References
- Barile, D., Marotta, M., Chu, C., Mehra, R., Grimm, R., Lebrilla, C. B., and German, J. B. (2010) Neutral and acidic oligosacchrarides in Hostein-Friesian colostrums during the first 3 days of lactation measured by high performance liquid chromatography on a microfluidic chip and time-of-flight mass spectrometry. J. Dairy Sci. 93, 3940-3949. https://doi.org/10.3168/jds.2010-3156
- Barile, D., Tao, N., Lebrilla, C. B., Coisson. J-D., Arlorio, M., and German, J. B. (2009) Permeate from cheese whey ultrafiltration is a source of milk oligosaccharides. Int. Dairy J. 19, 524-530. https://doi.org/10.1016/j.idairyj.2009.03.008
- Bode, L. (2006) Recent advances on structure, metabolism and function of human milk oligosaccharides. J. Nutr. 136, 2127-2130.
- Bode, L., Kunz, C., Muhly-Reinholz, M., Mayer, K., Seeger, W., and Rudloff, S. (2004a) Inhibition of monocyte, lymphocyte and neutrophil adhesion to endothelial cells by human milk oligosaccharides. J. Throm. Haemost. 92, 1402-1410.
- Bode, L., Rudloff, S., Kunz, C., Strobel, S., and Klein, N. (2004b) Human milk oligosaccharides reduce platelet-neutrophil complex formation leading to a decrease in neutrophil beta 2 integrin expression. J. Leukocyte Biol. 76, 820-826. https://doi.org/10.1189/jlb.0304198
- Boehm, G. and Moro, G. (2008) Structural and functional aspects of prebiotics used in infant nutrition. J. Nutr. 138, 1818S-1828S.
- Boehm, G. and Stahl, B. (2007) Oligosaccharides from milk. J. Nutr. 137, 847S-849S.
- Boehm, G. and Stahl, B. (2003) Oligosachardes. In: Functional dairy products. Mattila-Sandholm, T. (ed) Woodhead publishers, Cambridge, UK, pp. 203-243.
- Bogoch, S. (1977) Recognins and their chemoreciprocals. In: Behavioural neurochemistry. DeFeudis, F. V., and Delgado, J. M. (eds) Spectrum Publishers, New York, NY, USA, p. 270.
- Carden, D. L. and Granger, D. N. (2000) Pathophysiology of ischaemia-reperfusion injury. J. Pathol. 190, 255-266. https://doi.org/10.1002/(SICI)1096-9896(200002)190:3<255::AID-PATH526>3.0.CO;2-6
- Chonan, O. and Watanuki, M. (1996) The effect of 6'-galactooligosaccharides on bone mineralization of rats adapted to different levels of dietary calcium. Int. J. Vitam. Nutr. 66, 244-249.
- Coppa, G. V., Zampini, L., Galeazzi, T., and Gabrielli, O. (2006) Prebiotics in human milk: a review. Digest. Liver Dis. 38, S291-S294. https://doi.org/10.1016/S1590-8658(07)60013-9
- Coppa, G. V., Pierani, P. Zampini, L., Bruni, S., Carloni, I., and Gabrielli O. (2001) Characterization of oligosaccharides in milk and feces of breast-fed infants by high performance anion-exchange chromatography. Adv. Med. Biol. 501, 307-314. https://doi.org/10.1007/978-1-4615-1371-1_38
- Cumar, F. A., Ferchmin, P. A., and Caputto, R. (1965) Isolation and identification of a lactose phosphatase ester from cow colostrums. Biochem. Biophys. Res. Comm. 20, 60-62. https://doi.org/10.1016/0006-291X(65)90950-2
- Fergusson, D. M., Beautrais, A. L., and Silva, P. (1982) Breastfeeding and cognitive development in the first seven years of life. Soc. Sci. Med. 16, 1705-1708. https://doi.org/10.1016/0277-9536(82)90096-X
- Gibson, G. and Roberfroid, M. (1995) Dietary modulation of human colonic microbiota-introducing the concept of probiotics. J. Nutr. 125, 1401-1412.
- Gopal, P. K. and Gill, H. S. (2000) Oligosaccharides and glycoconjugates in bovine milk and colostrums. Brit. J. Nutr. 84, 69-74.
- Gronlund, M. M., Lehtonen, O. P., Eerola, E., and Kero, P. (1999) Fecal microflora in healthy infants born by different methods of delivery: permanent changes in intestinal flora after caesarean delivery. J. Pediat. Gastroenterol. Nutr. 28, 19-25. https://doi.org/10.1097/00005176-199901000-00007
- Gruber, C., van Stuijvenberg M., Mosca, F., Moro, G., Chirico, G., Braegger, C. P., Riedler, J., Boehm, G., and Wahn, U. (2010) Reduced occurrence of early atopic dermatitis because of immunoactive prebiotics among low-atopy-risk infants. J. Alergy Clin. Immunol. 126, 791-797. https://doi.org/10.1016/j.jaci.2010.07.022
- Hakkarainen, J., Toaiven, M., Leinonen, A., Frangsmyr, L., Stromberg, N., Lapinjoki, S., Nasssif, X., and Tikkanen-Kaukanen, C. (2005) Human and bovine milk oligosaccharides inhibit Neisseria meningitidis pili attachment in vitro. J. Nutr. 135, 2445-2448.
- Heuvel van den E. G., Schoteraman, M. H., and Muijs, T. (2000) Transgalacto-oligosaccharides stimulate calcium absorption in postmenopausal women. J. Nutr. 130, 2938-2942.
- Heuvel van den E. G., Schaafsma G., Muys T., and Dokkum van, W. (1998) Non digestible oligosaccharides do not interfere with calcium and nonhem-iron absorption in young, healthy men. Am. J. Clin. Nutr. 67, 445-451.
- IUPAC/IUBMB (1997) Joint Commission on Biochemical Nomenclature (JCBN) Nomenclature of Carbohydrates, Recommendations 1996. Carbohydr. Res. 297, 1-90. https://doi.org/10.1016/S0008-6215(97)83449-0
-
Johansson, P., Nilsson, J., Angstrom, J., and Meller-Podraza, H. (2005) Interaction of Helicobacter pylori with sialylated carbohydrates: the dependence on different parts of the binding trisaccharides
$Neu5Ac{\alpha}3Gal{\beta}4GlcNAc$ . Glycobiol. 15, 625-636. - Jungi, T. W., Spycher, M. O., Nydegger, U. E., and Barandun, S. (1986) Platelet-leukocyte interaction: selective binding of thrombin-stimulated platelets to human monocytes, polymorphonuclear leukocyte, and related cell lines. Blood 67, 629-636.
- Kimura, K., Watanabe, Y., Matsumoto, K., and Miyagi, A. (1997) Yakult Reports 17, 1-7.
- Kuhn, R., and Gauhe, A. (1965) Bestimmung der bindungsstellen von sialinsaure-resten in oligosacchariden mit hilfe von perjodat. Chem. Ber. 98, 395-413. https://doi.org/10.1002/cber.19650980211
- Kobata, A. (2010) Structures and application of oligosaccharides in human milk. Proc. Jpn. Acad., Ser. B. 86, 731-747. https://doi.org/10.2183/pjab.86.731
- Kobata, A., Grollman, E. F., Torain, B. F., and Ginsburg, V. (1970) Blood and tissue antigens. Academic press, New York, USA, pp. 497.
- Kunz, C. and Rudloff, S. (2006) Health promoting aspects of milk oligosaccharides. Int. Dairy J. 16, 1341-1346. https://doi.org/10.1016/j.idairyj.2006.06.020
- Kunz, C., Rudloff, S., Baier, W., Klein, N., and Strobel, S. (2000) Oligosaccharides in human milk. Structural, functional, and metabolic aspects. Annu. Rev. Nutr. 20, 699-722. https://doi.org/10.1146/annurev.nutr.20.1.699
- Lucas, A., Morley, R., Cole, T. J., Lister, G., and Leeson-Payne, C. (1992) Breast milk and subsequent intelligence quotient in children born preterm. Lancet 339, 261-264. https://doi.org/10.1016/0140-6736(92)91329-7
- Manning, T. S., and Gibson, G. R. (2004) Prebiotics. Best Prac. Res. Clin. Gastro. 18, 287-298. https://doi.org/10.1016/j.bpg.2003.10.008
- Martinez-Ferez, A., Rudloff, S., Guadix, A., Henkel, C. A., Phlents, G., Boza, J. J., Guadix, E. M., and Kunz, C. (2006) Goats' milk as a natural source of lactose-derived oligosaccharides: Isolation by membrane technology. Int. Dairy J. 16, 173-174. https://doi.org/10.1016/j.idairyj.2005.02.003
- Martin, M. J., Martin-Sosa, S., and Hueso, P. (2002) Binding of milk oligosaccharides by several enterotoxigenic Eschecrichia coli strains isolated from calves. Glycoconj. J. 19, 5-11.
- Martin, M. J., Marin-Sosa., S. Garcia-Pardo, L. A., and Hueso, P. (2001) Distribution of bovine sialoglycoconjugates during lactation. J. Dairy Sci. 84, 995-1000. https://doi.org/10.3168/jds.S0022-0302(01)74558-4
- Maslowski, K. M., Vieira, A. T., Ng, A., Kranich, J., Sierro, F., Yu, D., Schilter, H. C., Rolph, M. S., Mackay, F., Artis, D., Xavier, R. J., Teixeira, M. M., and Mackay, C. R. (2009) Regulation of inflammatory responses by gut microbiota and chemoattractant receptor GPR43. Nature 461, 1282-1286. https://doi.org/10.1038/nature08530
- McEver, R. P. (1997). Selectin-carbohydrate interactions during inflammation and metastasis. Glycoconj. J. 14, 585-591. https://doi.org/10.1023/A:1018584425879
- Mehra, R., and Kelly, P. (2006) Milk oligosaccharides: structural and technological aspects. Int. Dairy J. 16, 1334-1340. https://doi.org/10.1016/j.idairyj.2006.06.008
- Mills, S., Ross, R. P., Hill, C., Fitzgerald, G. F., and Stanton, C. (2011) Milk intelligence: Mining milk of bioactive substances associated with human health. Int. Dairy J. 21, 382-386.
- Monchois, V., Willemot, R. M., and Monsan, P. (1999) Glucansucrases: Mechanism of action and structure-function relationships. FEMS Microbiol. Rev. 23, 131-151.
- Mussatto, S. I., and Manchilha, I. M. (2007) Non-digestible oligosaccharides: A review. Carbohydr. Polymers 68, 587-597. https://doi.org/10.1016/j.carbpol.2006.12.011
- Nakamura, T., Kawase, H., Kimura, K., Watanabe, Y., Ohtani, M., Arai, I., and Urashima, T. (2003) Concentrations of sialyloligosaccharides in bovine colostrums and milk during the prepartum and early lactation. J. Dairy Sci. 86, 1315-1320. https://doi.org/10.3168/jds.S0022-0302(03)73715-1
- Newburg, D. S. (1999) Human milk glycocnjugates that inhibit pathogens. Curr. Med. Chem. 6, 117-127.
- Ngo, D.-N., Kim, M.-M., and Km, S.-K. (2008) Chitin oligosaccharides inhibit oxidative stress in live cells. Carbohyd. Polym. 74, 228-234. https://doi.org/10.1016/j.carbpol.2008.02.005
-
Niess, J. H., Brand, S., Gu, X., Landsman, L., Jung, S., McCormick, B. A., Vyas, J. M., Boes, M., Ploegh, H. L., Fox, J. G., Littman, D. R., and Reinecker, H. C. (2005)
$CX_{3}CR1$ -mediated dendritic cell access to the intestinal lumen and bacterial clearance. Science 307, 254-258. https://doi.org/10.1126/science.1102901 - Ninonuevo, M. R., Park, Y., Yin, H., Zhang, J., Ward, R. E., Clowers, B. H., German, J. B., Freeman S. L., Killeen, K., Grimm, R., and Lebrilla, C. B. (2006) A strategy for annotating the human milk glycome. J. Agric. Food Chem. 54, 7471-7480. https://doi.org/10.1021/jf0615810
- Parkkinen, J., and Finne, J. (1987) Isolation of sialyl oligosaccharides and sialyl oligosaccharide phosphates from bovine colostrums and human urine. In: Methods in Enzymology Ginsberg, V. (ed) Academic Press, New York. Vol. 138, pp. 289-300.
- Peters, M. J., Dixon, G., Kotowicz, K. T., Hatch, D. J., Heyderman, R. S., and Klein, N. J. (1999) Circulating plateletneutrophil complexes represent a subpopulation of activated neutrophils primed for adhesion, phagocytosis and intracellular killing. Brit. J. Haematol. 106, 391-399. https://doi.org/10.1046/j.1365-2141.1999.01553.x
- Qiang, X., YongLie, C., and QiaBing, W. (2009) Health benefit application of functional oligosaccharides. Carbohyd. Polym. 77, 435-441. https://doi.org/10.1016/j.carbpol.2009.03.016
- Rescigno, M. and Di Sabatino, A. (2009) Dendritic cells in intestinal homeostasis and disease. J. Clin. Invest. 119, 2441-2450. https://doi.org/10.1172/JCI39134
- Rivero-Urgell M., and Santamaria-Orleans, A. (2001) Oligosaccharides: application in infant food. Early Human Develop. 65, S43-S45. https://doi.org/10.1016/S0378-3782(01)00202-X
- Rousseu, V., Lepargneur, J. P., Roques, C., Remaud-Simeon, M., and Paul, F. (2005) Prebiotic effects of oligosaccharides on selected vaginal lactobacilli and pathogenic microorganisms. Anaerobe 11, 145-153. https://doi.org/10.1016/j.anaerobe.2004.12.002
- Rudloff, S., Phlentz, G., Diekmann, L., Egge, H., and Kunz, C. (1996) Urinary excretion of lactose and oligosaccharides n preterm infants fed human milk or infant formula. Acta Paedeatr. 85, 598-603. https://doi.org/10.1111/j.1651-2227.1996.tb14095.x
-
Ruiz-Palacios, G. M., Cervantes, L. E., Ramos, P., Chavez- Munguia, B., and Newburg, D. S. (2003) Campylobacter jejuni binds intestinal H(O) antigen (
$Fuc{\alpha}1,\;2\;Gal{\beta}1,4$ GlcNAc), and fucosyloligosaccharides of human milk inhibit its binding and infection. J. Biol. Chem. 278, 14112-14120. https://doi.org/10.1074/jbc.M207744200 - Sabharwal, H., Sjoblad, S., and Lundblad, A. (1991) Affinity chromatographic identification and quantification of blood group A-active oligosaccharides in human milk and feces of breast-fed infants. J. Pediatr. Gastroenterol. Nutr. 12, 474-479. https://doi.org/10.1097/00005176-199105000-00011
- Saito, T., Itoh, T., and Adachis, S. (1987) Chemical structure of three neutral trisaccharides isolated in free form from bovine colostrums. Carbohydr Res. 165, 43-51. https://doi.org/10.1016/0008-6215(87)80076-9
- Saito, T., Itoh, T., and Adachi, S. (1984) Presence of two neutral disaccharides containing N-acetylhexosamine in bovine colostrums as free forms. Biochem. Biophys. Acta 801, 147-150. https://doi.org/10.1016/0304-4165(84)90223-X
- Schaur, R., and Kamerling, J. P. (1997) Chemistry, biochemistry and biology of sialic acids. In: Glycoproteins II, Schachter, H., Montreuil, and Vilegenthart, J. F. G. (eds) Elsvier, Amsterdam, The Netherlands, pp. 243-372.
- Scheneir, M. L. and Rafelson, M. E. (1996) Isolation of two structural isomers of N-acetylneuraminyllactose from bovine colostrum. Biochem. Biophys. Acta 130, 1-11.
- Schimdt, R. (1989) Glycoproteins involved in long-lasting plasticity in the teleost brain. Forts. Zool. 37, 327-339.
- Scholz-Ahrens, K., Schsafsma, G., Van Del Heuvel E. G. M. J., and Schrezenmeir J (2001) Effect of Prebiotics in mineral metabolism. Am. J. Clin. Nutr. 73, 459S-464S.
- Schon, M. P., Krahn, T., Schon, M., Rodriquez, M. -L., Antonicek, H., Schultz, J. E., Ludwiq, R. J., Zollner, T. M., Bischoff, E., Bremm, K. D., Schramm, M., Henninger, K., Kaufmann, R., Gollnick, H. P. Parker, C. M., and Boenchke, W. H. (2002) Efomycine M, a new specific inhibitor of selectin, impairs leukocyte adhesion and alleviates cutaneous inflammation. Nature Med. 8, 366-372. https://doi.org/10.1038/nm0402-366
- Schumacher, G., Bendas, G., Stahl, B., and Beermann, C. (2006) Human milk oligosaccharides affect P-selectin binding capacities: in vitro investigation. Nutr. 22, 620-627. https://doi.org/10.1016/j.nut.2005.12.009
- Schwertmann, A., Rudloff, S., and Kunz, C. (1996) Potential ligands for cell adhesion molecules in human milk. Ann. Nutr. Metab. 40, 252-262. https://doi.org/10.1159/000177965
- Smith, M. M., Durkin, M., Hinton, V. J., Bellinger, D., and Kuhn, L. (2003) Influence of breastfeeding on cognitive outcomes at age 6-8 years: follow-up of very low birth weight infants. Am. J. Epidem. 158, 1075-1082. https://doi.org/10.1093/aje/kwg257
- Tao, N., DePeters, E. J., Freeman, S. German, J. B., Grimm, R., and Lebrilla, C. B. (2009) Variations in bovine milk oligosaccharides during early and middle lactation stages analyzed by high-performance liquid chromatography-chip/mass spectrometry. J. Dairy Sci. 92, 2991-3001. https://doi.org/10.3168/jds.2008-1642
- Tao, N., DePeters, E. J., Freeman, S., German, J. B., Grimm, R., and Lebrilla, C. B. (2008) Bovine milk glycome. J. Dairy Sci. 91, 3768-3778. https://doi.org/10.3168/jds.2008-1305
- Urashima, T. and Taufik, T. (2010) Oligosaccharides in milk: Their benefits and future utilization. J. Anim. Sci. Technol. 33, 189-197. https://doi.org/10.5398/medpet.2010.33.3.189
- Urashima, T., Saito, T., Nakamura, T., and Messer, M. (2001) Oligosaccharides of milk and colostrums in non-human mammals. Glycoconj. J. 18, 357-371. https://doi.org/10.1023/A:1014881913541
- Urashima, T., Saito, T., and Nakamura, T. (1997b) Structural determination of mono-sialyltrisaccharides obtained from caprine colostrum. Comp. Biochem. Physiol. 116, 431-435. https://doi.org/10.1016/S0305-0491(96)00269-6
-
Urashima, T., Bubb, W. A., Messer, M., Tsujii, Y., and Taneda, Y. (1994) Studies of the neutral trisaccharides of goat (Capra hircus) and of the one- and two-dimensional
$^{1}H\;and\;^{13}C$ NMR spectra of 6'-N-acetylglucosaminyllactose. Carbhydr. Res. 269, 173-184. - Urashima, T., Saitu, T., and Kimura, T. (1991b) Structural determination of three neutral oligosaccharides in bovine (Holstein-Friesian) colostrum. Comp. Biochem. Biophys. Acta 1073, 225-229. https://doi.org/10.1016/0304-4165(91)90207-W
- Veh, R. W., Michalski, J. C., Corfield, A. P., Sander-Wewer, M., Gies, D., and Schauer, R. (1981) New chromatographic system for the rapid analysis and preparation of colostrum sialyloligosaccharides. J. Chromatogr. 212, 313-322. https://doi.org/10.1016/S0021-9673(01)84044-9
- Viverge, D., Grimmonprez, L., and Solere, M. (1997) Chemical characterization of sialyl oligosaccharides isolated from goat (capra hircus) milk. Biochem. Biophys. Acta 1336, 157-164. https://doi.org/10.1016/S0304-4165(97)00021-4
- Von Itzstein, M. and Thomson, R. J. (1997) Sialic acid and sialic acid-recognizing proteins: drug discovery targets and potential glycopharmaceuticals. Curr. Med. Chem. 4, 185-210.
- Wang, B., Yu, B., Karim, M., Hu, H., Sun, Y., McGreevy, P., et al. (2007b) Dietary sialic acid supplementation improves learning and memory in piglets. Am. J. Clin. Nutr. 85, 561-569.
- Wang, B. and Brand-Miller, J. (2003) The role and potential of sialic acid in human nutrition. Eur. J. Clin. Nutr. 57, 1351-1369. https://doi.org/10.1038/sj.ejcn.1601704
- Zivkovic, A. M. and Barile, D. (2011) Bovine milk as a source of functional oligosaccharides for improving human health. Adv. Nutr. 2, 284-288. https://doi.org/10.3945/an.111.000455
Cited by
- Milk Inhibits the Biological Activity of Ricin vol.287, pp.33, 2012, https://doi.org/10.1074/jbc.M112.362988