Genistein ( born Genistein ) is an organic substance of plant origin from the class of isoflavones . It was first obtained in 1899 from a gorse dye ( Latin Genísta tinctória ), which is why it got its name. In 1926, the structure of genistein was discovered, in 1928 it was chemically synthesized. [one]
| Genistein | |
|---|---|
 | |
 | |
| Are common | |
| Systematic name | 5,7-dihydroxy-3- (4-hydroxyphenyl) chromen-4-one |
| Chem. formula | C 15 H 10 O 5 |
| Physical properties | |
| Molar mass | 270.24 g / mol |
| Classification | |
| Reg. CAS number | 446-72-0 |
| PubChem | |
| Reg. EINECS number | |
| Smiles | |
| Inchi | |
| RTECS | |
| Chebi | and |
| ChemSpider | |
Content
Occurrence in nature
Isoflavones, such as genistein and daidzein , are found in several plants. They are found in lupine , garden beans , soybeans , lobed Pueraria , psoralea , [2] [3] in the medicinal plants Flemingia vestita [4] and Flemingia macrophylla , [5] [6] and in coffee . [7]
Genistein is also found in Maackia amurensis . [eight]
Biological Activity
Isoflavones act as antioxidant and anthelmintic drugs. Due to their structural similarities with estrogen hormones in animal and human cells, they can interact with estrogen receptors, which leads to effects similar to the hormonal effects of estrogens.
Genistein has numerous biochemical functions in living cells:
- activation of PPAR receptors;
- inhibition of several tyrosine kinases ;
- inhibition of topoisomerase ;
- direct antioxidant effect with some prooxidant properties;
- activation of the Nrf2- dependent antioxidant response;
- autophagy stimulation [9] [10] [11]
- beta estrogen receptor activation;
- mammalian hexose transporter inhibition GLUT1 ;
- contraction of several types of smooth muscles;
- modulation of the CFTR channel (potentiation of its opening at low concentrations and inhibition at high);
- inhibition of cytosine methylation.
Notes
- ↑ Walter ED Genistin (an isoflavone glucoside) and its aglucone, genistein, from soybeans (English) // J Am Chem Soc : journal. - 1941. - Vol. 62 , no. 12 . - P. 3273–3276 . - DOI : 10.1021 / ja01857a013 .
- ↑ Coward L., Barnes NC, Setchell KDR, Barnes S. Genistein, daidzein, and their β-glycoside conjugates: antitumor isoflavones in soybean foods from American and Asian diets (Eng.) // J Agric Food Chem : journal. - 1993. - Vol. 41 , no. 11 . - P. 1961-1967 . - DOI : 10.1021 / jf00035a027 .
- ↑ Kaufman PB, Duke JA, Brielmann H., Boik J., Hoyt JE A comparative survey of leguminous plants as sources of the isoflavones, genistein and daidzein: implications for human nutrition and health. (Eng.) // J Altern Complement Med : journal. - 1997. - Vol. 3 , no. 1 . - P. 7-12 . - DOI : 10.1089 / acm.1997.3.7 . - PMID 9395689 .
- ↑ Rao, HSP; Reddy, KS Isofavones from Flemingia vestita (English) // Fitoterapia : journal. - 1991. - Vol. 62 , no. 5 . - P. 458 .
- ↑ Li BQ, Song QS Chemical constituents in roots of Flemingia macrophylla (Eng.) // Chinese Traditional and Herbal Drugs: journal. - 2009. - Vol. 40 , no. 2 . - P. epub . - DOI : 10.1016 / S0031-9422 (00) 80163-6 .
- ↑ Wang BS, Juang LJ, Yang JJ, Chen LY, Tai HM, Huan MH Antioxidant and antityrosinase activity of Flemingia macrophylla and Glycine tomentella roots (English) // Evidence-Based Complementary and Alternative Medicine : journal. - 2012. - P. 1-7 . - DOI : 10.1155 / 2012/431081 . - PMID 22997529 .
- ↑ Alves RC, Almeida IM, Casal S., Oliveira MB. Isoflavones in coffee: influence of species, roast degree, and brewing method. (Eng.) // J Agric Food Chem : journal. - 2010 .-- Vol. 58 , no. 5 . - P. 3002-3007 . - DOI : 10.1021 / jf9039205 . - PMID 20131840 .
- ↑ Fedoreyev SA, Pokushalov TV, Veselova MV, Glebko LI, Kulesh NI, Muzarok TI, Seletskaya LD, Bulgakov VP and Zhuravlev YN Isoflavonoid production by callus cultures of Maackia amurensis (English) // Fitoterapia : journal. - 2000. - Vol. 71 , no. 4 . - P. 365-372 . - DOI : 10.1016 / S0367-326X (00) 00129-5 . - PMID 10925005 .
- ↑ Gossner, G .; Choi, M .; Tan, L .; Fogoros, S .; Griffith, KA .; Kuenker, M .; Liu, JR. Genistein-induced apoptosis and autophagocytosis in ovarian cancer cells (English) // Gynecol Oncol : journal. - 2007 .-- April ( vol. 105 , no. 1 ). - P. 23-30 . - DOI : 10.1016 / j.ygyno.2006.11.009 . - PMID 17234261 .
- ↑ Singletary, K .; Milner, J. Diet, autophagy, and cancer: a review (English) // Cancer Epidemiol Biomarkers Prev : journal. - 2008 .-- July ( vol. 17 , no. 7 ). - P. 1596-1610 . - DOI : 10.1158 / 1055-9965.EPI-07-2917 . - PMID 18628411 .
- ↑ Nakamura, Y .; Yogosawa, S .; Izutani, Y .; Watanabe, H .; Otsuji, E .; Sakai, T. A combination of indol-3-carbinol and genistein synergistically induces apoptosis in human colon cancer HT-29 cells by inhibiting Akt phosphorylation and progression of autophagy (Eng.) // Mol Cancer: journal. - 2009. - Vol. 8 . - P. 100 . - DOI : 10.1186 / 1476-4598-8-100 . - PMID 19909554 .