Isovitexin

Isovitexin
Names
IUPAC name
6-(β-D-Glucopyranosyl)-4′,5,7-trihydroxyflavone
Systematic IUPAC name
5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-1-benzopyran-4-one
Other names
Homovitexin, saponaretin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.126.529
UNII
  • InChI=1S/C21H20O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14-,17-,19+,20-,21+/m1/s1
    Key: MYXNWGACZJSMBT-VJXVFPJBSA-N
  • C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C=C3O2)O)C4C(C(C(C(O4)CO)O)O)O)O)O
Properties
C21H20O10
Molar mass 432.381 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Isovitexin (homovitexin or saponaretin) is a flavonoid,[1] namely the apigenin-6-C-glucoside. In this case, the prefix 'iso' does not imply an isoflavonoid (the position of the B-ring on the C-ring), but the position of the glucoside on the flavone, in comparison to vitexin.

Natural occurrence

Isovitexin has been found in passion flower, Cannabis, oat, and the açaí palm. Buckwheat contained the highest concentration among the sources tested.[2]

Metabolism

Isovitexin beta-glucosyltransferase is an enzyme characterised from Silene alba that forms the glucoside, 2"-O-(β-D-glucosyl)isovitexin from isovitexin and UDP-glucose.[3]

2D representation of the chemical structure of isovitexin .
isovitexin
+ UDP-glucose
 
 
 
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of Q27145302.
2"-O-(β-D-glucosyl)isovitexin
Saponarin

Saponarin is a related compound where the second glucose unit is attached at the 7-position of isovitexin.[4]

See also

References

  1. ↑ Lin, Jinquan; Ran, Hao; Feng, Qiqian; Shen, Qun; Zhou, Sumei; Sun, Yuanlin; Hou, Dianzhi (2025-09-01). "Unveiling the differences between vitexin and isovitexin: From the perspective of sources, green advanced extraction technologies, biological activities, and safety". Food Chemistry. 485 144600. doi:10.1016/j.foodchem.2025.144600. ISSN 0308-8146.
  2. ↑ Kalinová, Jana Pexová; Vrchotová, Naděžda; Tříska, Jan (2021). "Vitexin and isovitexin levels in sprouts of selected plants". Journal of Food Composition and Analysis. 100 103895. doi:10.1016/j.jfca.2021.103895.
  3. ↑ 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.
  4. ↑ Takeda, Kosaku; Fujii, Aki; Senda, Yohko; Iwashina, Tsukasa (2010). "Greenish blue flower colour of Strongylodon macrobotrys". Biochemical Systematics and Ecology. 38 (4): 630–633. doi:10.1016/j.bse.2010.07.014.
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