Silibinin | Silybin | Silymarin | CAS#22888-70-6

MedKoo Cat#: 202610 | Name: Silibinin

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Silibinin, also known as silybin, contains both A and B diastereomers. Silibinin is the major active constituent of silymarin, standardized extract of the milk thistle seeds, containing mixture of flavonolignans consisting of among others of silibinin, isosilibinin, silicristin and silidianin. Silibinin itself is mixture of two diastereomers Silibinin A and Silybinin B in approximately equimolar ratio. Both in vitro and animal research suggest that silibinin has hepatoprotective (antihepatotoxic) properties that protect liver cells against toxins.

Chemical Structure

Silibinin

CAS#22888-70-6

Theoretical Analysis

MedKoo Cat#: 202610

Name: Silibinin

CAS#: 22888-70-6

Chemical Formula: C25H22O10

Exact Mass: 482.1213

Molecular Weight: 482.44

Elemental Analysis: C, 62.24; H, 4.60; O, 33.16

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
5g	USD 350.00	2 Weeks
10g	USD 500.00	2 Weeks
50g	USD 1,100.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Flavobin; Silibinin; Silybin; NSC 651520; Silybine; Silymarin I; Silymarine I;

IUPAC/Chemical Name

(2R,3R)-3,5,7-trihydroxy-2-((2S,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one

InChi Key

SEBFKMXJBCUCAI-MNPDLOSFSA-N

InChi Code

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

SMILES Code

O=C1[C@H](O)[C@@H](C2=CC=C3O[C@@H](CO)[C@@H](C4=CC=C(O)C(OC)=C4)OC3=C2)OC5=C1C(O)=CC(O)=C5

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>5 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Silibinin (INN), also known as silybin, is the major active constituent of silymarin, the mixture of flavonolignans extracted from blessed milk thistle. Poor water solubility and bioavailability of silymarin led to the development of enhanced formulations. Silipide (trade name Siliphos), a complex of silymarin and phosphatidylcholine (lecithin), is about ten times more bioavailable than silymarin. It has been also reported that silymarin inclusion complex with β-cyclodextrin is much more soluble than silymarin itself. There have also been prepared glycosides of silybin, which show better water solubility and even stronger hepatoprotective effect. Silymarin, as other flavonoids, has been shown to inhibit P-glycoprotein-mediated cellular efflux. The modulation of P-glycoprotein activity may result in altered absorption and bioavailability of drugs that are P-glycoprotein substrates. It has been reported that silymarin inhibit cytochrome P450 enzymes and an interaction with drugs primarily cleared by P450s cannot be excluded. [source: http://en.wikipedia.org/wiki/Silibinin]. Toxicity: The acute toxicity of silymarin and silybin were investigated by oral and intravenous route in various animal species. No mortality or any signs of adverse effects were observed after silymarin at oral doses of 20 g/kg in mice and 1 g/kg in dogs. The 50% lethal dose (LD50) after intravenous infusion values are 400 mg/kg in mice, 385 mg/kg in rats and 140 mg/kg in rabbits and dogs. These data demonstrate that the acute toxicity of silymarin is very low [source: http://en.wikipedia.org/wiki/Silibinin].

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Silibinin is an effective anti-cancer and chemopreventive agent and has been shown to exert multiple effects on cancer cells, including inhibition of both cell proliferation and migration.

In vitro activity:

Silibinin may have an inhibitory effect on the enzymes involved in the invasion of human fibrosarcoma cells, potentially influenceing the metastatic ability of tumor cells. in HT1080 cells, silibinin above 20 μM remarkably inhibited the levels of MMP-2 and MMP-9 activation under PMA treatment conditions. Silibinin at 25 μM reduced the levels of MMP-2, IL-1β, ERK-1/2, and p-p38 expression and silibinin above 10 μM inhibited cell invasion on HT1080 cells. Reference: Front Biosci (Landmark Ed). 2023 Apr 6;28(4):64. https://pubmed.ncbi.nlm.nih.gov/37114542/

In vivo activity:

Silibinin is a safe drug with low toxicity and demonstrates significant antipsychotic activity against the positive and negative symptoms of schizophrenia. SIL prevented and reversed ketamine-induced increase in stereotypy and behavioral despair in the forced swim and tail suspension tests. Reference: Front Pharmacol. 2023 Feb 2;14:1111915. https://pubmed.ncbi.nlm.nih.gov/36817163/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	250.0	518.20

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 482.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Jo AI, Kim MM. Silibinin Inhibits Cell Invasion through the Inhibition of MMPs, p-p38, and IL-1β in Human Fibrosarcoma Cells. Front Biosci (Landmark Ed). 2023 Apr 6;28(4):64. doi: 10.31083/j.fbl2804064. PMID: 37114542. 2. Ranapour S, Motamed N. Effect of Silibinin on the Expression of Mir-20b, Bcl2L11, and Erbb2 in Breast Cancer Cell Lines. Mol Biotechnol. 2023 Dec;65(12):1979-1990. doi: 10.1007/s12033-023-00702-5. Epub 2023 Mar 11. PMID: 36905464. 3. Liu P, Chen W, Kang Y, Wang C, Wang X, Liu W, Hayashi T, Qiu Z, Mizuno K, Hattori S, Fujisaki H, Ikejima T. Silibinin ameliorates STING-mediated neuroinflammation via downregulation of ferroptotic damage in a sporadic Alzheimer's disease model. Arch Biochem Biophys. 2023 Aug;744:109691. doi: 10.1016/j.abb.2023.109691. Epub 2023 Jul 18. PMID: 37473980. 4. Ain QU, Saleem U, Ahmad B, Khalid I. Pharmacological screening of silibinin for antischizophrenic activity along with its acute toxicity evaluation in experimental animals. Front Pharmacol. 2023 Feb 2;14:1111915. doi: 10.3389/fphar.2023.1111915. PMID: 36817163; PMCID: PMC9936411.

In vitro protocol:

In vivo protocol:

1. Liu P, Chen W, Kang Y, Wang C, Wang X, Liu W, Hayashi T, Qiu Z, Mizuno K, Hattori S, Fujisaki H, Ikejima T. Silibinin ameliorates STING-mediated neuroinflammation via downregulation of ferroptotic damage in a sporadic Alzheimer's disease model. Arch Biochem Biophys. 2023 Aug;744:109691. doi: 10.1016/j.abb.2023.109691. Epub 2023 Jul 18. PMID: 37473980. 2. Ain QU, Saleem U, Ahmad B, Khalid I. Pharmacological screening of silibinin for antischizophrenic activity along with its acute toxicity evaluation in experimental animals. Front Pharmacol. 2023 Feb 2;14:1111915. doi: 10.3389/fphar.2023.1111915. PMID: 36817163; PMCID: PMC9936411.

1: Kaur M, Velmurugan B, Tyagi A, Agarwal C, Singh RP, Agarwal R. Silibinin suppresses growth of human colorectal carcinoma SW480 cells in culture and xenograft through down-regulation of beta-catenin-dependent signaling. Neoplasia. 2010 May;12(5):415-24. PubMed PMID: 20454513; PubMed Central PMCID: PMC2864479. 2: Duan W, Jin X, Li Q, Tashiro S, Onodera S, Ikejima T. Silibinin induced autophagic and apoptotic cell death in HT1080 cells through a reactive oxygen species pathway. J Pharmacol Sci. 2010;113(1):48-56. Epub 2010 Apr 22. PubMed PMID: 20431246. 3: Wu K, Zeng J, Li L, Fan J, Zhang D, Xue Y, Zhu G, Yang L, Wang X, He D. Silibinin reverses epithelial-to-mesenchymal transition in metastatic prostate cancer cells by targeting transcription factors. Oncol Rep. 2010 Jun;23(6):1545-52. PubMed PMID: 20428808. 4: Li L, Zeng J, Gao Y, He D. Targeting silibinin in the antiproliferative pathway. Expert Opin Investig Drugs. 2010 Feb;19(2):243-55. Review. PubMed PMID: 20047507. 5: Mateen S, Tyagi A, Agarwal C, Singh RP, Agarwal R. Silibinin inhibits human nonsmall cell lung cancer cell growth through cell-cycle arrest by modulating expression and function of key cell-cycle regulators. Mol Carcinog. 2010 Mar;49(3):247-58. PubMed PMID: 19908243. 6: Kidd PM. Bioavailability and activity of phytosome complexes from botanical polyphenols: the silymarin, curcumin, green tea, and grape seed extracts. Altern Med Rev. 2009 Sep;14(3):226-46. Review. PubMed PMID: 19803548. 7: Jung HJ, Park JW, Lee JS, Lee SR, Jang BC, Suh SI, Suh MH, Baek WK. Silibinin inhibits expression of HIF-1alpha through suppression of protein translation in prostate cancer cells. Biochem Biophys Res Commun. 2009 Dec 4;390(1):71-6. Epub 2009 Sep 22. PubMed PMID: 19778521. 8: Kaur M, Velmurugan B, Tyagi A, Deep G, Katiyar S, Agarwal C, Agarwal R. Silibinin suppresses growth and induces apoptotic death of human colorectal carcinoma LoVo cells in culture and tumor xenograft. Mol Cancer Ther. 2009 Aug;8(8):2366-74. Epub 2009 Jul 28. PubMed PMID: 19638451; PubMed Central PMCID: PMC2728169. 9: Lin CJ, Sukarieh R, Pelletier J. Silibinin inhibits translation initiation: implications for anticancer therapy. Mol Cancer Ther. 2009 Jun;8(6):1606-12. Epub 2009 Jun 9. PubMed PMID: 19509268. 10: Kim KW, Choi CH, Kim TH, Kwon CH, Woo JS, Kim YK. Silibinin inhibits glioma cell proliferation via Ca2+/ROS/MAPK-dependent mechanism in vitro and glioma tumor growth in vivo. Neurochem Res. 2009 Aug;34(8):1479-90. Epub 2009 Mar 5. PubMed PMID: 19263218. 11: Bhatt RS, Bubley GJ. The challenge of herbal therapies for prostate cancer. Clin Cancer Res. 2008 Dec 1;14(23):7581-2. Review. PubMed PMID: 19047081. 12: Thongphasuk P, Stremmel W, Chamulitrat W. 2,3-dehydrosilybin is a better DNA topoisomerase I inhibitor than its parental silybin. Chemotherapy. 2009;55(1):42-8. Epub 2008 Nov 21. PubMed PMID: 19023201. 13: GarcÃa-Maceira P, Mateo J. Silibinin inhibits hypoxia-inducible factor-1alpha and mTOR/p70S6K/4E-BP1 signalling pathway in human cervical and hepatoma cancer cells: implications for anticancer therapy. Oncogene. 2009 Jan 22;28(3):313-24. Epub 2008 Nov 3. PubMed PMID: 18978810. 14: Wang HJ, Tashiro S, Onodera S, Ikejima T. Inhibition of insulin-like growth factor 1 receptor signaling enhanced silibinin-induced activation of death receptor and mitochondrial apoptotic pathways in human breast cancer MCF-7 cells. J Pharmacol Sci. 2008 Jul;107(3):260-9. PubMed PMID: 18635919. 15: Zhou L, Liu P, Chen B, Wang Y, Wang X, Chiriva Internati M, Wachtel MS, Frezza EE. Silibinin restores paclitaxel sensitivity to paclitaxel-resistant human ovarian carcinoma cells. Anticancer Res. 2008 Mar-Apr;28(2A):1119-27. PubMed PMID: 18507063. 16: Deep G, Oberlies NH, Kroll DJ, Agarwal R. Identifying the differential effects of silymarin constituents on cell growth and cell cycle regulatory molecules in human prostate cancer cells. Int J Cancer. 2008 Jul 1;123(1):41-50. PubMed PMID: 18435416. 17: Huber A, Thongphasuk P, Erben G, Lehmann WD, Tuma S, Stremmel W, Chamulitrat W. Significantly greater antioxidant anticancer activities of 2,3-dehydrosilybin than silybin. Biochim Biophys Acta. 2008 May;1780(5):837-47. Epub 2008 Jan 3. PubMed PMID: 18222181. 18: Thongphasuk P, Stremmel W, Chamulitrat W. Potent direct or TNF-alpha-promoted anticancer effects of 2,3-dehydrosilybin: comparison study with silybin. Chemotherapy. 2008;54(1):23-30. Epub 2007 Dec 7. PubMed PMID: 18063863. 19: Raina K, Agarwal R. Combinatorial strategies for cancer eradication by silibinin and cytotoxic agents: efficacy and mechanisms. Acta Pharmacol Sin. 2007 Sep;28(9):1466-75. Review. PubMed PMID: 17723180. 20: JancovÃ¡ P, AnzenbacherovÃ¡ E, PapouskovÃ¡ B, Lemr K, LuznÃ¡ P, VeinlichovÃ¡ A, Anzenbacher P, SimÃ¡nek V. Silybin is metabolized by cytochrome P450 2C8 in vitro. Drug Metab Dispos. 2007 Nov;35(11):2035-9. Epub 2007 Aug 1. PubMed PMID: 17670841.