Flavan-3-ol C-glycosides - Preparation and model experiments mimicking their human intestinal transit

Molecular Nutrition and Food Research

Volumn 54, Issue 11, 2010, Pages 1546-1555

  Hasslauer, Iris ^a   Oehme, Anett ^a   Locher, Sanja ^a   Valotis, Anagnostis ^a   Van't Slot, Gordon ^b   Humpf, Hans Ulrich ^b   Schreier, Peter ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Colostomy fluid; Flavan 3 ol C glycosides; Gastric Juice; Ileostomy fluid

Indexed keywords

C GLYCOSIDE; C-GLYCOSIDE; CATECHIN; DRUG DERIVATIVE; FLAVAN 3 OL; FLAVAN-3-OL; FLAVONOID; MONOSACCHARIDE;

ADULT; AGED; ARTICLE; BIOLOGICAL MODEL; BODY FLUID; CIRCULAR DICHROISM; COLOSTOMY; GASTROINTESTINAL TRANSIT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; ILEOSTOMY; INTESTINE; METABOLISM; SALIVA; STOMACH JUICE;

ADULT; AGED; BODY FLUIDS; CATECHIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; COLOSTOMY; FLAVONOIDS; GASTRIC JUICE; GASTROINTESTINAL TRANSIT; HUMANS; ILEOSTOMY; INTESTINES; MODELS, BIOLOGICAL; MONOSACCHARIDES; SALIVA;

EID: 77955674941     PISSN: 16134125     EISSN: 16134133     Source Type: Journal    
DOI: 10.1002/mnfr.201000003     Document Type: Article

References (43)

1. Sanugul, K., Akao, T., Li, Y., Kakiuchi, N. et al., Isolation of a human intestinal bacterium that transforms mangiferin to norathyriol and inducibility of the enzyme that cleaves a C-glucosyl bond. Biol. Pharm. Bull. 2005, 28, 1672-1678.
2. Colombo, R., Yariwake, J. H., Queiroz, E. F., Ndjok, K., Hostettmann, K., On-line identification of further flavone C- and O-glycosides from sugarcane (Saccharum officinarum L., Gramineae) by HPLC-UV-MS. Phytochem. Anal. 2006, 17, 337-343.
3. Hong, Y. J., Tomas-Barberan, F. A., Kader, A. A., Mitchell, A. E., The flavonoid glycosides and procyanidin composition of deglet noor dates (Phoenix dactylifera). J. Agric. Food Chem. 2006, 54, 2405-2411.
4. Feng, Y., McDonald, C. E., Vick, B. A., C-glycosylflavones form hard red spring wheat bran. Cereal Chem. 1988, 65, 452-456.
5. Rabe, C., Steenkamp, J. A., Joubert, E., Burger, J. F. W., Ferreira, D., Phenolic metabolites from rooibos tea (Aspalathus linearis). Phytochemistry 1994, 35, 1559-1565.
6. Stalmach, A., Mullen, W., Pecorari, M., Serafini, M., Crozier, A., Bioavailability of C-linked dihydrochalcone and flavanone glucosides in humans following ingestion of unfermented and fermented rooibos teas. J. Agric. Food Chem. 2009, 57, 7104-7111.
7. Zhou, Z.-H., Zhang, Y.-J., Xu, M., Yang, G.-R., Puerins A and B, two new 8-C substituted flavan-3-ols from Pu-er tea. J. Agric. Food Chem. 2005, 53, 8614-8617.
8. Morimoto, S., Nonaka, G.-I., Nishioka, T., Tannins and related compounds. XXXVIII. Isolation and characterization of flavan-3-ol glucosides and procyanidin oligomers from Cassia bark (Cinnamomum cassia BLUME). Chem. Pharm. Bull. 1986, 34, 633-642.
9. Stark, T., Hofmann, T., Application of a molecular sensory science approach to alkalized cocoa (Theobroma cacao): Structure determination and sensory activity of nonenzymatically C-glycosylated flavan-3-ols. J. Agric. Food Chem. 2006, 54, 9510-9521.
10. Kim, H. P., Son, H. K., Chang, H. W., Kang, S. S., Anti-inflammatory plant flavonoids and cellular action mechanisms. J. Pharmacol. Sci. 2004, 96, 229-245.
11. Scalbert, A., Manach, C., Morand, C., Rémésy, C., Dietary polyphenols and the prevention of disease. Crit. Rev. Food Sci. Nutr. 2005, 45, 287-306.
12. U.S. Food and Drug Administration, Federal Food, Drug, and Cosmetic Act, 2004, Chapter V, 505.
13. Scalbert, A., Williamson, G., Dietary intake and bioavailability of polyphenols. J. Nutr. 2000, 130, 2073-2085.
14. Hein, E.-M., Rose, K., van't Slot, G., Friedrich, A. W., Humpf, H.-U., Deconjugation and degradation of flavonol glycosides by pig cecal microbiota characterized by fluorescence in situ hyridization (FISH). J. Agric. Food Chem. 2008, 56, 2281-2290.
15. Stoupi, S., Williamson, G., Drynan, J. W., Barron, D., Clifford, M. N., A comparison of the in vitro biotransformation of (-)-epicatechin and procyanidin B2 by human faecal microbiota. Mol. Nutr. Food Res. 2009. DOI: 10.1002/mnfr.200900123.
16. Stalmach, A., Mullen, W., Steiling, H., Williamson, G. et al., Absorption, metabolism, and excretion of green tea flavan-3-ols in humans with an ileostomy. Mol. Nutr. Food Res. 2009. DOI: 10.1002/mnfr.200900056.
17. van't Slot, G., Humpf, H.-U., Degradation and metabolisation of catechin, epigallocatechin-3-gallate (EGCG) and related compounds by the intestinal microbiota in the pig cecum model. J. Agric. Food Chem. 2009, 57, 8041-8048.
18. Manach, C., Scalbert, A., Morand, C., Remesy, C., Jimenez, L., Polyphenols: food sources and bioavailability. Am. J. Clin. Nutr. 2004, 79, 727-747.
19. Kobayashi, S., Konishi, Y., Transepithelial transport of flavanone in intestinal Caco-2 cell monolayers, Biochem. Biophys. Res. Commun. 2008, 368, 23-29.
20. Zhang, Y., Tie, X., Bao, B., Wu, X., Zhang, Y., Metabolism of flavone C-glucosides and p-coumaric acid from antioxidant of bamboo leaves (AOB) in rats. Br. J. Nutr. 2007, 97, 484-494.
21. Kahle, K., Kraus, M., Richling, E., Polyphenol profiles of apple juices. Mol. Nutr. Food Res. 2005, 49, 797-806.
22. Kahle, K., Kraus, M., Scheppach, W., Ackermann, M. et al., Studies on apple and blueberry fruit constituents: Do the polyphenols reach the colon after ingestion? Mol. Nutr. Food Res. 2006, 50, 418-423.
23. Walle, T., Browning, A. M., Steed, L. L., Reed, S. G., Walle, U. K., Flavonoid glucosides are hydrolyzed and thus activated in the oral cavity in humans. J. Nutr. 2005, 135, 48-52.
24. Gillatt, P. N., Palmer, R. C., Smith, P. L. R., Walters, C. L., Susceptibilities of drugs to nitrosation under simulated gastric conditions. Food Chem. Toxicol. 1985, 23, 849-855.
25. Labib, S., Hummel, S., Richling, E., Humpf, H. U., Schreier, P., Use of the pig caecum model to mimic the human intestinal metabolism of hispidulin and related compounds. Mol. Nutr. Food Res. 2006, 50, 78-86.
26. Courbat, T., Weith, A., Albert, A., 167. Contribution à l' étude du comportement de la catéchine en milieu alcline. Helv. Chim. Acta, 1977, 60, 1665-1667.
27. Kiatgrajai, P., Wellons, J. D., Gollob, L., White, J. D., Kinetics of epimerization of (+)-catechin and its rearrangement to catechinic acid. J. Org. Chem. 1982, 47, 2910-2912.
28. Stark, T., Keller, D., Wenker, K., Hillmann, H., Hofmann, T., Nonenzymatic C-glycosylation of flavan-3-ols by oligo- and polysaccharides. J. Agric. Food Chem. 2007, 55, 9685-9697.
29. Mehta, P., Whalley, W. B., The Stereochemistry of some catechin derivatives. J. Chem. Soc. 1963, 5327-5332.
30. Korver, O., Wilkins, C. K., Circular dichroism spectra of flavanols. Tetrahedron 1971, 27, 5459-5465.
31. Kiatgrajai, P., Wellons, J. D., Gollob, L., White, J. D., Kinetics of epimerization of (+)-catechin and its rearrangement to catechinic acid. J. Org. Chem. 1982, 47, 2910-2910.
32. Neilson, A. P., Hopf, A. S., Cooper, B. R., Pereira, M. A. et al., Catechin degradation with concurrent formation of homo- and heterocatechin dimers during in vitro digestion. J. Agric. Food Chem. 2007, 55, 8941-8949.
33. Knaup, B., Kahle, K., Erk, T., Valotis, A. et al., Human intestinal hydrolysis of phenol glycosides-a study with quercetin and p-nitrophenol glycosides using ileostomy fluid. Mol. Nutr. Food Res. 2007, 51, 1423-1429.
34. Berg, R. D., The indigenous gastrointestinal microflora. Trends Mircrobiol. 1996, 4, 430-435.
35. Selma, M. V., Espin, J. C., Tomas-Barberan, F. A., Interaction between phenolics and gut microbiota: role in human health. J. Agric. Food Chem. 2009, 57, 6485-6501.
36. Jin, J. S., Nishihata, T., Kakiuchi, N., Hattori, M., Biotransformation of C-glucosyl-isoflavone puerarin to estrogenic (3S)-equol in co-culture of two human intestinal bacteria. Biol. Pharm. Bull. 2008, 31, 1621-1625.
37. Kreuz, S., Joubert, E., Waldmann, K.-H., Ternes, W., Aspalathin, a flavonoid in Aspalathus linearis (rooibos), is absorbed by pig intestine as C-glycoside. Nutr. Res. 2008, 28, 690-701.
38. Courts, F. L., Williamson, G., The C-glycosyl flavonoid, aspalathin, is absorbed, methylated and glucuronidated intact in humans. Mol. Nutr. Food Res. 2009, 53, 1104-1111.
39. Liang, M. L., Xu, W., Zhang, W., Zhang, C. et al., Quantitative LC/MS/MS method and in vivo pharmcokinetic studies of vitexin rhamnoside, a bioactive constituent on cardiovascular system from hawthorn. Biomed. Chromatogr. 2007, 21, 422-429.
40. Kawano, A., Nakamura, H., Hata, S., Minakawa, M. et al., Hypoglycemic effect of aspalathin, a rooibos tea component from Aspalathus linearis, in type 2 diabetic model db/db mice. Phytomedicine 2009, 16, 437-443.
41. Cheel, J., Theoduloz, C., Rodríguez, J., Schmeda-Hirschmann, G., Free radical scavengers and antioxidants from lemongrass (Cymbopogon citratus (DC.) Stapf.). J. Agric. Food Chem. 2005, 53, 2511-2517.
42. Hsu, F.-L., Liu, I.-M., Kuo, D.-H., Antihyperglycemic effect of puerarin in streptozotocin-induced diabetic rats. J. Nat. Prod. 2003, 66, 788-792.
43. Rauter, A. P., Lopes, R. G., Marins, A., C-Glycosylflavonoids: Identification, bioactivity and synthesis. Nat. Prod. Commun. 2007, 2, 1175-1196.