Coumestrol

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==Description==
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[http://crdd.osdd.net/raghava/hmrbase/test_extract.php?db=arun&table=nphormonet&id=1034&show=SHOW-3D Show 3-D Structure]
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[http://172.141.127.22/raghava/hmrbase/test_extract.php?db=arun&table=nphormonet&id=1034&show=SHOW-3D Show 3-D Structure]
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{{Drugbox
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| IUPAC_name        = 3,9-dihydroxy-[1]benzoxolo[3,2-c]chromen-6-one
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| CAS_number        = 479-13-0
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| CAS_supplemental  =
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| ATC_suffix =
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| ATC_supplemental  =
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| PubChem          = 5281707
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| ChemSpiderID      =
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| chemical_formula  =C<sub>1</sub><sub>5</sub>H<sub>8</sub>O<sub>5</sub>
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| molecular_weight  = 268.22
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| smiles            = C1=CC2=C(C=C1O)OC3=C2C(=O)OC4=C3C=CC(=C4)O
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| synonyms          =Chrysanthin
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| density          =
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| melting_point    = 385(EXP)
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| solubility        =
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A daidzein derivative occurring naturally in forage crops which has  some estrogenic activity.'''Coumestrol''' is a natural [[organic compound]] in the class of [[phytochemical]]s known as [[coumestan]]s.  It has garnered research interest because of its estrogenic activity and its prevalence in some foods, such as [[soybean]]s and herbs such as [[Pueraria mirifica]].
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A daidzein derivative occurring naturally in forage crops which has  some estrogenic activity.'''Daidzein''' is one of several known [[isoflavone]]s. Isoflavones compounds, such as daidzein and [[genistein]], are found in a number of [[plant]]s and herbs like the Thai [[Kwao Krua]] or Pueraria Mirifica, but [[soybean]]s and soy products like [[tofu]] and [[textured vegetable protein]] are the primary food source. Soy isoflavones are a group of compounds found in and isolated from the soybean. Besides functioning as [[antioxidant]]s, many isoflavones have been shown to interact with [[animal]] and [[human]] [[estrogen receptor]]s, and are therefore known as [[phytoestrogens]]. Soy isoflavones also produce non-hormonal effects.
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Coumestrol was first identified by E. M. Bickoff in [[alfalfa]] in 1957.<ref>{{cite journal|title=Coumestrol, a New Estrogen Isolated from Forage Crops|author=E. M. Bickoff, A. N. Booth, R. L. Lyman, A. L. Livingston, C. R. Thompson, and F. Deeds|journal=Science|year=1957|volume=126|pages=969–970|doi=10.1126/science.126.3280.969-a}}</ref>  It has since be found in a variety of [[legume]]s, [[soybean]]s, [[brussels sprout]]s, and [[spinach]].  [[Clover]] and soybeans have the highest concentrations.<ref name="Amin">{{cite journal|author=Amr Amin and 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}}</ref>
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Isoflavones act as antioxidants to counteract damaging effects of free radicals in tissues. Isoflavones can act like estrogen in stimulating development and maintenance of female characteristics or they can block cells from using other forms of estrogen{{Fact|date=June 2007}}. Isoflavones also have been found to have antiangiogenic effects (blocking formation of new blood vessels){{Fact|date=June 2007}}, and may block the uncontrolled cell growth associated with cancer, most likely by inhibiting the activity of substances in the body that regulate cell division and cell survival (growth factors){{Fact|date=June 2007}}.
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Coumestrol is a [[phytoestrogen]], mimicking the biological activity of [[estrogen]]s. The chemical shape of coumestrol orients its two [[hydroxy]] groups in the same position as the two hydroxy groups in [[estradiol]], allowing it to [[enzyme inhibition|inhibit]] the activity of [[aromatase]] and [[hydroxysteroid dehydrogenase]].<ref>{{cite journal|author=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}}</ref>  These enzymes are involved in the biosynthesis of [[steroid]] hormones, and inhibition of these enzymes results in the modulation of hormone production.<ref name="Amin"/>
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Studies show that groups of people who eat large amounts of soy-based products have lower incidences of breast, colon, endometrial, and prostate cancers than the general (US) population{{Fact|date=June 2007}}. Initial studies of soy and Kwao Krua isoflavone mixtures containing genistein, daidzein, and glycitein have found them safe for human use<ref>Safety of soy-based infant formulas containing isoflavones PMID 15113975</ref>. Laboratory studies using animals models have shown that both soy and isoflavones can be protective against cancer when given during early life but can stimulate response to cancer-causing chemicals when given during fetal development or when circulating levels of estrogen are low (menopause){{Fact|date=June 2007}}.
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'''[[Pueraria mirifica]]''' or White Kawo Krua has been found to contain concentrations of daidzein where the Cu²+ at 300 ppm is shown to contain as much as 44.69 ppm of daidzein. Another source of daidzein is Kudzu also known as Pueraria Lobata.
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'''Pueraria mirifica''' or White Kawo Krua has been found to contain concentration of Coumestrol where Cu<sup>2+</sup> at 1000 ppm the highest concentration was to be found where CuCl<sub>2</sub>, MnCl<sub>2</sub> and FeCl<sub>2</sub> at 1,000 ppm can in fact stimulate coumestrol accumulation.
==General Properties==
==General Properties==
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[[Categories:Hormones]]
[[Categories:Hormones]]
[[Category:Flavonoids]]
[[Category:Flavonoids]]
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[[de:Daidzein]]
 

Revision as of 08:09, 20 February 2009

Show 3-D Structure

Coumestrol
Systematic (IUPAC) name
3,9-dihydroxy-[1]benzoxolo[3,2-c]chromen-6-one
Identifiers
CAS number 479-13-0
ATC code  ?
PubChem 5281707
Chemical data
Formula C15H8O5
Mol. mass 268.22
SMILES eMolecules & PubChem
Synonyms Chrysanthin
Physical data
Melt. point 385(EXP) °C
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?

Legal status
Routes  ?

A daidzein derivative occurring naturally in forage crops which has some estrogenic activity.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.<ref>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:10.1126/science.126.3280.969-a. </ref> It has since be found in a variety of legumes, soybeans, brussels sprouts, and spinach. Clover and soybeans have the highest concentrations.<ref name="Amin">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. </ref>

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.<ref>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. </ref> These enzymes are involved in the biosynthesis of steroid hormones, and inhibition of these enzymes results in the modulation of hormone production.<ref name="Amin"/>

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.

General Properties

*Molecular Weight

268.22

*Molecular Formula

C15H8O5

*IUPAC NAME

3,9-dihydroxy-[1]benzoxolo[3,2-c]chromen-6-one

*Canonical Smiles

C1=CC2=C(C=C1O)OC3=C2C(=O)OC4=C3C=CC(=C4)O

*Isomeric Smiles



PhysioChemical Properties

*Melting Point

385(EXP)

*LogP

1.57(EST)

*Water Solubility


External Links

  • [1]Pubchem
  • [2]]KEGG Compound
  • [3]Human Metabolome DataBase


Categories:Hormones

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