Cloning and regiospecificity studies of two flavonoid glucosyltransferases from Allium cepa

Phytochemistry

Volumn 64, Issue 6, 2003, Pages 1069-1076

  Kramer, Catherine M ^a   Prata, Rogerio T N ^a   Willits, Michael G ^a   De Luca, Vincenzo ^b   Steffens, John C ^a   Graser, Gerson ^a  

^a SYNGENTA BIOTECHNOLOGY INC   (United States)

^b BROCK UNIVERSITY   (Canada)

Author keywords

Alliaceae; Allium cepa; Flavonoids; Glucosyltransferases; Onion; Quercetin; Regiospecificity; Substrate specificity

Indexed keywords

FLAVONOID; FLAVONOID GLUCOTRANSFERASE; GENISTEIN; HYDROXYL GROUP; ISOFLAVONE; ISOQUERCETIN; QUERCETIN; UNCLASSIFIED DRUG; URIDINE DIPHOSPHATE GLUCOSE;

ARTICLE; BIOAVAILABILITY; BIOSYNTHESIS; CHEMICAL STRUCTURE; ENZYME ASSAY; ENZYME MECHANISM; ENZYME PURIFICATION; ENZYME SPECIFICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR CLONING; NONHUMAN; NUCLEOTIDE SEQUENCE; ONION; PROTEIN EXPRESSION; SMALL INTESTINE ABSORPTION; STEREOSPECIFICITY;

ALLIACEAE; ALLIUM; ALLIUM CEPA; ESCHERICHIA COLI;

EID: 0142121395     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(03)00507-7     Document Type: Article

References (30)

1. Arend, J., Warzecha, H., Hefner, T., Stockigt, J., 2001. Utilizing genetically engineered bacteria to produce plant specific glucosides. Biotechnol. Bioeng. 76, 126-131.
2. Aziz, A.A., Edwards, C.A., Lean, M.E.J., Crozier, A., 1998. Absorption and excretion of conjugated flavonols, including quercetin-4′-O-β -glucoside and isorhamnetin-4′-O-β-glucosides by human volunteers after the consumption of onions. Free Radic. Res. 29, 257-269.
3. Campbell, J.A., Davies, G.J., Bulone, V., Henrissat, B., 1997. A classification of nucleotide-diphospho-sugar glycosyltransferases based on amino acid sequence similarities. Biochem. J. 326, 929-939.
4. Dorant, E., van den Brandt, P.A., Goldbohm, R.A., Sturmans, F., 1996. Consumption of onions and a reduced risk of stomach carcinoma. Gastroenterology 110, 12-20.
5. Harborne, J.B., Baxter, H., 1999. Handbook of Natural Flavonoids. 2 Vols. John Wiley & Sons, Chichester, New York.
6. Harborne, J.B., Williams, C.A., 2000. Advances in flavonoid research since 1992. Phytochemistry 55, 481-504.
7. Hertog, M.G.L., Hollman, P.C.H., Katan, M.B., 1992. Content of potentially anticarcinogenic flavonoids of 28 vegetables and 9 fruits commonly consumed in the Netherlands. J. Agric. Food Chem. 40, 2379-2383.
8. Hertog, M.G.L., Kromhout, D., Aravanis, C., Blackburn, H., Buzina, R., Fidanza, F., Giampaoli, S., Jansen, A., Menotti, A., Nedeljkovic, S., Pekkarinen, M., Simic, B.S., Toshima, H., Feskens, E.J.M., Hollman, P.C.H., Katan, M.B., 1995. Flavonoid intake and long-term risk of coronary heart disease and cancer in the seven countries study. Arch. Intern. Med. 155, 381-386.
9. Hirotani, M., Kuroda, R., Suzuki, H., Yoshikawa, T., 2000. Cloning and expression of UDP-glucose: flavonoid 7-O-glucosyltransferase from hairy root cultures of Scutellaria baicalensis. Planta 210, 1006-1013.
10. Hollman, P.C.H., de Vries, J.H.M., van Leeuwen, S.D., Mengelers, M.J.B., Katan, M.B., 1995. Absorption of dietary quercetin glycosides and quercetin in healthy ileostomy volunteers. Am. J. Clin. Nutr. 62, 1276-1282.
11. Hollman, P.C.H., van Trijp, J.M.P., Buysman, M.N.C.P., Gaag, M.S.v.d., Mengelers, M.J.B., de Vries, J.H.M., Katan, M.B., 1997. Relative bioavailability of the antioxidants flavonoid quercetin from various foods in man. FEBS Lett. 418, 152-156.
12. Hollman, P.C.H., Bijsman, M.N.C.P., van Gameren, Y., Cnossen, E.P.J., de Vries, J.H.M., Katan, M.B., 1999. The sugar moiety is a major determinant of the absorption of dietary flavonoid glycosides in man. Free Radic. Res. 31, 569-573.
13. Iwashina, T., Kitajima, J., 2000. Chalcone and flavonol glycosides from Asarum canadense (Aristochiaceae). Phytochemistry 55, 971-974.
14. Keli, S.O., Hertog, M.G.L., Feskens, E.J.M., Kromhout, D., 1996. Flavonoids, antioxidant vitamins and risk of stroke. The Zutphen study. Arch. Intern. Med. 156, 637-642.
15. Lagrimini, L.M., Burkhart, W., Moyer, M., Rothstein, S., 1987. Molecular cloning of complementary DNA encoding lignin-forming peroxidase from tobacco: molecular analysis and tissue-specific expression. Proc. Natl. Acad. Sci. U.S.A. 84, 7542-7546.
16. Latchinian-Sadek, L., Ibrahim, R.K., 1991. Partial purification and some properties of a ring β-O-glucosyltransferase from onion bulbs. Phytochemistry 30, 1767-1771.
17. Lim, E.-K., Doucet, C.J., Li, Y., Elias, L., Worrall, D., Spencer, S.P., Ross, J., Bowles, D.J., 2002. The activity of Arabidopsis glycosyltransferases toward salicylic acid 4-hvdroxybenzoic acid, and other benzoates. J. Biol. Chem. 277, 586-592.
18. Markham, K.R., 1982. Techniques of Flavonoid Identification. Academic Press, London.
19. Messner, B., Thulke, O., Schaffner, A.R., 2003. Arabidopsis glucosyltransferases with activities towards both endogenous and xenobiotic substrates. Planta 217, 138-146.
20. Olthof, M.R., Hollman, P.C.H., Vree, T.B., Katan, M.B., 2000. Bioavailability of quercetin-3-glucoside and quercetin-4′-glucoside do not differ in humans. J. Nutr. 130, 1200-1203.
21. Price, K.R., Rhodes, M.J.C., 1997. Analysis of the major flavonol glycosides present in four varieties of onion (Allium cepa) and changes in composition resulting from autolysis. J. Sci. Food Agric. 74, 331-339.
22. Rhodes, M.J.C., Price, K.R., 1996. Analytical problems in the study of flavonoid compounds in onions. Food Chem. 57, 113-117.
23. Sambrook, J., Fritsch, E.F., Maniatis, T., 1989. Molecular Cloning: A Laboratory Manual. Cold Spring Harbor Laboratory Press, New York.
24. Scalbert, A., Williamson, G., 2000. Dietary intake and bioavailability of polyphenols. J. Nutr. 130, 2073S-2085S.
25. Tsushida, T., Suzuki, M., 1996. Content of flavonol glucosides and some properties of enzymes metabolizing the glucosides in onion. Nippon Shokuhin Kagaku Kaishi 43, 642-649.
26. Vogt, T., Zimmermann, E., Grimm, R., Meyer, M., Strack, D., 1997. Are the characteristics of betanidin glucosyltransferase from cell-suspension cultures of Dorotheanthus bellidiformis indicative of their phylogenetic relationship with flavonoid glucosyltransferases? Planta 203, 349-361.
27. Vogt, T., Jones, P., 2000. Glycosyltransferases in plant natural product synthesis: characterization of a supergene family. Trends Plant Sci. 5, 380-386.
28. Walgren, R.A., Karnaky, K.J., Lindenmayer, G.E., Walle, T., 2000a. Efflux of dietary flavonoid quercetin 4′-β-glucoside across human intestinal caco-2 cell monolayers by apical multidrug resistance-associated protein-2. J. Pharmacol. Exp. Ther. 294. 830-836.
29. Walgren, R.A., Lin, J.-T., Kinne, R.K.-H., Walle, T., 2000b. Cellular uptake of dietary flavonoid quercetin 4′-β-glucoside by sodium-dependent glucose transporter SGLT1. J. Pharmacol. Exp. Ther, 294, 837-843.
30. Willits, M.G., Giovanni, M., Prata, R.T.N., Kramer, C.M., De Luca, V., Steffens, J.C., Graser, G., 2003. Biofermentation of modified flavonoids: an example of in vivo diversification of plant secondary metabolites. Photochemistry (submitted for publication).