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6,8-diprenylnaringenin

Names

[ CAS No. ]:
68236-11-3

[ Name ]:
6,8-diprenylnaringenin

[Synonym ]:
Senegalensien
Lonchocarpol A
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Senegalensein
Senegalensin
4H-1-Benzopyran-4-one,2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis(3-methyl-2-butenyl)-,(S)
6,8-Diprenylnaringenin

Biological Activity

[Description]:

6,8-Diprenylnaringenin (Lonchocarpol A; Senegalensin), a hop prenylflavonoid, is a inhibitor of breast cancer resistance protein (BCRP/ABCG2). 6,8-Diprenylnaringenin inhibits ABCG2-mediated efflux of Mitoxantrone, and 3H-Methotrexate transport (IC50=0.41 μM) in HEK293 cells. 6,8-Diprenylnaringenin exhibits some estrogenicity, but its potency is less than 1% of that of 8-Prenylnaringenin[1][2].

[Related Catalog]:

Research Areas >> Cancer
Research Areas >> Metabolic Disease
Signaling Pathways >> Membrane Transporter/Ion Channel >> BCRP

[References]

[1]. Tan KW, et al. Hop-derived prenylflavonoids are substrates and inhibitors of the efflux transporter breast cancer resistance protein (BCRP/ABCG2). Mol Nutr Food Res. 2014 Nov;58(11):2099-110.

[2]. Milligan SR, et al. The endocrine activities of 8-prenylnaringenin and related hop (Humulus lupulus L.) flavonoids. J Clin Endocrinol Metab. 2000 Dec;85(12):4912-5.

Chemical & Physical Properties

[ Density]:
1.22g/cm3

[ Boiling Point ]:
639.245°C at 760 mmHg

[ Molecular Formula ]:
C25H28O5

[ Molecular Weight ]:
408.48700

[ Flash Point ]:
218.297°C

[ Exact Mass ]:
408.19400

[ PSA ]:
86.99000

[ LogP ]:
5.52730

Related Compounds