Reversed-phase HPLC-ESI/MS analysis of birch leaf proanthocyanidins after their acidic degradation in the presence of nucleophiles

Phytochemical Analysis

Volumn 18, Issue 5, 2007, Pages 378-386

  Karonen, Maarit ^a   Leikas, Anne ^a   Loponen, Jyrki ^a   Sinkkonen, Jari ^a   Ossipov, Vladimir ^a   Pihlaja, Kalevi ^a  

^a UNIVERSITY OF TURKU   (Finland)

Author keywords

Betula sp.; Condensed tannins; Liquid chromatography; Mass spectrometry; Phloroglucinol degradation; Thiolysis

Indexed keywords

COLUMN CHROMATOGRAPHY; DEGRADATION; DRUG PRODUCTS; ELECTROSPRAY IONIZATION; FLAVONOIDS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH PRESSURE LIQUID CHROMATOGRAPHY; ION EXCHANGE; TANNINS;

ACIDIC DEGRADATION; BETULA SP.; CONDENSED TANNINS; FLAVAN-3-OLS; HPLC-ESI MS; PHLOROGLUCINOL; PHLOROGLUCINOL DEGRADATION; PROANTHOCYANIDINS; REVERSED PHASE HPLC; THIOLYSIS;

MASS SPECTROMETRY;

CATECHIN; EPICATECHIN; EPIGALLOCATECHIN; FLAVANOL DERIVATIVE; PHLOROGLUCINOL; PROANTHOCYANIDIN; THIOL DERIVATIVE;

ACIDITY; ARTICLE; BIRCH; CATALYSIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; DEGRADATION; DEPOLYMERIZATION; ELECTROSPRAY MASS SPECTROMETRY; LIQUID LIQUID EXTRACTION; NONHUMAN; PLANT LEAF; POLYMERIZATION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ULTRAVIOLET SPECTROPHOTOMETRY;

BETULA PUBESCENS SUBSP. TORTUOSA; BETULA SP.;

EID: 34548723991     PISSN: 09580344     EISSN: 10991565     Source Type: Journal    
DOI: 10.1002/pca.992     Document Type: Article

References (25)

1. Ayres MP, Clausen TP, MacLean SF, Redman AM, Reichardt, PB. 1997. Diversity of structure and antiherbivore activity in condensed tannins. Ecology 78: 1696-1712.
2. Cheynier V, Labarbe B, Moutounet M. 2001. Estimation of procyanidin chain length. Methods Enzymol 335: 82-94.
3. De Bruyne T, Pieters LAC, Dommisse RA, Kolodziej H, Wray V, Domke T, Vlietinck AJ. 1996. Unambiguous assignments for free dimeric proanthocyanidin phenols from 2D NMR, Phytochemistry 43: 265-272.
4. Foo LY, Lu Y. 1999. Isolation and identification of procyanidins in apple pomace. Food Chem 64: 511-518.
5. Fulcrand H, Remy S, Souquet J-M, Cheynier V, Moutounet M. 1999. Study of wine tannin oligomers by on-line liquid chromatography electrospray ionization mass spectrometry. J Agric Food Chem. 47: 1023-1028.
6. Gu L, Kelm MA, Hammerstone JF, Zhang Z, Beecher G, Holden J, Haytowltz D, Prior RL. 2003. Liquid chromatographic/electrospray ionization mass spectrometric studies of proanthocyanidins in foods. J Mass Spectrom 38: 1272-1280.
7. Guyot S, Doco T, Souquet J-M, Moutounet M, Drilieau J-F. 1997. Characterization of highly polymerized procyanidins in cider apple ( Malus sylvestris var. kermerrien) skin and pulp. Phytochemistry 44: 351-357.
8. Guyot S, Marnet N, Sanoner P, Drilleau J-F. 2001. Direct thiolysis on crude apple materials for high-performance liquid chromatography characterization and quantification of polyphenols in cider apple tissues and juices. Methods Enzymo1 335: 57-70.
9. Hagerman AE. 2005. Determination of degree of polymerization-HPLC of phloroglusinol derivatives, www.users.muohio.edu/hagermae/tannin.pdf.
10. Hatano T, Hemingway RW. 1997. Conformational isomerism of phenolic procyanidins: preferred conformations in organic solvents and water. J Chem Soc, Perkin Trans 25: 1035-1043.
11. Karonen M, Loponen J, Ossipov V, Pihlaja K. 2004a. Analysis of procyanidins in pine bark with reversed-phase and normal-phase high-performance liquid chromatography-electrospray ionization mass spectrometry. Anal Chim Acta 522: 105-112.
12. 2. J Agric Food Chem 52: 7532-7540.
13. Karonen M, Ossipov V, Sinkkonen J, Loponen J, Haukioja E, Pihlaja K. 2006. Quantitative analysis of polymeric proanthocyanidins in birch leaves with normal-phase HPLC. Phytochem. Anal. 17: 149-156.
14. Kennedy JA, Jones GP. 2001. Analysis of proanthocyanidin cleavage products following acid-catalysis in the presence of excess phloroglucinol. J Agric Food Chem 49: 1740-1746.
15. Kennedy JA, Matthews MA, Waterhouse AL. 2000. Changes in grape seed polyphenols during fruit ripening. Phytochemistry 55: 77-85.
16. Koupai-Abyazani MR, McCallum J, Bohm BA. 1992. Identification of the constituent flavonoid units in sainfoin proanthocyanidins by reversed-phase high-performance liquid chromatography. J Chromatogr 594: 117-123.
17. Matthews S, Mila I, Scalbert A, Donnelly DMX. 1997a. Extractable and non-extractable proanthocyanidins in barks. Phytochemistry 45: 405-410.
18. Matthews S, Mila I, Scalbert A, Pollet B, Lapierre C, Hervé du Penhoat CLM, Rolando C, Donnelly DMX. 1997b. Method for estimation of proanthocyanidins based on their acid depolymerization in the presence of nucleophiles. J Agric Food Chem 45: 1195-1201.
19. Ossipov V, Nurmi K, Loponen J, Haukioja E, Pihlaja K. 1996. High-performance liquid chromatographic separation and identification of phenolic compounds from leaves of Betula pubescens and Betula pendula. J Chromatogr A 721: 59-68.
20. Ossipova S, Ossipov V, Haukloja E, Loponen J, Pihlaja K. 2001. Proanthocyanidins of mountain birch leaves: quantification and properties. Phytochem Anal 12: 128-133.
21. Shoji T, Mutsuga M, Nakamura T, Kanda T, Akiyama H, Goda, Y. 2003. Isolation and structural elucidation of some procyanidins from apple by low-temperature nuclear magnetic resonance. J Agric Food Chem 51: 3806-3813.
22. Sun D, Wong H, Foo LY. 1986. Proanthocyanidin dimers and polymers from Quercus dentata. Phytochemistry 26: 1825-1829.
23. Thompson RS, Jacques D, Haslam E, Tanner RJN. 1972. Plant proanthocyanidins. Part I. Introduction; the isolation, structure and distribution in nature of plant procyanidins. J Chem Soc, Perkin Trans 1 11: 1387-1399.
24. Vivas N, Nonier M-F, Vivas de GauleJac N, Absalon C, Bertrand A, Mirabel M. 2004. Differentiation of proanthocyanidin tannins from seeds, skins and stems of grapes (Vittis vinifera) and heartwood of Quebracho (Schinopsis balansae) by matrix-assisted laser desorption/ ionlzation time-of-flight mass spectrometry and thioacidolysis/liquld chromatography/electrospray ionization mass spectrometry. Anal Chim Acta 513: 247-256.
25. Waterman PG, Mole S (eds) 1994. Analysis of Phenolic Plant Metabolites. Blackwell Scientific: Oxford.