8-PRENYLNARINGENIN Chemical Properties

Boiling point:

597.6±50.0 °C(Predicted)

Density 

1.314±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in DMSO

pka

7.70±0.40(Predicted)

BRN 

5611472

InChI

InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9,18,21-23H,8,10H2,1-2H3/t18-/m0/s1

InChIKey

LPEPZZAVFJPLNZ-SFHVURJKSA-N

SMILES

[C@H]1(C2=CC=C(O)C=C2)OC2=C(C/C=C(/C)\C)C(O)=CC(O)=C2C(=O)C1

LogP

4.037 (est)

Safety Information

WGK Germany 

3

8-PRENYLNARINGENIN Usage And Synthesis

Uses

(-)-8-Prenylnaringin is a prenylflavonoid, a class on non-steroidal phytoestrogen that mimicks and/or modulating endogenous estrogens via estrogen receptor binding.

Definition

ChEBI: Sophoraflavanone B is a trihydroxyflavanone that is (S)-naringenin having a prenyl group at position 8. It has a role as a platelet aggregation inhibitor and a plant metabolite. It is a trihydroxyflavanone, a member of 4'-hydroxyflavanones and a (2S)-flavan-4-one. It is functionally related to a (S)-naringenin. It is a conjugate acid of a sophoraflavanone B(1-).

Biological Activity

8-prenylnaringenin is an estrogen receptor inhibitor.the two estrogen receptors erα and erβ belong to the nuclear receptor superfamily and are ligand-regulated transcription factors accounting for mediating the physiological effects of the steroid hormone 17α-estradiol. er is an established target for the development of synthetic ligands for therapeutic applications.

in vitro

previous study identified 8-prenylnaringenin as a potent phytoestrogen in hops, which had an activity greater than other known plant estrogens. the estrogenic activity of 8-prenylnaringenin was reflected in its relative binding affinity to estrogen receptors from rat uteri. in addition, the presence of 8-prenylnaringenin in hops might explane the accounts of menstrual disturbances in female hop workers [1].

in vivo

previous animal data demonstrated that 8-prenylnaringenin treatment could result in ampk signaling pathway activation, therefore suppressing lipogenesis. the consumption of 8-prenylnaringenin was able to prevent body weight gain and improve plasma lipid profile, with significant improvement of insulin resistance and glucose tolerance. moreove, it was found that 8-prenylnaringenin-enriched diet could ameliorate diabetic-associated metabolic disturbances via regulating glucose and lipid pathways [2].

IC 50

57 and 68 nm for erα and erβ, respectively

References

[1] milligan sr, kalita jc, heyerick a, rong h, de cooman l, de keukeleire d. identification of a potent phytoestrogen in hops (humulus lupulus l.) and beer. j clin endocrinol metab. 1999 jun;84(6):2249-52.
[2] costa r et al. xanthohumol and 8-prenylnaringenin ameliorate diabetic-related metabolic dysfunctions in mice. j nutr biochem. 2017 apr 6;45:39-47.

8-PRENYLNARINGENIN(53846-50-7)Related Product Information

• PONCIRIN
• 2-(3,4-Dihydroxyphenyl)-8-(2-O-beta-L-galactopyranosyl-beta-D-glucopyranosyl)-5,7-dihydroxy-4H-1-Benzopyran-4-one
• LUPULONE
• Xanthohumol
• MOSLOFLAVONE
• HUMULONE
• hydroxygenkwanin
• GARDENIN B
• Naringenin 7-O-β-D-Glucuronide (Mixture of Diastereomers)
• MEDICAGOL
• Quercetin-7-O-β-D-glucopyranoside
• 4',5-DIHYDROXY-7-METHOXYFLAVONE
• 3,3-Dimethylallyl bromide
• ISOXANTHOHUMOL
• 8-PRENYLNARINGENIN
• 6,8-DIPRENYLNARINGENIN
• LUPINIFOLINOL
• LUPINIFOLIN