daidzin

{{distinguish|Daidzein}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 396323607

| Name = Daidzin

| ImageFile = Daidzin.svg

| ImageSize =

| IUPACName = 7-(β-D-Glucopyranosyloxy)-4′-hydroxyisoflavone

| SystematicName = 7-{[(2S,3R,4S,5S,6R)-6-(Hydroxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

| OtherNames = Daidzoside
Daidzein 7-glucoside
Daidzein-7-glucoside
Daidzein 7-O-glucoside
daidzein 7-O-beta-D-glucoside

|Section1={{Chembox Identifiers

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4R2X91A5M5

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C10216

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 97088

| SMILES = c1cc(ccc1c2coc3cc(ccc3c2=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O

| 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

| InChIKey = KYQZWONCHDNPDP-QNDFHXLGBS

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = KYQZWONCHDNPDP-QNDFHXLGSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 552-66-9

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 42202

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 486422

| PubChem = 107971

| SMILES2 = O=C3c4ccc(OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)cc4O/C=C3/c2ccc(O)cc2

}}

|Section2={{Chembox Properties

| Formula = C21H20O9

| MolarMass = 416.38

| Appearance =

| Density =

| MeltingPt =

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

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.{{cite journal |doi=10.1016/0031-9422(83)80013-2 |title=Isoflavone glucoside stress metabolites of soybean leaves |year=1983 |last1=Osman |first1=S |last2=Fett |first2=W |journal=Phytochemistry |volume=22 |pages=1921 |issue=9|bibcode=1983PChem..22.1921O }}

Daidzin is the 7-O-glucoside of daidzein.

Daidzin has shown the potential for the treatment of alcohol dependency (antidipsotropic) based on animal models.{{cite journal |doi=10.1016/S0091-3057(03)00124-2 |title=Plant derivatives in the treatment of alcohol dependency |year=2003 |last1=Rezvani |first1=A |journal=Pharmacology Biochemistry and Behavior |volume=75 |pages=593–606 |last2=Overstreet |first2=David H |last3=Perfumi |first3=Marina |last4=Massi |first4=Maurizio |issue=3|pmid=12895677 |s2cid=23298356 }}{{cite journal |author=Keung WM |author2=Vallee BL |title=Kudzu root: an ancient Chinese source of modern antidipsotropic agents |journal=Phytochemistry |volume=47 |issue=4 |pages=499–506 |date=February 1998 |pmid=9461670 |doi=10.1016/S0031-9422(97)00723-1|bibcode=1998PChem..47..499K }}

List of plants that contain the chemical

  • Pueraria candollei{{cite journal |author=Pongkitwitoon B |author2=Sakamoto S |author3=Tanaka H |title=Enzyme-Linked Immunosorbent Assay for Total Isoflavonoids in Pueraria candollei Using Anti-Puerarin and Anti-Daidzin Polyclonal Antibodies |journal=Planta Medica |volume= 76|issue= 8|pages= 831–6|date=December 2009 |pmid=20033865 |doi=10.1055/s-0029-1240725|display-authors=etal}}
  • Pueraria lobata{{cite journal |author=Jin WS |author2= Tan YY |author3=Chen YG|author4=Wang Y |title=[Determination of puerarin, daidzin and daidzein in root of Pueraria lobata of different origin by HPLC] |language=Chinese |journal=Zhongguo Zhong Yao Za Zhi |volume=28 |issue=1 |pages=49–51 |date=January 2003 |pmid=15015267}}
  • Pueraria thomsonii{{cite journal |author=Zhou HY |author2= Wang JH |author3=Yan FY |title=[Separation and determination of puerarin, daidzin and daidzein in stems and leaves of Pueraria thomsonii by RP-HPLC] |language=Chinese |journal=Zhongguo Zhong Yao Za Zhi |volume=32 |issue=10 |pages=937–9 |date=May 2007 |pmid=17655152}}
  • Pueraria thunbergiana{{cite journal |author=Park EK |author2=Shin J |author3=Bae EA|author4= Lee YC |author5=Kim DH |title=Intestinal bacteria activate estrogenic effect of main constituents puerarin and daidzin of Pueraria thunbergiana |journal=Biological & Pharmaceutical Bulletin |volume=29 |issue=12 |pages=2432–5 |date=December 2006 |pmid=17142977 |doi=10.1248/bpb.29.2432|doi-access=free }}

Notes and references

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See also