(2S)-6-Prenylnaringenin

Names

[ Name ]:
(2S)-6-Prenylnaringenin

[Synonym ]:
YS03
6-Prenylnaringenin
5,7,4'-Trihydroxy-6-prenylflavanone
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one

Biological Activity

[Description]:

(2S)-6-Prenylnaringenin is the most efficient compound in forebrain. (2S)-6-Prenylnaringenin acts as a GABAA positive allosteric modulator at α+β- binding interface[1].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Research Areas >> Neurological Disease

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

[In Vitro]

(2S)-6-Prenylnaringenin (6-Prenylnaringenin) displays a modulatory activity at low micromolar concentrations. (2S)-6-Prenylnaringenin potentiates GABA-induced displacement of [3H]EBOB binding in a concentration-dependent manner where the IC50 value for this potentiation in native GABAA receptors is 3.7 μM, respectively[1].

[References]

[1]. Ali Y Benkherouf, et al. Hops Compounds Modulatory Effects and 6-prenylnaringenin Dual Mode of Action on GABA AReceptors. Eur J Pharmacol. 2020 Apr 15;873:172962.

Chemical & Physical Properties

[ Density]:
1.314±0.06 g/cm3

[ Molecular Formula ]:
C₂₀H₂₀O₅

[ Molecular Weight ]:
340.37000

[ Exact Mass ]:
340.13100

[ PSA ]:
86.99000

[ LogP ]:
4.01860

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
Insuluble (9.2E-3 g/L) (25 ºC)

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Articles

Involvement of a Hydrophobic Pocket and Helix 11 in Determining the Modes of Action of Prenylated Flavonoids and Isoflavonoids in the Human Estrogen Receptor.

ChemBioChem. 16 , 2668-77, (2016)

Six prenylated (iso)flavonoids were purified from a licorice root extract and subjected to competition experiments with six commercially available (iso)flavonoids. The agonistic and antagonistic activ...