| Identification | Back Directory | [Name]
KURARINONE | [CAS]
34981-26-5 | [Synonyms]
Marini
Kurarinon
KURARINONE
Kurarinone >=98% (HPLC)
2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-(5-methyl-2-prop-1-en-2-ylhex-4-enyl)-2,3-dihydrochromen-4-one
(S)-2-(2,4-Dihydroxyphenyl)-7-hydroxy-5-methoxy-8-((R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl)chroman-4-one
2-(2,4-Dihydroxyphenyl)-2,3-dihydro-7-hydroxy-5-methoxy-8-[5-methyl-2-(1-methylethenyl)-4-hexenyl]-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one,2-(2,4-dihydroxyphenyl)-2,3-dihydro-7-hydroxy-5-methoxy-8-[(2R)-5-methyl-2-(1-methylethenyl)-4-hexen-1-yl]-,(2S)- | [EINECS(EC#)]
233-305-4 | [Molecular Formula]
C26H30O6 | [MDL Number]
MFCD03411889 | [MOL File]
34981-26-5.mol | [Molecular Weight]
438.51 |
| Chemical Properties | Back Directory | [Melting point ]
117-119℃ | [Boiling point ]
651.4±55.0 °C(Predicted) | [density ]
1?+-.0.06 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Powder | [pka]
7.49±0.40(Predicted) | [color ]
Light yellow to yellow | [biological source]
(isolated from Caragana sinica) | [InChI]
1S/C25H28O6/c1-13(2)5-6-15(14(3)4)9-18-20(28)11-21(29)24-22(30)12-23(31-25(18)24)17-8-7-16(26)10-19(17)27/h5,7-8,10-11,15,23,26-29H,3,6,9,12H2,1-2,4H3 | [InChIKey]
XRYVAQQLDYTHCL-UHFFFAOYSA-N | [SMILES]
CC([C@H](CC=C(C)C)CC1=C2C(C(C[C@@H](C3=CC=C(O)C=C3O)O2)=O)=C(OC)C=C1O)=C |
| Hazard Information | Back Directory | [Uses]
Kurarinone is an orally active flavonoid isolated from matrine that inhibits the pathogenesis of experimental autoimmune encephalomyelitis by inhibiting cell differentiation of Th1 and Th17. Kurarinone has antitumor and anti-inflammatory activity[1][2][3]. | [Definition]
ChEBI: (2S)-(-)-kurarinone is a trihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 7, 2' and 4', a lavandulyl group at position 8 and a methoxy group at position 5. Isolated from the roots of Sophora flavescens, it exhibits cytotoxicity against human myeloid leukemia HL-60 cells. It has a role as a metabolite and an antineoplastic agent. It is a trihydroxyflavanone, a monomethoxyflavanone and a member of 4'-hydroxyflavanones. It is functionally related to a (2S)-flavanone. | [Biological Activity]
Kurarinone, a flavonoid isolated from Sophora flavescens, inhibits the pathogenesis of experimental autoimmune encephalomyelitis by inhibiting the differentiation of Th1 and Th17 cells. | [Physiological effects]
Kurarinon has an anti-endothelial cell proliferative activity, and it has a significant inhibitory effect on endothelial cell proliferation with a median inhibitory concentration (IC50) of 12ug/ml. | [in vivo]
Kurarinone (100 mg/kg，口服，第 21-42 天) 在胶原诱导关节炎 (CIA) 小鼠模型中具有治疗作用[3]。
? Kurarinone (100 mg/kg，p.o.，from day 21-42) has a therapeutic effect in a mouse model of collagen-induced arthritis (CIA)[3].
| Animal Model: | CIA Mouse Model[3] | | Dosage: | 100 mg/kg | | Administration: | p.o. | | Result: | Reduced the levels of proinflammatory cytokines, TNF-α, IL-6, IFN-γ, and IL-17A.
Reduced STAT1 and STAT3 phosphorylation and the proportions of Th1 and Th17 cells in lymph nodes.
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| [References]
[1] Xie L, et al. The flavonoid kurarinone inhibits clinical progression of EAE through inhibiting Th1 and Th17 cell differentiation and proliferation. Int Immunopharmacol. 2018 Sep;62:227-236. DOI:10.1016/j.intimp.2018.06.022
[2] Nishikawa S, et al. Kurarinone from Sophora Flavescens Roots Triggers ATF4 Activation and Cytostatic Effects Through PERK Phosphorylation. Molecules. 2019 Aug 27;24(17):3110. DOI:10.3390/molecules24173110
[3] Tang KT, et al. Kurarinone Attenuates Collagen-Induced Arthritis in Mice by Inhibiting Th1/Th17 Cell Responses and Oxidative Stress. Int J Mol Sci. 2021 Apr 13;22(8):4002. DOI:10.3390/ijms22084002 |
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