Chemical Properties
Yellow Crystalline Solid
Definition
ChEBI: 7-Hydroxyisoflavone with additional hydroxy groups at positions 5 and 4'. It is a phytoestrogenic isoflavone with antioxidant properties.
General Description
Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards
Biological Activity
Phytoestrogen with a wide range of biological actions. Inhibits protein tyrosine kinases including epidermal growth factor receptor kinase. Also binds to PPAR γ and estrogen receptors and acts as an agonist at GPR30. Also available as part of the MAPK Cascade Inhibitor Tocriset™ .
Biochem/physiol Actions
Inhibitor of tyrosine protein kinase; competitive inhibitor of ATP in other protein kinase reactions. Antiangiogenic agent, down-regulates the transcription of genes involved in controlling angiogenesis.
Anticancer Research
It is an isoflavone and is obtained from a variety of plants like psoralea (Psoraleacorylifolia), kudzu (Pueraria lobata), faba beans (Vicia faba), and soybeans(Glycine max). It exhibits anticancer effect by inhibiting NF-κB and protein kinaseB (Akt) signaling pathways (Singh et al. 2016b). It blocks the proliferation of cancercells via the inhibition of cell growth enzymes and survival like tyrosine kinase andtopoisomerase II; hence it is used to treat leukemia. Genistein increases the growthrate of some estrogen receptors in breast cancer cells and the rate of proliferation of estrogen-dependent breast cancer by competitive binding to the estrogen-β receptors.It may be involved in JNK pathway in inducing activator protein-1(AP-1) activity(Wang et al. 2012; Dixon and Ferreira 2002).
storage
-20°C (desiccate)
Purification Methods
Crystallise it from EtOH or aqueous EtOH. It has UV: max at 290nm (EtOH). The S(-)-enantiomer (natural form) has m 255-256o (from EtOH) and [] D 20 -28.0o (c 2, EtOH), [ ] D 20 -35.2o (c 1, pyridine).[Beilstein 18 H 503, 18 II 164, 18 III/IV 2630.] Genistein (4',5,7-trihydroxyisoflavone) [446-72-0]M 270.2 crystallises from 60% aqueous EtOH or water with m 297-298o and [] D 20 -28o (c 0.6, 20mM NaOH). [Beilstein 18/4 V 594.]For Naringin (naringenin 7-rhamnoglucoside) See “Carbohydrates” in Chapter 6.
References
1) Akiyama?et al.?(1987),?Genistein, a specific inhibitor of tyrosine-specific protein kinases; J. Biol. Chem.,?262?5592
2) Linassier?et al.?(1990),?Mechanisms of action in NIH-3T3 cells of genistein, an inhibitor if EGF receptor tyrosine kinase?Biochem. Pharmacol.,?39?187
3) Dang?et al.?(2003),?Peroxisome proliferator-activated receptor gamma (PPARgamma) as a molecular target for the soy phytoestrogen genistein; J. Biol. Chem.,?278?962
4) Vivacqua?et al.?(2006),?17beta-estradiol, genistein, and 4-hydroxytamoxifen induce the proliferation of thyroid cancer cells through the g protein-coupled receptor GPR30; Mol. Pharmacol., 70?1414
5) Sarker and Li (2002),?Mechanisms of cancer chemoprevention by soy isoflavone genistein; Cancer Metastasis Rev.,?21?265
