Silibinin
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| Systematic (IUPAC) name | |
| (2R,3R)-3,5,7-trihydroxy- 2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl) -2,3-dihydrobenzob[1,4]dioxin-6-yl]chroman-4-one |
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| Identifiers | |
| CAS number | 22888-70-6 |
| ATC code | A05BA03 |
| PubChem | CID 31553 |
| Chemical data | |
| Formula | C25H22O10 |
| Mol. mass | 482.44 g/mol |
| Therapeutic considerations | |
| Pregnancy cat. | ? |
| Legal status | |
Silibinin (INN), also known as silybin, is the major active constituent of silymarin, the mixture of flavonolignans extracted from blessed milk thistle (Silybum marianum) consisting of silibinin A and B, isosibilinin A and B, silicristin, silidianin. Both in vitro and animal research suggest that silibinin has hepatoprotective (antihepatotoxic) properties that protect liver cells against toxins.12 Silibinin has also demonstrated anti-cancer effects against human prostate adenocarcinoma cells, estrogen-dependent and -independent human breast carcinoma cells, human ectocervical carcinoma cells, human colon cancer cells, and both small and nonsmall human lung carcinoma cells.3456
Chemically modified silibinin, silibinin dihydrogen disuccinate disodium (trade name Legalon SIL) a solution for injection, is used in treatment of severe intoxications with hepatotoxic substances, such as death cap (Amanita phalloides) poisoning.7
Contents
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Pharmacology
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.citation needed It has been also reportedwho? that silymarin inclusion complex with β-cyclodextrin is much more soluble than silymarin itselfcitation needed. There have also been prepared glycosides of silybin, which show better water solubility and even stronger hepatoprotective effectcitation needed.
Silymarin, as other flavonoids, has been shown to inhibit P-glycoprotein-mediated cellular efflux.8 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.citation needed
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.citation needed
Similarly, its subacute and chronic toxicity are very low; the compound is also devoid of embryotoxic potential.citation needed
Complementary and alternative medicine
A recent study suggested that silymarin may help patients with type II diabetes by assisting in blood sugar control.9
References
- ^ Al-Anati L, Essid E, Reinehr R, Petzinger E (April 2009). "Silibinin protects OTA-mediated TNF-alpha release from perfused rat livers and isolated rat Kupffer cells". Mol Nutr Food Res 53 (4): 460–6. doi:10.1002/mnfr.20080011010.1002/mnfr.200800110 (inactive 2009-06-26). PMID 19156713.
- ^ Jayaraj R, Deb U, Bhaskar AS, Prasad GB, Rao PV (October 2007). "Hepatoprotective efficacy of certain flavonoids against microcystin induced toxicity in mice". Environ. Toxicol. 22 (5): 472–9. doi:10.1002/tox.2028310.1002/tox.20283 (inactive 2009-06-26). PMID 17696131.
- ^ Mokhtari MJ, Motamed N, Shokrgozar MA (August 2008). "Evaluation of silibinin on the viability, migration and adhesion of the human prostate adenocarcinoma (PC-3) cell line". Cell Biol. Int. 32 (8): 888–92. doi:10.1016/j.cellbi.2008.03.019. PMID 18538589. http://linkinghub.elsevier.com/retrieve/pii/S1065-6995(08)00384-3.
- ^ Bhatia N, Zhao J, Wolf DM, Agarwal R (December 1999). "Inhibition of human carcinoma cell growth and DNA synthesis by silibinin, an active constituent of milk thistle: comparison with silymarin". Cancer Lett. 147 (1-2): 77–84. doi:10.1016/S0304-3835(99)00276-1. PMID 10660092.
- ^ Hogan FS, Krishnegowda NK, Mikhailova M, Kahlenberg MS (November 2007). "Flavonoid, silibinin, inhibits proliferation and promotes cell-cycle arrest of human colon cancer". J. Surg. Res. 143 (1): 58–65. doi:10.1016/j.jss.2007.03.080. PMID 17950073. http://linkinghub.elsevier.com/retrieve/pii/S0022-4804(07)00241-7.
- ^ Sharma G, Singh RP, Chan DC, Agarwal R (2003). "Silibinin induces growth inhibition and apoptotic cell death in human lung carcinoma cells". Anticancer Res. 23 (3B): 2649–55. PMID 12894553.
- ^ Mitchell, T (2009). "Intravenous Milk Thistle (Silibinin-Legalon) for Hepatic Failure Induced by Amatoxin/Amanita Mushroom Poisoning". (Clinical study). http://clinicaltrials.gov/ct2/show/NCT00915681.
- ^ Zhou S, Lim LY, Chowbay B (February 2004). "Herbal modulation of P-glycoprotein". Drug Metab. Rev. 36 (1): 57–104. doi:10.1081/DMR-120028427. PMID 15072439. http://www.informapharmascience.com/doi/abs/10.1081/DMR-120028427.
- ^ Huseini HF, Larijani B, Heshmat R, et al. (December 2006). "The efficacy of Silybum marianum (L.) Gaertn. (silymarin) in the treatment of type II diabetes: a randomized, double-blind, placebo-controlled, clinical trial". Phytother Res 20 (12): 1036–9. doi:10.1002/ptr.198810.1002/ptr.1988 (inactive 2009-06-26). PMID 17072885.
- Morazzoni P, Bombardelli E (1994). "Silybum marianum (cardus marianus)". Fitoterapia 66: 3–42.
- Saller R, Meier R, Brignoli R (2001). "The use of silymarin in the treatment of liver diseases". Drugs 61 (14): 2035–63. doi:10.2165/00003495-200161140-00003. PMID 11735632.
External links
- Review of the Quality of Evidence for Milk Thistle Use from MayoClinic.com
- Intravenous Milk Thistle Compound Used to Save Victims of Poisonous Mushrooms
- MeSH Silymarin
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