isosilybin
4H-1-benzopyran-4-one, 2-(2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-1,4-benzodioxin-6-yl)-2,3-dihydro-3,5,7-trihydroxy-
Identification
| Name | isosilybin |
| IUPAC | 3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one |
| CAS Number | 72581-71-6 |
| FDA UNII | Search |
| Molecular Formula | C25 H22 O10 |
| Molecular Weight | 482.44234000 |
| MDL Number | MFCD09842608 |
| Nikkaji Number | J458.501A |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 77.36 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for isosilybin usage levels up to | not for fragrance use. |
| Recommendation for isosilybin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
4H-1-
benzopyran-4-one, 2-(2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-1,4-benzodioxin-6-yl)-2,3-dihydro-3,5,7-trihydroxy-
3,5,7-
trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
PubMed:
Chemoenzymatic Synthesis, Characterization, and Scale-up of Milk Thistle Flavonolignan Glucuronides.
PubMed:
Synchronous microencapsulation of multiple components in silymarin into PLGA nanoparticles by an emulsification/solvent evaporation method.
PubMed:
Pyranone natural products as inspirations for catalytic reaction discovery and development.
PubMed:
Accumulation of silymarin in milk thistle seeds under drought stress.
PubMed:
A biomimetic strategy to access the silybins: total synthesis of (-)-isosilybin A.
PubMed:
The effects of milk thistle (Silybum marianum) on human cytochrome P450 activity.
PubMed:
Isolation and purification of diastereoisomeric flavonolignans from silymarin by binary-column recycling preparative high-performance liquid chromatography.
PubMed:
Simplified procedure of silymarin extraction from Silybum marianum L. Gaertner.
PubMed:
Identification of isosilybin a from milk thistle seeds as an agonist of peroxisome proliferator-activated receptor gamma.
PubMed:
Flavonolignans from Aspergillus iizukae, a fungal endophyte of milk thistle (Silybum marianum).
PubMed:
Biotransformation on the flavonolignan constituents of Silybi Fructus by an intestinal bacterial strain Eubacterium limosum ZL-II.
PubMed:
Mechanistic study of the biomimetic synthesis of flavonolignan diastereoisomers in milk thistle.
PubMed:
An assessment of pharmacokinetics and antioxidant activity of free silymarin flavonolignans in healthy volunteers: a dose escalation study.
PubMed:
A systematic approach to evaluate herb-drug interaction mechanisms: investigation of milk thistle extracts and eight isolated constituents as CYP3A inhibitors.
PubMed:
Milk thistle's active components silybin and isosilybin: novel inhibitors of PXR-mediated CYP3A4 induction.
PubMed:
HiFSA fingerprinting applied to isomers with near-identical NMR spectra: the silybin/isosilybin case.
PubMed:
Synchronized and controlled release of multiple components in silymarin achieved by the osmotic release strategy.
PubMed:
Absolute configuration of isosilybin A by X-ray crystallography of the heavy atom analogue 7-(4-Bromobenzoyl)isosilybin A.
PubMed:
Absorption and metabolism of milk thistle flavanolignans in humans.
PubMed:
A sensitive LC-MS/MS assay for the simultaneous analysis of the major active components of silymarin in human plasma.
PubMed:
Angiopreventive efficacy of pure flavonolignans from milk thistle extract against prostate cancer: targeting VEGF-VEGFR signaling.
PubMed:
Pyrazinecarboxamides as potential elicitors of flavonolignan and flavonoid production in Silybum marianum and Ononis arvensis cultures in vitro.
PubMed:
Electrochemical investigation of flavonolignans and study of their interactions with DNA in the presence of Cu(II).
PubMed:
Effects of silymarin nanoemulsion against carbon tetrachloride-induced hepatic damage.
PubMed:
Isosilybin A induces apoptosis in human prostate cancer cells via targeting Akt, NF-κB, and androgen receptor signaling.
PubMed:
Enhanced production of silymarin by Ag+ elicitor in cell suspension cultures of Silybum marianum.
PubMed:
Identification of hepatoprotective flavonolignans from silymarin.
PubMed:
Large-scale isolation of flavonolignans from Silybum marianum extract affords new minor constituents and preliminary structure-activity relationships.
PubMed:
Two flavonolignans from milk thistle (Silybum marianum) inhibit CYP2C9-mediated warfarin metabolism at clinically achievable concentrations.
PubMed:
Influence of exogenous salicylic acid on flavonolignans and lipoxygenase activity in the hairy root cultures of Silybum marianum.
PubMed:
[Silymarin in the treatment of chronic liver diseases: past and future].
PubMed:
Isosilibinin inhibits advanced human prostate cancer growth in athymic nude mice: comparison with silymarin and silibinin.
PubMed:
Hepatic metabolism and biliary excretion of silymarin flavonolignans in isolated perfused rat livers: role of multidrug resistance-associated protein 2 (Abcc2).
PubMed:
Identifying the differential effects of silymarin constituents on cell growth and cell cycle regulatory molecules in human prostate cancer cells.
PubMed:
New insight into the biosynthesis of flavanolignans in the white-flowered variant of Silybum marianum.
PubMed:
Isosilybin B causes androgen receptor degradation in human prostate carcinoma cells via PI3K-Akt-Mdm2-mediated pathway.
PubMed:
Gram-scale purification of flavonolignan diastereoisomers from Silybum marianum (Milk Thistle) extract in support of preclinical in vivo studies for prostate cancer chemoprevention.
PubMed:
Pharmacokinetics and metabolic profile of free, conjugated, and total silymarin flavonolignans in human plasma after oral administration of milk thistle extract.
PubMed:
Inhibition of T-cell inflammatory cytokines, hepatocyte NF-kappaB signaling, and HCV infection by standardized Silymarin.
PubMed:
Isosilybin B and isosilybin A inhibit growth, induce G1 arrest and cause apoptosis in human prostate cancer LNCaP and 22Rv1 cells.
PubMed:
Hepatoprotective herbal drug, silymarin from experimental pharmacology to clinical medicine.
PubMed:
Anticancer potential of silymarin: from bench to bed side.
PubMed:
Synchronized and sustained release of multiple components in silymarin from erodible glyceryl monostearate matrix system.
PubMed:
Structure elucidation and antioxidant activity of (-)-isosilandrin isolated from Silybum marianum L.
PubMed:
Analysis and comparison of active constituents in commercial standardized silymarin extracts by liquid chromatography-electrospray ionization mass spectrometry.
PubMed:
Separation and characterization of silybin, isosilybin, silydianin and silychristin in milk thistle extract by liquid chromatography-electrospray tandem mass spectrometry.
PubMed:
Silymarin and silibinin cause G1 and G2-M cell cycle arrest via distinct circuitries in human prostate cancer PC3 cells: a comparison of flavanone silibinin with flavanolignan mixture silymarin.
PubMed:
Milk thistle and prostate cancer: differential effects of pure flavonolignans from Silybum marianum on antiproliferative end points in human prostate carcinoma cells.
PubMed:
Molecular structure and stereochemistry of silybin A, silybin B, isosilybin A, and isosilybin B, Isolated from Silybum marianum (milk thistle).
PubMed:
Analysis of the active components of silymarin.
PubMed:
Primary cultures of human hepatocytes as a tool in cytotoxicity studies: cell protection against model toxins by flavonolignans obtained from Silybum marianum.
PubMed:
[Determination of the active flavonoids in silymarine].
PubMed:
Inhibition of the superoxide anion release and hydrogen peroxide formation in PMNLs by flavonolignans.
PubMed:
Determination of active component in silymarin by RP-LC and LC/MS.
PubMed:
[Separation and determination of effective components in silymarin and preparations of silymarin by MECC].
PubMed:
Flavonolignan production from Silybum marianum transformed and untransformed root cultures.
PubMed:
Comparative pharmacokinetics of silipide and silymarin in rats.
PubMed:
Pharmacokinetics of silybin in bile following administration of silipide and silymarin in cholecystectomy patients.
PubMed:
Effect of the flavanolignans of Silybum marianum L. on lipid peroxidation in rat liver microsomes and freshly isolated hepatocytes.
PubMed:
[Structure of silandrin and silymonin, two new flavanolignans from a white blooming Silybum marianum variety].