Pratensein

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Pratensein
Pratensein.svg
Pratensein-3D-balls.png
Names
IUPAC name
3′,5,7-Trihydroxy-4′-methoxyisoflavone
Systematic IUPAC name
5,7-Dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
Other names
4′-Methoxy-3′,5,7-trihydroxyisoflavone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C16H12O6/c1-21-13-3-2-8(4-11(13)18)10-7-22-14-6-9(17)5-12(19)15(14)16(10)20/h2-7,17-19H,1H3 X mark.svgN
    Key: FPIOBTBNRZPWJW-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C16H12O6/c1-21-13-3-2-8(4-11(13)18)10-7-22-14-6-9(17)5-12(19)15(14)16(10)20/h2-7,17-19H,1H3
    Key: FPIOBTBNRZPWJW-UHFFFAOYAF
  • COC1=C(C=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O)O
Properties
C16H12O6
Molar mass 300.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pratensein is an O-methylated isoflavone, a type of flavonoid. It can be found in Trifolium pratense (red clover) [1] and can have effects for the prevention of atherosclerosis. [2]

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<span class="mw-page-title-main">Phytoestrogen</span> Plant-derived xenoestrogen

A phytoestrogen is a plant-derived xenoestrogen not generated within the endocrine system, but consumed by eating plants or manufactured foods. Also called a "dietary estrogen", it is a diverse group of naturally occurring nonsteroidal plant compounds that, because of its structural similarity with estradiol (17-β-estradiol), have the ability to cause estrogenic or antiestrogenic effects. Phytoestrogens are not essential nutrients because their absence from the diet does not cause a disease, nor are they known to participate in any normal biological function. Common foods containing phytoestrogens are soy protein, beans, oats, barley, rice, coffee, apples, carrots.

<span class="mw-page-title-main">Equol</span> Isoflavandiol estrogen metabolized from daidzein

Equol (4',7-isoflavandiol) is an isoflavandiol estrogen metabolized from daidzein, a type of isoflavone found in soybeans and other plant sources, by bacterial flora in the intestines. While endogenous estrogenic hormones such as estradiol are steroids, equol is a nonsteroidal estrogen. Only about 30–50% of people have intestinal bacteria that make equol.

Isoflavones are substituted derivatives of isoflavone, a type of naturally occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones are produced almost exclusively by the members of the bean family, Fabaceae (Leguminosae).

<span class="mw-page-title-main">Daidzein</span> Chemical compound

Daidzein is a naturally occurring compound found exclusively in soybeans and other legumes and structurally belongs to a class of compounds known as isoflavones. Daidzein and other isoflavones are produced in plants through the phenylpropanoid pathway of secondary metabolism and are used as signal carriers, and defense responses to pathogenic attacks. In humans, recent research has shown the viability of using daidzein in medicine for menopausal relief, osteoporosis, blood cholesterol, and lowering the risk of some hormone-related cancers, and heart disease. Despite the known health benefits, the use of both puerarin and daidzein is limited by their poor bioavailability and low water solubility.

<span class="mw-page-title-main">Coumestrol</span> Chemical compound

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. 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, and Alfalfa sprouts.

<span class="mw-page-title-main">Glycitein</span> Chemical compound

Glycitein is an O-methylated isoflavone which accounts for 5-10% of the total isoflavones in soy food products. Glycitein is a phytoestrogen with weak estrogenic activity, comparable to that of the other soy isoflavones.

<span class="mw-page-title-main">Biochanin A</span> Chemical compound

Biochanin A is an O-methylated isoflavone. It is a natural organic compound in the class of phytochemicals known as flavonoids. Biochanin A can be found in red clover in soy, in alfalfa sprouts, in peanuts, in chickpea and in other legumes.

<span class="mw-page-title-main">Formononetin</span> Chemical compound

Formononetin is an O-methylated isoflavone.

<span class="mw-page-title-main">Tectorigenin</span> Chemical compound

Tectorigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from leopard lily, in Iris unguicularis or Pueraria thunbergiana.

<span class="mw-page-title-main">Iridin</span> Chemical compound

Iridin is an isoflavone, a type of flavonoid. It is the 7-glucoside of irigenin and can be isolated from several species of irises like orris root, Iris florentina or Iris versicolor, also commonly known as the larger blue flag. It can also be found in Iris kemaonensis.

<span class="mw-page-title-main">Tectoridin</span> Chemical compound

Tectoridin is an isoflavone, a type of flavonoid. It is the 7-glucoside of tectorigenin and can be isolated from flowers of Pueraria thunbergiana (Leguminosae).

<span class="mw-page-title-main">Irilone</span> Chemical compound

Irilone is an isoflavone, a type of flavonoid. It can be found in Trifolium pratense, in Iris unguicularis and in Iris germanica.

<span class="mw-page-title-main">Prunetin</span> Chemical compound

Prunetin is an O-methylated isoflavone, a type of flavonoid. It has been isolated for the first time by Finnemore in 1910 in the bark of Prunus emarginata. Prunetin isolated from pea roots can act as an attractant for Aphanomyces euteiches zoospores. It is also an allosteric inhibitor of human liver aldehyde dehydrogenase.

<span class="mw-page-title-main">Calycosin</span> Chemical compound

Calycosin is an O-methylated isoflavone. It can be isolated from Astragalus membranaceus Bge. var. mongholicus and Trifolium pratense L..

<span class="mw-page-title-main">Pseudobaptigenin</span> Chemical compound

Pseudobaptigenin is an isoflavone, a type of flavonoid. It can be isolated in Trifolium pratense.

<span class="mw-page-title-main">Luteone (isoflavone)</span> Chemical compound

Luteone is a prenylated isoflavone, a type of flavonoid. It can be found in the pods of Laburnum anagyroides and can be synthesized.

<span class="mw-page-title-main">Rimostil</span>

Rimostil is a dietary supplement and extract of isoflavones from red clover which was under development by Kazia Therapeutics for the prevention of postmenopausal osteoporosis and cardiovascular disease and for the treatment of menopausal symptoms and hyperlipidemia but was never approved for medical use. It is enriched with isoflavone phytoestrogens such as formononetin, biochanin A, daidzein, and genistein, and is proposed to act as a selective estrogen receptor modulator, with both estrogenic and antiestrogenic effects in different tissues. The extract reached phase II clinical trials for cardiovascular disorders, hyperlipidemia, and postmenopausal osteoporosis prior to the discontinuation of its development in 2007.

<span class="mw-page-title-main">Glycitin</span> Chemical compound

Glycitin is an isoflavone found in soy, and remains to various degrees in soy products like tofu, soymilk and soy sauce. Although glycitin has its own health associated properties (below), it can be transformed to glycitein by human intestinal flora by the action of beta-glucosidases.

References