Biotransformation of procyanidins by a purified fungal dioxygenase: Identification and characterization of the products using mass spectrometry

Process Biochemistry

Volumn 45, Issue 6, 2010, Pages 904-913

  Roopesh, Krishnankutty ^a   Guyot, Sylvain ^b   Sabu, Abdulhameed ^c   Haridas, M ^c   Isabelle, Perraud Gaime ^a   Roussos, Sevastianos ^a   Augur, Christopher ^a  

^a INSTITUT DE RECHERCHE POUR LE DÉVELOPPEMENT   (France)

^b CEMAGREF   (France)

^c School of Life Sciences   (India)

Author keywords

Aspergillus fumigatus; Dioxygenase; Electrospray Ionization Mass Spectrometry; Procyanidins; Purification; Reversed Phase High Performance Liquid Chromatography

Indexed keywords

ASPERGILLUS FUMIGATUS; DIOXYGENASES; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; PROCYANIDINS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

CHROMATOGRAPHY; ELECTROSPRAY IONIZATION; ENZYMES; FREE RADICAL REACTIONS; FREE RADICALS; IONIZATION; LIQUIDS; MASS SPECTROMETRY; PARTICLE DETECTORS; PURIFICATION;

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

ASPERGILLUS FUMIGATUS;

EID: 77950994154     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2010.02.019     Document Type: Article

References (32)

1. Cheynier V. Polyphenols in foods are more complex than often thought. Am J Clin Nutr 81 1 (2005) 223S-229S
2. Waghorn G.C., and McNabb W.C. Consequences of plant phenolic compounds for productivity and health of ruminants. Proc Nutr Soc 62 2 (2003) 383-392
3. Ursini F., Rapuzzi I., Toniolo R., Tubaro F., and Bontempelly J. Characterization of antioxidant effect of procyanidins: flavonoids and other polyphenols. Meth Enzymol 335 (2001) 338-350
4. Landraut N., Poucheret P., Ravel P., Gasc F., Cros G., and Teisseidre P.-L. Antioxidant capacities and phenolics levels of French wines from different varieties and vintages. J Agric Food Chem 49 (2001) 3341-3348
5. Matthews S., Mila I., Scalbert A., Pollet B., Lapierre C., duPenhoat C., Rolando C., and Donnelly D.M.X. Method for estimation of procyanidins based on their acid depolymerization in the presence of nucleophiles. J Agric Food Chem 45 4 (1997) 1195-1201
6. Scalbert A. Antimicrobial properties of tannins. Phytochem 30 12 (1991) 3875-3883
7. Bhat T.K., Sing B., and Sharma P.O. Microbial degradation of tannins-a current perspective. Biodegrad 9 5 (1998) 343-357
8. Augilar C.N., Cruz M., Rodriguez R., Gutierrez-Sanchez G., Ramirez-Coronel A., and Augur C. Catechin degradation by several fungal strains isolated from Mexican desert. J Microbial Biotechnol 14 2 (2004) 426-429
9. Contreras-Dominguez M., Roopesh K., Ramirez Coronel A., Garcia Oduardo N., Guyot S., Saucedo-Castañeda G., Gaime Perraud I., Roussos S., and Augur C. Use of fungal enzymes to study the degradation of specific plant polyphenols. In: Koutinas A., Pandey A., and Larroche C. (Eds). Current topics on bioprocess in food industry vol. II (2008), Asiatech Publishers 508-518
10. Waterman P.G., and Mole S. Analysis of phenolic plant metabolites (1994), Black-Well Scientific Publications, Oxford p. 238
11. Nguz K., Demey L., and Huyghebaert A. Evaluation of the degradation of sorghum condensed tannins by a Penicillium sp. by determination of proanthocyanidins and flavan-3-ols. Sci Aliment 14 1 (1994) 51-59
12. Shen Z., Haslam E., Falshaw C.P., and Begley M.J. Plant proanthocyanidins. 8. Procyanidins and polyphenols of larix-gmelini bark. Phytochem 25 11 (1986) 2629-2635
13. Rigaud J., Perezilzarbe J., Dasilva J.M.R., and Cheynier V. Micro method for the identification of proanthocyanidin using thiolysis monitored by high performance liquid chromatography. J Chromatogr A 540 1-2 (1991) 401-405
14. Guyot S., Marnet N., Sanoner P., and 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, Meth Enzymol. (2001), Acad. Press Inc., San Diego p. 57-70
15. Wollgast J., Pallaroni L., Agazzi M.E., and Anklam E. Analysis of procyanidins in chocolate by reversed-phase high-performance liquid chromatography with electrospray ionisation mass spectrometric and tandem mass spectrometric detection. J Chromatogr A 926 1 (2001) 211-220
16. Guyot S., Bernillon S., Poupard P., and Renard C.M.G.C. Multiplicity of phenolic oxidation products in apple juices and ciders, from synthetic medium to commercial products. Recent advances in polyphenol research (2008), Wiley-Blackwell p. 278-92
17. Wang C.L., You S.L., and Wang S.L. Purification and characterization of a novel catechol 1,2-dioxygenase from Pseudomonas aeruginosa with benzoic acid as carbon source. Process Biochem 41 (2006) 1594-1601
18. Contreras-Domínguez M., Guyot S., Marnet N., Le Petit J., Perraud-Gaime I., Roussos S., and Augur C. Degradation of procyanidins by Aspergillus fumigatus: Identification of an aromatic ring cleavage product using thiolysis-high performance liquid chromatography and mass spectrometry. Biochimie 88 12 (2006) 1899-1908
19. Roussos S. Mise au point d'une méthode pour l'etude des cractères morphologiques, biochimiques et nutrionnels des champignons imparfaits. Cah. ORSTOM, ser. Biol 45 (1982) 25-34
20. Guyot S., Doco T., Souquet J.M., Moutounet M., and Drilleau J.F. Characterization of highly polymerized procyanidins in cider apple (Malus sylvestris var. Kermerrien) skin and pulp. Phytochem 44 2 (1997) 351-357
21. Gessiner O.M., and Steiner D. Acid Butanol assay for proanthocyanidins (condensed tannins). In: Graça M.A.S., Bärlocher F., and Gessiner M.O. (Eds). Methods to study litter decomposition: a practical guide (2005), Springer 107-114
22. Bradford M.M. A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Analytical Biochem 72 (1976) 248-254
23. Laemmli U.K. Cleavage of structural proteins during the assembly of head of bacteriophage T4. Nature (London) 227 (1970) 680-685
24. Guyot S., Marnet N., Laraba D., Sanoner P., and Drilleau J.F. Reversed-phase HPLC following thiolysis for quantitative estimation and characterization of the four main classes of phenolic compounds in different tissue zones of a French cider apple variety (Malus domestica var. Kermerrien). J Agric Food Chem 46 5 (1998) 1698-1705
25. Friedrich W., Eberhardt A., and Galensa R. Investigation of proanthocyanidins by HPLC with electrospray ionization mass spectrometry. Eur Food Res Technol 211 (2000) 56-64
26. Gu L.W., Kelm M.A., Hammerstone J.F., Beecher G., Holden J., Haytowitz D., and Prioir R.L. Screening of foods containing proanthocyanidins and their structural characterization using LC-MS/MS and thiolytic degradation. J Agric Food Chem 51 25 (2003) 7513-7521
27. Miketova P., Schram K.H., Whitney J., Li M., Huang R., Kerns E., Valcic S., Timmerman B.N., Rourick R., and Klohr S. Tandem mass spectrometry studies of green tea catechins. Identification of three minor components in the polyphenolic extract of green tea. J Mass Spectrom 35 7 (2000) 860-869
28. Ramirez-Coronel M.A., Marnet N., Kolli K.V.S., Roussos S., Guyot S., and Augur C. Characterization and estimation of proanthocyanidins and other phenolics in coffe pulp (Coffea arabica) by thiolysis-high-performance liquid chromatography. J Agric Food Chem 52 (2004) 1344-1349
29. Thompson R.S., Jacques D., Haslam E., and Tanner R.J.N. Plant proanthocyanidins. Part I. Introduction, the isolation, structure and distribution in nature of plant procyanidins. J Chem Soc Perkin Trans (1972) 1387-1399
30. Schofield P., Mbugua D.M., and Pell A.N. Analysis of condensed tannins: a review. Anim Feed Sci Technol 91 (2001) 21-40
31. Fan P.H., Lou H.X., Yu W.T., Ren D.M., Ma B., and Ji M. Novel flavanol derivatives from grape seeds. Tetrahedron Lett 45 15 (2004) 31363-33166
32. Fan P.H., and Lou H.X. Effects of polyphenols from grape seeds on oxidative damage to cellular DNA. Mol Cell Biochem 267 1-2 (2004) 67-74