Coumestrol

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Coumestrol
Coumestrol.png
Identifiers
CAS number 479-13-0 YesY
PubChem 5281707
ChemSpider 4445024 YesY
UNII V7NW98OB34 YesY
KEGG C10205 YesY
ChEBI CHEBI:3908 N
ChEMBL CHEMBL30707 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C15H8O5
Molar mass 268.22 g mol−1
Melting point 385 °C (725 °F; 658 K) (decomp)[1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

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.

Coumestrol was first identified by E. M. Bickoff in alfalfa in 1957.[2] It has since be found in a variety of legumes, soybeans, brussels sprouts, and spinach. Clover and soybeans have the highest concentrations.[3]

Coumestrol is a phytoestrogen, mimicking the biological activity of estrogens. Coumestrol has about the same binding affinity for the ER-β estrogen receptor as 17β-estradiol, but much less affinity than 17α-estradiol, although the estrogenic potency of coumestrol at both receptors is much less than that of 17β-estradiol.[4]

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.[5] These enzymes are involved in the biosynthesis of steroid hormones, and inhibition of these enzymes results in the modulation of hormone production.[3]

References[edit]

  1. ^ 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:10.1002/jps.2600531213. PMID 14255129. 
  2. ^ 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 (3280): 969–970. doi:10.1126/science.126.3280.969-a. PMID 13486041. 
  3. ^ 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:10.2174/157489207780832414. PMID 18221056. 
  4. ^ Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA (1998). "Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta". Endocrinology 139 (10): 4252–4263. doi:10.1210/en.139.10.4252. PMID 9751507. 
  5. ^ 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:10.1016/j.steroids.2005.01.004. PMID 15894034.