Daidzin
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 Edit this at Wikidata
KEGG
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 ☒N
    Key: KYQZWONCHDNPDP-QNDFHXLGSA-N ☒N
  • 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 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]

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. 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. 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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