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Merck
CN

S0417

Silibinin

≥98% (HPLC)

Synonym(s):

2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-6-(3,5,7-trihydroxy-4-oxobenzopyran-2-yl)benzodioxin, Silybin

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About This Item

Empirical Formula (Hill Notation):
C25H22O10
CAS Number:
Molecular Weight:
482.44
NACRES:
NA.83
PubChem Substance ID:
UNSPSC Code:
12352204
EC Number:
245-302-5
MDL number:
Assay:
≥98% (HPLC)
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Quality Level

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

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.

Other Notes

Contains both A and B diastereomers


pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves



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Articles

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

Chronic inflammation is an underlying factor in the development and progression of many of the chronic diseases of aging, such as arthritis, atherosclerosis, diabetes, and cancer.

抗氧化剂可保护生物系统免受含氧自由基和氧化还原过渡金属离子(如铁、铜和镉)引起的氧化损伤。

Related Content


Silibinin Inhibits Platelet-Derived Growth Factor-Driven Cell Proliferation via Downregulation of N-Glycosylation in Human Tenon's Fibroblasts in a Proteasome-Dependent Manner
Chen YH, et al.
Testing, 11(12), e0168765-e0168765 (2016)
Silibinin efficacy against human hepatocellular carcinoma
Varghese L, et al.
Clinical Cancer Research, 11(23), 8441-8448 (2005)
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



Global Trade Item Number

SKUGTIN
S0417-10G04061836830250
S0417-1G04061836830267