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Vitexin - Wikipedia

From Wikipedia, the free encyclopedia

Vitexin
Names

IUPAC name 8-(β-D-Glucopyranosyl)-4′,5,7-trihydroxyflavone
Systematic IUPAC name 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
Other names Apigenin-8-C-glucoside
Identifiers
CAS Number	3681-93-4^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16954^Y
ChEMBL	ChEMBL487417^Y
ChemSpider	4444098^Y
ECHA InfoCard	100.020.876
KEGG	C01460^Y
PubChem CID	5280441
UNII	9VP70K75OK^Y
CompTox Dashboard (EPA)	DTXSID90190287
InChI InChI=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^Y Key: SGEWCQFRYRRZDC-VPRICQMDSA-N^Y 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 Key: SGEWCQFRYRRZDC-VPRICQMDBU
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
Properties
Chemical formula	C₂₁H₂₀O₁₀
Molar mass	432.38 g/mol
Appearance	Light yellow powder
Melting point	203 to 204 °C (397 to 399 °F; 476 to 477 K)
Supplementary data page
Vitexin (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

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,^[1] in the pearl millet (Pennisetum millet),^[2] and in Hawthorn.^[3]

Metabolism

Goitrogenicity of millet flavones : Vitexin inhibits thyroid peroxidase thus contributing to goiter.^[4]^[5]

^ Zhang Y, Jiao J, Liu C, Wu X, Zhang Y (2007). "Isolation and purification of four flavone C-glycosides from antioxidant of bamboo leaves by macroporous resin column chromatography and preparative high-performance liquid chromatography". Food Chemistry. doi:10.1016/j.foodchem.2007.09.037.
^ J.O. AKINGBALA (1991). "Effect of Processing on Flavonoids in Millet (Pennisetum americanum) Flour" (PDF). Cereal Chem. 68 (2): 180–183. Archived from the original (PDF) on 2009-05-14. Retrieved 2009-08-21.
^ Scholz H (1995). Gustav Hegi. Illustrierte Flora von Mitteleuropa IV(2B). Spermatophyta: Angiospermae: Dicotyledones 2(3). Rosaceae 2 (2nd ed.). Berlin: Blackwell Wissenschafts-Verlag. p. 431. ISBN 978-3-8263-2533-5.
^ Gaitan E (1990). "Goitrogens in food and water". Annual Review of Nutrition. 10: 21–39. doi:10.1146/annurev.nu.10.070190.000321. PMID 1696490.
^ Birzer DM, Klopfenstein CF, Leipold HW (1987). "Goitre causing compounds found in pearl millet". Nutr. Rep. Int. 36: 131–141. ISSN 0029-6635.

Flavones and their conjugates

Aglycones

Monohydroxyflavone	3-Hydroxyflavone 6-Hydroxyflavone
Dihydroxyflavones	Chrysin 4',7-Dihydroxyflavone 7,8-Dihydroxyflavone
Trihydroxyflavones	Apigenin Baicalein Galangin Norwogonin 7,8,3'-Trihydroxyflavone 6,7,4'-Trihydroxyflavone
Tetrahydroxyflavones	Fisetin Kaempferol Isoscutellarein Luteolin Norartocarpetin Scutellarein
Pentahydroxyflavones	Herbacetin Morin Quercetin Nortangeretin 6-Hydroxyluteolin Norwightin Hypolaetin Tricetin
O-methylated flavones	4',7-Dihydroxy-6-methoxyflavone Acacetin Alnetin Artocarpetin Chrysoeriol Cirsilineol Cirsiliol Cirsimaritin Diosmetin Eupatilin Genkwanin Hispidulin Nepetin Nobiletin Oroxylin A Pratol Salvigenin Sinensetin Tangeretin Techtochrysin Tricin Wogonin Zapotin

of apigenin	Apiin Apigetrin Isovitexin Rhoifolin Saponarin Schaftoside Vicenin-2 Vitexin
of baicalein	Baicalin Tetuin
of hypolaetin	Hypolaetin 8-glucoside Hypolaetin 8-glucuronide
of luteolin	Cynaroside Isoorientin Orientin Veronicastroside Luteolin-7-O-glucuronide

Acetylated

Sulfated glycosides

Polymers

Drugs

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