Names | |
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IUPAC name 7-Hydroxy-4′-methoxyisoflavone | |
Systematic IUPAC name 7-Hydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one | |
Other names Biochanin B Formononetol 4'-O-methyldaidzein | |
Identifiers | |
3D model (JSmol) | |
237979 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.006.931 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C16H12O4 | |
Molar mass | 268.26 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Formononetin is an O-methylated isoflavone.
Formononetin is found in a number of plants and herbs such as red clover. [1] Along with other phytoestrogens, it predominantly occurs in leguminous plants and Fabaceae, particularly in beans, such as green beans, lima beans, soy and many others, as the free aglycone or in form of its glucoside ononin. [2]
It can also be found in Maackia amurensis cell cultures. [3]
Formononetin promotes angiogenesis. [4] It is also involved in expressing the gene and proteins that are needed to make IgE. [5]
Hot flashes are a form of flushing, often caused by the changing hormone levels that are characteristic of menopause. They are typically experienced as a feeling of intense heat with sweating and rapid heartbeat, and may typically last from two to 30 minutes for each occurrence.
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 to 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.
Isoflavones are substituted derivatives of isoflavone, a type of naturally occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones occur in many plant species, but are especially high in soybeans.
An angiogenesis inhibitor is a substance that inhibits the growth of new blood vessels (angiogenesis). Some angiogenesis inhibitors are endogenous and a normal part of the body's control and others are obtained exogenously through pharmaceutical drugs or diet.
Genistein (C15H10O5) is a naturally occurring compound that structurally belongs to a class of compounds known as isoflavones. It is described as an angiogenesis inhibitor and a phytoestrogen.
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.
Angiopoietin is part of a family of vascular growth factors that play a role in embryonic and postnatal angiogenesis. Angiopoietin signaling most directly corresponds with angiogenesis, the process by which new arteries and veins form from preexisting blood vessels. Angiogenesis proceeds through sprouting, endothelial cell migration, proliferation, and vessel destabilization and stabilization. They are responsible for assembling and disassembling the endothelial lining of blood vessels. Angiopoietin cytokines are involved with controlling microvascular permeability, vasodilation, and vasoconstriction by signaling smooth muscle cells surrounding vessels. There are now four identified angiopoietins: ANGPT1, ANGPT2, ANGPTL3, ANGPT4.
Astragalus mongholicus, synonyms including Astragalus propinquus and Astragalus membranaceus, commonly known as Mongolian milkvetch in English; 'Хунчир' in Mongolian; huáng qí, běi qí or huáng huā huáng qí, in Mongolia, is a flowering plant in the family Fabaceae. It is one of the 50 fundamental herbs used in traditional Mongolian medicine. It is a perennial plant and it is not listed as being threatened.
Maackia amurensis, commonly known as the Amur maackia, is a species of tree in the family Fabaceae that can grow 15 metres (49 ft) tall. The species epithet and common names are from the Amur River region, where the tree originated; it occurs in northeastern China, Korea, and Russia.
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.
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.
Ononin is an isoflavone glycoside, the 7-O-β-D-glucopyranoside of formononetin, which in turn is the 4'-O-methoxy derivative of the parent isoflavone daidzein.
Taxifolin (5,7,3',4'-flavan-on-ol), also known as dihydroquercetin, belongs to the subclass flavanonols in the flavonoids, which in turn is a class of polyphenols. It is extracted from plants such as Siberian larch and milk thistle.
The O-methylated flavonoids or methoxyflavonoids are flavonoids with methylations on hydroxyl groups. O-methylation has an effect on the solubility of flavonoids.
Retusin is an O-methylated isoflavone, a type of flavonoid. It can be found in Fabaceae species like Dipteryx odorata, in Dalbergia retusa and in Millettia nitida. It can also be found in Maackia amurensis cell cultures.
Pratensein is an O-methylated isoflavone, a type of flavonoid. It can be found in Trifolium pratense and can have effects for the prevention of atherosclerosis.
Calycosin is an O-methylated isoflavone. It can be isolated from Astragalus membranaceus Bge. var. mongholicus and Trifolium pratense L..
Pterocarpans are derivatives of isoflavonoids found in the family Fabaceae. It is a group of compounds which can be described as benzo-pyrano-furano-benzenes which can be formed by coupling of the B ring to the 4-one position.
Meso-Papilionoideae is a monophyletic clade of the flowering plant subfamily Faboideae that includes the majority of papilionoid legumes. This clade is consistently resolved in molecular phylogenies. It contains many agronomically important genera, including Arachis (peanut), Cicer (chickpea), Glycine (soybean), Medicago (alfalfa), Phaseolus, Trifolium (clover), Vicia (vetch), and Vigna.
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.