Coumestrol
From Wikipedia, the free encyclopedia
| Coumestrol | |
|---|---|
 |
|
| IUPAC name | 3,9-Dihydroxy-6-benzofurano[3,2-c]chromenone |
| Identifiers | |
| CAS number | [479-13-0] |
| PubChem | |
| SMILES | C1=CC2=C(C=C1O)OC3=C2C(=O)OC4=C3C=CC(=C4)O |
| Properties | |
| Molecular formula | C15H8O5 |
| Molar mass | 268.22102 |
| Melting point |
385 °C (decomp)[1] |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Coumestrol is a natural organic compound in the class of phytochemicals known as coumestans. It has garnered research interest because of its estrogenic activity and its prevalence in some foods, such as soybeans and herbs such as Pueraria mirifica.
Coumestrol was first identified by E. M. Bickoff in alfalfa in 1957.[2] It has since be found in a variety of legumes, soybeans, brussel sprouts, and spinach. Clover and soybeans have the highest concentrations.[3]
Coumestrol is a phytoestrogen, mimicking the biological activity of estrogens. The chemical shape of coumestrol orients its two hydroxy groups in the same position as the two hydroxy groups in estradiol, allowing it to inhibit the activity of aromatase and hydroxysteroid dehydrogenase.[4] These enzymes are involved in the biosynthesis of steroid hormones, and inhibition of these enzymes results in the modulation of hormone production.[3]
Pueraria mirifica or White Kawo Krua has been found to contain concentration of Coumestrol where Cu²+ at 1000 ppm the highest concentration was to be found where CuCl2, MnCl² and FeCl² at 1,000 ppm can in fact stimulate coumestrol accumulation.
[edit] References
- ^ Bickoff, E. M.; Livingston, A. L.; Witt, S. C.; Knuckles, B. E.; Guggolz, Jack; Spencer, R. R. (1964). "Isolation of coumestrol and other phenolics from alfalfa by countercurrent distribution". Journal of Pharmaceutical Sciences 53 (12): 1496–9. doi:.
- ^ E. M. Bickoff, A. N. Booth, R. L. Lyman, A. L. Livingston, C. R. Thompson, and F. Deeds (1957). "Coumestrol, a New Estrogen Isolated from Forage Crops". Science 126: 969–970. doi:.
- ^ a b Amr Amin and Michael Buratovich (2007). ""The Anti-Cancer Charm of Flavonoids: A Cup-of-Tea Will Do!". Recent Patents on Anti-Cancer Drug Discovery 2 (2): 109–117. doi:.
- ^ Blomquist CH, Lima PH, Hotchkiss JR (2005). "Inhibition of 3a-hydroxysteoid dehydogenase (3a-HSD) activity of human lung microsomes by genistein, daidzein, coumestrol and C18-, C19- and C21 hydroxysteroids and ketosteroids". Steroids 70 (8): 507–514. doi:.
