Coumestrolのソースを表示

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443542489
| ImageFile =Coumestrol.png
| ImageSize = 
| IUPACName = 3,9-Dihydroxypterocarp-6a(11a)-en-6-one
| SystematicName = 3,9-Dihydroxy-6''H''-[1]benzofuro[3,2-''c''][1]benzopyran-6-one
| OtherNames =
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4445024
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C10205
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 3908
| EC_number = 207-525-6 
| 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
| InChIKey = ZZIALNLLNHEQPJ-UHFFFAOYAN
| SMILES1 = O=C3Oc4cc(O)ccc4c2oc1c(ccc(O)c1)c23
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 30707
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZZIALNLLNHEQPJ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo =479-13-0
| PubChem =5281707
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = V7NW98OB34
| SMILES =C1=CC2=C(C=C1O)OC3=C2C(=O)OC4=C3C=CC(=C4)O
  }}
|Section2={{Chembox Properties
| C=15 | H=8 | O=5
| Appearance =
| Density =
| MeltingPtC =385
| MeltingPt_notes = (decomposes)<ref>{{cite journal|title=Isolation of coumestrol and other phenolics from alfalfa by countercurrent distribution|author1=Bickoff, E. M. |author2=Livingston, A. L. |author3=Witt, S. C. |author4=Knuckles, B. E. |author5=Guggolz, Jack |author6=Spencer, R. R. |journal=Journal of Pharmaceutical Sciences|year=1964|volume=53|issue=12|pages=1496–9|doi=10.1002/jps.2600531213|pmid=14255129}}</ref>
| BoilingPt =
| Solubility =
  }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = 
 }}
}}

'''Coumestrol''' is a natural [[organic compound]] in the class of [[phytochemical]]s known as [[coumestan]]s. Coumestrol was first identified as a compound with estrogenic properties by E. M. Bickoff in ladino [[clover]] and [[alfalfa]] in 1957.<ref>{{cite journal |title=Coumestrol, a New Estrogen Isolated from Forage Crops |author1=E. M. Bickoff |author2=A. N. Booth |author3=R. L. Lyman |author4=A. L. Livingston |author5=C. R. Thompson |author6=F. Deeds |journal=Science |year=1957 |volume=126 |pages=969–970 |doi=10.1126/science.126.3280.969-a |pmid=13486041 |issue=3280|bibcode=1957Sci...126..969B }}</ref>  It has garnered research interest because of its estrogenic activity and prevalence in some foods, including [[soybean]]s, [[brussels sprout]]s, [[spinach]] and a variety of [[legume]]s. The highest concentrations of coumestrol are found in [[clover]], Kala Chana (a type of [[chick pea]]), and [[Alfalfa|Alfalfa sprouts]].<ref name =Bhagwat>{{cite book|last1=Bhagwat|first1=Seema|last2=Haytowitz|first2=David|last3=Holden|first3=Joanne|title=USDA Database for the Isoflavone Content of Selected Foods|date=September 2008|publisher=U.S. Department of Agriculture|location=Beltsville, Maryland|edition=Release 2.0|url=http://www.ars.usda.gov/SP2UserFiles/Place/80400525/Data/isoflav/Isoflav_R2.pdf|access-date=10 March 2015}}</ref>

Coumestrol is a [[phytoestrogen]], mimicking the [[biological activity]] of [[estrogen]]s. 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.<ref name=ososki>{{cite journal|last1=Ososki|first1=Andreana L.|last2=Kennelly|first2=Edward J.|title=Phytoestrogens: a Review of the Present State of Research|journal=Phytotherapy Research|date=2003|volume=17|issue=8|pages=845–869|pmid=13680814|doi=10.1002/ptr.1364|s2cid=32550431}}<!--|access-date=16 April 2015--></ref> Coumestrol binds to the [[ERα]] and [[ERβ]] with similar [[affinity (pharmacology)|affinity]] to that of [[estradiol]] (94% and 185% of the [[relative binding affinity]] of estradiol at the ERα and ERβ, respectively),<ref name="pmid9048584">{{cite journal | vauthors = Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA | title = Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta | journal = Endocrinology | volume = 138 | issue = 3 | pages = 863–70 | year = 1997 | pmid = 9048584 | doi = 10.1210/endo.138.3.4979 | doi-access = free }}</ref> although the estrogenic activity of coumestrol at both receptors is much less than that of estradiol.<ref>{{cite journal |vauthors=Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA | title=Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta | journal=Endocrinology  | volume=139 | issue=10 | year=1998 | pages=4252–4263  | url = http://endo.endojournals.org/cgi/content/full/139/10/4252 | pmid=9751507 | doi=10.1210/endo.139.10.6216| doi-access= }}</ref> In any case, coumestrol has estrogenic activity that is 30 to 100 times greater than that of isoflavones.<ref>{{Cite journal|last=Konar|first=Nevzat|title=Non-isoflavone phytoestrogenic compound contents of various legumes|journal=European Food Research and Technology|language=en|volume=236|issue=3|pages=523–530|doi=10.1007/s00217-013-1914-0|issn=1438-2377|year=2013|s2cid=85373016}}</ref>

The chemical shape of coumestrol orients its two [[hydroxyl|hydroxy]] groups in the same position as the two hydroxy groups in estradiol, allowing it to [[enzyme inhibition|inhibit]] the activity of [[aromatase]] and [[3α-hydroxysteroid dehydrogenase]].<ref>{{cite journal|vauthors=Blomquist CH, Lima PH, Hotchkiss JR |title=Inhibition of 3a-hydroxysteoid dehydogenase (3a-HSD) activity of human lung microsomes by genistein, daidzein, coumestrol and C18-, C19- and C21 hydroxysteroids and ketosteroids|journal=Steroids|year=2005|volume=70|issue=8|pages=507–514|doi=10.1016/j.steroids.2005.01.004|pmid=15894034|s2cid=54388469}}</ref> These enzymes are involved in the biosynthesis of [[steroid]] hormones, and inhibition of these enzymes results in the interference with hormone [[metabolism]].<ref name="Amin">{{cite journal|author1=Amr Amin |author2=Michael Buratovich |title=The Anti-Cancer Charm of Flavonoids: A Cup-of-Tea Will Do!|journal=Recent Patents on Anti-Cancer Drug Discovery|year=2007|issue=2|pages=109–117|doi=10.2174/157489207780832414|volume=2|pmid=18221056}}</ref>