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Coumestrol

Coumestrol
Names
IUPAC name
3,9-Dihydroxypterocarp-6a(11a)-en-6-one
Systematic IUPAC name
3,9-Dihydroxy-6H-[1]benzofuro[3,2-c][1]benzopyran-6-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.842 Edit this at Wikidata
EC Number
  • 207-525-6
KEGG
UNII
  • InChI=1S/C15H8O5/c16-7-1-3-9-11(5-7)19-14-10-4-2-8(17)6-12(10)20-15(18)13(9)14/h1-6,16-17H checkY
    Key: ZZIALNLLNHEQPJ-UHFFFAOYSA-N checkY
  • InChI=1/C15H8O5/c16-7-1-3-9-11(5-7)19-14-10-4-2-8(17)6-12(10)20-15(18)13(9)14/h1-6,16-17H
    Key: ZZIALNLLNHEQPJ-UHFFFAOYAN
  • C1=CC2=C(C=C1O)OC3=C2C(=O)OC4=C3C=CC(=C4)O
  • O=C3Oc4cc(O)ccc4c2oc1c(ccc(O)c1)c23
Properties
C15H8O5
Molar mass 268.224 g·mol−1
Melting point 385 °C (725 °F; 658 K) (decomposes)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Coumestrol is a natural organic compound in the class of phytochemicals known as coumestans. Coumestrol was first identified as a compound with estrogenic properties by E. M. Bickoff in ladino clover and alfalfa in 1957.[2] It has garnered research interest because of its estrogenic activity and prevalence in some foods, including soybeans, brussels sprouts, spinach and a variety of legumes. The highest concentrations of coumestrol are found in clover, Kala Chana (a type of chick pea), and Alfalfa sprouts.[3]

Coumestrol is a phytoestrogen, mimicking the biological activity of estrogens. Phytoestrogens are able to pass through cell membranes due to their low molecular weight and stable structure, and they are able to interact with the enzymes and receptors of cells.[4] Coumestrol binds to the ERα and ERβ with similar affinity to that of estradiol (94% and 185% of the relative binding affinity of estradiol at the ERα and ERβ, respectively),[5] although the estrogenic activity of coumestrol at both receptors is much less than that of estradiol.[6] In any case, coumestrol has estrogenic activity that is 30 to 100 times greater than that of isoflavones.[7]

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 3α-hydroxysteroid dehydrogenase.[8] These enzymes are involved in the biosynthesis of steroid hormones, and inhibition of these enzymes results in the interference with hormone metabolism.[9]

  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; F. Deeds (1957). "Coumestrol, a New Estrogen Isolated from Forage Crops". Science. 126 (3280): 969–970. Bibcode:1957Sci...126..969B. doi:10.1126/science.126.3280.969-a. PMID 13486041.
  3. ^ Bhagwat, Seema; Haytowitz, David; Holden, Joanne (September 2008). USDA Database for the Isoflavone Content of Selected Foods (PDF) (Release 2.0 ed.). Beltsville, Maryland: U.S. Department of Agriculture. Retrieved 10 March 2015.
  4. ^ Ososki, Andreana L.; Kennelly, Edward J. (2003). "Phytoestrogens: a Review of the Present State of Research". Phytotherapy Research. 17 (8): 845–869. doi:10.1002/ptr.1364. PMID 13680814. S2CID 32550431.
  5. ^ Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA (1997). "Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta". Endocrinology. 138 (3): 863–70. doi:10.1210/endo.138.3.4979. PMID 9048584.
  6. ^ 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/endo.139.10.6216. PMID 9751507.
  7. ^ Konar, Nevzat (2013). "Non-isoflavone phytoestrogenic compound contents of various legumes". European Food Research and Technology. 236 (3): 523–530. doi:10.1007/s00217-013-1914-0. ISSN 1438-2377. S2CID 85373016.
  8. ^ 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. S2CID 54388469.
  9. ^ Amr Amin; 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.
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