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Glabrene Sale

(Synonyms: 光甘草素) 目录号 : GC36144

Glabrene 是一种来源于甘草根的异黄酮,具有雌激素样活性。Glabrene 是 tyrosinase 抑制剂,IC50 值为 3.5 μM。

Glabrene Chemical Structure

Cas No.:60008-03-9

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产品描述

Glabrene, an isoflavene derived from licorice root, shows estrogen-like activity. Glabrene is a tyrosinase inhibitor with an IC50 of 3.5 μM[1][2]. IC50: 3.5 μM (Tyrosinase)[2]

[1]. Somjen D, et al. Estrogenic activity of glabridin and glabrene from licorice roots on human osteoblasts and prepubertal rat skeletal tissues. J Steroid Biochem Mol Biol. 2004 Aug;91(4-5):241-6. [2]. Nerya O, et al. Glabrene and isoliquiritigenin as tyrosinase inhibitors from licorice roots. J Agric Food Chem. 2003 Feb 26;51(5):1201-7

Chemical Properties

Cas No. 60008-03-9 SDF
别名 光甘草素
Canonical SMILES OC1=C2C=CC(C)(C)OC2=C(C3=CC4=CC=C(O)C=C4OC3)C=C1
分子式 C20H18O4 分子量 322.35
溶解度 Soluble in DMSO 储存条件 Store at -20°C
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1 mM 3.1022 mL 15.5111 mL 31.0222 mL
5 mM 0.6204 mL 3.1022 mL 6.2044 mL
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Research Update

The phytoestrogen Glabrene prevents osteoporosis in ovariectomized rats through upregulation of the canonical Wnt/β-catenin signaling pathway

J Biochem Mol Toxicol 2021 Feb;35(2):e22653.PMID:33113278DOI:10.1002/jbt.22653.

This study systematically investigated the effects of phytoestrogen Glabrene on postmenopausal osteoporosis in an ovariectomy (OVX) rat model. Glabrene administration (25, 50, and 100 mg/kg) for 13 weeks can significantly slow down the body weight gain and slightly increase the uterus weight of OVX rats. The increased levels of U-Ca, U-P levels, urine DPD/creatinine, serum ALP, OCN, triglycerides, and total cholesterol induced by OVX were dramatically inhibited in rats, whereas no difference occurred for S-Ca and S-P in all groups. Furthermore, Glabrene can enhance bone mineral density of the right femur, fourth-lumbar vertebra and tibia and improve biomechanical parameters, such as femoral neck loading force, three-point bending of the tibia, and vertebral compression in OVX rats. Moreover, Glabrene greatly suppressed the expression of TRAP protein but increased OPG and BGP protein expression in tibia tissue of OVX rats. In addition, OVX-induced reduction of Lrp-5, β-catenin, Runx2, and Osx protein expression was all restored by Glabrene treatment. The present study indicated that Glabrene might be a potential alternative medicine for the prevention and treatment of postmenopausal osteoporosis via activation of the Wnt/β-catenin signaling pathway.

Glabrene and isoliquiritigenin as tyrosinase inhibitors from licorice roots

J Agric Food Chem 2003 Feb 26;51(5):1201-7.PMID:12590456DOI:10.1021/jf020935u.

Tyrosinase is known to be a key enzyme in melanin biosynthesis, involved in determining the color of mammalian skin and hair. Various dermatological disorders, such as melasama, age spots, and sites of actinic damage, arise from the accumulation of an excessive level of epidermal pigmentation. The inadequacy of current therapies to treat these conditions as well as high cytotoxicity and mutagenicity, poor skin penetration, and low stability of formulations led us to seek new whitening agents to meet the medical requirements for depigmenting agents. The inhibitory effect of licorice extract on tyrosinase activity was higher than that expected from the level of glabridin in the extract. This led us to test for other components that may contribute to this strong inhibitory activity. Results indicated that Glabrene and isoliquiritigenin (2',4',4-trihydroxychalcone) in the licorice extract can inhibit both mono- and diphenolase tyrosinase activities. The IC(50) values for Glabrene and isoliquiritigenin were 3.5 and 8.1 microM, respectively, when tyrosine was used as substrate. The effects of Glabrene and isoliquiritigenin on tyrosinase activity were dose-dependent and correlated to their ability to inhibit melanin formation in melanocytes. This is the first study indicating that Glabrene and isoliquiritigenin exert varying degrees of inhibition on tyrosinase-dependent melanin biosynthesis, suggesting that isoflavenes and chalcones may serve as candidates for skin-lightening agents.

Estrogen-like activity of Glabrene and other constituents isolated from licorice root

J Steroid Biochem Mol Biol 2001 Sep;78(3):291-8.PMID:11595510DOI:10.1016/s0960-0760(01)00093-0.

Licorice root extract and its major isoflavan, glabridin, exhibited varying degrees of estrogen receptor (ER) agonism in different tissues in vitro and in vivo. Animals fed with licorice extract, compared with estradiol and glabridin, showed an increase in creatine kinase (CK) activity, a known marker for estrogen responsive genes, which was higher than expected from the levels of glabridin in the extract. This led us to test for other components that may contribute to this strong estrogen agonist activity. Results indicated that Glabrene and isoliquiritigenin, (2',4',4-three hydroxy chalcone) (ILC) in the licorice extract can bind to the human ER with higher affinity (IC50, 1 and 0.5 microM) than glabridin (IC50, 5 microM). The stimulatory effects of Glabrene in vivo were tissue specific and similar to those of estradiol. The effect of increasing concentrations of Glabrene and ILC on the growth of breast tumor cell were biphasic. Both showed an ER-dependent growth-promoting effect at low concentrations (10 nM-10 microM), and ER-independent antiproliferative activity at concentrations >15 microM. This is the first study to indicate that Glabrene, an isoflavene exerted varying degrees of ER agonism in different tissues.

Estrogenic activity of glabridin and Glabrene from licorice roots on human osteoblasts and prepubertal rat skeletal tissues

J Steroid Biochem Mol Biol 2004 Aug;91(4-5):241-6.PMID:15336701DOI:10.1016/j.jsbmb.2004.04.008.

Data from both in vivo and in vitro experiments demonstrated that glabridin and Glabrene are similar to estradiol-17beta in their stimulation of the specific activity of creatine kinase, although at higher concentrations, but differ in their extent of action and interaction with other drugs. In pre-menopausal human bone cells, the response to estradiol-17beta and glabridin (at higher concentration) was higher than in post-menopausal cells; whereas, Glabrene (at higher concentration) was more effective in post-menopausal cells. At both ages, the response to estradiol-17beta and glabridin was enhanced by pretreatment with the less-calcemic Vitamin D analog CB 1093 (CB) and the demonstrably non-calcemic analog JK 1624 F(2)-2 (JKF). The response to Glabrene was reduced by this pretreatment. Both glabridin and Glabrene stimulated creatine kinase specific activity in diaphyseal bone and epiphyseal cartilage of prepubertal female rats. Daily feeding (3-14 days) of prepubertal female rats with glabridin, estradiol-17beta or their combination, also stimulated creatine kinase specific activity. Glabridine, similarly to estradiol-17beta, also stimulated creatine kinase specific activity in ovariectomized female rats. Raloxifene, in combination with glabridin or estradiol-17beta, demonstrated the phenomenon of mutual annihilation of stimulation of creatine kinase specific activity in both epiphysis and diaphysis. Glabrene activity was not inhibited by raloxifene. Therefore, glabridin shows greater similarity to estradiol-17beta and thus greater potential, with or without Vitamin D, to modulate bone disorders in post-menopausal women.

Bioactive Phytoconstituents as Potent Inhibitors of Tyrosine-Protein Kinase Yes (YES1): Implications in Anticancer Therapeutics

Molecules 2022 May 10;27(10):3060.PMID:35630545DOI:10.3390/molecules27103060.

Tyrosine-protein kinase Yes (YES1) belongs to the Tyrosine-protein kinase family and is involved in several biological activities, including cell survival, cell-cell adhesion, cell differentiation, and cytoskeleton remodeling. It is highly expressed in esophageal, lung, and bladder cancers, and thus considered as an attractive drug target for cancer therapy. In this study, we performed a virtual screening of phytoconstituents from the IMPPAT database to identify potential inhibitors of YES1. Initially, the molecules were retrieved on their physicochemical properties following the Lipinski rule of five. Then binding affinities calculation, PAINS filter, ADMET, and PASS analyses followed by an interaction analysis to select safe and clinically better hits. Finally, two compounds, Glabrene and Lupinisoflavone C (LIC), with appreciable affinities and a specific interaction towards the AlphaFold predicted structure of YES1, were identified. Their time-evolution analyses were carried out using an all-atom molecular dynamics (MD) simulation, principal component analysis, and free energy landscapes. Altogether, we propose that Glabrene and LIC can be further explored in clinical settings to develop anticancer therapeutics targeting YES1 kinase.