Characterization of oxidized tannins: Comparison of depolymerization methods, asymmetric flow field-flow fractionation and small-angle X-ray scattering

Analytical and Bioanalytical Chemistry

Volumn 401, Issue 5, 2011, Pages 1563-1573

  Vernhet, Aude ^a   Dubascoux, Stéphane ^b   Cabane, Bernard ^c   Fulcrand, Hélène ^a   Dubreucq, Eric ^b   Poncet Legrand, Céline ^a  

^a SPO   (France)

^b UMR IATE   (France)

^c ESPCI   (France)

Author keywords

AF4 MALLS; Depolymerization; Molecular weight determination; Oxidation; Small angle X ray scattering; Tannins

Indexed keywords

AF4-MALLS; ASYMMETRIC FLOWS; AVERAGE DEGREE; CONDENSED TANNINS; HIGH CONCENTRATION; LOW CONCENTRATIONS; MOLECULAR WEIGHT DETERMINATION; NATIVE STRUCTURES; PLANT POLYPHENOLS; SMALL ANGLE X-RAY SCATTERING; STRUCTURAL CHANGE; TANNINS; WEIGHT-AVERAGE MOLECULAR WEIGHT;

ETHANOL; FLOW FIELDS; FRACTIONATION; LIQUID CHROMATOGRAPHY; MACROMOLECULES; MOLECULAR WEIGHT; ORGANIC SOLVENTS; OXIDATION; PHENOLS; SCATTERING; X RAYS;

X RAY SCATTERING;

TANNIN DERIVATIVE;

ARTICLE; CHEMISTRY; COMPARATIVE STUDY; FIELD FLOW FRACTIONATION; ISOLATION AND PURIFICATION; METHODOLOGY; OXIDATION REDUCTION REACTION; PLANT SEED; POLYMERIZATION; SMALL ANGLE SCATTERING; VITIS; X RAY DIFFRACTION;

FRACTIONATION, FIELD FLOW; OXIDATION-REDUCTION; POLYMERIZATION; SCATTERING, SMALL ANGLE; SEEDS; TANNINS; VITIS; X-RAY DIFFRACTION;

EID: 80052571835     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-011-5076-2     Document Type: Article

References (28)

1. V Cheynier M Duenas-Paton E Salas C Maury JM Souquet P Sarni-Manchado H Fulcrand 2006 Structure and properties of wine pigments and tannins Am J Enol Vitic 57 298 305 1:CAS:528:DC%2BD28XhtFKmur3J (Pubitemid 44496960)
2. H Fulcrand M Duenas E Salas V Cheynier 2006 Phenolic reactions during winemaking and aging Am J Enol Vitic 57 289 297 1:CAS:528:DC%2BD28XhtFKmur3P (Pubitemid 44496959)
3. VL Singleton JA Rossi Jr 1965 Colorimetry of total phenolics with phosphomolybdic-phosphotungstic acid reagents Am J Enol Vitic 16 144 158 1:CAS:528:DyaF28Xit1yhuw%3D%3D
4. T Swain WE Hillis 1959 The phenolic constituents of Prunus domestica. I.-The quantitative analysis of phenolic constituents J Sci Food Agric 10 63 68 10.1002/jsfa.2740100110 1:CAS:528:DyaG1MXltFylug%3D%3D
5. I McMurrough J McDowell 1978 Chromatographic separation and automated analysis of flavanols Anal Biochem 91 92 100 10.1016/0003-2697(78)90819-9 1:CAS:528:DyaE1MXotlWhsQ%3D%3D (Pubitemid 9066801)
6. B Sun JM RicardodaSilva I Spranger 1998 Critical factors of vanillin assay for catechins and proanthocyanidins J Agr Food Chem 46 4267 4274 10.1021/jf980366j 1:CAS:528:DyaK1cXmtFakur0%3D (Pubitemid 128488527)
7. KA Cooper E Campos-Gimenez D JimenezAlvarez K Nagy JL Donovan G Williamson 2007 Rapid reversed phase ultra-performance liquid chromatography analysis of the major cocoa polyphenols and inter-relationships of their concentrations in chocolate J Agr Food Chem 55 2841 2847 10.1021/jf063277c 1:CAS:528:DC%2BD2sXivVaqsbw%3D (Pubitemid 46668287)
8. MA Kelm JC Johnson RJ Robbins JF Hammerstone HH Schmitz 2006 High-performance liquid chromatography separation and purification of cacao (Theobroma cacao L.) procyanidins according to degree of polymerization using a diol stationary phase J Agr Food Chem 54 1571 1576 10.1021/jf0525941 1:CAS:528:DC%2BD28XhtFKntL0%3D
9. 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 Agr Food Chem 51 4101 4110 10.1021/jf0340409 1:CAS:528:DC%2BD3sXkvFOmt78%3D
10. A Yanagida T Kanda T Shoji M Ohnishi-Kameyama T Nagata 1999 Fractionation of apple procyanidins by size-exclusion chromatography J Chromatogr A 855 181 190 10.1016/S0021-9673(99)00684-6 1:CAS:528:DyaK1MXmsFWrs7Y%3D (Pubitemid 29413097)
11. 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)
12. S Matthews I Mila A Scalbert B Pollet C Lapierre C duPenhoat C Rolando DMX Donnelly 1997 Method for estimation of proanthocyanidins based on their acid depolymerization in the presence of nucleophiles J Agr Food Chem 45 1195 1201 10.1021/jf9607573 1:CAS:528:DyaK2sXitVGhsrk%3D (Pubitemid 127476891)
13. J Rigaud J Perezilzarbe 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
14. JM Souquet V Cheynier F Brossaud M Moutounet 1996 Polymeric proanthocyanidins from grape skins Phytochemistry 43 509 512 10.1016/0031-9422(96)00301-9 1:CAS:528:DyaK28Xls1yrtr8%3D (Pubitemid 27065579)
15. S Guyot J Vercauteren V Cheynier 1996 Colourless and yellow dimers resulting from (+)-catechin oxidative coupling catalysed by grape polyphenoloxidase Phytochemistry 42 1279 1288 10.1016/0031-9422(96)00127-6 1:CAS:528:DyaK28Xkt1SksLY%3D (Pubitemid 27063268)
16. R Kusano T Tanaka Y Matsuo I Kouno 2007 Structures of epicatechin gallate trimer and tetramer produced by enzymatic oxidation Chem & Pharml Bull 55 1768 1772 10.1248/cpb.55.1768 1:CAS:528:DC%2BD1cXht1yls70%3D (Pubitemid 350232555)
17. T Tanaka Y Matsuo I Kouno 2005 A novel black tea pigment and two new oxidation products of epigallocatechin-3-O-gallate J Agr Food Chem 53 7571 7578 10.1021/jf0512656 1:CAS:528:DC%2BD2MXptVCntr8%3D (Pubitemid 41413557)
18. Schimpf ME, Caldwell K, Giddings JC (2000) Field flow fractionation handbook. Wiley-Interscience, New York
19. S Purawatt A Siripinyanond J Shiowatana 2007 Flow field-flow fractionation-inductively coupled optical emission spectrometric investigation of the size-based distribution of iron complexed to phytic and tannic acids in a food suspension: implications for iron availability Anal Bioanal Chem 389 733 742 10.1007/s00216-007-1308-x 1:CAS:528:DC%2BD2sXhtVOmtLbK (Pubitemid 47462442)
20. JS Pedersen 1997 Analysis of small-angle scattering data from colloids and polymer solutions: modeling and least-squares fitting Adv Colloid Interface Sci 70 171 210 10.1016/S0001-8686(97)00312-6 1:CAS:528:DyaK2sXmvVSkt7Y%3D (Pubitemid 127403556)
21. C Poncet-Legrand B Cabane AB Bautista-Ortin S Carrillo H Fulcrand J Perez A Vernhet 2010 Tannin oxidation: intra-versus intermolecular reactions Biomacromolecules 11 2376 2386 10.1021/bm100515e 1:CAS:528:DC%2BC3cXpt12iurc%3D
22. C Poncet-Legrand D Cartalade J-L Putaux V Cheynier A Vernhet 2003 Flavan-3-ol aggregation in model ethanolic solutions: incidence of polyphenol structure, concentration, ethanol content and ionic strength Langmuir 19 10563 10572 10.1021/la034927z 1:CAS:528:DC%2BD3sXosl2nurY%3D
23. W Burchard 1974 Statistics of star-shaped molecules. I. Stars with polydisperse side chains Macromolecules 7 835 841 10.1021/ma60042a027 1:CAS:528:DyaE2MXkslWr
24. P Debye 1947 Molecular weight determination by light scattering J Phys Colloid Chem 51 18 32 10.1021/j150451a002 1:CAS:528:DyaH2sXhtFalsw%3D%3D
25. ME Fisher RJ Burford 1967 Theory of critical-point scattering and correlations. I. The Ising model Phys Rev 156 583 10.1103/PhysRev.156.583 1:CAS:528:DyaF2sXktFCqu74%3D
26. G Beaucage 1996 Small-angle scattering from polymeric mass fractals of arbitrary mass-fractal dimension J Appl Crystallogr 29 134 146 10.1107/S0021889895011605 1:CAS:528:DyaK28XjtVSltbc%3D (Pubitemid 126466797)
27. M Takeshita Y Ishida E Akamatsu Y Ohmori M Sudoh H Uto H Tsubouchi H Kataoka 2009 Proanthocyanidin from blueberry leaves suppresses expression of subgenomic hepatitis C virus RNA J Biol Chem 284 21165 21176 10.1074/jbc.M109.004945 1:CAS:528:DC%2BD1MXpt1Wjur4%3D
28. de Gennes PG (1979) Scaling concepts in polymer physics. Cornell University Press, Ithaca, New York