Daidzin

Last updated
Daidzin
Daidzin.svg
Names
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16-,18-,19+,20-,21-/m1/s1 X mark.svgN
    Key: KYQZWONCHDNPDP-QNDFHXLGSA-N X mark.svgN
  • InChI=1/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16-,18-,19+,20-,21-/m1/s1
    Key: KYQZWONCHDNPDP-QNDFHXLGBS
  • c1cc(ccc1c2coc3cc(ccc3c2=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
  • O=C3c4ccc(OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)cc4O/C=C3/c2ccc(O)cc2
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).
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Daidzin is a natural organic compound in the class of phytochemicals known as isoflavones. Daidzin can be found in Chinese plant kudzu (Pueraria lobata, Fabaceae) and from soybean leaves. [1]

Contents

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]

List of plants that contain the chemical

Notes and references

  1. Osman, S; Fett, W (1983). "Isoflavone glucoside stress metabolites of soybean leaves". Phytochemistry. 22 (9): 1921. Bibcode:1983PChem..22.1921O. doi:10.1016/0031-9422(83)80013-2.
  2. Rezvani, A; Overstreet, David H; Perfumi, Marina; Massi, Maurizio (2003). "Plant derivatives in the treatment of alcohol dependency". Pharmacology Biochemistry and Behavior. 75 (3): 593–606. doi:10.1016/S0091-3057(03)00124-2. PMID   12895677. S2CID   23298356.
  3. Keung WM; Vallee BL (February 1998). "Kudzu root: an ancient Chinese source of modern antidipsotropic agents". Phytochemistry. 47 (4): 499–506. Bibcode:1998PChem..47..499K. doi:10.1016/S0031-9422(97)00723-1. PMID   9461670.
  4. Pongkitwitoon B; Sakamoto S; Tanaka H; et al. (December 2009). "Enzyme-Linked Immunosorbent Assay for Total Isoflavonoids in Pueraria candollei Using Anti-Puerarin and Anti-Daidzin Polyclonal Antibodies". Planta Medica. 76 (8): 831–6. doi:10.1055/s-0029-1240725. PMID   20033865.
  5. Jin WS; Tan YY; Chen YG; Wang Y (January 2003). "[Determination of puerarin, daidzin and daidzein in root of Pueraria lobata of different origin by HPLC]". Zhongguo Zhong Yao Za Zhi (in Chinese). 28 (1): 49–51. PMID   15015267.
  6. Zhou HY; Wang JH; Yan FY (May 2007). "[Separation and determination of puerarin, daidzin and daidzein in stems and leaves of Pueraria thomsonii by RP-HPLC]". Zhongguo Zhong Yao Za Zhi (in Chinese). 32 (10): 937–9. PMID   17655152.
  7. Park EK; Shin J; Bae EA; Lee YC; Kim DH (December 2006). "Intestinal bacteria activate estrogenic effect of main constituents puerarin and daidzin of Pueraria thunbergiana". Biological & Pharmaceutical Bulletin. 29 (12): 2432–5. doi: 10.1248/bpb.29.2432 . PMID   17142977.

See also


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<i>Pueraria montana</i> Species of legume

Pueraria montana is a species of plant in the botanical family Fabaceae. At least three sub-species are known. It is closely related to other species in the genus Pueraria and the common name kudzu is used for all of these species and hybrids between them. The morphological differences between them are subtle, they can breed with each other, and it appears that introduced kudzu populations in the United States have ancestry from more than one of the species.

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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.

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