8-PRENYLNARINGENIN

Bezeichnung:8-PRENYLNARINGENIN

CAS-Nr53846-50-7

Englisch Name:8-PRENYLNARINGENIN

CBNumberCB31484307

SummenformelC20H20O5

Molgewicht340.37

MOL-Datei53846-50-7.mol

8-PRENYLNARINGENIN physikalisch-chemischer Eigenschaften

Siedepunkt	597.6±50.0 °C(Predicted)
Dichte	1.314±0.06 g/cm3(Predicted)
storage temp.	2-8°C
Löslichkeit	Soluble in DMSO
pka	7.70±0.40(Predicted)
Aggregatzustand	Solid
Farbe	White to off-white
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)

Sicherheit

WGK Germany

Gefahreninformationscode (GHS)

8-PRENYLNARINGENIN Chemische Eigenschaften,Einsatz,Produktion Methoden

Verwenden
(-)-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-).
Biologische Aktivität
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
Einzelnachweise
[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 Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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