(±)-8-Prenylnaringenin 

(±)-8-Prenylnaringenin, a natural prenylated flavonoid, is a potent phytoestrogen. (±)-8-Prenylnaringenin is an orally active selective estrogen receptor modulator (SERM) (Estrogen Receptor/ERR) that inhibits ERα and ERβ with IC₅₀s of 57 nM and 68 nM, respectively. (±)-8-Prenylnaringenin has anticancer effects, and can be used for osteoporosis research^[1][2].

In rabbit bone marrow cells, (±)-8-Prenylnaringenin inhibits the formation and induces apoptosis of Osteoclasts to a greater extent than naringenin. (±)-8-Prenylnaringenin is applied to the MC3T3-E1 osteoblast cell line, where it enhances differentiation and maturation, and also inhibits the differentiation of the RAW264.7 osteoclast cell line. (±)-8-Prenylnaringenin inhibits the expression of receptor activator of nuclear factor-κB ligand (RANKL), and leads to increased expression of osteoprotegerin^[1].
A significant, dose-dependent inhibition of proliferation is observed in PC-3 human prostate cancer cells and UO.31 human renal carcinoma cells after exposure to (±)-8-Prenylnaringenin. In MCF-10A, a human breast cancer cell line, (±)-8-Prenylnaringenin modulats the metabolic pathways of estradiol conversion into cancer-promoting metabolites, and thereby inhibits malignant transformation^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

(±)-8-Prenylnaringenin (50 mg/kg; orally gavage; once daily; for 12 days) ameliorates impaired glucose homeostasis and islet dysfunction induced by STZ treatment. (±)-8-Prenylnaringenin increases the protein expression levels of ERα in the pancreas and liver and of fibroblast growth factor 21 in the liver^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

340.37

C₂₀H₂₀O₅

68682-02-0

O=C1CC(OC2=C(C(O)=CC(O)=C21)C/C=C(C)\C)C3=CC=C(C=C3)O

Room temperature in continental US; may vary elsewhere.

Please store the product under the recommended conditions in the Certificate of Analysis.

• [1]. Kateřina Štulíková, et al. Therapeutic Perspectives of 8-Prenylnaringenin, a Potent Phytoestrogen from Hops. Molecules. 2018 Mar 15;23(3):660.  [Content Brief]

  [2]. Frederik Roelens, et al. Subtle side-chain modifications of the hop phytoestrogen 8-prenylnaringenin result in distinct agonist/antagonist activity profiles for estrogen receptors alpha and beta. J Med Chem. 2006 Dec 14;49(25):7357-65.  [Content Brief]

  [3]. Song Park, et al. Naringenin and Phytoestrogen 8-Prenylnaringenin Protect against Islet Dysfunction and Inhibit Apoptotic Signaling in Insulin-Deficient Diabetic Mice. Molecules. 2022 Jun 30;27(13):4227.  [Content Brief]