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

Xenobiotica

Volumn 33, Issue 3, 2003, Pages 255-264

  Wilkinson, A P ^a   Gee, J M ^a   Dupont, M S ^a   Needs, P W ^a   Mellon, F A ^a   Williamson, G ^a,b   Johnson, I T ^a  

^a INSTITUTE OF FOOD RESEARCH   (United Kingdom)

^b NESTLÉ RESEARCH CENTER   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DAIDZIN; ENZYME; ENZYME INHIBITOR; INTESTINE ENZYME; LACTASE PHLORIZIN HYDROLASE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BRUSH BORDER; CONCENTRATION RESPONSE; CONTROLLED STUDY; DEGLYCOSYLATION; DRUG ABSORPTION; DRUG GLUCURONIDATION; DRUG HYDROLYSIS; ENZYME ACTIVITY; ENZYME INHIBITION; GLUCOSE TRANSPORT; INTESTINE ABSORPTION; JEJUNUM; JEJUNUM MUCOSA; MALE; NONHUMAN; RAT; SEROSA; SMALL INTESTINE ABSORPTION;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENZYME-LINKED IMMUNOSORBENT ASSAY; GLYCOSIDES; GLYCOSYLCERAMIDASE; HYDROLYSIS; INTESTINAL ABSORPTION; INTESTINAL MUCOSA; INTESTINE, SMALL; ISOFLAVONES; JEJUNUM; MALE; MICROVILLI; RATS;

ANIMALIA;

EID: 0037354625     PISSN: 00498254     EISSN: None     Source Type: Journal    
DOI: 10.1080/0049825021000058088     Document Type: Article

References (30)

1. ADLERCREUTZ, H. and MAZUR, W., 1997, Phyto-oestrogens and Western diseases. Annals of Medicine, 29, 95-120.
2. ANDERSSON, U., BUTTERS, T. D., DWEK, R. A. and PLATT, F. M., 2000, N-butyldeoxygalactonojirimycin: a more selective inhibitor of glycosphingolipid biosynthesis than N-butyldeoxynojirimycin, in vitro and in vivo. Biochemical Pharmacology, 59, 821-829.
3. ANDLAUER, W., KOLB, J. and FURST, P., 2000a, Absorption and metabolism of genistin in the isolated rat small intestine. FEBS Letters, 475, 127-130.
4. 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.
5. 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.
6. BURCHELL, B. and COUGHTRIE, M. W. H., 1989, UDP-glucuronyltransferases. Pharmacology and Therapeutics, 43, 261-289.
7. 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.
8. 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.
9. DAY, A. J., CAǸADA, 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.
10. 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.
11. 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.
12. 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.
13. 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.
14. GRIFFITHS, L. A. and BARROW, A., 1972, Metabolism of flavonoid compounds in germ free rats. Biochemical Journal, 130, 1161-1162.
15. 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.
16. HOLLMAN, P. C., VAN DER GAAG, M., MENGELERS, M. J., VAN TRIJP, 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.
17. 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.
18. 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.
19. 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.
20. KREN, V. and MARTINKOVA, L., 2001, Glycosides in medicine: 'The role of glycosidic residue in biological activity'. Current Medicinal Chemistry, 8, 1303-1328.
21. 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.
22. NEEDS, P. W. and WILLIAMSON, G., 2001, Syntheses of daidzein-7-yl beta-D-glucopyranosiduronic acid and daidzein-4,7-yl di-beta-D-glucopyranosiduronic acid. Carbohydrate Research, 330, 511-515.
23. PISKULA, M. K., 2000, Factors affecting flavonoids absorption. Biofactors, 12, 175-180.
24. PISKULA, M. K., YAMAKOSHI, J. and IWAI, Y., 1999, Daidzein and genistein but not their glucosides are absorbed from the rat stomach. FEBS Letters, 447, 287-291.
25. 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.
26. 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.
27. SETCHELL, K. D. and CASSIDY, A., 1999, Dietary isoflavones: biological effects and relevance to human health. Journal of Nutrition, 129, 758S-767S.
28. 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.
29. 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.
30. 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.