Hydrolysis by lactase phlorizin hydrolase is the first step in the uptake of daidzein glucosides by rat small intestine in vitro

References

• ADLERCREUTZ, H. and MAZUR, W., 1997, Phyto-oestrogens and Western diseases. Annals of Medicine, 29, 95–120.
   PubMed Web of Science ®Google Scholar
• ANDERSSON, U., BUTTERS, T. D., DWEK, R. A. and PLATT, F. M., 2000, N-butyldeoxygalactonojir-imycin: a more selective inhibitor of glycosphingolipid biosynthesis than N-butyldeoxynojir-imycin, in vitro and in vivo. Biochemical Pharmacology, 59, 821–829.
   PubMed Web of Science ®Google Scholar
• ANDLAUER, W., KOLB, J. and FURST, P., 2000a, Absorption and metabolism of genistin in the isolated rat small intestine. FEBS Letters, 475, 127–130.
   PubMed Web of Science ®Google Scholar
• ANDLAUER, W., KOLB, J. and FURST, P., 2000b, Isoflavones from tofu are absorbed and metabolized in the isolated rat small intestine. Journal of Nutrition, 130, 3021–3027.
   PubMed Web of Science ®Google Scholar
• BARNES, S., KIRK, M. and COWARD, L., 1994, Isoflavones and their conjugates in soy foods: extraction conditions and analysis by HPLC-mass spectrometry. Journal of Agricultural and Food Chemistry, 42, 2466–2474.
   Web of Science ®Google Scholar
• BURCHELL, B. and COUGHTRIE, M. W. H., 1989, UDP-glucuronyltransferases. Pharmacology and Therapeutics, 43, 261–289.
   PubMed Web of Science ®Google Scholar
• CREEKE, P. I., WILKINSON, A. P., LEE, H. A., MORGAN, M. R. A., PRICE, K. R. and RHODES, M. J. C., 1998, Development of ELISAs for the measurement of the dietary phytoestrogens daidzein and equol in human plasma. Food and Agricultural Immunology, 10, 325–333.
   Google Scholar
• DAY, A. J., BAO, Y., MORGAN, M. R. A. and WILLIAMSON, G., 2000a, Conjugation position of quercetin glucuronides and effect on biological activity. Free Radicals in Biology and Medicine, 29, 1234–1243.
   Google Scholar
• DAY, A. J., CANADA, F. J., DiAz, J. C., KROON, P. A., MCLAUCHLAN, R., FAULDS, C. B., PLUMB, G. W., MORGAN, M. R. A. and WILLIAMSON, G., 2000b, Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase. FEBS Letters, 468, 166–170.
   Google Scholar
• DAY, A. J., DUPONT, M. S., RIDLEY, S., RHODES, M., RHODES, M. J., MORGAN, M. R. A. and WILLIAMSON, G., 1998, Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver beta-glucosidase activity. FEBS Letters, 436, 71–75.
   Google Scholar
• DUPONT, M. S., MONDIN, Z., WILLIAMSON, G. and PRICE, K. P., 2000, Effect of variety, processing and storage on the flavonoid glycoside content and composition of lettuce and endive. Journal of Agriculture and Food Chemistry, 48, 3957–3964.
   PubMed Web of Science ®Google Scholar
• GEE, J. M., DUPONT, M. S., DAY, A. J., PLUMB, G. W., WILLIAMSON, G. and JOHNSON, I. T., 2000, Intestinal transport of quercetin glycosides in rats involves both deglycosylation and interaction with the hexose transport pathway. Journal of Nutrition, 130, 2765–2771.
   PubMed Web of Science ®Google Scholar
• GEE, J. M., DUPONT, M. S., RHODES, M. J. and JOHNSON, I. T., 1998, Quercetin glucosides interact with the intestinal glucose transport pathway. Free Radicals in Biology and Medicine, 25, 19–25.
   PubMed Web of Science ®Google Scholar
• GRIFFITHS, L. A. and BARROW, A., 1972, Metabolism of flavonoid compounds in germ free rats. Biochemical Journal, 130, 1161–1162.
   PubMed Web of Science ®Google Scholar
• HOLLMAN, P. C., DE VRIES, J. H., VAN LEEUWEN, S. D., MENGELERS, M. J. and KATAN, M. B., 1995, Absorption of dietary quercetin glycosides and quercetin in healthy ileostomy volunteers. American Journal of Clinical Nutrition, 62, 1276–1282.
   PubMed Web of Science ®Google Scholar
• HOLLMAN, P. C., VAN DER GAAG, M., MENGELERS, M. J., VAN TRIP, J. M., DE VRIES, J. H. and KATAN, M. B., 1996, Absorption and disposition kinetics of the dietary antioxidant quercetin in man. Free Radicals in Biology and Medicine, 21, 703–707.
   PubMed Web of Science ®Google Scholar
• HOUBA, P. H., BOVEN, E., VAN DER MEULEN-MUILEMAN, I. H., LEENDERS, R. G., SCHEEREN, J. W., PINEDO, H. M. and HAISMA, H. J., 2001, A novel doxorubicin-glucuronide prodrug DOX-GA3 for tumour-selective chemotherapy: distribution and efficacy in experimental human ovarian cancer. British Journal of Cancer, 84, 550–557.
   Google Scholar
• HWANG, J., SEVANIAN, A., HODIS, H. N. and URSINI, F., 2000, Synergistic inhibition of LDL oxidation by phytoestrogens and ascorbic acid. Free Radicals in Biology and Medicine, 29, 79–89.
   PubMed Web of Science ®Google Scholar
• KING, R. A. and BURSILL, D. B., 1998, Plasma and urinary kinetics of the isoflavones daidzein and genistein after a single soy meal in humans. American Journal of Clinical Nutrition, 67, 867–872.
   PubMed Web of Science ®Google Scholar
• KREN, V. and MARTINKOVA, L., 2001, Glycosides in medicine: 'The role of glycosidic residue in abiological activity'. Current Medicinal Chemistry, 8, 1303–1328.
   PubMed Web of Science ®Google Scholar
• MORTON, M. S., MATOS-FERREIRA, A., ABRANCHES-MONTEIRO, L., CORREIA, R., BLACKLOCK, N., CHAN, P. S. F., CHENG, C., LLOYD, S., Wu, C.P. and GRIFFITHS, K., 1997, Measurement and metabolism of isoflavonoids and lignans in the human male. Cancer Letters, 114, 145–151.
   Google Scholar
• NEEDS, P. W. and WILLIAMSON, G., 2001, Syntheses of daidzein-7-ylbeta-D-glucopyranosiduronic acid and daidzein-4,7-y1 di-beta-D-glucopyranosiduronic acid. Carbohydrate Research, 330, 511–515.
   PubMed Web of Science ®Google Scholar
• PISKULA, M. K., 2000, Factors affecting flavonoids absorption. Biofactors, 12, 175–180.
   PubMed Web of Science ®Google Scholar
• PISKULA, M. K., YAMAKOSHI, J. and Iwm, Y., 1999, Daidzein and genistein but not their glucosides are absorbed from the rat stomach. FEBS Letters, 447, 287–291.
   PubMed Web of Science ®Google Scholar
• PRICE, K. R., COLQUHOUN, I. J., BARNES, K. A. and RHODES, M. J. C., 1998, The composition and content of flavonol glycosides in green beans and their fate during processing. Journal of Food Chemistry, 46, 4898–4903.
   Web of Science ®Google Scholar
• RUIZ-LARREA, M. B., MOHAN, A. R., PAGANGA, G., MILLER, N. J., BOLWELL G. P. and RICE-EVANS, C. A., 1997, Antioxidant activity of phytoestrogenic isoflavones. Free Radical Research, 26, 63–70.
   Google Scholar
• SETCHELL, K. D. and CASSIDY, A., 1999, Dietary isoflavones: biological effects and relevance to human health. Journal of Nutrition, 129, 758S–767S.
   Google Scholar
• WACKER, H., KELLER, P., FALCHETTO, R., LEGLER, G., SEMENZA, G., ROAL, F. and FREUND, J. N., 1992, Location of the two catalytic sites in intestinal lactase phloridzin hydrolase. Journal of Biological Chemistry, 267, 18744–18752.
   PubMed Web of Science ®Google Scholar
• WISEMAN, H., O'REILLY, J. D., ADLERCREUTZ, H., MALLET, A. I., BOWEY, E. A., ROWLAND, I. R. and SANDERS, T. A., 2000, Isoflavone phytoestrogens consumed in soy decrease F(2)-isoprostane concentrations and increase resistance of low-density lipoprotein to oxidation in humans. American Journal of Clinical Nutrition, 72, 395–400.
   Google Scholar
• ZHANG, Y., SONG, T. T., CUNNICK, J. E., MURPHY, P. A. and HENDRICH, S., 1999, Daidzein and genistein glucuronides in vitro are weakly estrogenic and activate human natural killer cells at nutritionally relevant concentrations. Journal of Nutrition, 129, 399–405.
   PubMed Web of Science ®Google Scholar