Vitexin

Vitexin
Other names Apigenin-8-C-glucoside
Identifiers
CAS number	3681-93-4 Y
PubChem	5280441
ChemSpider	4444098 Y
ChEBI	CHEBI:16954 N
ChEMBL	CHEMBL487417 Y
Jmol-3D images	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
Exact mass	432.105647
Appearance	Light yellow powder
Melting point	203–204 °C
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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]

Metabolism

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

• Vitexin beta-glucosyltransferase
• Vitexin 2"-O-rhamnoside 7-O-methyltransferase
• Isovitexin beta-glucosyltransferase

Isovitexin

Isovitexin (or homovitexin, saponaretin) is the apigenin-6-C-glucoside. It can be found in the passion flower and the açaí palm.

References

1. ^ 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. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6T6R-4PRRBT7-4&_user=10&_rdoc=1&_fmt=&_orig=search&_sort=d&_docanchor=&view=c&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=19496ba79336a2655fdc3c321290cad3. 
2. ^ J.O. AKINGBALA (1991). "Effect of Processing on Flavonoids in Millet (Pennisetum americanum) Flour". Cereal Chem. 68 (2): 180–183. http://www.aaccnet.org/cerealchemistry/backissues/1991/68_180.pdf. 
3. ^ 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. 
4. ^ Birzer, D. M., Klopfenstein, C. F., Leipold, H. W. (1987). "Goitre causing compounds found in pearl millet". Nutr. Rep. Int. 36: 131. 

External links

• Vitexin on RDchemicals.com
• Isovitexin on pubchem