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Merck
CN

SML1843

Kurarinone

isolated from Caragana sinica, ≥98% (HPLC), BKCa channel blocker, powder

Synonym(s):

(-)-Kurarinone, (2S)-2-(2,4-Dihydroxyphenyl)-2,3-dihydro-7-hydroxy-5-methoxy-8-[(2R)-5-methyl-2-(1-methylethenyl)-4-hexen-1-yl]-4H-1-benzopyran-4-one, Marini

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About This Item

Empirical Formula (Hill Notation):
C26H30O6
CAS Number:
34981-26-5
Molecular Weight:
438.51
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Product Name

Kurarinone, ≥98% (HPLC)

SMILES string

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

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

InChI key

XRYVAQQLDYTHCL-UHFFFAOYSA-N

biological source

(isolated from Caragana sinica)

assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Kurarinone, a flavanone from Sophora flavescens roots, is a potent activator of the large-conductance calcium-activated potassium channel (BKCa channel).
Kurarinone, a flavanone from Sophora flavescens roots, is a potent activator of the large-conductance calcium-activated potassium channel (BKCa channel). Kurarinone exhibits strong preference to potentiate the homomeric BKCa channel composed only of the α subunits. Kurarinone reduces acetylcholine induced contraction of rat urinary bladder strips and decreased the voiding frequency in a rat OAB model. Kurarinone exhibits cytotoxic and antiinflamatory activity. Kurarinone sensitizes TRAIL-induced tumor cell apoptosis via suppression of NF-KB-dependent cFLIP expression.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000398012
0000398012
017M4756V

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Ok Won Seo et al.
Experimental & molecular medicine, 44(11), 653-664 (2012-08-31)
This study was designed to investigate the effects of the prenylated flavonoid kurarinone on TNF-related apoptosis inducing ligand (TRAIL)-induced apoptosis and its underlying mechanism. A low dose of kurarinone had no significant effect on apoptosis, but this compound markedly promoted
Sojung Lee et al.
Molecular pharmacology, 90(2), 140-150 (2016-06-03)
The large-conductance calcium-activated potassium channel (BKCa channel) plays critical roles in smooth muscle relaxation. In urinary bladder smooth muscle, BKCa channel activity underlies the maintenance of the resting membrane potential and repolarization of the spontaneous action potential triggering the phasic

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