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HomeProduct name list8-PRENYLNARINGENIN

8-PRENYLNARINGENIN

8-PRENYLNARINGENIN Structural

What is 8-PRENYLNARINGENIN?

The Uses of 8-PRENYLNARINGENIN

(-)-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].

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.

Properties of 8-PRENYLNARINGENIN

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
form  neat
pka 7.70±0.40(Predicted)
form  Solid
color  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

Safety information for 8-PRENYLNARINGENIN

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for 8-PRENYLNARINGENIN

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

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