Genistein
Compound Structure: |
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Synonyms: | 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one; genistein; Prunetol; 4',5,7-Trihydroxyisoflavone; Genisterin; Genisteol; Sophoricol; 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one; 5,7,4'-Trihydroxyisoflavone; Bonistein; Genestein | ||||||||||||||||||||||||||||||||||||||||||||
Compound ID: | NMPC-1070 | ||||||||||||||||||||||||||||||||||||||||||||
PubChem ID: | |||||||||||||||||||||||||||||||||||||||||||||
Molecular Formula: | C15H10O5 | ||||||||||||||||||||||||||||||||||||||||||||
Canonical SMILES: | C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O | ||||||||||||||||||||||||||||||||||||||||||||
InChIKey: | TZBJGXHYKVUXJN-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||
About the compound: | Genistein, a 7-hydroxyisoflavone with additional hydroxy groups at positions 5 and 4', is a phytoestrogenic isoflavone known for its antioxidant properties. It serves various roles, including as an antineoplastic agent, a tyrosine kinase inhibitor, a DNA topoisomerase inhibitor, a phytoestrogen, a plant metabolite, a geroprotector, and a human urinary metabolite. It is the conjugate acid of a genistein(1-) and is functionally related to emodin anthrone. Derived from soy products, genistein inhibits protein-tyrosine kinase and topoisomerase-II activities, making it useful as an antineoplastic and antitumor agent. It has been shown to induce G2 phase arrest in human and murine cell lines. Additionally, genistein possesses antihelmintic activity, having been identified as the active ingredient in Felmingia vestita, a plant traditionally used against worms. It has demonstrated effectiveness against common liver fluke, pork trematode, and poultry cestode. As a phytoestrogen with selective estrogen receptor modulator properties, genistein has been investigated in clinical trials as an alternative to hormone therapy for preventing cardiovascular disease in postmenopausal women. Natural sources of genistein include tofu, fava beans, soybeans, kudzu, and lupin. Genistein (C15H10O5) is part of the isoflavone class and is described as an angiogenesis inhibitor and a phytoestrogen. It was first isolated in 1899 from the dyer's broom, Genista tinctoria, leading to its chemical name. The structure was established in 1926, and it was chemically synthesized in 1928. It is a primary secondary metabolite of the Trifolium species and Glycine max. Apart from its roles as an antioxidant and anthelmintic, genistein interacts with estrogen receptors in animals and humans, producing effects similar to the hormone estrogen. It also exhibits non-hormonal effects. Genistein and daidzein bind to and transactivate all three PPAR isoforms, influencing both ERs and PPARs, thereby inducing differential effects. As a tyrosine kinase inhibitor, genistein primarily inhibits the epidermal growth factor receptor (EGFR). Additionally, it may act as a direct antioxidant and poison topoisomerase II by generating free radicals. It also triggers the activation of the beneficial, detoxifying Nrf2 factor in response to its insult. In studies on rodents, genistein has shown promise in the treatment of leukemia and can be used in combination with other antileukemic drugs. Due to its structural similarity to 17β-estradiol (estrogen), genistein can bind to estrogen receptors, though it shows a higher affinity toward estrogen receptor β than α. However, genistein can increase the growth rate of some ER-expressing breast cancers and may decrease the efficiency of certain breast cancer therapies. Isoflavones like genistein can also impact male fertility, with studies showing varying effects. In high doses, genistein is toxic to normal cells, exhibiting both anticarcinogenic and carcinogenic potential. It has been found to deteriorate DNA of cultured blood stem cells, potentially leading to leukemia, and is suspected of increasing the risk of infant leukemia when consumed during pregnancy. Genistein shows potential in treating Sanfilippo syndrome by decreasing the pathological accumulation of glycosaminoglycans. It also possesses toxic properties toward brain cells and stimulates pathways like autophagy, which may explain its observed efficiency. In terms of cognitive effects, a study among Italians over 50 found that high genistein intake was associated with lower odds of cognitive impairment. https://en.wikipedia.org/wiki/Genistein GHS Hazard Statements • H302 (96.48%): Harmful if swallowed [Warning Acute toxicity, oral] • H315 (65.49%): Causes skin irritation [Warning Skin corrosion/irritation] • H319 (65.49%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] • H335 (65.49%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] • H400 (62.68%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard] • H410 (62.68%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard] |
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Properties: |
Source: PubChem |
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Source Species: |
Talinum triangulare |