Intestinal metabolism of two A-type procyanidins using the pig cecum model: Detailed structure elucidation of unknown catabolites with Fourier transform mass spectrometry (FTMS)

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 3, 2012, Pages 749-757

  Engemann, Anna ^a   Hübner, Florian ^a   Rzeppa, Sebastian ^a   Humpf, Hans Ulrich ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

bioavailability; cinnamtannin B1; FTMS; heterocyclic ring fission (HRF); intestinal metabolism; microbial catabolites; pig cecum; Procyanidin A2; quinone methide pathway (QM); retro Diels Alder fission (RDA); structure elucidation

Indexed keywords

BIOAVAILABILITY; CINNAMTANNIN B1; FTMS; HETEROCYCLIC RINGS; MICROBIAL CATABOLITES; PIG CECUM; PROCYANIDINS; QUINONE METHIDE; RETRO-DIELS-ALDER FISSION (RDA); STRUCTURE ELUCIDATION;

BIOCHEMISTRY; DEGRADATION; DIMERS; ETHERS; FRUITS; MAMMALS; MASS SPECTROMETRY; METABOLITES; PHENOLS; PHYSIOLOGY;

METABOLISM;

PROANTHOCYANIDIN;

ANIMAL; ARTICLE; BIOLOGICAL MODEL; CECUM; CHEMICAL STRUCTURE; CHEMISTRY; IN VITRO STUDY; INTESTINE; MASS SPECTROMETRY; METABOLISM; SWINE;

ANIMALS; CECUM; INTESTINES; MASS SPECTROMETRY; MODELS, BIOLOGICAL; MOLECULAR STRUCTURE; PROANTHOCYANIDINS; SWINE;

ALNUS; SUIDAE; THEOBROMA CACAO;

EID: 84856251116     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf203927g     Document Type: Article

References (28)

1. Williamson, G.; Manach, C. Bioavailability and bioefficacy of polyphenols in humans. II. Review of 93 intervention studies Am. J. Clin. Nutr. 2005, 81 (1 Suppl.) 243S-255S
2. da Silva Porto, P. A.; Laranjinha, J. A.; de Freitas, V. A. Antioxidant protection of low density lipoprotein by procyanidins: structure/activity relationships Biochem. Pharmacol. 2003, 66 (6) 947-954 (Pubitemid 37083591)
3. Miura, T.; Chiba, M.; Kasai, K.; Nozaka, H.; Nakamura, T.; Shoji, T.; Kanda, T.; Ohtake, Y.; Sato, T. Apple procyanidins induce tumor cell apoptosis through mitochondrial pathway activation of caspase-3 Carcinogenesis 2008, 29 (3) 585-593 (Pubitemid 351404876)
4. Lopez, J. J.; Jardin, I.; Salido, G. M.; Rosado, J. A. Cinnamtannin B-1 as an antioxidant and platelet aggregation inhibitor Life Sci 2008, 82 (19-20) 977-982
5. Rasmussen, S. E.; Frederiksen, H.; Krogholm, K. S.; Poulsen, L. Dietary proanthocyanidins: occurrence, dietary intake, bioavailability, and protection against cardiovascular disease Mol. Nutr. Food Res. 2005, 49, 159-174 (Pubitemid 40379813)
6. Rzeppa, S.; von Bargen, C.; Bittner, K.; Humpf, H. U. Analysis of flavan-3-ols and procyanidins in food samples by reversed phase high-performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry (RP-HPLC-ESI-MS/MS) J. Agric. Food Chem. 2011, 59 (19) 10594-10603
7. Serra, A.; Macia, A.; Romero, M. P.; Valls, J.; Blade, C.; Arola, L.; Motilva, M. J. Bioavailability of procyanidin dimers and trimers and matrix food effects in in vitro and in vivo models Br. J. Nutr. 2009, 103 (7) 944-952
8. Rios, L. Y.; Bennett, R. N.; Lazarus, S. A.; Remesy, C.; Scalbert, A.; Williamson, G. Cocoa procyanidins are stable during gastric transit in humans Am. J. Clin. Nutr. 2002, 76 (5) 1106-1110 (Pubitemid 35244685)
9. Kahle, K.; Kempf, M.; Schreier, P.; Scheppach, W.; Schrenk, D.; Kautenburger, T.; Hecker, D.; Huemmer, W.; Ackermann, M.; Richling, E. Intestinal transit and systematic metabolism of apple polyphenols Eur. J. Nutr. 2011, 50, 507-522
10. Appeldoorn, M. M.; Vincken, J. P.; Gruppen, H.; Hollman, P. C. Procyanidin dimers A1, A2, and B2 are absorbed without conjugation or methylation from the small intestine of rats J. Nutr. 2009, 139 (8) 1469-1473
11. Manach, C.; Scalbert, A.; Morand, C.; Remesy, C.; Jimenez, L. Polyphenols: food sources and bioavailability Am. J. Clin. Nutr. 2004, 79 (5) 727-747 (Pubitemid 41103873)
12. Seefelder, W. Fumonisine und deren Reaktionsprodukte: Vorkommen, Bedeutung, biologische Aktivität und Metabolsimus; Würzburg, Bayrische Julius-Maximilian-Universität, Institut für Lebensmittelchemie: Würzburg, Germany, 2002.
13. 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 hybridization (FISH) J. Agric. Food Chem. 2008, 56 (6) 2281-2290 (Pubitemid 351497897)
14. Keppler, K.; Humpf, H.-U. Metabolism of anthocyanins and their phenolic degradation products by the intestinal microflora Bioorg. Med. Chem. 2005, 13 (17) 5195-5205 (Pubitemid 41039980)
15. Wang, L.-Q.; Meselhy, M. R.; Li, Y.; Nakamura, N.; Min, B.-S.; Qin, G.-W.; Hattori, M. The heterocyclic ring fission and dehydroxylation of catechins and related compounds by Eubacterium sp. strain SDG-2, a human intestinal bacterium Chem. Pharm. Bull. 2001, 49 (12) 1640-1643 (Pubitemid 33126597)
16. Keppler, K.; Hein, E. M.; Humpf, H.-U. Metabolism of quercetin and rutin by the pig caecal microflora prepared by freeze-preservation Mol. Nutr. Food Res. 2006, 50 (8) 686-695 (Pubitemid 44342465)
17. van't Slot, G.; Humpf, H. U. Degradation and metabolism of catechin, epigallocatechin-3-gallate (EGCG), and related compounds by the intestinal microbiota in the pig cecum model J. Agric. Food Chem. 2009, 57 (17) 8041-8048
18. van't Slot, G.; Mattern, W.; Rzeppa, S.; Grewe, D.; Humpf, H. U. Complex flavonoids in cocoa: synthesis and degradation by intestinal microbiota J. Agric. Food Chem. 2010, 58 (15) 8879-8886
19. Stoupi, S.; Williamson, G.; Drynan, J. W.; Barron, D.; Clifford, M. N. Procyanidin B2 catabolism by human fecal microflora: partial characterization of 'dimeric' intermediates Arch. Biochem. Biophys. 2010, 501 (1) 73-78
20. Liu, L.; Xie, B.; Cao, S.; Yang, E.; Xu, X.; Guo, S. A-type procyanidins from Litchi chinensis pericarp with antioxidant activity Food Chem. 2007, 105, 1446-1451 (Pubitemid 47095164)
21. Virtbauer, J.; Krenn, L.; Kahlig, H.; Hufner, A.; Donath, O.; Marian, B. Chemical and pharmacological investigations of Metaxya rostrata Z. Naturforsch. C 2008, 63 (7-8) 469-475
22. Jayaprakasha, G. K.; Ohnishi-Kameyama, M.; Ono, H.; Yoshida, M.; Jaganmohan Rao, L. Phenolic constituents in the fruits of Cinnamomum zeylanicum and their antioxidant activity J. Agric. Food Chem. 2006, 54 (5) 1672-1679
23. Kamiya, K.; Watanabe, C.; Endang, H.; Umar, M.; Satake, T. Studies on the constituents of bark of Parameria laevigata Moldenke Chem. Pharm. Bull. (Tokyo) 2001, 49 (5) 551-557 (Pubitemid 32505879)
24. Appeldoorn, M. M.; Vincken, J. P.; Aura, A. M.; Hollman, P. C.; Gruppen, H. Procyanidin dimers are metabolized by human microbiota with 2-(3,4-dihydroxyphenyl)acetic acid and 5-(3,4-dihydroxyphenyl)-γ- valerolactone as the major metabolites J. Agric. Food Chem. 2009, 57 (3) 1084-1092
25. Kondo, K.; Kurihara, M.; Fukuhara, K.; Tanaka, T.; Suzuki, T.; Miyata, N.; Toyoda, M. Conversion of procyanidin B-type (catechin dimer) to A-type: evidence for abstraction of C-2 hydrogen in catechin during radical oxidation Tetrahedron Lett. 2000, 41, 485-488 (Pubitemid 30059254)
26. Osman, A. M.; Wong, K. K. Y. Laccase (EC 1.10.3.2) catalyses the conversion of procyanidin B-2 (epicatechin dimer) to type A-2 Tetrahedron Lett. 2007, 48, 1163-1167 (Pubitemid 46097049)
27. Friedrich, W.; Eberhardt, A.; Galensa, R. Investigation of proanthocyanidins by HPLC with electrospray ionization mass spectrometry Eur. Food Res. Technol. 1999, 211, 56-64
28. Karchesy, J. J.; Foo, L. Y.; Barofsky, E.; Arbogast, B.; Barofsky, D. F. Negative-ion fast-atom-bombardment mass spectrometry of procyanidin oligomers J. Wood Chem. Technol. 1989, 9 (3) 313-331 (Pubitemid 20635597)