Formononetin

Last updated
Formononetin
Formononetin.svg
Formononetin-3D-balls.png
Names
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3 Yes check.svgY
    Key: HKQYGTCOTHHOMP-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3
    Key: HKQYGTCOTHHOMP-UHFFFAOYAJ
  • O=C\1c3c(O/C=C/1c2ccc(OC)cc2)cc(O)cc3
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Formononetin is an O-methylated isoflavone.

Natural occurrences

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]

Contents

It can also be found in Maackia amurensis cell cultures. [3]

Pharmacodynamics

Formononetin promotes angiogenesis. [4] It is also involved in expressing the gene and proteins that are needed to make IgE. [5]

Derivatives

Ononin is the 7-O-β-D-glucopyranoside of formononetin. [6]

Related Research Articles

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.

<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 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 are produced almost exclusively by the members of the bean family, Fabaceae (Leguminosae).

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.

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

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.

<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">Angiopoietin</span> Protein family

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.

<i>Astragalus mongholicus</i> Species of plant

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.

<i>Maackia amurensis</i> Species of legume

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.

<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">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">Ononin</span> Chemical compound

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.

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

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.

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

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.

<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">Pterocarpan</span> Class of chemical compounds

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.

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

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.

<i>Soy boy</i> Pejorative term for men perceived as non-masculine

Soy boy is a pejorative term sometimes used in online communities to describe men perceived to be lacking masculine characteristics. The term bears many similarities and has been compared to the slang terms cuck, nu-male and low-T – terms sometimes used as an insult for male femininity by online communities.

References

  1. Medjakovic, S.; Jungbauer, A. (2008). "Red Clover Isoflavones Biochanin A and Formononetin are Potent Ligands of the Human Aryl Hydrocarbon Receptor". The Journal of Steroid Biochemistry and Molecular Biology. 108 (1–2): 171–177. doi:10.1016/j.jsbmb.2007.10.001. PMID   18060767. S2CID   206495959.
  2. "Iowa State University Database on the Isoflavone Content of Foods, Release 1.3". USDA. 2002. Archived from the original on 2012-11-02. Retrieved 2011-02-13.
  3. Fedoreyev, S.A; Pokushalova, T.V; Veselova, M.V; Glebko, L.I; Kulesh, N.I; Muzarok, T.I; Seletskaya, L.D; Bulgakov, V.P; Zhuravlev, Yu.N (2000). "Isoflavonoid production by callus cultures of Maackia amurensis". Fitoterapia. 71 (4): 365–72. doi:10.1016/S0367-326X(00)00129-5. PMID   10925005.
  4. Li, Shang; Dang, Yuanye; Zhou, Xuelin; Huang, Bin; Huang, Xiaohui; Zhang, Zherui; Kwan, Yiu Wa; Chan, Shun Wan; Leung, George Pak Heng; Lee, Simon Ming Yuen; Hoi, Maggie Pui Man (2015). "Formononetin promotes angiogenesis through the estrogen receptor alpha-enhanced ROCK pathway". Scientific Reports. 5: 16815. Bibcode:2015NatSR...516815L. doi:10.1038/srep16815. PMC   4645220 . PMID   26568398.
  5. "This plant-based compound could finally cure food allergies". ZME Science. 2022-04-01. Retrieved 2022-04-04.
  6. You-Ping Zhu (1998-05-28). Chinese Materia Medica: Chemistry, Pharmacology and Applications . CRC Press. p.  622. ISBN   9057022850.