68682-02-0

68682-02-0 structure

Name: rac 8-Prenylnaringenin
Chemical Name: rac 8-Prenylnaringenin
CAS Number: 68682-02-0
Molecular Formula: C₂₀H₂₀O₅
Molecular Weight: 340.37000
Catalog: Signaling Pathways Apoptosis Apoptosis
Create Date: 2016-07-31 19:34:13
Modify Date: 2024-01-03 12:19:37
(±)-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].

Name	rac 8-Prenylnaringenin
Synonyms	5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one

Description	(±)-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].
Related Catalog	Signaling Pathways >> Others >> Estrogen Receptor/ERR Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Research Areas >> Endocrinology Research Areas >> Metabolic Disease
Target	ERα:57 nM (IC50) ERβ:68 nM (IC50)
In Vitro	在兔骨髓细胞中，(±)-8-Prenylnaringenin 比 Osteoclasts 更能抑制破骨细胞的形成并诱导破骨细胞凋亡。(±)-8-Prenylnaringenin 应用于 MC3T3-E1 成骨细胞系，可促进分化和成熟，同时抑制 RAW264.7 破骨细胞系的分化。(±)-8-Prenylnaringenin 抑制核因子-κB配体受体激活剂 (RANKL) 的表达，并导致骨保护素的表达增加[1]。在暴露于 (±)-8-Prenylnaringenin 后，在 PC-3 人前列腺癌细胞和 UO.31 人肾癌细胞中观察到显着的剂量依赖性增殖抑制。在人乳腺癌细胞系 MCF-10A 中，(±)-8-Prenylnaringenin 调节雌二醇转化为促癌代谢物的代谢途径，从而抑制恶性转化[1]。
In Vivo	(±)-8-Prenylnaringenin（50 mg/kg；口服强饲法；每天一次；持续 12 天）改善由 STZ 治疗引起的葡萄糖稳态受损和胰岛功能障碍。 (±)-8-Prenylnaringenin 增加胰腺和肝脏中 ERα 和肝脏中成纤维细胞生长因子 21 的蛋白表达水平[3]。 Animal Model: Male C57BL/6J mice (Seven-week-old) injected with Streptozotocin (STZ)[3] Dosage: 50 mg/kg Administration: Orally gavage; once daily; for 12 days Result: Ameliorated impaired glucose homeostasis and islet dysfunction induced by STZ treatment.
References	[1]. Kateřina Štulíková, et al. Therapeutic Perspectives of 8-Prenylnaringenin, a Potent Phytoestrogen from Hops. Molecules. 2018 Mar 15;23(3):660. [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. [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.

Molecular Formula	C₂₀H₂₀O₅
Molecular Weight	340.37000
Exact Mass	340.13100
PSA	86.99000
LogP	4.01860
Appearance	Light yellow powder
Storage condition	−20°C

Safety Phrases	22-24/25
WGK Germany	3

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