Structural identification of novel oligosaccharides produced by Lactobacillus bulgaricus and Lactobacillus plantarum

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 19, 2012, Pages 4886-4894

  Black, Brenna A ^a   Lee, Vivian S Y ^a   Zhao, Yuan Yuan ^a   Hu, Ying ^a   Curtis, Jonathan M ^a   Gänzle, Michael G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

galactosidase; fucose; hetero oligosaccharides; Lactobacillus bulgaricus; LC ESI MS MS; N acetylglucosamine

Indexed keywords

FUCOSE; GALACTOSIDASES; LACTOBACILLUS BULGARICUS; LC-ESI-MS/MS; N-ACETYLGLUCOSAMINE;

BACILLI; CARBOHYDRATES; LACTIC ACID; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY;

OLIGOSACCHARIDES;

OLIGOSACCHARIDE;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMISTRY; LACTOBACILLUS; LACTOBACILLUS PLANTARUM; MASS SPECTROMETRY; METABOLISM; MOLECULAR GENETICS;

CARBOHYDRATE SEQUENCE; LACTOBACILLUS; LACTOBACILLUS PLANTARUM; MASS SPECTROMETRY; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES;

LACTOBACILLUS DELBRUECKII SUBSP. BULGARICUS; LACTOBACILLUS PLANTARUM;

EID: 84861137220     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf300917m     Document Type: Article

References (33)

1. Macfarlane, G.; Steed, H.; Macfarlane, S. Bacterial metabolism and health-related effects of galacto-oligosaccharides and other prebiotics J. Appl. Microbiol. 2008, 104, 305-344
2. Oku, T.; Nakamura, S. Digestion, absorption, fermentation, and metabolism of functional sugar substitutes and their available energy Pure Appl. Chem. 2002, 74, 1253-1261
3. Venema, K. Intestinal fermentation of lactose and prebiotic lactose derivatives, including human milk oligosaccharides Int. Dairy J. 2012, 22, 123-140
4. Kulkarni, A.; Weiss, A.; Iyver, S. Glycan-based high affinity ligands for toxins and pathogen receptors Med. Res. Rev. 2010, 30, 327-393
5. Johannes, L.; Römer, W. Shiga toxins - from cell biology to biomedical applications Nat. Rev. Microbiol. 2010, 8, 105-116
6. Shoaf, K.; Mulvey, G.; Armstrong, G.; Hutkins, R. Prebiotic galactooligosaccharides reduce adherence of enteropathogenic Escherichia coli to tissue culture cells Infect. Immun. 2006, 74, 6920-6928
7. Searle, L.; Best, A.; Nunez, A.; Salguero, F.; Johnson, L.; Weyer, U.; Dugdale, A.; Cooley, W.; Carter, B.; Jones, G.; Tzortzis, G.; Woodward, M.; Ragione, R. A mixture containing galactooligosaccharide, produced by the enzymic activity of Bifidobacterium bifidum, reduces Salmonella enterica serovar Typhimurium infection in mice J. Med. Microbiol. 2009, 58, 37-48
8. Gänzle, M. G. Enzymatic synthesis of galactooligosaccharides and other lactose derivatives (hetero-oligosaccharides) from lactose Int. Dairy J. 2012, 22, 116-122
9. Torres, D. P. M.; Gonçalves, M. D. P. F.; Teixeira, J. A.; Rodrigues, L. R. Galacto-oligosaccharides: production, properties, applications, and significance as prebiotics Comp. Rev. Food Sci. Food Saf. 2010, 9, 438-454
10. Li, W.; Sun, Y.; Ye, H.; Zeng, X. Synthesis of oligosaccharides with lactose and N -acetylglucosamine as substrates by using β- d -galactosidase from Bacillus circulans Eur. Food Res. Technol. 2010, 231, 55-63
11. Kunz, C.; Rudloff, S.; Baier, W.; Klein, N.; Strobel, S. Oligosaccharides in human milk: structural, functional, and metabolic aspects Annu. Rev. Nutr. 2000, 20, 699-722
12. Schwab, C.; Gänzle, M. G. Lactic acid bacteria fermentation of human milk oligosaccharide components, human milk oligosaccharides and galactooligosaccharides FEMS Microbiol. Lett. 2011, 315, 141-148
13. Chai, W.; Piskarev, V.; Lawson, A. Negative-ion electrospray mass spectrometry of neutral underivatized oligosaccharides Anal. Chem. 2001, 73, 651-657
14. n (part 1: methodology) J. Am. Soc. Mass Spectrom. 2002, 13, 1331-1340
15. Liu, Y.; Urgaonkar, S.; Verkade, J.; Armstrong, D. Separation and characterization of underivatized oligosaccharides using liquid chromatography and liquid chromatography-electrospray ionization mass spectrometry J. Chromatogr., A 2005, 1079, 146-152
16. 1H NMR spectroscopy Arch. Biochem. Biophys. 2005, 434, 116-127
17. Nguyen, T.; Splechtna, B.; Krasteva, S.; Kneifel, W.; Kulbe, K.; Divne, C.; Haltrich, D. Characterization and molecular cloning of a heterodimeric β-galactosidase from the probiotic strain Lactobacillus acidophilus R22 FEMS Microbiol. Lett. 2007, 269, 136-144
18. Splechtna, B.; Nguyen, T.; Zehetner, R.; Lettner, H.; Lorenz, W.; Haltrich, D. Process development for the production of prebiotic galacto-oligosaccharides from lactose using β-galactosidase from Lactobacillus sp Biotechnol. J. 2007, 2, 480-485
19. Schwab, C.; Lee, V.; Sørensen, K.; Gänzle, M. Production of galactooligosaccharides and heterooligosaccharides with disrupted cell extracts and whole cells of lactic acid bacteria and bifidobacteria Int. Dairy J. 2011, 21, 748-754
20. Schwab, C.; Sørensen, K. I.; Gänzle, M. G. Heterologous expression of glycoside-hydrolase family 2 and 42 β-galactosidases of lactic acid bacteria in Lactococcus lactis System. Appl. Microbiol. 2010, 33, 300-307
21. Domon, B.; Costello, C. A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates Glycoconjugate J. 1988, 5, 397-409
22. Guan, B.; Cole, R. MALDI linear-field reflectron TOF post-source decay analysis of underivatized oligosaccharides: determination of glycosidic linkages and anomeric configurations using anion attachment J. Am. Soc. Mass Spectrom. 2008, 19, 1119-1131
23. Carroll, J.; Ngoka, L.; Beggs, C.; Lebrilla, C. Liquid secondary ion mass spectrometry/fourier transform mass spectrometry of oligosaccharide anions Anal. Chem. 1993, 65, 1582-1587
24. Dallinga, J.; Heerma, W. Reaction mechanism and fragment ion structure determination of deprotonated small oligosaccharides, studied by negative ion fast atom bombardment (tandem) mass spectrometry Biol. Mass. Spectrom. 1991, 20, 215-231
25. Seymour, J.; Costello, C.; Zaia, J. The influence of sialylation on glycan negative ion dissociation and energetics J. Am. Soc. Mass Spectrom. 2006, 17, 844-854
26. Carroll, J.; Willard, D.; Lebrilla, C. Energetics of cross-ring cleavages and their relevance to the linkage determination of oligosaccharides Anal. Chim. Acta 1995, 307, 431-447
27. Splechtna, B.; Nguyen, T.; Steinböck, M.; Kulbe, K.; Lorenz, W.; Haltrich, D. Production of prebiotic galacto-oligosaccharides from lactose using β-galactosidase from Lactobacillus reuteri J. Agric. Food Chem. 2006, 54, 4999-5006
28. Toba, T.; Tomita, Y.; Itoh, T.; Adachi, S. β-Galactosidases of lactic acid bacteria: characterization by oligosaccharides formed during hydrolysis of lactose J. Dairy Sci. 1981, 64, 185-192
29. Vasiljevic, T.; Jelen, P. Lactose hydrolysis in milk as affected by neutralizers used for the preparation of crude β-galactosidase extracts from Lactobacillus bulgaricus 11842 Innovative Food Sci. Emerging Technol. 2002, 3, 175-184
30. Kurita, K. Controlled functionalization of the polysaccharide chitin Prog. Polym. Sci. 2001, 26, 1921-1971
31. Boehm, G.; Stahl, B. Oligosaccharides from milk J. Nutr. 2007, 137, 847S-849S
32. Zivkovic, A.; German, B.; Lebrilla, C.; Mills, D. Human milk glycobiome and its impact on the infant gastrointestinal microbiota Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 4653S-4658S
33. Hyland, R.; Sun, J.; Griener, T.; Mulvey, G.; Klassen, J.; Donnenberg, M.; Armstrong, G. The bundin pilin protein of enteropathogenic Escherichia coli is an N -acetyllactosamine-specific lectin Cell. Microbiol. 2008, 10, 177-187