Daidzin

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 checkY
    Key: KYQZWONCHDNPDP-QNDFHXLGSA-N checkY
  • 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).

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.

Daidzin is the 7-O-glucoside of daidzein.

Daidzin has shown the potential for the treatment of alcohol dependency (antidipsotropic) based on animal models.

List of plants that contain the chemical

Biosynthesis

Daidzin is an isoflavone, which are isomers of the large group of plant metabolites called flavones. Its biosynthesis begins in a phenylpropanoid metabolic pathway from the amino acid phenylalanine. After several steps, the intermediate daidzein is formed. The enzyme isoflavone 7-O-glucosyltransferase then adds a glycosyl group by transfer from UDP-glucose.

2D representation of the chemical structure of daidzein .
daidzein
+ UDP-glucose
 
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of daidzin.
daidzin
+ UDP
 

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.
  8. ↑ Ververidis Filippos, F; Trantas Emmanouil; Douglas Carl; Vollmer Guenter; Kretzschmar Georg; Panopoulos Nickolas (October 2007). "Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: Chemical diversity, impacts on plant biology and human health". Biotechnology Journal. 2 (10): 1214–34. doi:10.1002/biot.200700084. PMID 17935117.
  9. ↑ Koster J, Barz W (1981). "UDP-glucose:isoflavone 7-O-glucosyltransferase from roots of chick pea (Cicer arietinum L.)". Arch. Biochem. Biophys. 212 (1): 98–104. doi:10.1016/0003-9861(81)90347-7. PMID 6458246.

See also