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S0417

Sigma-Aldrich

Silibinin

≥98% (HPLC)

Synonim(y):

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

Wzór empiryczny (zapis Hilla):
C25H22O10
Numer CAS:
22888-70-6
Masa cząsteczkowa:
482.44
Numer WE:
245-302-5
Numer MDL:
MFCD03225424
Kod UNSPSC:
12352204
Identyfikator substancji w PubChem:
24899437
NACRES:
NA.83

Poziom jakości

200

Próba

≥98% (HPLC)

temp. przechowywania

−20°C

ciąg SMILES

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

Klucz InChI

SEBFKMXJBCUCAI-ILJKEPSESA-N

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Opis ogólny

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).

Zastosowanie

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

Działania biochem./fizjol.

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.

Komponenty

Contains both A and B diastereomers
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Piktogramy

Exclamation mark
GHS07

Hasło ostrzegawcze

Warning

Zwroty wskazujące rodzaj zagrożenia

H302

Zwroty wskazujące środki ostrożności

P264 - P270 - P301 + P312 - P501

Klasyfikacja zagrożeń

Acute Tox. 4 Oral

Kod klasy składowania

11 - Combustible Solids

Klasa zagrożenia wodnego (WGK)

WGK 2

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable

Środki ochrony indywidualnej

dust mask type N95 (US), Eyeshields, Gloves

Wybierz jedną z najnowszych wersji:

Certyfikaty analizy (CoA)

Lot/Batch Number
BCCG4575
BCCD0563
BCCD1066
BCCB3782
BCCB3721

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Katharina Esser-Nobis et al.
Hepatology (Baltimore, Md.), 57(3), 953-963 (2013-01-17)
Intravenous silibinin (SIL) is an approved therapeutic that has recently been applied to patients with chronic hepatitis C, successfully clearing hepatitis C virus (HCV) infection in some patients even in monotherapy. Previous studies suggested multiple antiviral mechanisms of SIL; however
Gagan Deep et al.
Cancer metastasis reviews, 29(3), 447-463 (2010-08-18)
Cancer is a major health problem around the world. Research efforts in the last few decades have been successful in providing better and effective treatments against both early stage and localized cancer, but clinical options against advanced metastatic stage/s of
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)
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
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
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