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S0417

Sigma-Aldrich

Silibinin

≥98% (HPLC)

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Synonym(s):
2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-6-(3,5,7-trihydroxy-4-oxobenzopyran-2-yl)benzodioxin, Silybin
Empirical Formula (Hill Notation):
C25H22O10
CAS Number:
22888-70-6
Molecular Weight:
482.44
EC Number:
245-302-5
MDL number:
MFCD03225424
UNSPSC Code:
12352204
PubChem Substance ID:
24899437
NACRES:
NA.83

Quality Level

200

Assay

≥98% (HPLC)

storage temp.

−20°C

SMILES string

COc1cc(ccc1O)[C@@H]2Oc3cc(ccc3O[C@H]2CO)[C@H]4Oc5cc(O)cc(O)c5C(=O)[C@H]4O

InChI

1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23+,24-,25?/m0/s1

InChI key

SEBFKMXJBCUCAI-ILJKEPSESA-N

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General description

Silibinin, a principal component of silymarin, is a flavonolignan and an orally active flavonoid. It is isolated from the seeds of milk thistle (Sylibum marianum L).

Application

Silibinin has been used:
  • to study its effect on gene expression levels of various proteins involved in chromatin regulations of prostate cancer, by real time polymerase chain reaction (RT-PCR)
  • to study its effect on cell proliferation in platelet-derived growth factor (PDGF)-treated human tenon′s fibroblasts (HTFs) by investigating the expression of proliferating cell nuclear antigen (PCNA) and by water-soluble tetrazolium salt (WST-1) assay
  • to examine its effect on gene expression levels of stromelysine 1 (STM1), acetyl hexoseamines and collagen production during skin wound healing
  • to study its inhibitory effect on Escherichia coli ATP synthase

Biochem/physiol Actions

Silibinin functions as a hepatoprotectant in patients with acute and chronic liver injury. This flavonoid fights against various cancer cells including, prostate, skin, breast, colon, lung, bladder and hepatocellular carcinoma (HCC). Silibinin exhibits its efficacy as an anti-cancer agent by blocking the secretion of proangiogenic factors from tumor cells, and by hindering growth and inducing apoptotic death of endothelial cells. In addition, it also interrupts capillary tube formation on Matrigel. Silibinin might be a good candidate for chemoprevention of prostate cancer (PC). It might be used as a potential therapeutic regimen for the treatment of endometriosis in vitro and in vivo.

Components

Contains both A and B diastereomers

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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C H Lin et al.
British journal of pharmacology, 168(4), 920-931 (2012-09-26)
Hypoxia-mediated neovascularization plays an important role in age-related macular degeneration (AMD). There are few animal models or effective treatments for AMD. Here, we investigated the effects of the flavonoid silibinin on hypoxia-induced angiogenesis in a rat AMD model. Retinal pigmented
A novel role of silibinin as a putative epigenetic modulator in human prostate carcinoma
Anestopoulos L, et al.
Molecules (Basel), 22(1), 62-62 (2017)
Zoe Mariño et al.
Journal of hepatology, 58(3), 415-420 (2012-10-16)
Hepatitis C recurrence after liver transplantation (LT) is the main problem of most transplant programs. We aimed at assessing the antiviral activity and safety of intravenous silibinin (SIL) administered daily during the peri-transplant period. This was a single-centre, prospective, randomized
Silibinin efficacy against human hepatocellular carcinoma
Varghese L, et al.
Clinical Cancer Research, 11(23), 8441-8448 (2005)
Chapla Agarwal et al.
Oncogene, 22(51), 8271-8282 (2003-11-14)
Silymarin, a defined mixture of natural flavonoid, has recently been shown to have potent cancer chemopreventive efficacy against colon carcinogenesis in rat model; however, the mechanism of such efficacy is not elucidated. Here, using pure active agent in silymarin, namely
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