Comprehensive study of condensed tannins by ESI mass spectrometry: Average degree of polymerisation and polymer distribution determination from mass spectra

Analytical and Bioanalytical Chemistry

Volumn 400, Issue 2, 2011, Pages 613-623

  Mouls, Laetitia ^a,b,c   Mazauric, Jean Paul ^a,b,c   Sommerer, Nicolas ^a,b,c   Fulcrand, Hélène ^a,b,c   Mazerolles, Gérard ^a,b,c  

^a SPO   (France)

^b MONTPELLIER SUPAGRO   (France)

^c UNIV MONTPELLIER   (France)

Author keywords

Chemometrics; Degree of polymerisation; Electrospray ionisation mass spectrometry (ESI MS); Polymer distribution; Polyphenols; Tannins

Indexed keywords

CHEMOMETRICS; DEGREE OF POLYMERISATION; ELECTROSPRAYS; POLYMER DISTRIBUTION; POLYPHENOLS; TANNINS;

IONIZATION; MASS SPECTROMETERS; MASS SPECTROMETRY; MOLECULAR MASS; PHENOLS; POLYMERIZATION; POLYMERS;

ELECTROSPRAY IONIZATION;

PLANT EXTRACT; PROANTHOCYANIDIN;

ARTICLE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; EVALUATION; METHODOLOGY; POLYMERIZATION; VEGETABLE;

PLANT EXTRACTS; POLYMERIZATION; PROANTHOCYANIDINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; VEGETABLES;

EID: 79954628290     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-011-4751-7     Document Type: Article

References (33)

1. Fulcrand H, Guyot S, Le Roux E, Remy S, Souquet J-M, Doco T, Cheynier V (1999) In: Gross (ed) Plant polyphenols 2: chemistry, biology, pharmacology, ecology. Springer, Berlin, pp 223-244
2. D Zanchi PV Konarev C Tribet A Baron DI Svergun S Guyot 2009 Rigidity, conformation, and solvation of native and oxidized tannin macromolecules in water-ethanol solution J Chem Phys 130 245103 10.1063/1.3156020
3. E Haslam TH Lilley 1988 Natural astringency in foodstuffs - a molecular interpretation Crit Rev Food Sci Nutr 27 1 40 10.1080/10408398809527476 1:CAS:528:DyaL1MXntlyqtQ%3D%3D
4. G Cao RM Russell N Lischner RL Prior 1998 Serum antioxidant capacity is increased by consumption of strawberries, spinach, red wine or vitamin C in elderly women J Nutr 128 2383 2390 1:CAS:528:DyaK1cXotVOktLw%3D (Pubitemid 29012987)
5. JF Young SE Nielsen J Haraldsdottir B Daneshvar ST Lauridsen P Knuthsen A Crozie B Sandstrom LO Dragsted 1999 Effect of fruit juice intake on urinary quercetin excretion and biomarkers of antioxidative status Am J Clin Nutr 69 87 94 1:CAS:528:DyaK1MXjvFSmug%3D%3D (Pubitemid 29031256)
6. D Rein S Lotito RR Holt CL Keen HH Schmitz CG Fraga 2000 Epicatechin in human plasma: In vivo determination and effect of chocolate consumption on plasma oxidation status J Nutr 130 2109S 2114S 1:CAS:528:DC%2BD3cXltl2gsLk%3D (Pubitemid 30619391)
7. T Koga M Meydani 2001 Effect of plasma metabolites of (+)-catechin and quercetin on monocyte adhesion to human aortic endothelial cells Am J Clin Nutr 73 941 948 1:CAS:528:DC%2BD3MXjsValtrg%3D (Pubitemid 32405992)
8. JA Kennedy AW Taylor 2003 Analysis of proanthocyanidins by high-performance gel permeation chromatography J Chromatogr A 995 99 107 10.1016/S0021-9673(03)00420-5 1:CAS:528:DC%2BD3sXjs1Wrs7g%3D (Pubitemid 36579046)
9. J Rigaud J Perez-Ilzarbe JM Ricardo Da Silva V Cheynier 1991 Micro method for the identification of proanthocyanidin using thiolysis monitored by high-performance liquid-chromatography J Chromatogr 540 401 405 10.1016/S0021-9673(01)88830-0 1:CAS:528:DyaK3MXit1Crsbs%3D
10. MJ Telepchack 1973 New uses for molecular-size exclusion chromatography J Chromatogr 83 125 134 10.1016/S0021-9673(00)97033-X
11. N Kasai G Nakatsubo 2006 Size-exclusion chromatography of tea tannins and intercepting potentials of peptides for the inhibition of trypsin-caseinolytic activity by tea tannins J Agric Food Chem 54 5149 5156 10.1021/jf060435r 1:CAS:528:DC%2BD28XlsFOqsb0%3D (Pubitemid 44140915)
12. A Ikegami A Sato M Yamado A Kitajuma K Yonemori 2005 Molecular size profiles of tannins in persimmon fruits of Japanese and Chinese pollination-constant non-astringent (PCNA)-type cultivars and their offspring revealed by size-exclusion chromatography J Japan Soc Hort Sci 74 437 443 10.2503/jjshs.74.437 1:CAS:528:DC%2BD2MXht1GktrnO (Pubitemid 41769687)
13. RC Kaufman M Tilley SR Bean MR Tuinstra 2009 Improved characterization of sorghum tannins using size-exclusion chromatography Cereal Chem 86 369 371 10.1094/CCHEM-86-4-0369 1:CAS:528:DC%2BD1MXps1els7w%3D
14. C Viriot A Scalbert CLMH Dupenhoat C Rolando M Moutounet 1994 Methylation, acetylation and gel-permeation of hydrolysable tannins J Chromatogr A 662 77 85 10.1016/0021-9673(94)85297-9 1:CAS:528:DyaK2cXitFWqt7c%3D (Pubitemid 24065375)
15. JB Fenn M Mann CK Meng SF Wong CM Whitehouse 1989 Electrospray ionization for masse-spectrometry of large biomolecules Sci 246 64 71 10.1126/science. 2675315 1:CAS:528:DyaL1MXmtFWhs7w%3D (Pubitemid 19252085)
16. M Karas F Hillenkamp 1988 Laser desorption ionization of proteins with molecular masses exceeding 10000 daltons Anal Chem 60 2299 2301 10.1021/ac00171a028 1:CAS:528:DyaL1cXlsVGmu7g%3D
17. JF Hammerstone SA Lazarus AE Mitchell R Rucker HH Schmitz 1999 Identification of procyanidins in cocoa (Theobroma cacao) and chocolate using high-performance liquid chromatography mass spectrometry J Agric Food Chem 47 490 496 10.1021/jf980760h 1:CAS:528:DyaK1MXivFGjsQ%3D%3D (Pubitemid 29185214)
18. Z Peng Y Hayasaka PG Iland M Sefton P Hoj EJ Waters 2001 Quantitative analysis of polymeric procyanidins (tannins) from grape (Vitis vinifera) seeds by reverse phase high performance liquid chromatography J Agric Food Chem 49 26 31 10.1021/jf000670o 1:CAS:528:DC%2BD3cXoslGrsbk%3D (Pubitemid 32104483)
19. W Hümmer P Schreier 2008 Analysis of proanthocyanidins Mol Nutr Food Res 52 1381 1398 10.1002/mnfr.200700463
20. AW Taylor E Barofsky JA Kennedy ML Deinzer 2003 Hop (Humulus lupulus L) proanthocyanidins characterized by mass spectrometry, acid catalysis, and gel permeation chromatography J Agric Food Chem 51 4101 4110 10.1021/jf0340409 1:CAS:528:DC%2BD3sXkvFOmt78%3D
21. Y Ishida K Kuniyuki K Goto H Ohtani 2005 Solid sampling technique for direct detection of condensed tannins in bark by matrix-assisted laser desorption/ionization mass spectrometry Rapid Commun Mass Spectrom 19 706 710 10.1002/rcm.1845 1:CAS:528:DC%2BD2MXitFyhsr0%3D (Pubitemid 40332768)
22. X Ping L Yiming L Peng X Cheng 2006 Effects of adduct ions on matrix-assisted laser desorption/ionization time of flight mass spectrometry of condensed tannins: a prerequisite knowledge Chinese J Anal Chem 34 1019 1022 10.1016/S1872-2040(06)60047-9 (Pubitemid 44693510)
23. C Mané N Sommerer T Yalcin V Cheynier RB Cole H Fulcrand 2007 Assessment of the molecular weight distribution of tannin fractions through MALDI-TOF MS analysis of protein-tannin complexes Anal Chem 79 2239 2248 10.1021/ac061685+ (Pubitemid 46449002)
24. N-E Es-Safi S Guyot PH Ducrot 2006 NMR, ESI/MS, and MALDI-TOF/MS analysis of pear juice polymeric proanthocyanidins with potent free radical scavenging activity J Agric Food Chem 54 6969 6977 10.1021/jf061090f 1:CAS:528: DC%2BD28XosVylsLw%3D (Pubitemid 44554909)
25. S Guyot N Marnet P Sanoner J-F Drilleau 2003 Variability of the polyphenolic composition of cider apple (Malus domestica) fruits and juices J Agric Food Chem 51 6240 6247 10.1021/jf0301798 1:CAS:528:DC%2BD3sXnt1Knu7k%3D
26. G Derdelinckx J Jerumanis 1984 Separation of malt and hop proanthocyanidins on Fractogel TSK HW-40 (S) J Chromatogr 285 231 244 10.1016/S0021-9673(01)87758-X 1:CAS:528:DyaL2cXhtlOhtb8%3D
27. J Ricardo Da Silva J Rigaud V Cheynier A Cheminat M Moutounet 1991 Procyanidin dimers and trimers from grape seeds Phytochem 30 1259 1264 10.1016/S0031-9422(00)95213-0 1:CAS:528:DyaK3MXks1ynsL4%3D
28. S Guyot N Marnet J-F Drilleau 2001 Thiolysis-HPLC characterization of apple procyanidins covering a large range of polymerization states J Agric Food Chem 49 14 20 10.1021/jf000814z 1:CAS:528:DC%2BD3cXosFWmtLs%3D (Pubitemid 32104481)
29. A Savitzky MJE Golay 1964 Smoothing and differentiation of data by simplified least squares procedures Anal Chem 36 1627 1639 10.1021/ac60214a047 1:CAS:528:DyaF2cXksVCjur8%3D
30. P Sanoner S Guyot N Marnet D Molle J-F Drilleau 1999 Polyphenol profiles of French cider apple varieties (Malus domestica sp) J Agric Food Chem 47 4847 4853 10.1021/jf990563y 1:CAS:528:DyaK1MXmvVOiur0%3D (Pubitemid 30016907)
31. Guyot S, Doco T, Souquet J-M, Moutounet M, Drilleau J-F Phytochem (1997) Characterization of highly polymerized procyanidins in cider apple (Malus sylvestris var kermerrien) skin and pulp. 44:351-357
32. L Gu MA Kelm JF Hammerstone G Beecher J Holden D Haytowitz RL Prior 2003 Screening of foods containing proanthocyanidins and their structural characterization using LC-MS/MS and thiolytic degradation J Agric Food Chem 51 7513 7521 10.1021/jf034815d 1:CAS:528:DC%2BD3sXosl2ms7Y%3D
33. RL Prior L Gu 2005 Occurrence and biological significance of proanthocyanidins in the American diet Phytochem 66 2264 2280 10.1016/j.phytochem.2005.03.025 1:CAS:528:DC%2BD2MXpvV2ks7c%3D (Pubitemid 41254100)