UHPLC-PDA-ESI/HRMSnprofiling method to identify and quantify oligomeric proanthocyanidins in plant products

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 39, 2014, Pages 9387-9400

  Lin, Long Ze ^a   Sun, Jianghao ^a   Chen, Pei ^a   Monagas, Maria J ^b   Harnly, James M ^a  

^a BELTSVILLE HUMAN NUTRITION RESEARCH CENTER   (United States)

^b UNITED STATES PHARMACOPEIA   (United States)

Author keywords

identification; oligomeric proanthocyanidins; plant products; quantification; UHPLC PDA ESI HRMSnprofiling method

Indexed keywords

OLIGOMERIC PROANTHOCYANIDINS; PLANT PRODUCTS; PROFILING METHODS; QUANTIFICATION;

IDENTIFICATION (CONTROL SYSTEMS);

PLANT EXTRACT; PROANTHOCYANIDIN;

CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; EVALUATION STUDY; FRUIT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PLANT; PLANT SEED; PROCEDURES;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FRUIT; PLANT EXTRACTS; PLANTS; PROANTHOCYANIDINS; SEEDS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84907480635     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf501011y     Document Type: Article

References (34)

1. Hümmer, W.; Schreier, P. Analysis of proanthocyanidins Mol. Nutr. Food Res. 2008, 52, 1381-1398
2. Hellström, J. K.; Mattila, P. H. HPLC determination of extractable and unextractable proanthocyanidins in plant materials J. Agric. Food Chem. 2008, 56, 7617-7624
3. Hellström, J. K.; Törrönen, A. R.; Mattila, P. H. Proanthocyanidins in common food products of plant origin J. Agric. Food Chem. 2009, 57, 7899-7906
4. Gu, L.; Kelm, M. A.; Hammerstone, J. F.; Beecher, G.; Holden, J.; Haytowitz, D.; Gebhardt, S.; Prior, R. L. Screening of foods containing proanthocyanidins and their structural characterization using LC-MS/MS and thiolytic degradation J. Agric. Food Chem. 2003, 51, 7513-7521
5. Aron, P. M.; Kennedy, J. A. Flavan-3-ols: nature, occurrence and biological activity Mol. Nutr. Food Res. 2008, 52, 79-104
6. Prior, R. L.; Gu, L. Occurrence and biological significance of proanthocyanidins in the American diet Phytochemistry 2005, 66, 2264-2280
7. Monagas, M.; Quintanilla-López, J. E.; Gómez-Cordovés, C.; Bartolomé, B.; Lebrón-Aguilar, R. MALDI-TOF MS analysis of plant proanthocyanidins J. Pharm. Biomed. Anal. 2010, 51, 358-372
8. 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
9. Zhou, H.-C.; Lin, Y.-M.; Li, Y.-Y.; Li, M.; Wei, S.-D.; Chai, W.-M.; Tam, F.-Y. Antioxidant properties of polymeric proanthocyanidins from fruit stones and pericarps of Litchi chinensis Sonn Food Res. Int. 2011, 44, 613-620
10. Chai, W.-M.; Shi, Y.; Feng, H.-L.; Qiu, L.; Zhou, H.-C.; Deng, Z.-W.; Yan, C.-L.; Chen, Q.-S. NMR, HPLC-ESI-MS, and MALDI-TOF MS analysis of condensed tannins from Delonix regia (Bojer ex Hook.) Raf. and their bioactivities J. Agric. Food Chem. 2012, 60, 5013-5022
11. Fu, C.; Loo, A. E.; Chia, F. P.; Huang, D. Oligomeric proanthocyanidins from mangosteen pericarps J. Agric. Food Chem. 2007, 55, 7689-7694
12. Zhou, H.-C.; Lin, Y.-M.; Wei, S.-D.; Tam, F.-Y. Structural diversity and antioxidant activity of condensed tannins fractionated from mangosteen pericarp Food Chem. 2011, 129, 1710-1720
13. Mouls, L.; Mazauric, J.-P.; Sommerer, N.; Fulcrand, H.; Mazerolles, G. Comprehensive study of condensed tannins by ESI mass spectrometry: average degree of polymerisation and polymer distribution determination from mass spectra Anal. Bioanal. Chem. 2011, 400, 613-623
14. Gu, L.; Kelm, M. A.; Hammerstone, J. F.; Zhang, Z.; Beecher, G.; Holden, J.; Haytowitz, D.; Prior, R. L. Liquid chromatographic/electrospray ionization mass spectrometric studies of proanthocyanidins in foods J. Mass Spectrom. 2003, 38, 1272-1280
15. Hayasaka, Y.; Waters, E. J.; Cheynier, V.; Herderich, M. J.; Vidal, S. Characterization of proanthocyanidins in grape seeds using electrospray mass spectrometry Rapid Commun. Mass Spectrom. 2003, 17, 9-16
16. Roux, E. L.; Doco, T.; Sarni-Manchado, P.; Lozano, Y.; Cheynier, V. A-type proanthocyanidins from pericarp of Litchi chinensis Phytochemistry 1998, 48, 1251-1258
17. Wollgast, J.; Pallaroni, L.; Agazzi, M.-E.; Anklam, E. Analysis of procyanidins in chocolate by reversed-phase highperformance liquid chromatography with electrospray ionization mass spectrometric and tandem mass spectrometric detection J. Chromatogr. A 2001, 926, 211-220
18. Núñez, V.; Gómez-Cordovés, C.; Bartolomé, B.; Hong, Y.-J.; Mitchell, A. E. Non-galloylated and galloylated proanthocyanidin oligomers in grape seeds from Vitus vinifera L. cv. Graciano, Tempranillo and Cabernet Sauvignon J. Sci. Food Agric. 2006, 86, 915-921
19. Sarnosk, P. J.; Johnson, J. V.; Reed, K. V.; Tanko, J. M.; O'Keefe, S. F. Separation and characterisation of proanthocyanidins in Virginia type peanut skins by LC-MS Food Chem. 2012, 131, 927-939
20. Appeldoorn, M. M.; Vincken, J. P.; Sanders, M.; Hollman, P. C. H.; Gruppen, H. Combined normal-phase and reversed-phase liquid chromatography/ESI-MS as a tool to determine the molecular diversity of A-type procyanidins in peanut skins J. Agric. Food Chem. 2009, 57, 6007-6013
21. Cooper, K. A.; Campos-Giménez, E.; Jiménez Alvarez, D.; Nagy, K.; Donovan, J. L.; Williamson, G. Rapid reversed phase ultra-performance liquid chromatography analysis of the major cocoa polyphenols and inter-relationships of their concentrations in chocolate J. Agric. Food Chem. 2007, 55, 2841-2847
22. Li, S.; Xiao, J.; Chen, L.; Hu, C.; Chen, P.; Xie, B.; Sun, Z. Identification of A-series oligomeric procyanidins from pericarp of Litchi chinensis by FT-ICR-MS and LC-MS Food Chem. 2012, 135, 31-38
23. Hokkanen, J.; Mattila, S.; Jaakola, L.; Pirttilä, A. M.; Tolonen, A. Identification of phenolic compounds from lingonberry (Vaccinium vitis-idaea L.), bilberry (Vaccinium myrtillus L.) and hybrid bilberry (Vaccinium × intermedium Ruthe L.) leaves J. Agric. Food Chem. 2009, 57, 9437-9447
24. Lin, L.-Z.; Harnly, J. M. A screening method for the identification of glycosylated flavonoids and other phenolic compounds using a standard analytical approach for all plant materials J. Agric. Food Chem. 2007, 55, 1084-1096
25. Lin, L.-Z.; Harnly, J. M. Quantitation of flavanols, proanthocyanidins, isoflavones, flavananes, dihydroxychalcones, stilbens and benzoic acid derivatives using UV absorbance after identification by LC-MS J. Agric. Food Chem. 2012, 60, 5832-5840
26. nanalysis of anthocyanins, flavonol glycosides and hydroxycinnamic acid derivatives in red mustard green (Brassica juncea Coss variety) J. Agric. Food Chem. 2011, 59, 12059-12072
27. Li, H.-J.; Deinzer, M. L. The mass spectral analysis of isolated hops A-type proanthocyanidins by electrospray ionization tandem mass spectrometry J. Mass Spectrom. 2008, 43, 1353-1363
28. Monagas, M.; Gómez-Cordovés, C.; Bartolomé, B.; Laureano, O.; Ricardo da Silva, J. M. Monomeric, oligomeric, and polymeric flavan-ol composition of wines and grapes from Vitis vinifera L. cv. Graciano, Tempranillo, and Cabernet Sauvignon J. Agric. Food Chem. 2003, 51, 6475-6481
29. Escribano-Bailón, M. T.; Guitiérrez-Fernández, Y.; Rivas-Gonzalo, J. C.; Santos-Buelga, C. Characterization of procyanidins of Vitis vinifera variety Tinta del Pais grape seeds J. Agric. Food Chem. 1992, 40, 1794-1799
30. Ricardo da Silva, J. M.; Rigaud, J.; Cheynier, V.; Cheminat, A.; Moutounet, M. Procyanidin dimers and trimers from grape seeds Phytochemistry 1991, 30, 1259-1264
31. Ricardo da Silva, J. M.; Rosec, J.-Ph.; Bourzeix, M.; Mourgues, J.; Moutounet, M. Dimer and trimer procyanidins in Carignan and Mourvèdre grapes and red wines Vitis 1992, 31, 55-63
32. Malik, A.; Kuliev, Z. A.; Akhmedov, Y. A.; Vdovin, A. D.; Abdullaev, N. D. Proanthocyanidins of Ziziphus jujuba Chem. Nat. Compd. 1997, 33, 165-173
33. Prasain, J. K.; Wang, C. C.; Barnes, S. Mass spectrometric methods for the determination of flavonoids in biological samples Free Radical Biol. Med. 2004, 37, 1324-1350
34. Redeuil, K.; Bertholet, R.; Kussmann, M.; Steiling, H.; Rezzi, S.; Nagy, K. Quantification of flavan-3-ols and phenolic acids in milk-based food products by reversed-phase liquid chromatography-tandem mass spectrometry J. Chromatogr. A 2009, 1216, 8362-8370