Vitexin

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Vitexin

Other names Apigenin-8-C-glucoside
Identifiers
CAS number	3681-93-4^Y
PubChem	5280441
ChemSpider	4444098^Y
ChEBI	CHEBI:16954^Y
ChEMBL	CHEMBL487417^Y
Jmol-3D images	{{#if: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\|Image 1
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
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
Properties
Molecular formula	C₂₁H₂₀O₁₀
Molar mass	432.38 g/mol
Appearance	Light yellow powder
Melting point	203–204 °C
Supplementary data page
Structure and properties	n, ε_r, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Vitexin is an apigenin flavone glucoside, a chemical coupound found in the passion flower, Vitex agnus-castus (chaste tree or chasteberry) and in the Phyllostachys nigra bamboo leaves.^[1] It is also found in the pearl millet (Pennisetum millet).^[2] Vitexin is also found in Hawthorn.^{[citation needed]}

Metabolism

Goitrogenicity of millet flavones : Vitexin inhibits thyroid peroxidase thus contributing to goiter.^[3]^[4]

↑ 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". Cereal Chem. 68 (2): 180–183.
↑ 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, D. M., Klopfenstein, C. F., Leipold, H. W. (1987). "Goitre causing compounds found in pearl millet". Nutr. Rep. Int. 36: 131.

Flavones and their conjugates

Aglycones

Monohydroxyflavone	6-Hydroxyflavone

Dihydroxyflavones	Chrysin (5,7-dihydroxyflavone) 4',7-Dihydroxyflavone

Trihydroxyflavones	Apigenin (5,7,4'-trihydroxyflavone) Baicalein (5,6,7-trihydroxyflavone) Norwogonin (5,7,8-Trihydroxyflavone)

Tetrahydroxyflavones	Isoscutellarein (5,7,8,4'-Tetrahydroxyflavone or 8-Hydroxyapigenin) Luteolin (3',4',5,7-Tetrahydroxyflavone) Norartocarpetin (2',4',5,7-Tetrahydroxyflavone) Scutellarein (5,6,7,4'-Tetrahydroxyflavone)

Pentahydroxyflavones	6-Hydroxyluteolin Hypolaetin (8-Hydroxyluteolin) Tricetin (5,7,3',4',5'-Pentahydroxyflavone)

O-methylated flavones	Acacetin (Apigenin 4'-methyl ether) Artocarpetin (Norartocarpetin 7-methyl ether) Chrysoeriol (Luteolin 3'-methyl ether) Cirsilineol (4',5-Dihydroxy-3',6,7-trimethoxyflavone) Cirsiliol (3',4',5-trihydoxy-6,7-dimethoxyflavone) Cirsimaritin (Scutellarein 6,7-dimethyl ether) Diosmetin (Luteolin 4'-methyl ether) Eupatilin (5,7-Dihydroxy-3',4',6-trimethoxyflavone) Genkwanin (Apigenin 7-methyl ether) Nepetin (Luteolin 6-methyl ether) Nobiletin (3',4',5,6,7,8-Hexamethoxyflavone) Oroxylin A (Baicalein 6-methyl ether) Pratol (7-Hydroxy-4-methoxyflavone) Salvigenin (5-Hydroxy-6,7,4'-trimethoxyflavone) Sinensetin (3',4',5,6,7-Pentamethoxyflavone) Tangeritin (4',5,6,7,8-Pentamethoxyflavone) Techtochrysin (Chrysin 7-methyl ether) Tricin (Tricetin 3',5'-dimethyl ether) Wogonin (Norwogonin 8-methyl ether) Zapotin (2,6,5,6-tetramethoxyflavone)

of apigenin	Apiin (Apigenin-7-O-apioglucoside) Apigetrin (Apigenin 7-O-glucoside) Isovitexin (Apigenin 6-C-glucoside) Rhoifolin (Apigenin 7-O-neohesperidoside) Saponarin (Isovitexin-7-O-glucoside) Schaftoside (Apigenin 6-C-glucoside 8-C-arabinoside) Vicenin-2 (Apigenin 6,8-di-C-glucoside) Vitexin (Apigenin-8-C-glucoside)

of baicalein	Baicalin (Baicalein 7-O-glucuronide) Tetuin (Baicalein 6-O-glucoside)

of hypolaetin	Hypolaetin 8-glucoside Hypolaetin 8-glucuronide

of luteolin	Cynaroside (Luteolin 7-O-glucoside) Isoorientin (Luteolin 6-C-glucoside) Orientin (Luteolin 8-C-glucoside) Veronicastroside (Luteolin 7-O-neohesperidoside) Luteolin-7-O-glucuronide

Giraldiin A (4',5,5',7-Tetrahydroxy-3-methoxy-3'-O-α-L-arabinopyranosyloxyflavone) and B (5,5',7'-Trihydroxy-2',3-dimethoxy-4'-O-β-D-glucopyranosyloxyflavone)
Nepitrin (Nepetin 7-O-glucoside)
Oroxindin (Wogonin 7-O-glucuronide)
Scutellarin (Scutellarein 7-O-glucuronide)

Acetylated

Sulfated glycosides

Theograndin I (sulfated glucuronide of isoscutellarein) and II

Polymers

Drugs

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