Dietary quercetin glycosides: antioxidant activity and induction of the anticarcinogenic phase II marker enzyme quinone reductase in Hepalclc7 cells.
It has recently been shown by Hollman et al. (Am. J. Clin. Nutr., 62, 1276-1282) that flavonoid glycosides are preferentially absorbed from dietary onions compared to the flavonoid aglycone. In the light of this, we have compared the bioactivities of the two most abundant flavonoid glycosides that we have purified from onions (quercetin-3,4'-diglucoside and quercetin-4'-glucoside) to the quercetin aglycone, and also to the more commonly studied commercially-available flavonoid glycosides, rutin (quercetin-3-rutinoside) and isoquercitrin (quercetin-3-glucoside). Quercetin aglycone was the most effective inducer of the anticarcinogenic phase II marker enzyme, quinone reductase (QR), in mouse Hepalclc7 cells. Of the glycosides, only quercetin-4'-glucoside was able to induce QR activity in this assay. Inhibition of NADPH/iron- and ascorbate/iron-induced lipid peroxidation of human liver microsomes, and the Trolox C-equivalent antioxidant capacity (TEAC), were also measured. The 4'-glycosylation dramatically decreased activity in the 'antioxidant' assays, whereas 3-substitutions produced much smaller changes. These results show that the preferentially-absorbed quercetin glycosides in onions have markedly different biological properties compared with the aglycone.
Williamson
G
G
Biochemistry Department, Institute of Food Research, Colney, Norwich, UK.
Plumb
G W
GW
Uda
Y
Y
Price
K R
KR
Rhodes
M J
MJ
D000818:Animals; D016588:Anticarcinogenic Agents / Q000494:pharmacology*; D000975:Antioxidants / Q000494:pharmacology*; D002839:Chromans / Q000494:pharmacology; D004790:Enzyme Induction / Q000187:drug effects; D006027:Glycosides / Q000494:pharmacology*; D006031:Glycosylation; D006801:Humans; D015227:Lipid Peroxidation; D051379:Mice; D008862:Microsomes, Liver / Q000187:drug effects* / Q000201:enzymology*; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000096:biosynthesis*; D011794:Quercetin / Q000031:analogs & derivatives* / Q000494:pharmacology
D016588:Anticarcinogenic Agents; D000975:Antioxidants; D002839:Chromans; D006027:Glycosides; D011794:Quercetin; D016660:NAD(P)H Dehydrogenase (Quinone); C080613:spiraeoside; C010643:6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid