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Isotopic Labelling of Dietary Polyphenols for Bioavailability Studies

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Plant Polyphenols 2

Part of the book series: Basic Life Sciences ((BLSC,volume 66))

Abstract

People are increasingly concerned by the effect of their diet on health. Excessive consumption of some dietary components (fat, sugar) may have negative effects, whereas the consumption of other components (fiber, micronutrients, etc.) is encouraged. Epidemiology studies have suggested a protective role for different constituents of our diet against diseases. The reduced prevalence of various cancers by the consumption of fruit and vegetables is now well established.1 Other associations, such as the protective role of wine against cardiovascular diseases2 or of soya against breast cancer3 have been suggested. Many researchers try today to identify the molecules in food responsible for these protective effects.

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References

  1. Steinmetz K.A.; Potter J.D. Vegetables, fruit, and cancer prevention: a review. J. Am. Diet. Assoc. 96:1027 (1996).

    Article  PubMed  CAS  Google Scholar 

  2. St. Leger, A.S.; Cochrane, A.L.; Moore, F. Factors associated with cardiac mortality in developed countries with particular reference to the consumption of wine. Lancet:1017 (1979).

    Google Scholar 

  3. Adlercreutz H.; Mazur W. Phyto-oestrogens and Western diseases. Ann. Med. 29:95 (1997).

    PubMed  CAS  Google Scholar 

  4. Swain, T. Economic importance of flavonoid compounds: foodstuffs. In: Geissman, T.A. (ed.). The chemistry of flavonoid compounds. Pergamon Press, Oxford p. 513 (1962).

    Google Scholar 

  5. Shahidi, F.; Naczk, M. Food phenolics, sources, chemistry, effects, applications. Technomic Publishing Co. Inc., Lancaster, (1995).

    Google Scholar 

  6. Kühnau, J. The flavonoids. A class of semi-essential food components: their role in human nutrition. World Rev. Nutr. Diet. 24:117 (1976).

    PubMed  Google Scholar 

  7. Bender, A.E. Nutritional significance of bioavailability. In: Southgate, D.; Johnson, I.; Fenwik, G.R. (eds.). Nutrient availability: Chemical and biological aspects. Royal Society of Chemistry, Cambridge, p. 3 (1989).

    Google Scholar 

  8. Terrill T.H.; Waghorn G.C.; Woolley D.J.; McNabb W.C.; Barry T.N. Assay and digestion of 14C-labelled condensed tannins in the gastrointestinal tract of sheep. Brit. J. Nutr. 72:467 (1994).

    Article  PubMed  CAS  Google Scholar 

  9. Hackett A.M.; Griffiths L.A.; Broillet A.; Wermeille M. The metabolism and excretion of (+)-[14C]cyanidol-3 in man following oral administration. Xenobiotica 13:279 (1983).

    Article  PubMed  CAS  Google Scholar 

  10. Klein, P.D.; Hachey, D.L.; Kreek, M.J.; Shoeller, D.A. Stable isotopes: essential tools in biological and medical research. In: Baillie, T.A. (ed.). Stable isotopes—Applications in pharmacology, toxicology and clinical research. Macmillan Press Ltd., London, p. 3 (1978).

    Google Scholar 

  11. Draffan, G.H. Stable isotopes in human drug metabolism studies. In: Baillie, T.A. (ed.). Stable isotopes—Applications in pharmacology, toxicology and clinical research. Macmillan Press Ltd., London, p. 27 (1978).

    Google Scholar 

  12. Adlercreutz H.; Fotsis T.; Bannwart C.; Wähälä, K.; Brunow G.; Hase T. Isotope dilution gas chromatographic-mass spectrometric method for the determination of lignans and isoflavonoids in human urine, including identification of genistein. Clin. Chem. Acta 199:263 (1991).

    Article  CAS  Google Scholar 

  13. Adlercreutz H.; Fotsis T.; Kurzer M.S.; Wähälä, K.; Makela T.; Hase T. Isotope dilution gas Chromatographic mass spectrometric method for the determination of unconjugated lignans and isoflavonoids in human feces, with preliminary results in omnivorous and vegetarian women. Anal. Biochem. 225:101 (1995).

    Article  PubMed  CAS  Google Scholar 

  14. Baba S.; Furuta T.; Fujioka M.; Goromaru T. Studies on drug metabolism by use of isotopes. XXVII. Urinary metabolites of rutin in rats and the role of intestinal microflora in the metabolism of rutin. J. Pharm. Sci. 72:1155 (1983).

    Article  PubMed  CAS  Google Scholar 

  15. Peterson T.G.; Coward L.; Kirk M.; Falany C.N.; Barnes S. The role of metabolism in mammary epithelial cell growth inhibition by the isoflavones genistein and biochanin A. Carcinogenesis 17:1861 (1996).

    Article  PubMed  CAS  Google Scholar 

  16. Hackett, A.M.; Shaw, I.C.; Griffiths, L.A. 3′-O-Methyl-(+)-catechin glucuronide and 3′-O-methyl-(+)-catechin sulphate: new urinary metabolites of (+)-catechin in the rat and the marmoset. Experientia 38:538 (1982).

    Article  PubMed  CAS  Google Scholar 

  17. Petrakis P.L.; Kallianos A.G.; Wender S.H.; Shetlar M.R. Metabolic studies of quercetin labeled with C14. Arch. Biochem. Biophys. 85:264 (1959).

    Article  PubMed  CAS  Google Scholar 

  18. Ueno I.; Nakano N.; Hirono I. Metabolic fate of [14C]quercetin in the ACI rat. Jap. J. Exp. Med. 53:41 (1983).

    PubMed  CAS  Google Scholar 

  19. Honohan T.; Hale R.L.; Brown J.P.; Wingard R.E. Synthesis and metabolic fate of hesperetin-3-14C. J. Agric. Food Chem. 24:906 (1976).

    Article  PubMed  CAS  Google Scholar 

  20. Oustrin J.; Fauran M.J.; Commanay L. A pharmacokinetic study of 3H-diosmine. Arzneim. Forsch. 27 (II): 1688 (1977).

    CAS  Google Scholar 

  21. Harmand M.F.; Blanquet P. The fate of total flavanolic oligomers (OFT) extracted from Vitis vinifera L. in the rat. Eur. J. Drug Metabol. Pharmacokinet. 3:15 (1978).

    Article  CAS  Google Scholar 

  22. Laparra J.; Michaud J.; Lesca M.F.; Blanquet P.; Masquelier J. Etude pharmacocinétique des oligomères procyanidoliques totaux du raisin. Acta Ther. 4:233 (1978).

    Google Scholar 

  23. Jimenez-Ramsey L.M.; Rogler J.C.; Housley T.L.; Butler L.G.; Elkin R.G. Absorption and distribution of 14C-labelled condensed tannins and related sorghum phenolics in chickens. J. Agric. Food Chem. 42:963 (1994).

    Article  CAS  Google Scholar 

  24. Peterson T.G.; Coward L.; Kirk M.; Falany C.N.; Barnes S. Isoflavones and breast epithelial cell growth: the importance of genistein biochanin A metabolism in the breast. Carcinogenesis 17:101 (1996).

    Article  Google Scholar 

  25. Sfakianos J.; Coward L.; Kirk M.; Barnes S. Intestinal uptake and biliary excretion of the isoflavone genistein in rats. J. Nutr. 127:1260 (1997).

    PubMed  CAS  Google Scholar 

  26. Gooderham M.J.; Adlercreutz H.; Ojala S.T.; Wähälä, K.; Holub B.J. A soy protein isolate rich in genistein and daidzein and its effects on plasma isoflavone concentrations, platelet aggregation, blood lipids and fatty acid composition of plasma phospholipid in normal men. J. Nutr. 126:2000 (1996).

    PubMed  CAS  Google Scholar 

  27. Déprez, S.; Buffnoir S.; Scalbert A.; Rolando C. Isotopic labelling of proanthocyanidins. Analusis 25:M43 (1997).

    Google Scholar 

  28. Pierre M.C.; Chèze, C.; Vercauteren J. Deuterium labeled procyanidin syntheses. Tetrahedron Lett. 38:5639 (1997).

    Article  CAS  Google Scholar 

  29. Wähälä, K.; Mäkelä, T.; Bäckström, R.; Brunow G.; Hase T. Synthesis of the [2H]-labelled urinary lignans, enterolactone and enterodiol, and the phytoestrogen daidzein and its metabolites equol and O-demetylangolensin. J. Chem. Soc., Perkin Trans. 1:95 (1986).

    Article  Google Scholar 

  30. Wähälä, K.; Rasku S. Synthesis of D-4-genistein, a stable deutero labeled isoflavone, by a predeuteration—selective dedeuteration approach. Tetrahedron. Lett. 38:7287 (1997).

    Article  Google Scholar 

  31. Mazur W.; Fotsis T.; Wähälä, K.; Ojala S.; Salakka A.; Adlercreutz H. Isotope dilution gas Chromatographic mass spectrometric method for the determination of isoflavonoids, coumestrol, and lignans in food samples. Anal. Biochem. 233:169 (1996).

    Article  PubMed  CAS  Google Scholar 

  32. Das N.P.; Griffiths L.A. Studies on flavonoid metabolism. Biosynthesis of (+)-[14C]catechin by the plant Uncaria gambir Roxb. Biochem. J. 105:73 (1967).

    PubMed  CAS  Google Scholar 

  33. Déprez, S.; Sealbert, A. Carbon-14 biolabelling of (+)-catechin and proanthocyanidin oligomers in willow-tree cuttings. J. Agric. Food Chem. (in press) (1999).

    Google Scholar 

  34. Scalbert A.; Haslam E. Polyphenols and chemical defence of the leaves of Quercus robur. Phytochemistry 26:3191 (1987).

    Article  CAS  Google Scholar 

  35. Lister C.E.; Lancaster J.E.; Sutton K.H.; Walker R.L. Developmental changes in the concentration and composition of flavanoids in skin of a red and a green apple cultivar. J. Sci. Food Agric. 64:155 (1994).

    Article  CAS  Google Scholar 

  36. Böhm, B.A.; Singh, S.; Koupai-Abyazani, M.R. Biosynthesis and turnover of tannins in sainfoin (Onobrychis viciifolia). Polyphénols Actualités no11:18 (1994).

    Google Scholar 

  37. Feeny P.P.; Bostock H. Seasonal changes in the tannin content of oak leaves. Phytochemistry 7:871 (1968).

    Article  CAS  Google Scholar 

  38. Tissut M. Etude du cycle annuel des dérivés phénoliques de la feuille de hêtre, Fagus sylvatica L. Physiol. Vég. 6:351 (1968).

    CAS  Google Scholar 

  39. Koupai-Abyazani M.R.; McCallum J.; Muir A.D.; Böhm, B.A.; Towers G.H.N.; Gruber M.Y. Developmental changes in the composition of proanthocyanidins from leaves of sainfoin (Onobrychis viciifolia Scop.) as determined by HPLC analysis. J. Agric. Food Chem. 41:1066 (1993).

    Article  CAS  Google Scholar 

  40. Fukushima, K. Biolabelling of polyphenols in woody plants. I. Feeding methods. Polyphénols Actualités no 16:11 (1997).

    CAS  Google Scholar 

  41. Rausch H.; Gross G.G. Preparation of [14C]-labelled 1,2,3,4,6-penta-O-galloyl-β-D-glucose and related gallotannins. Z. Naturforsch. 51:473 (1996).

    CAS  Google Scholar 

  42. Fry S.C. Incorporation of 14C-cinnamate into hydrolase-resistant components of the primary cell wall of spinach. Phytochemistry 23:59 (1984).

    Article  CAS  Google Scholar 

  43. Jacques D.; Opie C.T.; Porter L.J.; Haslam E. Plant proanthocyanidins. Part 4._Biosynthesis of procyanidins and observations on the metabolism of cyanidin in plants. J. Chem. Soc., Perkin Trans. 1:1637 (1977).

    Article  Google Scholar 

  44. Stafford H.A.; Shimamoto M.; Lester H.H. Incorporation of (14C)phenylalanine into flavan3-ols and procyanidins in cell suspension cultures of Douglas fir. Plant Physiol. 69:1055 (1982).

    Article  PubMed  CAS  Google Scholar 

  45. Krisa, S.; Waffo Teguo, P.; Vitrac, X.; Vercauteren, J.; Deffieux, G.; Mérillon, J.M. Production de polyphénols marqués en 13C à l’aide de culture cellulaire. Proc. 19th International Conference on Polyphenols, Lille, France, p. 245 (1998).

    Google Scholar 

  46. Zaprometov M.N.; Bukhlaeva V.Y. Two pathways of biosynthesis of gallic acid. Biochemistry 33:317 (1968).

    Google Scholar 

  47. Hillis W.E.; Hasegawa M. The formation of polyphenols in trees-I: Administration of 14C glucose and subsequent distribution of radioactivity. Phytochemistry 2:195 (1963).

    Article  CAS  Google Scholar 

  48. Hillis W.E.; Isoi K. The biosynthesis of polyphenols in Eucalyptus species. Phytochemistry 4:905 (1965).

    Article  CAS  Google Scholar 

  49. Ellis B.E. Degradation of aromatic compounds in plants. Lloydia 37:168 (1974).

    CAS  Google Scholar 

  50. Zaprometov, M.N. Bohl. Akad. Nauk SSSR 125:1359 (1959).

    CAS  Google Scholar 

  51. Reed D.J.; Vimmerstedt J.; Jerina D.M.; Daly J.W. Formation of phenols from aromatic substrates by plant and animal mono-oxygenases: the effect of adjacent deuteriums on the magnitude of the NIH shift of tritium. Arch. Biochem. Biophys. 154:642 (1973).

    Article  PubMed  CAS  Google Scholar 

  52. Michaud J.; Laparra J.; Lesca M.F.; Harmand M.F.; Masquelier J.; Blanquet P. Phytosynthèse de rutoside marqué au 14C. Bull Soc. Pharm. Bordeaux 108:133 (1969).

    CAS  Google Scholar 

  53. Lapierre C.; Gaudillère, J.P.; Monties B.; Guittet E.; Rolando C.; Lallemand J.Y. Enrichissement photosynthetique en carbone 13 de peuplier: caracterisation préliminaire par acidolyse et RMN 13C. Holzforschung 37:217 (1983).

    Article  CAS  Google Scholar 

  54. Lewis, N.G.; Inciong, M.E.; Razal, R.A.; Yamamoto, E.; Davin, L.B. Monolignol biogenesis, lignin structure and biodegradation. Proc. 15émes Journées Internationales du Groupe Polyphenols, Strasbourg, p. 365 (1990).

    Google Scholar 

  55. Eastmond, R.; Gardner, R.J. [14C]-Epicatechin and [14C]-procyanidins from seed shells of Aesculus hippocastaneum. Phytochemistry 13:1477 (1974).

    Article  CAS  Google Scholar 

  56. Reddy V.; Butler L.G. Incorporation of 14C from [14C]-phenylalanine into condensed tannin of sorghum grain. J. Agric. Food Chem. 37:383 (1989).

    Article  CAS  Google Scholar 

  57. Bernays E.A.; Woodhead S. Incorporation of dietary phenols into the cuticle in the tree locust Anacridium melanorhodon. J. Insect Physiol. 28:601 (1982).

    Article  CAS  Google Scholar 

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© 1999 Kluwer Academic / Plenum Publishers, New York

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Déprez, S., Scalbert, A. (1999). Isotopic Labelling of Dietary Polyphenols for Bioavailability Studies. In: Gross, G.G., Hemingway, R.W., Yoshida, T., Branham, S.J. (eds) Plant Polyphenols 2. Basic Life Sciences, vol 66. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4139-4_19

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  • DOI: https://doi.org/10.1007/978-1-4615-4139-4_19

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-0-306-46218-4

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