Regioselective formation of quercetin 5-O-glucoside from orally administered quercetin in the silkworm, Bombyx mori.
The cocoons of some races of the silkworm, Bombyx mori, have been shown to contain 5-O-glucosylated flavonoids, which do not occur naturally in the leaves of their host plant, mulberry (Morus alba). Thus, dietary flavonoids could be biotransformed in this insect. In this study, we found that after feeding silkworms a diet rich in the flavonol quercetin, quercetin 5-O-glucoside was the predominant metabolite in the midgut tissue, while quercetin 5,4'-di-O-glucoside was the major constituent in the hemolymph and silk glands. UDP-glucosyltransferase (UGT) in the midgut could transfer glucose to each of the hydroxyl groups of quercetin, with a preference for formation of 5-O-glucoside, while quercetin 5,4'-di-O-glucoside was predominantly produced if the enzyme extracts of either the fat body or silk glands were incubated with quercetin 5-O-glucoside and UDP-glucose. These results suggest that dietary quercetin was glucosylated at the 5-O position in the midgut as the first-pass metabolite of quercetin after oral absorption, then glucosylated at the 4'-O position in the fat body or silk glands. The 5-O-glucosylated flavonoids retained biological activity in the insect, since the total free radical scavenging capacity of several tissues increased after oral administration of quercetin.
Hirayama
Chikara
C
National Institute of Agrobiological Sciences, Tsukuba, Ibaraki 305-8634, Japan. hirayam@nias.affrc.go.jp
Ono
Hiroshi
H
Tamura
Yasumori
Y
Konno
Kotaro
K
Nakamura
Masatoshi
M
D000284:Administration, Oral; D000818:Animals; D000975:Antioxidants / Q000737:chemistry / Q000378:metabolism; D001711:Biotransformation; D012831:Bombyx / Q000737:chemistry* / Q000378:metabolism; D004789:Enzyme Activation; D005260:Female; D005960:Glucosides / Q000096:biosynthesis* / Q000737:chemistry; D014453:Glucuronosyltransferase / Q000032:analysis / Q000378:metabolism; D007814:Larva / Q000378:metabolism; D015394:Molecular Structure; D009928:Organ Specificity; D011794:Quercetin / Q000008:administration & dosage / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism; D013997:Time Factors
D000975:Antioxidants; D005960:Glucosides; C530520:quercetin 5-O-glucoside; D011794:Quercetin; D014453:Glucuronosyltransferase