Description
Isovitexin, a food phytochemical contained in dietary rice products, or as a natural plant flavonoid isolated from the seeds of Vitex trifolia L, suppresses lipopolysaccharide-mediated inducible nitric oxide synthase through inhibition of NF-kappa B in mouse macrophages. Isovitexin exhibits anti-inflammatory and anti-oxidant activities on lipopolysaccharide-induced acute lung injury by inhibiting MAPK and NF-κB and activating HO-1/Nrf2 pathways. Isovitexin can inhibit xanthine oxidase with an IC50 value of 15.2 microM, and it may protect cells from oxidative stress.
Synonyms
Saponaretin; Homovitexin; (1S)-1,5-anhydro-1-[5,7-dihydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-6-yl]-D-glucitol; 4H-1-Benzopyran-4-one, 6-β-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-; 6-β-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; Flavone, 6-β-D-glucopyranosyl-4',5,7-trihydroxy-; Homovitexin; 6-C-Glucosylapigenin; 6-C-β-D-Glucopyranosylapigenin; Apigenin 6-C-β-D-glucoside; Apigenin 6-C-β-glucopyranoside; Apigenin-6-C-glucoside; Apigenin-6-C-β-D-glucopyranoside; Avroside; Isoavroside; Isovitexin (C-6 isomer); Saponaretin
IUPAC Name
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
Molecular Formula
C21H20O10
Canonical SMILES
C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)C4C(C(C(C(O4)CO)O)O)O)O)O
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
InChIKey
MYXNWGACZJSMBT-VJXVFPJBSA-N
Boiling Point
807.0±65.0°C (Predicted)
Solubility
Soluble in DMF, DMSO
Uses
Isovitexin is known as a flavones, a class of flavonoids. Isovitexin have been studied for their antiradical activities in the process of metabolisms. Isovitexin have also been studied for beneficial
effcts against atherosclerosis, osteoporosis and certain cancers.