22888-70-6 Usage
Chemical Properties
solid
Originator
Legalon,Madaus,W. Germany,1969
Uses
Different sources of media describe the Uses of 22888-70-6 differently. You can refer to the following data:
1. 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) assayto examine its effect on gene expression levels of stromelysine 1 (STM1), acetyl hexoseamines and collagen production during skin wound healingto study its inhibitory effect on Escherichia coli ATP synthase
2. Labelled Silybin (S465850). Hepatoprotectant.
Definition
ChEBI: A flavonolignan isolated from milk thistle, Silybum marianum, that has been shown to exhibit antioxidant and antineoplastic activities.
Manufacturing Process
Silymarin comprising polyhydroxyphenyl chromanones is recovered from the
dried fruit of Silybum marianum Gaertn. by separating the fatty oils
therefrom, extracting the remaining solid residue with ethyl acetate,
evaporating the ethyl acetate and dissolving the dry residue in a solvent
mixture comprising methanol, water and petroleum ether to form a two-phase
system wherein the chromanones are contained in the lower phase,
recovering the polyhydroxyphenyl chromanones from the lower phase after
subjecting same to multiple counter-current contact with petroleum ether.
Therapeutic Function
Hepatoprotectant
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).
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.
Check Digit Verification of cas no
The CAS Registry Mumber 22888-70-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,8,8 and 8 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 22888-70:
(7*2)+(6*2)+(5*8)+(4*8)+(3*8)+(2*7)+(1*0)=136
136 % 10 = 6
So 22888-70-6 is a valid CAS Registry Number.
InChI:InChI=1/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
22888-70-6Relevant articles and documents
Bioavailability of silymarin. III. Splitting of silybin dihemisuccinate by plasma and liver esterases
Koch,Tscherny
, p. 426 - 430 (1983)
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Mechanistic study of the biomimetic synthesis of flavonolignan diastereoisomers in milk thistle
Althagafy, Hanan S.,Meza-Avina, Maria Elena,Oberlies, Nicholas H.,Croatt, Mitchell P.
, p. 7594 - 7600 (2013/09/02)
The mechanism for the biomimetic synthesis of flavonolignan diastereoisomers in milk thistle is proposed to proceed by single-electron oxidation of coniferyl alcohol, subsequent reaction with one of the oxygen atoms of taxifolin's catechol moiety, and finally, further oxidation to form four of the major components of silymarin: silybin A, silybin B, isosilybin A, and isosilybin B. This mechanism is significantly different from a previously proposed process that involves the coupling of two independently formed radicals.
Enzymatic kinetic resolution of silybin diastereoisomers
Monti, Daniela,Gazak, Radek,Marhol, Petr,Biedermann, David,Purchartova, Katerina,Fedrigo, Mirko,Riva, Sergio,Kren, Vladimir
experimental part, p. 613 - 619 (2010/07/13)
In nature, the flavonolignan silybin (1) occurs as a mixture of two diastereomers, silybin A and silybin B, which in a number of biological assays exhibit different activities. A library of hydrolases (lipases, esterases, and proteases) was tested for separating the silybin A and B diastereomers by selective transesterification or by stereoselective alcoholysis of 23-O-acetylsilybin (2). Novozym 435 proved to be the most suitable enzyme for the preparative production of both optically pure silybins A and B by enzymatic discrimination. Gram amounts of the optically pure substances can be produced within one week, and the new method is robust and readily scalable to tens of grams.
