In situ analysis and structural elucidation of sainfoin (Onobrychis viciifolia) tannins for high-throughput germplasm screening

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 2, 2011, Pages 495-503

  Gea, An ^a   Stringano, Elisabetta ^a   Brown, Ron H ^a   Mueller Harvey, Irene ^a  

^a UNIVERSITY OF READING   (United Kingdom)

Author keywords

germplasm screening; green plants; in situ analysis; Onobrychis viciifolia; sainfoin; Tannins; thiolysis

Indexed keywords

GERMPLASM SCREENING; GREEN PLANTS; IN-SITU ANALYSIS; ONOBRYCHIS VICIIFOLIA; SAINFOIN; TANNINS; THIOLYSIS;

ACETONE; CHLOROPHYLL; DEGRADATION; PHENOLS; SOLVENT EXTRACTION;

STRUCTURAL ANALYSIS;

PLANT EXTRACT; TANNIN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; EVALUATION; FLOWER; HIGH THROUGHPUT SCREENING; LEGUME; METHODOLOGY;

FABACEAE; GERM CELLS, PLANT; HIGH-THROUGHPUT SCREENING ASSAYS; MOLECULAR STRUCTURE; PLANT EXTRACTS; TANNINS;

ONOBRYCHIS; ONOBRYCHIS VICIIFOLIA; VIRIDIPLANTAE;

EID: 78751496069     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf103609p     Document Type: Article

References (49)

1. Mueller-Harvey, I. Unravelling the conundrum of tannins in animal nutrition and health J. Sci. Food Agric. 2006, 86, 2010-2037
2. Marais, J. P. J.; Mueller-Harvey, I.; Brandt, E. V.; Ferreira, D. Polyphenols, condensed tannins, and other natural products in Onobrychis viciifolia (sainfoin) J. Agric. Food Chem. 2000, 48, 3440-3447
3. Foo, L. Y.; Lu, Y. R.; Howell, A. B.; Vorsa, N. The structure of cranberry proanthocyanidins which inhibit adherence of uropathogenic P-fimbriated Escherichia coli in vitro Phytochemistry 2000, 54 (2) 173-181
4. Hedqvist, H.; Mueller-Harvey, I.; Reed, J. D.; Krueger, C. G.; Murphy, M. Characterisation of tannins and in vitro protein digestibility of several Lotus corniculatus varieties Anim. Feed Sci. Technol. 2000, 87, 41-56
5. Reed, J. D.; Krueger, C. G.; Vestling, M. M. MALDI-TOF mass spectrometry of oligomeric food polyphenols Phytochemistry 2005, 66, 2248-2263
6. Guyot, S.; Marnet, N.; Drilleau, J. F. Thiolysis-HPLC characterization of apple procyanidins covering a large range of polymerization states J. Agric. Food Chem. 2001, 49, 14-20
7. Matthews, S.; Mila, I.; Scalbert, A.; Pollet, B.; Lapierre, C.; Dupenhoat, C. L. M. H.; Rolando, C.; Donnelly, D. M. X. Method for estimation of proanthocyanidins based on their acid depolymerization in the presence of nucleophiles J. Agric. Food Chem. 1997, 45 (4) 1195-1201
8. Matthews, S.; Mila, I.; Scalbert, A.; Donnelly, D. M. X. Extractable and non-extractable proanthocyanidins in barks Phytochemistry 1997, 45 (2) 405-410
9. Taylor, A. W.; Barofsky, E.; Kennedy, J. A.; Deinzer, M. L. Hop (Humulus lupulus L.) proanthocyanidins characterized by mass spectrometry, acid catalysis, and gel permeation chromatography J. Agric. Food Chem. 2003, 51, 4101-4110
10. Guyot, S.; Marnet, N.; Sanoner, P.; Drilleau, J. F. Direct thiolysis on crude apple materials for high-performance liquid chromatography characterization and quantification of polyphenols in cider apple tissues and juices Methods Enzymol. 2001, 335, 57-70
11. Labarbe, B.; Cheynier, V.; Brossaud, F.; Souquet, J. M.; Moutounet, M. Quantitative fractionation of grape proanthocyanidins according to their degree of polymerization J. Agric. Food Chem. 1999, 47, 2719-2723
12. Es-Safi, N.-E.; Guyot, S.; Ducrot, P.-H. NMR, ESI/MS, and MALDI-TOF/MS analysis of pear juice polymeric proanthocyanidins with potent free radical scavenging activity J. Agric. Food Chem. 2006, 54, 6969-6977
13. Le Bourvellec, C.; Guyot, S.; Renard, C. M. G. C. Non-covalent interaction between procyanidins and apple cell wall material. Part I. Effect of some environmental parameters Biochim. Biophys. Acta, Gen. Subj. 2004, 1672, 192-202
14. Peréz-Jiménez, J.; Arranz, S.; Saura-Calixto, F. Proanthocyanidin content in foods is largely underestimated in the literature data: An approach to quantification of the missing proanthocyanidins Food Res. Int. 2009, 42, 1381-1388
15. White, B. L.; Howard, R. L.; Prior, R. L. Release of bound procyanidins from cranberry pomace by alkaline hydrolysis J. Agric. Food Chem. 2010, 58, 7572-7579
16. Hellström, J. K.; Mattila, P. H. HPLC determination of extractable and unextractable proanthocyanidins in plant materials J. Agric. Food Chem. 2008, 56, 7617-7624
17. Guyot, S.; Le Bourvellec, C.; Marnet, N.; Drilleau, J. F. Procyanidins are the most abundant polyphenols in dessert apples at maturity Lebensm.-Wiss. Technol. 2002, 35, 289-291
18. Ramirez-Coronel, M. A. N.; Marnet, N.; Kolli, V. S. K.; Roussos, S.; Guyot, S.; Augur, C. Characterization and estimation of proanthocyanidins and other phenolics in coffee pulp (Coffea arabica) by thiolysis-high-performance liquid chromatography J. Agric. Food Chem. 2004, 52, 1344-1349
19. Nunes, C.; Guyot, S.; Marnet, N.; Barros, A. S.; Saraiva, J. A.; Renard, C. M. G. C.; Coimbra, M. Characterization of plum procyanidins by thiolytic depolymerization J. Agric. Food Chem. 2008, 56, 5188-5196
20. Meagher, L. P.; Lane, G.; Sivakumaran, S.; Tavendale, M. H.; Fraser, K. Characterization of condensed tannins from Lotus species by thiolytic degradation and electrospray mass spectrometry Anim. Feed Sci. Technol. 2004, 117, 151-163
21. Renard, C. M. G. C.; Dupont, N.; Guillermin, P. Concentrations and characteristics of procyanidins and other phenolics in apples during fruit growth Phytochemistry 2007, 68, 1128-1138
22. Stewart, J. L.; Mould, F.; Mueller-Harvey, I. The effect of drying treatment on the fodder quality and tannin content of two provenances of Calliandra calothyrsus Meissner J. Sci. Food Agric. 2000, 80, 1461-1468
23. Foo, L. Y.; Lu, Y.; Molan, A. L.; Woodfield, D. R.; McNabb, W. C. The phenols and prodelphinidins of white clover flowers Phytochemistry 2000, 54, 539-548
24. Koupai-Abyazani, M. R.; Muir, A. D.; Bohm, B. A.; Towers, G. H. N.; Gruber, M. Y. The proanthocyanidin polymers in some species of Onobrychis Phytochemistry 1993, 34, 113-117
25. Sivakumaran, S.; Molan, A. L.; Meagher, L. P.; Kolb, B.; Foo, L. Y.; Lane, G. A.; Attwood, G. A.; Fraser, K.; Tavendale, M. Variation in antimicrobial action of proanthocyanidins from Dorycnium rectum against rumen bacteria Phytochemistry 2004, 65, 2485-2497
26. Spencer, P.; Sivakumaran, S.; Fraser, K.; Foo, L. Y.; Lane, G. A.; Edwards, P. J. B.; Meagher, L. P. Isolation and characterisation of procyanidins from Rumex obtusifolius Phytochem. Anal. 2007, 18, 193-203
27. Meagher, L. P.; Spencer, P.; Lane, G.; Sivakumaran, S.; Fraser, K. What do green tea, grapes seeds, and docks have in common? Chem N. Z. 2005, September) 6-9
28. Steynberg, P. J.; Nel, R. J. J.; van Rensburg, H.; Bezuidenhardt, B. C. B.; Ferreira, D. Oligomeric flavanoids. Part 27. Interflavanyl bond formation in procyanidins under neutral conditions Tetrahedron 1998, 54, 8153-8158
29. Kolodziej, H. Thiolysis of birch bark procyanidins: structural dependence in formation of 2,3- cis -3,4- cis -flavan-4-benzylthioethers from procyanidins Phytochemistry 1990, 29, 1671-1674
30. Gu, L. W.; Kelm, M.; Hammerstone, J. F.; Beecher, G.; Cunningham, D.; Vannozzi, S.; Prior, R. L. Fractionation of polymeric procyanidins from lowbush blueberry and quantification of procyanidins in selected foods with an optimized normal-phase HPLC-MS fluorescent detection method J. Agric. Food Chem. 2002, 50, 4852-4860
31. Fan, J. L.; Ding, X. L.; Tao, G. J. Study of components in the thiolysis media of procyanidin B3 with different thiolysis conditions by high performance liquid chromatography/electrospray ionization-mass spectrometry Chin. J. Anal. Chem. 2006, 34, 251-254
32. Wang, H.; Helliwell, K. Epimerisation of catechins in green tea infusions Food Chem. 2000, 70, 337-344
33. Prieur, C.; Rigaud, J.; Cheynier, V.; Moutounet, M. Oligomeric and polymeric procyanidins from grape seeds Phytochemistry 1994, 36, 781-784
34. Betts, M. J.; Brown, B. R.; Shaw, M. R. Reaction of flavanoids with mercaptoacetic acid J. Chem. Soc. C 1969, 1178-1184
35. McGraw, G. W.; Steynberg, J. P.; Hemingay, R. W. Condensed tannins-a novel rearrangement of procyanidins and prodelphinidins in thiolytic cleavage Tetrahedron Lett. 1993, 34, 987-990
36. Czochanska, Z.; Foo, L. Y.; Newman, R. H.; Porter, L. J. Polymeric proanthocyanidins. Stereochemistry, structural units, and molecular weight J. Chem. Soc., Perkin Trans. 1 1980, 2278-2286
37. Hernes, P. J.; Hedges, J. I. Determination of condensed tannin monomers in environmental samples by capillary gas chromatography of acid depolymerization extracts Anal. Chem. 2000, 72, 5115-5124
38. Porter, L. J. Structure and chemical properties of the condensed tannins. In Plant Polyphenols; Hemingway, R. W.; Laks, P. E., Eds.; Plenum Press: New York, 1992; pp 245 - 258.
39. Brown, B. R.; Shaw, M. R. Reactions of flavanoids and condensed tannins with sulphur nucleophiles J. Chem. Soc., Perkin Trans. 1 1974, 2036-2049
40. Bate-Smith, E. C. Tannins of herbaceous Leguminosae Phytochemistry 1973, 12, 1809-1812
41. Dueñas, M.; Sun, B. S.; Hernandez, T.; Estrella, I.; Spranger, M. I. Proanthocyanidin composition in the seed coat of lentils (Lens culinaris L.) J. Agric. Food Chem. 2003, 51, 7999-8004
42. Kennedy, J. A.; Taylor, A. W. Analysis of proanthocyanidins by high-performance gel permeation chromatography J. Chromatogr., A 2003, 995, 99-107
43. Regos, I.; Urbanella, A.; Treutter, D. Idenficiation and quantification of phenolic compounds from the forage legume sainfoin (Onobrychis viciifolia) J. Agric. Food Chem. 2009, 57, 5843-5852
44. McAllister, T. A.; Martinez, T.; Bae, H. D.; Muir, A. D.; Yanke, L. J.; Jones, G. A. Characterization of condensed tannins purified from legume forages: Chromophore production, protein precipitation, and inhibitory effects on cellulose digestion J. Chem. Ecol. 2005, 31, 2049-2067
45. Jones, W. T.; Broadhurst, R. B.; Lyttleton, J. W. The condensed tannins of pasture legume species Phytochemistry 1976, 15, 1407-1409
46. Mangan, J. L. Nutritional effects of tannins in animal feeds Nutr. Res. Rev. 1988, 1, 209-231
47. Waghorn, G. C.; John, A.; Jones, W. R.; Shelton, I. D. Nutritive value of Lotus corniculatus L. containing low and medium concentrations of condensed tannins for sheep Proc. N. Z. Soc. Anim. Prod. 1987, 47, 25-30
48. Foo, L. Y.; Jones, W. T.; Porter, L. J.; Williams, V. M. Proanthocyanidin polymers of fodder legumes Phytochemistry 1982, 21, 933-935
49. Hayot-Carbonera, C.; Mueller-Harvey, I.; Brown, T. A.; Smith, L. Sainfoin (Onobrychis viciifolia): A beneficial forage legume. Plant Gen. Res. 2011, manuscript accepted.