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Vitexin

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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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.020.876 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: SGEWCQFRYRRZDC-VPRICQMDSA-N checkY
  • 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
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).

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

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Vitexin beta-glucosyltransferase is an enzyme characterised from Silene alba that converts vitexin to its 2"-O-β-D-glucoside (flavosativaside) using UDP-glucose as the source of the added glucose unit.[4]

2D representation of the chemical structure of vitexin .
vitexin
+ UDP-glucose
 
 
 
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of Q27102008.
vitexin 2"-O-β-D-glucoside

Properties

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Goitrogenicity of millet flavones : vitexin inhibits thyroid peroxidase thus contributing to goiter.[5][6]

See also

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

References

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  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.
  2. ^ Akingbala JO (1991). "Effect of Processing on Flavonoids in Millet (Pennisetum americanum) Flour" (PDF). Cereal Chemistry. 68 (2): 180–183. Archived from the original (PDF) on 2009-05-14. Retrieved 2009-08-21.
  3. ^ 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.
  4. ^ Kamsteeg J, Besson E, Chopin J (1980). "The 2"-O-glucosylation of vitexin and isovitexin in petals of Silene alba is catalysed by two different enzymes". Phytochemistry. 19 (9): 1935–1937. doi:10.1016/0031-9422(80)83007-X. hdl:1874/24857.
  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.
  6. ^ Birzer DM, Klopfenstein CF, Leipold HW (1987). "Goitre causing compounds found in pearl millet". Nutr. Rep. Int. 36: 131–141. ISSN 0029-6635.
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