybin
Silybin
Silybin A,B (mixture)

Biological Activity

[Description]:

Silybin is a flavonolignan isolated from milk thistle (Silybum marianum) seeds. Silybin induces apoptosis and exhibits hepatoprotective, antioxidant, anti-inflammatory, anti-cancer activity[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

[In Vitro]

Silybin (0-200 mM; for 72 hours) has growth inhibition in a time- and dose-dependent manner[1]. Silybin (68 μM; for 72 hours) induces apoptosis and increases the cells in G1-phase of ~22%[1]. Silybin (68 μM; for 72 hours) induces AKT activity inhibition[1]. Cell Viability Assay[1] Cell Line: HepG2 cell growth Concentration: 0-200 mM Incubation Time: For 72 hours Result: Had growth inhibition in a time- and dose-dependent manner with an IC50 of 68 μM. Apoptosis Analysis[1] Cell Line: HepG2 cell growth Concentration: 68 μM Incubation Time: For 72 hours Result: Induced apoptosis in a higher number of cells (60%) when compared to untreated cells. Cell Cycle Analysis[1] Cell Line: HepG2 cell growth Concentration: 68 μM Incubation Time: For 72 hours Result: Increased the cells in G1-phase of ~22% and decreased of 47% the cells in S-phase. Western Blot Analysis[1] Cell Line: HepG2 cell growth Concentration: 68 μM Incubation Time: For 72 hours Result: Induced AKT activity inhibition.

[In Vivo]

Silybin (50, 100 mg/kg/day; given intragastrically for the last 4 weeks) significantly lowers both serum and hepatic lipid accumulation[2]. Animal Model: Male C57BL/6J mice (6-8 weeks old) with nonalcoholic fatty liver disease (NAFLD)[2] Dosage: 50, 100 mg/kg Administration: Given intragastrically; daily; for the last 4 weeks Result: Significantly lowered both serum and hepatic lipid accumulation.

[References]

[1]. Silvia Zappavigna, et al. Silybin-Induced Apoptosis Occurs in Parallel to the Increase of Ceramides Synthesis and miRNAs Secretion in Human Hepatocarcinoma Cells. Int J Mol Sci. 2019 May 3;20(9):2190.

[2]. Runbin Sun, et al. Silybin ameliorates hepatic lipid accumulation and modulates global metabolism in an NAFLD mouse model. Biomed Pharmacother. 2020 Mar;123:109721.

Chemical & Physical Properties

[ Melting Point ]:
152-153°C

[ Molecular Formula ]:
C₂₅H₂₂O₁₀

[ Molecular Weight ]:
482.43600

[ Exact Mass ]:
482.12100

[ PSA ]:
155.14000

[ LogP ]:
2.36270

[ Storage condition ]:
Refrigerator

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-37/39

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
DJ2981770

Articles

The in-vitro effect of complementary and alternative medicines on cytochrome P450 2C9 activity.

J. Pharm. Pharmacol. 66(9) , 1339-46, (2014)

The aim of this study is to establish the inhibitory effects of 14 commonly used complementary and alternative medicines (CAM) on the metabolism of cytochrome P450 2C9 (CYP2C9) substrates 7-methoxy-4-...

Engineered silybin nanoparticles educe efficient control in experimental diabetes.

PLoS ONE 9(7) , e101818, (2014)

Silybin, is one imminent therapeutic for drug induced hepatotoxicity, human prostate adenocarcinoma and other degenerative organ diseases. Recent evidences suggest that silybin influences gluconeogene...

Isolation and purification of diastereoisomeric flavonolignans from silymarin by binary-column recycling preparative high-performance liquid chromatography.

J. Sep. Sci. 37(17) , 2300-6, (2014)

Silymarin extracted from Silybum marianum (L.) Gaertn consists of a large number of flavonolignans, of which diastereoisomeric flavonolignans including silybin A and silybin B, and isosilybin A and is...