| Identification | Back Directory | [Name]
3-(2,4-Dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one | [CAS]
94805-82-0 | [Synonyms]
Glycycoumarin
Glycocoumarin -
Glycocoumarin - Glycyrrhiza uralensis (liquorice)
3-(2,4-Dihydroxyphenyl)-5-methoxy-6-(3-methyl-2-butenyl)-7-hydroxy-2H-1-benzopyran-2-one
3-(2,4-Dihydroxyphenyl)-6-(3-methyl-2-butenyl)-5-methoxy-7-hydroxy-2H-1-benzopyran-2-one
3-(2,4-Dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one
3-(2,4-Dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methyl-2-buten-1-yl)-2H-1-benzopyran-2-one
2H-1-Benzopyran-2-one, 3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methyl-2-buten-1-yl)- | [Molecular Formula]
C21H20O6 | [MDL Number]
MFCD00272146 | [MOL File]
94805-82-0.mol | [Molecular Weight]
368.38 |
| Chemical Properties | Back Directory | [Melting point ]
243.5-244.5℃ | [Boiling point ]
646.9±55.0 °C(Predicted) | [density ]
1.342±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO | [form ]
solid | [pka]
7.86±0.20(Predicted) | [color ]
white to beige | [biological source]
plant | [Major Application]
metabolomics
vitamins, nutraceuticals, and natural products | [InChI]
1S/C21H20O6/c1-11(2)4-6-14-18(24)10-19-16(20(14)26-3)9-15(21(25)27-19)13-7-5-12(22)8-17(13)23/h4-5,7-10,22-24H,6H2,1-3H3 | [InChIKey]
NZYSZZDSYIBYLC-UHFFFAOYSA-N | [SMILES]
[o]1c2c(c(c(c(c2)O)CC=C(C)C)OC)cc([c]1=O)c3c(cc(cc3)O)O |
| Hazard Information | Back Directory | [Uses]
It is a natural product derived from plant source th at finds application in compound screening libraries, metabolomics, phytochemical, and pharmaceutical research. | [Definition]
ChEBI: A member of the class of coumarins that is coumarin substituted by a hydroxy group at position 7, a methoxy group at position 5, a prenyl group at position 6 and a 2,4-dihydroxyphenyl group at position 3. Isolated from Glycyrrhiza uralensis,
it exhibits antispasmodic activity. | [Biological Activity]
Glycycoumarin is an isoflavone from vegetable roots including licorice th at exhibits potent hepatoprotective effects. Glycycoumarin protects hepatocytes through activation of autophagy and mitigation of ER stress/GSK-3 –JNK/CHOP-mitochondria cascade activation. Alsoit appears to alleviate acetaminophen-induced liver injury through sustained autophagy. | [in vivo]
Glycycoumarin (30 μM-0.3 nM; 5 min) has an inhibitory effect on smooth muscle contraction induced by various types of stimulants through the inhibition of PDEs, especially isozyme 3, followed by the accumulation of intracellular cAMP[1].
Glycycoumarin (10 mg/kg; i.p.; once daily for 4 d) enhances tumor growth inhibition in HepG2 xenograft model in mice and shows synergistical effect with ABT-737 (HY-50907)[2].
| Animal Model: | Male ICR mice (aged 6 weeks, weight 25-30 g)[1] | | Dosage: | 30 μM-0.3 nM, 5 min | | Administration: | | | Result: | Inhibited the contraction induced by various types of stimulants, such as CCh, KCI, BaCI(2), and A23187 (calcium ionophore III).
Enhanced the relaxation induced by forskolin on CCh-evoked contraction and also enhances the relaxation effect of rolipram.
Associated with dose-dependent accumulation of cAMP.
|
| Animal Model: | HepG2 cancer cells xenograft model in male BALB/c athymic nude mice (6-7 weeks old)[2] | | Dosage: | 10 mg/kg | | Administration: | Intraperitoneal injection; once daily for 4 days; ABT-737 group was given 100 mg/kg i.p. | | Result: | Inhibited tumor growth and resulted a reduction of the final tumor weight by 17%. |
| [storage]
Store at -20°C |
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