| Identification | Back Directory | [Name]
Isosilybin | [CAS]
72581-71-6 | [Synonyms]
Q-100795
Isosilybin
indissolubly
ISOSILIBININ
Isosilybinin
Isosilybin，ISB
ISOSILYBIN hplc
Isosilybin USP/EP/BP
Isosilybin (A+B) mixture
Isosilybin (Isosilybinin)
ISOSILYBIN(PRIMARY STANDARD)
Isosilybin (Mixture of Diastereomers)
-(2,3-Dihydro-2-(4-hydroxy-3-Methoxyphenyl)-3-(hydroxyMethyl)-1,4-benzodioxin-6-yl)-2,3-dihydro-3,5,7-trihydroxy-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-4H-1-benzopyran-4-one
(2R,3R)-2-[2,3-Dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one
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-,(2R,3R)- | [Molecular Formula]
C25H22O10 | [MDL Number]
MFCD01075144 | [MOL File]
72581-71-6.mol | [Molecular Weight]
482.44 |
| Chemical Properties | Back Directory | [Boiling point ]
793.0±60.0 °C(Predicted) | [density ]
1.527±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20° C | [solubility ]
DMF: 20 mg/ml; DMF:PBS (pH 7.2) (1:9): 0.5 mg/ml; DMSO: 10 mg/ml; Ethanol: 0.1 mg/ml | [form ]
Solid | [pka]
7.39±0.60(Predicted) | [color ]
White-light yellow |
| Questions And Answer | Back Directory | [Structure]
Only silybins and isosilybins contain the 1,4-dioxane ring system in their structure during Silymarin’s primary constituents. Silybin and isosilybin have the same trans conformation of C-2, C-3, C-7′ and C-8′. Silybin is considered the major and most active component of silymarin. |
| Hazard Information | Back Directory | [Description]
Isosilybin is a flavanolignan found in the extract of S. marianum fruits with antioxidant and anticancer activities.1,2,3 It inhibits lipid peroxidation in rat liver microsomes (IC50 = 32 μM) and reduces ADP/Fe3+-induced malondialdehyde (MDA) production and lactate dehydrogenase (LDH) release in rat hepatocytes.1 Isosilybin inhibits the production of reactive oxygen species (ROS), MDA and LDH release, and reduction in total antioxidant capacity induced by amyloid-β (25-35) (Aβ25-35) in HT-22 hippocampal cells.2 It also increases protein and mRNA expression of heme oxygenase-1 (HO-1), glutathione S-transferase (GST), and the aldo-keto reductases (AKCR) 1C1 and AKCR1C2 in HT-22 cells. In vivo, isosilybin (50 and 100 mg/kg) reduces tumor volume and increases tumor cell apoptosis in a DU145 prostate cancer mouse xenograft model.3 It also reduces expression of the tumor angiogenesis markers CD31, nestin, VEGF, VEGFR1, VEGFR2, phospho-Akt, and HIF-1α in tumor tissue without reducing blood vessel count in non-cancerous liver, lung, and kidney tissue in DU145 tumor-bearing mice. | [Uses]
Isosilybin is useful in the treatment of liver disease
| [Definition]
ChEBI: A flavonolignan isolated from Silybum marianum. | [References]
[1] Radek Ga?ák . “Preparative method for isosilybin isolation based on enzymatic kinetic resolution of silymarin mixture.” Process Biochemistry 48 1 (2013): Pages 184-189.
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