Names | |
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IUPAC name 7-(β-D-Glucopyranosyloxy)-4′-hydroxyisoflavone | |
Systematic IUPAC name 7-{[(2S,3R,4S,5S,6R)-6-(Hydroxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | |
Other names Daidzoside Daidzein 7-glucoside Daidzein-7-glucoside Daidzein 7-O-glucoside daidzein 7-O-beta-D-glucoside | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.107.506 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C21H20O9 | |
Molar mass | 416.38 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Daidzin is a natural organic compound in the class of phytochemicals known as isoflavones. Daidzin can be found in Japanese plant kudzu (Pueraria lobata, Fabaceae) and from soybean leaves. [1]
Daidzin is the 7-O-glucoside of daidzein.
Daidzin has shown the potential for the treatment of alcohol dependency (antidipsotropic) based on animal models. [2] [3]
Kudzu, also called Japanese arrowroot or Chinese arrowroot, 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.
Pueraria is a genus of 15–20 species of legumes native to south, east, and southeast Asia and to New Guinea and northern Australia. 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.
Imperatorin is a furocoumarin and a phytochemical that has been isolated from Urena lobata L. (Malvaceae), Angelica archangelica, Angelica dahurica, Glehnia littoralis, Saposhnikovia divaricata, Cnidium monnieri, Incarvillea younghusbandii, and Zanthoxylum americanum mill. It is biosynthesized from umbelliferone, a coumarin derivative.
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.
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.
In enzymology, an isoflavone 7-O-methyltransferase is an enzyme that catalyzes the chemical reaction
The enzyme 2-hydroxyisoflavanone dehydratase (EC 4.2.1.105) catalyzes the chemical reaction
In enzymology, a sterol 3beta-glucosyltransferase is an enzyme that catalyzes the chemical reaction
A self-microemulsifying drug delivery system (SMEDDS) is a drug delivery system that uses a microemulsion achieved by chemical rather than mechanical means. That is, by an intrinsic property of the drug formulation, rather than by special mixing and handling. It employs the familiar ouzo effect displayed by anethole in many anise-flavored liquors. Microemulsions have significant potential for use in drug delivery, and SMEDDS are the best of these systems identified to date. SMEDDS are of particular value in increasing the absorption of lipophilic drugs taken by mouth.
Puerarin, one of several known isoflavones, is found in a number of plants and herbs, such as the root of the kudzu plant
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.
The flavanonols are a class of flavonoids that use the 3-hydroxy-2,3-dihydro-2-phenylchromen-4-one backbone.
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.
Tectorigenin is an O-methylated isoflavone, a type of flavonoid. It ha been isolated from leopard lily, Algerian iris and East Asian arrowroot.
Huáng bǎi, huáng bó or huáng bò is one of the fifty fundamental herbs of traditional Chinese medicine. Known also as Cortex Phellodendri, it is the bark of one of two species of Phellodendron tree: Phellodendron amurense or Phellodendron chinense.
Barbigerone is one of a few pyranoisoflavones among several groups of isoflavones. It was first isolated from the seed of a leguminous plant Tephrosia barbigera; hence the name "barbigerone". Members of the genus Millettia are now known to be rich in barbigerone, including M. dielsiena, M. ferruginea, M. usaramensis, and M. pachycarpa. It has also been isolated from the medicinal plant Sarcolobus globosus. Barbigerone from S. globosus is validated to have significant antioxidant property. Barbigerone exhibits profound antiplasmodial activity against the malarial parasite Plasmodium falciparum. It is also demonstrated that it has anti-cancer potential as it causes apoptosis of murine lung-cancer cells.
Xiyanping (喜炎平) is an anti-inflammatory and antiviral preparation developed and licensed for use in China. It is a semi-synthetic injectable product derived from the active component of the plant Andrographis paniculata, which is used in Traditional Chinese medicine. Xiyanping is primarily composed of 9-dehydro-17-hydro-andrographolide and sodium 9-dehydro-17-hydro-andrographolide-19-yl sulfate. It is used mainly in the treatment of hand, foot and mouth disease, diarrhea, upper respiratory tract infections and viral pneumonia, though one case report suggested it may also be useful in the treatment of Zika fever.
Mirificin, also known as daidzein 8-C-(6-apiofuranosylglucoside), is an isoflavone that is found in Pueraria mirifica and Pueraria lobata. It has estrogenic activity and hence is a phytoestrogen.
Securinine is an alkaloid found in Securinega suffruticosa and Phyllanthus niruri.