Names | |
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IUPAC name 8-[β-D-Apiofuranosyl-(1→6)-β-D-glucopyranosyloxy]-4′,7-dihydroxyisoflavone | |
Systematic IUPAC name 8-[(2S,3R,4R,5S,6R)-6-({[(2R,3R,4R)-3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]-7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | |
Other names Daidzein 8-C-(6-apiofuranosylglucoside) | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
PubChem CID | |
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Properties | |
C26H28O13 | |
Molar mass | 548.497 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Mirificin, also known as daidzein 8-C-(6-apiofuranosylglucoside), is an isoflavone that is found in Pueraria mirifica and Pueraria lobata . [1] [2] It has estrogenic activity and hence is a phytoestrogen. [1] [2]
Kudzu is a group of climbing, coiling, and trailing deciduous perennial vines native to much of East Asia, Southeast Asia, and some Pacific islands, but invasive in many parts of the world, primarily North America.
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.
Pueraria is a genus of 15–20 species of legumes native to Asia. The best known member is kudzu, also called Japanese arrowroot. The genus is named after 19th century Swiss botanist Marc Nicolas Puerari.
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.
Estrogen receptors (ERs) are a group of proteins found inside cells. They are receptors that are activated by the hormone estrogen (17β-estradiol). Two classes of ER exist: nuclear estrogen receptors, which are members of the nuclear receptor family of intracellular receptors, and membrane estrogen receptors (mERs), which are mostly G protein-coupled receptors. This article refers to the former (ER).
Pueraria mirifica, also known as กวาวเครือ Kwao Krua, is a plant found in northern and north eastern Thailand and Myanmar.
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).
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.
Estrogen receptor alpha (ERα), also known as NR3A1, is one of two main types of estrogen receptor, a nuclear receptor that is activated by the sex hormone estrogen. In humans, ERα is encoded by the gene ESR1.
Butea superba is a vining shrub in the legume family Fabaceae, native to India and mainland Southeast Asia. It is thought by locals to be an aphrodisiac, among other effects.
Estrogen receptor beta (ERβ) also known as NR3A2 is one of two main types of estrogen receptor—a nuclear receptor which is activated by the sex hormone estrogen. In humans ERβ is encoded by the ESR2 gene.
Estrogen-related receptor alpha (ERRα), also known as NR3B1, is a nuclear receptor that in humans is encoded by the ESRRA gene. ERRα was originally cloned by DNA sequence homology to the estrogen receptor alpha, but subsequent ligand binding and reporter-gene transfection experiments demonstrated that estrogens did not regulate ERRα. Currently, ERRα is considered an orphan nuclear receptor.
The enzyme 2-hydroxyisoflavanone dehydratase (EC 4.2.1.105) catalyzes the chemical reaction
Miroestrol is a phytoestrogen, a plant-derived chemical that mimics the biological activity of the hormone estrogen. Miroestrol was first reportedly isolated from the Thai herb Pueraria mirifica in 1960 and thought to be responsible for the supposed rejuvenating properties of the plant. However, more recent studies have suggested that the active ingredient may actually be the closely related chemical compound deoxymiroestrol, and the reported presence of miroestrol may only have been an artifact of the isolation procedure. When deoxymiroestrol is exposed to the oxygen in air, it is converted to miroestrol.
Daidzin is a natural organic compound in the class of phytochemicals known as isoflavones. Daidzin can be found in Japanese plant kudzu and from soybean leaves.
Puerarin, one of several known isoflavones, is found in a number of plants and herbs, such as the root of Pueraria notably of the kudzu plant.
Breast enlargement supplements are frequently portrayed as being a natural means to increase breast size, and with the suggestion that they are free from risk. The popularity of breast enlargement supplements stems from their heavy promotion toward women. Though there has been historical folklore about using herbs for breast enlargement, there is no scientific evidence to support the effectiveness of any breast enlargement supplement. At times, testimonials by companies have been faked. In the United States, both the Federal Trade Commission and the Food and Drug Administration have taken action against the manufacturers of these products for fraudulent practices. The Mayo Clinic advises that there may be serious drug interactions with their use.
A nonsteroidal estrogen is an estrogen with a nonsteroidal chemical structure. The most well-known example is the stilbestrol estrogen diethylstilbestrol (DES). Although nonsteroidal estrogens formerly had an important place in medicine, they have gradually fallen out of favor following the discovery of toxicities associated with high-dose DES starting in the early 1970s, and are now almost never used. On the other hand, virtually all selective estrogen receptor modulators (SERMs) are nonsteroidal, with triphenylethylenes like tamoxifen and clomifene having been derived from DES, and these drugs remain widely used in medicine for the treatment of breast cancer among other indications. In addition to pharmaceutical drugs, many xenoestrogens, including phytoestrogens, mycoestrogens, and synthetic endocrine disruptors like bisphenol A, are nonsteroidal substances with estrogenic activity.
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.