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Kushenol K

Names

[ CAS No. ]:
101236-49-1

[ Name ]:
Kushenol K

[Synonym ]:
4H-1-Benzopyran-4-one, 2-(2,4-dihydroxyphenyl)-2,3-dihydro-3,7-dihydroxy-8-[(2R)-5-hydroxy-5-methyl-2-(1-methylethenyl)hexyl]-5-methoxy-, (2R,3S)-
(2R,3S)-2-(2,4-Dihydroxyphenyl)-3,7-dihydroxy-8-[(2R)-5-hydroxy-2-isopropenyl-5-methylhexyl]-5-methoxy-2,3-dihydro-4H-chromen-4-one
(2R,3S)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-8-[(2R)-5-hydroxy-5-methyl-2-(prop-1-en-2-yl)hexyl]-5-methoxy-2,3-dihydro-4H-chromen-4-one

Biological Activity

[Description]:

Kushenol K, a flavonoid antioxidant isolated from the roots of Sophora flavescens. Kushenol K is a cytochrome P-450 3A4 (CYP3A4) inhibitor with a Ki value of 1.35 μM[1]. Kushenol K shows weak antiviral activity against HSV-2 (EC50 of 147 μM)[2]. Kushenol K also inhibits the activity of SGLT1 and SGLT2[3].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HSV
Research Areas >> Infection
Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450
Research Areas >> Metabolic Disease
Signaling Pathways >> Membrane Transporter/Ion Channel >> SGLT

[Target]

HSV-2:147 μM (EC50)

CYP3A4:1.35 μM (Ki)

SGLT


[In Vitro]

When Midazolam is used as the substrate of CYP3A4, Kushenol K exhibits the strong inhibition with an IC50 values of 1.62 µM[1]. At a concentration of 50 μM, the inhibition rate of Kushenol K on SGLT1 is 29.7%, and the inhibition rate on SGLT2 is 43.7%[3].

[References]

[1]. Yannan Li, et al. Drug interaction study of flavonoids toward CYP3A4 and their quantitative structure activity relationship (QSAR) analysis for predicting potential effects. Toxicol Lett. 2018 Sep 15;294:27-36.

[2]. E R Woo, et al. A new prenylated flavonol from the roots of Sophora flavescens. J Nat Prod. 1998 Dec;61(12):1552-4.

[3]. Seizo Sato, et al. Na+-glucose cotransporter (SGLT) inhibitory flavonoids from the roots of Sophora flavescens. Bioorg Med Chem. 2007 May 15;15(10):3445-9.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
722.4±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C26H32O8

[ Molecular Weight ]:
472.527

[ Flash Point ]:
242.4±26.4 °C

[ Exact Mass ]:
472.209717

[ LogP ]:
3.81

[ Vapour Pressure ]:
0.0±2.5 mmHg at 25°C

[ Index of Refraction ]:
1.614

Related Compounds