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'''Silibinin''' ([[International Nonproprietary Name|INN]]), also known as '''silybin''', is the major active constituent of '''silymarin''', the mixture of [[flavonolignan]]s extracted from [[Silybum marianum|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.<ref>{{cite journal |author=Al-Anati L, Essid E, Reinehr R, Petzinger E |title=Silibinin protects OTA-mediated TNF-alpha release from perfused rat livers and isolated rat Kupffer cells |journal=Mol Nutr Food Res |volume=53 |issue=4 |pages=460–6 |year=2009 |month=April |pmid=19156713 |doi=10.1002/mnfr.200800110 |doi_brokendate=2009-06-26}}</ref><ref>{{cite journal |author=Jayaraj R, Deb U, Bhaskar AS, Prasad GB, Rao PV |title=Hepatoprotective efficacy of certain flavonoids against microcystin induced toxicity in mice |journal=Environ. Toxicol. |volume=22 |issue=5 |pages=472–9 |year=2007 |month=October |pmid=17696131 |doi=10.1002/tox.20283 |doi_brokendate=2009-06-26}}</ref> 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.<ref>{{cite journal |author=Mokhtari MJ, Motamed N, Shokrgozar MA |title=Evaluation of silibinin on the viability, migration and adhesion of the human prostate adenocarcinoma (PC-3) cell line |journal=Cell Biol. Int. |volume=32 |issue=8 |pages=888–92 |year=2008 |month=August |pmid=18538589 |doi=10.1016/j.cellbi.2008.03.019 |url=http://linkinghub.elsevier.com/retrieve/pii/S1065-6995(08)00384-3}}</ref><ref>{{cite journal |author=Bhatia N, Zhao J, Wolf DM, Agarwal R |title=Inhibition of human carcinoma cell growth and DNA synthesis by silibinin, an active constituent of milk thistle: comparison with silymarin |journal=Cancer Lett. |volume=147 |issue=1-2 |pages=77–84 |year=1999 |month=December |pmid=10660092 |doi=10.1016/S0304-3835(99)00276-1 }}</ref><ref>{{cite journal |author=Hogan FS, Krishnegowda NK, Mikhailova M, Kahlenberg MS |title=Flavonoid, silibinin, inhibits proliferation and promotes cell-cycle arrest of human colon cancer |journal=J. Surg. Res. |volume=143 |issue=1 |pages=58–65 |year=2007 |month=November |pmid=17950073 |doi=10.1016/j.jss.2007.03.080 |url=http://linkinghub.elsevier.com/retrieve/pii/S0022-4804(07)00241-7}}</ref><ref>{{cite journal |author=Sharma G, Singh RP, Chan DC, Agarwal R |title=Silibinin induces growth inhibition and apoptotic cell death in human lung carcinoma cells |journal=Anticancer Res. |volume=23 |issue=3B |pages=2649–55 |year=2003 |pmid=12894553 }}</ref>
'''Silibinin''' ([[International Nonproprietary Name|INN]]), also known as '''silybin''', is the major active constituent of '''silymarin''', the mixture of [[flavonolignan]]s extracted from [[Silybum marianum|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.<ref>{{cite journal |author=Al-Anati L, Essid E, Reinehr R, Petzinger E |title=Silibinin protects OTA-mediated TNF-alpha release from perfused rat livers and isolated rat Kupffer cells |journal=Mol Nutr Food Res |volume=53 |issue=4 |pages=460–6 |year=2009 |month=April |pmid=19156713 |doi=10.1002/mnfr.200800110 |doi_brokendate=2009-06-26}}</ref><ref>{{cite journal |author=Jayaraj R, Deb U, Bhaskar AS, Prasad GB, Rao PV |title=Hepatoprotective efficacy of certain flavonoids against microcystin induced toxicity in mice |journal=Environ. Toxicol. |volume=22 |issue=5 |pages=472–9 |year=2007 |month=October |pmid=17696131 |doi=10.1002/tox.20283 |doi_brokendate=2009-06-26}}</ref> 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.<ref>{{cite journal |author=Mokhtari MJ, Motamed N, Shokrgozar MA |title=Evaluation of silibinin on the viability, migration and adhesion of the human prostate adenocarcinoma (PC-3) cell line |journal=Cell Biol. Int. |volume=32 |issue=8 |pages=888–92 |year=2008 |month=August |pmid=18538589 |doi=10.1016/j.cellbi.2008.03.019 |url=http://linkinghub.elsevier.com/retrieve/pii/S1065-6995(08)00384-3}}</ref><ref>{{cite journal |author=Bhatia N, Zhao J, Wolf DM, Agarwal R |title=Inhibition of human carcinoma cell growth and DNA synthesis by silibinin, an active constituent of milk thistle: comparison with silymarin |journal=Cancer Lett. |volume=147 |issue=1-2 |pages=77–84 |year=1999 |month=December |pmid=10660092 |doi=10.1016/S0304-3835(99)00276-1 }}</ref><ref>{{cite journal |author=Hogan FS, Krishnegowda NK, Mikhailova M, Kahlenberg MS |title=Flavonoid, silibinin, inhibits proliferation and promotes cell-cycle arrest of human colon cancer |journal=J. Surg. Res. |volume=143 |issue=1 |pages=58–65 |year=2007 |month=November |pmid=17950073 |doi=10.1016/j.jss.2007.03.080 |url=http://linkinghub.elsevier.com/retrieve/pii/S0022-4804(07)00241-7}}</ref><ref>{{cite journal |author=Sharma G, Singh RP, Chan DC, Agarwal R |title=Silibinin induces growth inhibition and apoptotic cell death in human lung carcinoma cells |journal=Anticancer Res. |volume=23 |issue=3B |pages=2649–55 |year=2003 |pmid=12894553 }}</ref>


Chemically modified silibinin, silibinin dihydrogen disuccinate disodium (trade name '''Legalon SIL''') a solution for [[injection (medicine)|injection]], is used in treatment of severe intoxications with hepatotoxic substances, such as [[Amanita phalloides|death cap]] (''Amanita phalloides'') poisoning.<ref>{{cite journal |author=Mitchell, T|title=Intravenous Milk Thistle (Silibinin-Legalon) for Hepatic Failure Induced by Amatoxin/Amanita Mushroom Poisoning|journal=(Clinical study)|year=2009|url=http://clinicaltrials.gov/ct2/show/NCT00915681}}</ref>
Chemically modified silibinin, silibinin dihydrogen disuccinate disodium (trade name '''Legalon SIL''') a solution for [[injection (medicine)|injection]], is used in treatment of severe intoxications with hepatotoxic substances, such as [[Amanita phalloides|death cap]] (''Amanita phalloides'') poisoning.<ref>{{cite journal |author=Mitchell, T|title=Intravenous Milk Thistle (Silibinin-Legalon) for Hepatic Failure Induced by Amatoxin/Amanita Mushroom Poisoning|journal=(Clinical study)|year=2009|url=http://clinicaltrials.gov/ct2/show/NCT00915681}}</ref> There is also clincial evidence for the use of silibinin as a supportive element in alcoholic and grade Child ‘A’ [[liver cirrhosis]].<ref>Saller R, Brignoli R, Melzer J, Meier R (2008). “An updated systematic review with meta-analysis for the clinical evidence of silymarin”. ''Forschende Komplementärmedizin'' 15 (1): 9-20. PMID 18334810</ref>


==Pharmacology==
==Pharmacology==

Revision as of 02:20, 11 October 2010

Silibinin
Clinical data
ATC code
Identifiers
  • (2R,3R)-3,5,7-trihydroxy-
    2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)
    -2,3-dihydrobenzo[b][1,4]dioxin-6-yl]chroman-4-one
CAS Number
PubChem CID
CompTox Dashboard (EPA)
ECHA InfoCard100.041.168 Edit this at Wikidata
Chemical and physical data
FormulaC25H22O10
Molar mass482.44 g/mol g·mol−1

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.[1][2] 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.[3][4][5][6]

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] There is also clincial evidence for the use of silibinin as a supportive element in alcoholic and grade Child ‘A’ liver cirrhosis.[8]

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 reported[who?] that silymarin inclusion complex with β-cyclodextrin is much more soluble than silymarin itself[citation needed]. There have also been prepared glycosides of silybin, which show better water solubility and even stronger hepatoprotective effect[citation needed].

Silymarin, as other flavonoids, has been shown to inhibit P-glycoprotein-mediated cellular efflux.[9] 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.[10]

References

  1. ^ Al-Anati L, Essid E, Reinehr R, Petzinger E (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.200800110. PMID 19156713. {{cite journal}}: Unknown parameter |doi_brokendate= ignored (|doi-broken-date= suggested) (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  2. ^ Jayaraj R, Deb U, Bhaskar AS, Prasad GB, Rao PV (2007). "Hepatoprotective efficacy of certain flavonoids against microcystin induced toxicity in mice". Environ. Toxicol. 22 (5): 472–9. doi:10.1002/tox.20283. PMID 17696131. {{cite journal}}: Unknown parameter |doi_brokendate= ignored (|doi-broken-date= suggested) (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. ^ Mokhtari MJ, Motamed N, Shokrgozar MA (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  4. ^ Bhatia N, Zhao J, Wolf DM, Agarwal R (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  5. ^ Hogan FS, Krishnegowda NK, Mikhailova M, Kahlenberg MS (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  6. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ Mitchell, T (2009). "Intravenous Milk Thistle (Silibinin-Legalon) for Hepatic Failure Induced by Amatoxin/Amanita Mushroom Poisoning". (Clinical study).
  8. ^ Saller R, Brignoli R, Melzer J, Meier R (2008). “An updated systematic review with meta-analysis for the clinical evidence of silymarin”. Forschende Komplementärmedizin 15 (1): 9-20. PMID 18334810
  9. ^ Zhou S, Lim LY, Chowbay B (2004). "Herbal modulation of P-glycoprotein". Drug Metab. Rev. 36 (1): 57–104. doi:10.1081/DMR-120028427. PMID 15072439. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  10. ^ Huseini HF, Larijani B, Heshmat R; et al. (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.1988. PMID 17072885. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |doi_brokendate= ignored (|doi-broken-date= suggested) (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  • 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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