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silybin
4H-1-benzopyran-4-one, 2-[(2R,3R)-2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-

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CAS Number: 22888-70-6Picture of molecule3D/inchi
Other(deleted CASRN):11054-49-2
ECHA EINECS - REACH Pre-Reg:245-302-5
FDA UNII: 33X338MNE4
Nikkaji Web:J11.473A
MDL:MFCD03225424
XlogP3-AA:2.40 (est)
Molecular Weight:482.44234000
Formula:C25 H22 O10
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:cosmetic agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:pale yellow to amber crystalline solid (est)
Assay: 70.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 793.03 °C. @ 760.00 mm Hg (est)
Flash Point: 526.00 °F. TCC ( 274.50 °C. ) (est)
logP (o/w): 4.232 (est)
Soluble in:
 water, 77.36 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: skin conditioning
 
Suppliers:
AIDP
Silymarin 80% Milk Thistle 80%
Alfa Biotechnology
For experimental / research use only.
Silybin 98%
BOC Sciences
For experimental / research use only.
Silybin A >98%
Odor: characteristic
Use: Silibinin (INN), also known as silybin, 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.
Charkit Chemical
MILK THISTLE 80% SILYMARIN
Charkit Chemical
SILYMARIN 80
Coompo
For experimental / research use only.
Silymarin from Plants ≥98%
Odor: characteristic
Use: Silymarin is a antioxidant or free radical scavenger. Both in vitro and animal research suggest that Silymarin has hepatoprotective (antihepatotoxic) properties that protect liver cells against toxins. Silymarin has also demonstrated in vitro 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. Chemically modified Silymarin, Silymarin dihydrogen disuccinate disodium (trade name Legalon SIL) a solution for injection, is currently being tested as a treatment of severe intoxications with hepatotoxic substances, such as death cap (Amanita phalloides) poisoning. There is also clinical evidence for the use of Silymarin as a supportive element in alcoholic and Child grade A’ liver cirrhosis. Silymarin should not be classified as an alternative medicine, because its composition is now defined, including 60 % of silibinin-1 with which many of the cited in vitro studies of efficacy have been performed. Silymarin treatment in type II diabetic patients for 4 months has a beneficial effect on improving the glycemic profile. Treatment with silymarin may reduce the lipoperoxidation of cell membranes and insulin resistance, significantly decreasing endogenous insulin overproduction and the need for exogenous insulin administration. Silymarin may exert a strong anticarcinogenic effect against prostate cancer and that this effect is likely to involve impairment of erbB1-SHC-mediated signaling pathway, induction of CDKIs, and a resultant G1 arrest. Silymarin was first evaluated for its protective effect against UV irradiation-induced apoptosis in human malignant melanoma cells. Silymarin and Prunella vulgaris improve antioxidant status in blood and liver and positively affect plasma lipoprotein profile in an experimental model of dietary induced hypertriglyceridemia.There is some evidence that silymarin bound to phosphatidylcholine may be better absorbed. This form should be taken at a dosage of 100 to 200 mg twice a day.
ExtraSynthese
For experimental / research use only.
Silybin
Glentham Life Sciences
Silybin
Indo World Trading
Silymarin
P.L. Thomas
Silybin
Penta International
MILK THISTLE EXTRACT 80%
Sigma-Aldrich: Sigma
For experimental / research use only.
Silybin ≥98% (HPLC)
Silver Fern Chemical
Silymarin Extract
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intravenous-mouse LD50 1056 mg/kg
Yaoxue Tongbao. Bulletin of Pharmacology. Vol. 18, Pg. 404, 1983.

unreported-rabbit LDLo 300 mg/kg
Yaoxue Tongbao. Bulletin of Pharmacology. Vol. 18, Pg. 404, 1983.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
cosmetic agents
Recommendation for silybin usage levels up to:
 not for fragrance use.
 
Recommendation for silybin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :31553
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
Chemidplus:0022888706
RTECS:DJ2981770 for cas# 22888-70-6
 
References:
 (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):31553
Pubchem (sid):134995169
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):D08515
HMDB (The Human Metabolome Database):HMDB30583
FooDB:FDB002476
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 milk thistle
Search Trop Picture
 milk thistle
Search Trop Picture
 
Synonyms:
4H-1-benzopyran-4-one, 2-[(2R,3R)-2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-
(2R,3R)-2-((2R,3R)-2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl)-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one
[2R-[2a,3b,6(2R*,3R*)]]-2-[2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one
 dura-silymarin
 flavobin
 silibinin
 silliver
 silybum substance E6
 silymarin
(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
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxy-phenyl)-2-hydroxymethyl-2,3-dihydro-benzo[1,4]dioxin-6-yl]-chroman-4-one
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-one
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
 

Articles:

PubMed:Taurine Attenuates Hepatic Inflammation in Chronic Alcohol-Fed Rats Through Inhibition of TLR4/MyD88 Signaling.
PubMed:Hepatopathy following consumption of a commercially available blue-green algae dietary supplement in a dog.
PubMed:Silymarin and lycopene administration in periparturient dairy cows: effects on milk production and oxidative status.
PubMed:Effects of aqueous extract of Withania somnifera on some liver biochemical and histopathological parameters in male guinea pigs.
PubMed:Self-nanoemulsifying drug delivery systems ameliorate the oral delivery of silymarin in rats with Roux-en-Y gastric bypass surgery.
PubMed:High-performance thin-layer chromatography linked with (bio)assays and mass spectrometry - a suited method for discovery and quantification of bioactive components? Exemplarily shown for turmeric and milk thistle extracts.
PubMed:Effects of Silybum marianum (L.) Gaertn. (silymarin) extract supplementation on antioxidant status and hs-CRP in patients with type 2 diabetes mellitus: a randomized, triple-blind, placebo-controlled clinical trial.
PubMed:Silybum marianum: Beyond Hepatoprotection.
PubMed:Silibinin mitigates zidovudine-induced hepatocellular degenerative changes, oxidative stress and hyperlipidaemia in rats.
PubMed:Proanthocyanidin-rich date seed extract protects against chemically induced hepatorenal toxicity.
PubMed:Blockade of lipid accumulation by silibinin in adipocytes and zebrafish.
PubMed:A comparative study on the therapeutic effects of silymarin and silymarin-loaded solid lipid nanoparticles on D-GaIN/TNF-α-induced liver damage in Balb/c mice.
PubMed:A novel approach for the efficient extraction of silybin from milk thistle fruits.
PubMed:CCl4 induced genotoxicity and DNA oxidative damages in rats: hepatoprotective effect of Sonchus arvensis.
PubMed:Silymarin in liposomes and ethosomes: pharmacokinetics and tissue distribution in free-moving rats by high-performance liquid chromatography-tandem mass spectrometry.
PubMed:Antioxidant and protective effect of inulin and catechin grafted inulin against CCl4-induced liver injury.
PubMed:Protective effects of Cholestin on ethanol induced oxidative stress in rats.
PubMed:Attenuation of anti-tuberculosis therapy induced hepatotoxicity by Spirulina fusiformis, a candidate food supplement.
PubMed:Silymarin inhibits the progression of fibrosis in the early stages of liver injury in CCl₄-treated rats.
PubMed:Serum oxidative stress markers and lipidomic profile to detect NASH patients responsive to an antioxidant treatment: a pilot study.
PubMed:Hepatoprotective effect of silymarin on di(2-ethylhexyl)phthalate (DEHP) induced injury in liver FL83B cells.
PubMed:Silybum marianum oil attenuates oxidative stress and ameliorates mitochondrial dysfunction in mice treated with D-galactose.
PubMed:Phyto-liposomes as nanoshuttles for water-insoluble silybin-phospholipid complex.
PubMed:Colostrum yield and piglet growth during lactation are related to gilt metabolic and hepatic status prepartum.
PubMed:Hepatoprotective activity of the neem-based constituent azadirachtin-A in carbon tetrachloride intoxicated Wistar rats.
PubMed:Silibinin attenuates MPP⁺-induced neurotoxicity in the substantia nigra in vivo.
PubMed:Hepatoprotective effect of polyphenols rich methanolic extract of Amorphophallus commutatus var. wayanadensis against CCl4 induced hepatic injury in swiss albino mice.
PubMed:Effects of the plant extract silymarin on prolactin concentrations, mammary gland development, and oxidative stress in gestating gilts.
PubMed:The role of milk thistle extract in breast carcinoma cell line (MCF-7) apoptosis with doxorubicin.
PubMed:Antioxidant, anti-inflammatory and hepatoprotective effects of silymarin on hepatic dysfunction induced by sodium nitrite.
PubMed:Hepatoprotective role of Nicotiana plumbaginifolia Linn. against carbon tetrachloride-induced injuries.
PubMed:Silibinin meglumine, a water-soluble form of milk thistle silymarin, is an orally active anti-cancer agent that impedes the epithelial-to-mesenchymal transition (EMT) in EGFR-mutant non-small-cell lung carcinoma cells.
PubMed:Increase of phosphatase and tensin homolog by silymarin to inhibit human pharynx squamous cancer.
PubMed:Protective effect of cordycepin-enriched Cordyceps militaris on alcoholic hepatotoxicity in Sprague-Dawley rats.
PubMed:Effects of yam peel extract against carbon tetrachloride-induced hepatotoxicity in rats.
PubMed:Antiosteoclastic activity of milk thistle extract after ovariectomy to suppress estrogen deficiency-induced osteoporosis.
PubMed:Resolution of liver fibrosis by isoquinoline alkaloid berberine in CCl₄-intoxicated mice is mediated by suppression of oxidative stress and upregulation of MMP-2 expression.
PubMed:Structure-activity relationship for (+)-taxifolin isolated from silymarin as an inhibitor of amyloid β aggregation.
PubMed:Silibinin inhibits tumor growth through downregulation of extracellular signal-regulated kinase and Akt in vitro and in vivo in human ovarian cancer cells.
PubMed:Antioxidant, free radical scavenging and liver protective effects of friedelin isolated from Azima tetracantha Lam. leaves.
PubMed:Protective effect of bark and empty pod extracts from Acacia auriculiformis against paracetamol intoxicated liver injury and alloxan induced type II diabetes.
PubMed:Biosafety and antioxidant effects of a beverage containing silymarin and arginine. A pilot, human intervention cross-over trial.
PubMed:Chemical composition and biological evaluation of Physalis peruviana root as hepato-renal protective agent.
PubMed:Protective effect of silymarin against ethanol-induced gastritis in rats: role of sulfhydryls, nitric oxide and gastric sensory afferents.
PubMed:Effects of monascin on anti-inflammation mediated by Nrf2 activation in advanced glycation end product-treated THP-1 monocytes and methylglyoxal-treated wistar rats.
PubMed:Antihepatotoxic activity of a quantified Desmodium adscendens decoction and D-pinitol against chemically-induced liver damage in rats.
PubMed:Hepatoprotective effect of 2,3-dehydrosilybin on carbon tetrachloride-induced liver injury in rats.
PubMed:Silibinin inhibits the invasion of IL-6-stimulated colon cancer cells via selective JNK/AP-1/MMP-2 modulation in vitro.
PubMed:Antioxidant activity, total phenolic and total flavonoid contents of whole plant extracts Torilis leptophylla L.
PubMed:Hepatoprotective effects of Gentiana asclepiadea L. extracts against carbon tetrachloride induced liver injury in rats.
PubMed:Potential antioxidant properties and hepatoprotective effects of an aqueous extract formula derived from three Chinese medicinal herbs against CCl(4)-induced liver injury in rats.
PubMed:Absorption and metabolism of milk thistle flavanolignans in humans.
PubMed:The use of galactogogues in the breastfeeding mother.
PubMed:Ameliorative effect of silibinin against N-nitrosodimethylamine-induced hepatic fibrosis in rats.
PubMed:Silymarin decreases connective tissue growth factor to improve liver fibrosis in rats treated with carbon tetrachloride.
PubMed:Hepatoprotection with a chloroform extract of Launaea procumbens against CCl4-induced injuries in rats.
PubMed:Beneficial Effects of Ocimum gratissimum Aqueous Extract on Rats with CCl(4)-Induced Acute Liver Injury.
PubMed:Food-related compounds that modulate expression of inducible nitric oxide synthase may act as its inhibitors.
PubMed:Edible oils for liver protection: hepatoprotective potentiality of Moringa oleifera seed oil against chemical-induced hepatitis in rats.
PubMed:Antioxidant effect of silymarin on paraquat-induced human lung adenocarcinoma A549 cell line.
PubMed:Mulberry water extracts (MWEs) ameliorated carbon tetrachloride-induced liver damages in rat.
PubMed:Novel antiosteoclastogenic activity of phloretin antagonizing RANKL-induced osteoclast differentiation of murine macrophages.
PubMed:Autophagy, polyphenols and healthy ageing.
PubMed:Osteogenic activity of silymarin through enhancement of alkaline phosphatase and osteocalcin in osteoblasts and tibia-fractured mice.
PubMed:A profile of bioactive compounds of Rumex vesicarius L.
PubMed:Identification of novel mechanisms of silymarin on the carbon tetrachloride-induced liver fibrosis in mice by nuclear factor-κB bioluminescent imaging-guided transcriptomic analysis.
PubMed:DPPH free radical scavenging activity and phenotypic difference in hepatoprotective plant (Silybum marianum L.).
PubMed:Flavonoids, a ubiquitous dietary phenolic subclass, exert extensive in vitro anti-invasive and in vivo anti-metastatic activities.
PubMed:In vitro determination of anticryptosporidial activity of phytogenic extracts and compounds.
PubMed:Hepatoprotection of Gentiana scabra extract and polyphenols in liver of carbon tetrachloride-intoxicated mice.
PubMed:[Determination of active components in silymarin by UPLC-ESIMS].
PubMed:Hepatoprotection of silymarin against thioacetamide-induced chronic liver fibrosis.
PubMed:Osteoblastogenesis and osteoprotection enhanced by flavonolignan silibinin in osteoblasts and osteoclasts.
PubMed:Hepatoprotective effects of methanol extract of Carissa opaca leaves on CCl4-induced damage in rat.
PubMed:Bioactive phytochemicals of leaf essential oils of Cinnamomum osmophloeum prevent lipopolysaccharide/D-galactosamine (LPS/D-GalN)-induced acute hepatitis in mice.
PubMed:Toxicology and carcinogenesis studies of milk thistle extract (CAS No. 84604-20-6) in F344/N rats and B6C3F1 mice (Feed Studies).
PubMed:Effects of long-term silymarin oral supplementation on the blood biochemical profile of rainbow trout (Oncorhynchus mykiss).
PubMed:In vitro and in vivo antioxidant activity of Symplocos cochinchinensis S. Moore leaves containing phenolic compounds.
PubMed:Effects of Antrodia camphorata on alcohol clearance and antifibrosis in livers of rats continuously fed alcohol.
PubMed:Oral administration of Trapa taiwanensis Nakai fruit skin extracts conferring hepatoprotection from CCl4-caused injury.
PubMed:Highly sensitive detection of silybin based on adsorptive stripping analysis at single-sided heated screen-printed carbon electrodes modified with multi-walled carbon nanotubes with direct current heating.
PubMed:Gentiana manshurica Kitagawa reverses acute alcohol-induced liver steatosis through blocking sterol regulatory element-binding protein-1 maturation.
PubMed:Hepatoprotection by freshwater clam extract against CCl4-induced hepatic damage in rats.
PubMed:Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals.
PubMed:Rapid separation and characterization of active flavonolignans of Silybum marianum by ultra-performance liquid chromatography coupled with electrospray tandem mass spectrometry.
PubMed:Silymarin: a novel antioxidant with antiglycation and antiinflammatory properties in vitro and in vivo.
PubMed:Effects of plant-derived polyphenols on TNF-alpha and nitric oxide production induced by advanced glycation endproducts.
PubMed:Involvement of multiple molecular events in pyrogallol-induced hepatotoxicity and silymarin-mediated protection: evidence from gene expression profiles.
PubMed:Influence of chrysin on hepatic marker enzymes and lipid profile against D-galactosamine-induced hepatotoxicity rats.
PubMed:Protective effects of silica hydride against carbon tetrachloride-induced hepatotoxicity in mice.
PubMed:Fruiting body of Niuchangchih (Antrodia camphorata) protects livers against chronic alcohol consumption damage.
PubMed:Establishment of a methodology for investigating protectants against ethanol-induced hepatotoxicity.
PubMed:Silymarin, the antioxidant component and Silybum marianum extracts prevent liver damage.
PubMed:Hepatoprotection of chlorella against carbon tetrachloride-induced oxidative damage in rats.
PubMed:Effect of carvacrol on hepatic marker enzymes and antioxidant status in D-galactosamine-induced hepatotoxicity in rats.
PubMed:Effect of silymarin on biochemical parameters of oxidative stress in aged and young rat brain.
PubMed:Protective effects of seabuckthorn (Hippophae rhamnoides L.) seed oil against carbon tetrachloride-induced hepatotoxicity in mice.
PubMed:Improvement for high fat diet-induced hepatic injuries and oxidative stress by flavonoid-enriched extract from Nelumbo nucifera leaf.
PubMed:Hepatoprotective activity of polyherbal formulation (Normeta) in oxidative stress induced by alcohol, polyunsaturated fatty acids and iron in rats.
PubMed:Hepatoprotective effect of electrolyzed reduced water against carbon tetrachloride-induced liver damage in mice.
PubMed:Mushroom poisoning in children: clinical presentation and outcome.
PubMed:PEGylated lactoferrin enhanced its hepatoprotective effects on acute liver injury induced by carbon tetrachloride in rats.
PubMed:Protective effect of Acacia confusa bark extract and its active compound gallic acid against carbon tetrachloride-induced chronic liver injury in rats.
PubMed:Silibinin protects OTA-mediated TNF-alpha release from perfused rat livers and isolated rat Kupffer cells.
PubMed:Synergistic anti-cancer effect of baicalein and silymarin on human hepatoma HepG2 Cells.
PubMed:Protective effects of Coriandrum sativum extracts on carbon tetrachloride-induced hepatotoxicity in rats.
PubMed:[The comparative analysis of two methods of an estimation a butter's quality at its long storage and influence of a thistle spotty extracts on a period of storage].
PubMed:Glycyrrhizic acid modulates t-BHP induced apoptosis in primary rat hepatocytes.
PubMed:In vitro antioxidant activity of silymarin.
PubMed:Effect of silymarin on metabolic factors of food-restricted over conditioned Wistar rats.
PubMed:Sodium borohydride/chloranil-based assay for quantifying total flavonoids.
PubMed:Protective effects of Dunaliella salina--a carotenoids-rich alga, against carbon tetrachloride-induced hepatotoxicity in mice.
PubMed:Hepatoprotective and antioxidant effects of Commiphora berryi (Arn) Engl bark extract against CCl(4)-induced oxidative damage in rats.
PubMed:Multiple treatment of propolis extract ameliorates carbon tetrachloride induced liver injury in rats.
PubMed:Moringa oleifera Lam prevents acetaminophen induced liver injury through restoration of glutathione level.
PubMed:Silymarin prevents adriamycin-induced cardiotoxicity and nephrotoxicity in rats.
PubMed:Milk thistle extracts inhibit the oxidation of low-density lipoprotein (LDL) and subsequent scavenger receptor-dependent monocyte adhesion.
PubMed:Separation and determination of flavonoids using microemulsion EKC with electrochemical detection.
PubMed:Plant-derived polyphenols attenuate lipopolysaccharide-induced nitric oxide and tumour necrosis factor production in murine microglia and macrophages.
PubMed:Maca (Lepidium meyenii) and yacon (Smallanthus sonchifolius) in combination with silymarin as food supplements: in vivo safety assessment.
PubMed:Cell cycle control as a basis for cancer chemoprevention through dietary agents.
PubMed:Inhibition effect of flavonoids on monocarboxylate transporter 1 (MCT1) in Caco-2 cells.
PubMed:Silymarin as an adjunct to glibenclamide therapy improves long-term and postprandial glycemic control and body mass index in type 2 diabetes.
PubMed:The potential of milk thistle (Silybum marianum L.), an Israeli native, as a source of edible sprouts rich in antioxidants.
PubMed:Therapeutic value of orally administered silibinin in renal cell carcinoma: manipulation of insulin-like growth factor binding protein-3 levels.
PubMed:Effects of Picrorrhiza rhizoma water extracts on the subacute liver damages induced by carbon tetrachloride.
PubMed:Antioxidant and protective effect of an oleanolic acid-enriched extract of A. deliciosa root on carbon tetrachloride induced rat liver injury.
PubMed:Quantitation of silibinin, a putative cancer chemopreventive agent derived from milk thistle (Silybum marianum), in human plasma by high-performance liquid chromatography and identification of possible metabolites.
PubMed:Hepatoprotective and antioxidative effects of total phenolics from Laggera pterodonta on chemical-induced injury in primary cultured neonatal rat hepatocytes.
PubMed:Effects of the plant flavonoids silymarin and quercetin on arsenite-induced oxidative stress in CHO-K1 cells.
PubMed:Silibinin suppresses PMA-induced MMP-9 expression by blocking the AP-1 activation via MAPK signaling pathways in MCF-7 human breast carcinoma cells.
PubMed:Phytochemicals induce breast cancer resistance protein in Caco-2 cells and enhance the transport of benzo[a]pyrene-3-sulfate.
PubMed:[The use of flavolignans of "Silybum marianum (L.) Gaertn." to create a new fat product--fortified butter].
PubMed:Molecular targets of dietary agents for prevention and therapy of cancer.
PubMed:A silychristin isomer and variation of flavonolignan levels in milk thistle (Silybum marianum) fruits.
PubMed:The protective effects of Hibiscus sabdariffa extract on CCl4-induced liver fibrosis in rats.
PubMed:Modulatory effects of plant phenols on human multidrug-resistance proteins 1, 4 and 5 (ABCC1, 4 and 5).
PubMed:Protective effect of ursolic acid on ethanol-mediated experimental liver damage in rats.
PubMed:Dietary antioxidant compounds and liver health.
PubMed:Efficacy of silymarin-phospholipid complex in reducing the toxicity of aflatoxin B1 in broiler chicks.
PubMed:[Hepatoprotective effects of silymarin in androgenic-anabolic steroid-induced liver damage].
PubMed:Effects of silymarin, a natural hepatoprotector, in periparturient dairy cows.
PubMed:Combined effects of multiple flavonoids on breast cancer resistance protein (ABCG2)-mediated transport.
PubMed:Silibinin inhibits the invasion of human lung cancer cells via decreased productions of urokinase-plasminogen activator and matrix metalloproteinase-2.
PubMed:Silymarin, a possible hepatoprotector in dairy cows: biochemical and histological observations.
PubMed:Antioxidant action of Moringa oleifera Lam. (drumstick) against antitubercular drugs induced lipid peroxidation in rats.
PubMed:Influence of Piper betle on hepatic marker enzymes and tissue antioxidant status in ethanol-treated Wistar rats.
PubMed:The evaluation of reno- and hepatoprotective effects of huai-shan-yao (Rhizome Dioscoreae).
PubMed:Hepatoprotective activity of Moringa oleifera on antitubercular drug-induced liver damage in rats.
PubMed:Dietary feeding of silibinin inhibits advance human prostate carcinoma growth in athymic nude mice and increases plasma insulin-like growth factor-binding protein-3 levels.
PubMed:Hepatoprotective and anti-Helicobacter pylori activities of constituents from Brazilian propolis.
PubMed:Allied studies on the effect of Rosmarinus officinalis L. on experimental hepatotoxicity and mutagenesis.
PubMed:Food constituents attenuate monoamine oxidase activity and peroxide levels in C6 astrocyte cells.
PubMed:Interference by carbohydrate substrates, flavonoids, and monosaccharide derivatives on bacterial beta-D-glucuronidase assays.
PubMed:[Biologically active additive from milk thistle in the solution of public health problems].
PubMed:In vitro attenuation of nitric oxide production in C6 astrocyte cell culture by various dietary compounds.
PubMed:Flavonoids modulate comet assay responses to food mutagens in human lymphocytes and sperm.
PubMed:Protective effect of flavonoids and tocopherol in high altitude hypoxia in the rat: comparison with ascorbic acid.
PubMed:Free radical scavenging and antioxidative properties of 'silibin' complexes on microsomal lipid peroxidation.
PubMed:Modulating effects of flavonoids on food mutagens in human blood and sperm samples in the comet assay.
PubMed:Effect of silymarin on different acute inflammation models and on leukocyte migration.
PubMed:Amanita poisoning during the second trimester of pregnancy. A case report and a review of the literature.
PubMed:Research note: efficacy of various flavonoids and simple phenolics in prevention of nutritional myopathy in the chick.
 
Notes:
the major component of flavonoids extracted from seeds of the milk thistle, silybum marianum; has antineoplastic activity. the major component of flavonoids extracted from seeds of the milk thistle, silybum marianum; has antineoplastic activity. Isol. from Silybum marianum (milk thistle)
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