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
CAS Number	38953-85-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18330 ;
ChemSpider	142556;
ECHA InfoCard	100.126.529
PubChem CID	162350;
UNII	KTQ9R9MS0Q ;
CompTox Dashboard (EPA)	DTXSID60952152 ;
	InChI 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;
	SMILES 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
Chemical formula	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^{[citation needed]}) 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]

isovitexin

+ UDP-glucose

UDP

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

References

↑ 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.
↑ 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.
↑ 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.
↑ 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.

[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.

[1]

[2]

[3]

[4]

Natural occurrence

Metabolism

See also

References