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)
Quality Segment
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
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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