Tags

Type your tag names separated by a space and hit enter

Regioselective formation of quercetin 5-O-glucoside from orally administered quercetin in the silkworm, Bombyx mori.
Phytochemistry. 2008 Mar; 69(5):1141-9.P

Abstract

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.

Authors+Show Affiliations

National Institute of Agrobiological Sciences, Tsukuba, Ibaraki 305-8634, Japan. hirayam@nias.affrc.go.jpNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

18164738

Citation

Hirayama, Chikara, et al. "Regioselective Formation of Quercetin 5-O-glucoside From Orally Administered Quercetin in the Silkworm, Bombyx Mori." Phytochemistry, vol. 69, no. 5, 2008, pp. 1141-9.
Hirayama C, Ono H, Tamura Y, et al. Regioselective formation of quercetin 5-O-glucoside from orally administered quercetin in the silkworm, Bombyx mori. Phytochemistry. 2008;69(5):1141-9.
Hirayama, C., Ono, H., Tamura, Y., Konno, K., & Nakamura, M. (2008). Regioselective formation of quercetin 5-O-glucoside from orally administered quercetin in the silkworm, Bombyx mori. Phytochemistry, 69(5), 1141-9. https://doi.org/10.1016/j.phytochem.2007.11.009
Hirayama C, et al. Regioselective Formation of Quercetin 5-O-glucoside From Orally Administered Quercetin in the Silkworm, Bombyx Mori. Phytochemistry. 2008;69(5):1141-9. PubMed PMID: 18164738.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Regioselective formation of quercetin 5-O-glucoside from orally administered quercetin in the silkworm, Bombyx mori. AU - Hirayama,Chikara, AU - Ono,Hiroshi, AU - Tamura,Yasumori, AU - Konno,Kotaro, AU - Nakamura,Masatoshi, Y1 - 2007/12/31/ PY - 2007/07/27/received PY - 2007/10/22/revised PY - 2007/11/14/accepted PY - 2008/1/1/pubmed PY - 2008/8/12/medline PY - 2008/1/1/entrez SP - 1141 EP - 9 JF - Phytochemistry JO - Phytochemistry VL - 69 IS - 5 N2 - 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. SN - 0031-9422 UR - https://www.unboundmedicine.com/medline/citation/18164738/Regioselective_formation_of_quercetin_5_O_glucoside_from_orally_administered_quercetin_in_the_silkworm_Bombyx_mori_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0031-9422(07)00677-2 DB - PRIME DP - Unbound Medicine ER -