vitexin

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{{chembox

| Watchedfields = changed

| verifiedrevid = 470631187

| ImageFile =Vitexin.svg

| ImageSize =

| IUPACName = 8-(β-{{small|D}}-Glucopyranosyl)-4′,5,7-trihydroxyflavone

| SystematicName = 5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-1-benzopyran-4-one

| OtherNames =Apigenin-8-C-glucoside

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4444098

| InChI = 1/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2/t14-,17-,18+,19-,21+/m1/s1

| InChIKey = SGEWCQFRYRRZDC-VPRICQMDBU

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2/t14-,17-,18+,19-,21+/m1/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = SGEWCQFRYRRZDC-VPRICQMDSA-N

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

| CASNo =3681-93-4

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

| UNII = 9VP70K75OK

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

| KEGG = C01460

| PubChem =5280441

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 487417

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 16954

| SMILES = O=C2\C=C(/Oc1c(c(O)cc(O)c12)[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)CO)c4ccc(O)cc4

}}

|Section2={{Chembox Properties

| Formula =C21H20O10

| MolarMass = 432.38 g/mol

| Appearance = Light yellow powder

| Density =

| MeltingPtC = 203 to 204

| MeltingPt_notes =

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

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Vitexin is an apigenin flavone glucoside, a chemical compound found in the passion flower, Vitex agnus-castus (chaste tree or chasteberry), in the Phyllostachys nigra bamboo leaves,{{cite journal | last1 = Zhang | first1 = Y | journal = Food Chemistry | last2 = Jiao | first2 = J | last3 = Liu | first3 = C | last4 = Wu | first4 = X | last5 = Zhang | first5 = Y | title = Isolation and purification of four flavone C-glycosides from antioxidant of bamboo leaves by macroporous resin column chromatography and preparative high-performance liquid chromatography | year = 2007|doi = 10.1016/j.foodchem.2007.09.037 }} in the pearl millet (Pennisetum millet),{{Cite journal | url = http://www.aaccnet.org/cerealchemistry/backissues/1991/68_180.pdf | title = Effect of Processing on Flavonoids in Millet (Pennisetum americanum) Flour | author = J.O. AKINGBALA | year = 1991 | journal = Cereal Chem. | volume = 68 | issue = 2 | pages = 180–183 | access-date = 2009-08-21 | archive-url = https://web.archive.org/web/20090514213426/http://www.aaccnet.org/cerealchemistry/backissues/1991/68_180.pdf | archive-date = 2009-05-14 | url-status = dead }} and in Hawthorn.{{Cite book|title=Gustav Hegi. Illustrierte Flora von Mitteleuropa IV(2B). Spermatophyta: Angiospermae: Dicotyledones 2(3). Rosaceae 2|last=Scholz|first=Hildemar|publisher=Blackwell Wissenschafts-Verlag|year=1995|isbn=978-3-8263-2533-5|edition=2nd|location=Berlin|pages=431}}

Metabolism

Goitrogenicity of millet flavones : Vitexin inhibits thyroid peroxidase thus contributing to goiter.{{cite journal | last1 = Gaitan | first1 = E | title = Goitrogens in food and water. | journal = Annual Review of Nutrition | volume = 10 | pages = 21–39 | year = 1990 | pmid = 1696490 | doi = 10.1146/annurev.nu.10.070190.000321}}{{cite journal | vauthors = Birzer DM, Klopfenstein CF, Leipold HW| year = 1987 | title = Goitre causing compounds found in pearl millet | journal = Nutr. Rep. Int. | volume = 36 | pages = 131–141|issn = 0029-6635}}

See also

  • Isovitexin (or homovitexin, saponaretin) is the apigenin-6-C-glucoside.
  • Orientin, the 3'-OH derivative

References

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