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Chemical characterization of milk oligosaccharides of the koala (Phascolarctos cinereus)


Tadasu Urashima1 & Epi Taufik1,2 & Rino Fukuda1 & Tadashi Nakamura1 & Kenji Fukuda1 & Tadao Saito3 & Michael Messer4


1 Graduate School of Animal and Food Hygiene, Obihiro University of Agriculture & Veterinary Medicine, Obihiro, Hokkaido 080-8555, Japan. e-mail:
2 Faculty of Animal Science, Bogor Agricultural University, Bogor 16680, Indonesia
3 Graduate School of Agriculture, Tohoku University, Sendai 981-8555, Japan
4 School of Molecular Biosciences, The University of Sydney, Sydney, NSW 2006, Australia


ABSTRACT

Previous structural characterizations of marsupial milk oligosaccharides had been performed in only two macropod species, the tammar wallaby and the red kangaroo. To clarify the homology and heterogeneity of milk oligosaccharides among marsupial species, which could provide information on their evolution, the oligosaccharides of the koala milk carbohydrate fraction were characterized in this study. Neutral and acidic oligosaccharides were separated from the carbohydrate fraction of milk of the koala, a non-macropod marsupial, and characterized by 1H-nuclear magnetic resonance spectroscopy. The structures of the neutral saccharides were found to be Gal(β1-4) Glc (lactose), Gal(β1-3)Gal(β1-4)Glc (3′-galactosyllactose), Gal(β1-3)Gal(β1-3)Gal(β1-4)Glc (3′,3″-digalactosyllactose), Gal(β1-3)[Gal(β1-4)GlcNAc(β1-6)]Gal(β1-4)Glc (lactoN-novopentaose I) and Gal(β1-3){Gal(β1-4)[Fuc(α1-3)]GlcNAc(β1-6)}Gal(β1-4)Glc (fucosyl lacto-Nnovopentaose I), while those of the acidic saccharides were Neu5Ac(α2-3)Gal(β1-4)Glc (3′-SL), Neu5Ac(α2-3)Gal(β1- 3)Gal(β1-4)Gal (sialyl 3′-galactosyllactose), Neu5Ac(α2- 3)Gal(β1-3)[Gal(β1-4)GlcNAc(β1-6)]Gal(β1-4)Glc (sialyl lacto-N-novopentaose a), Gal(β1-3)[Neu5Ac(α2-6)Gal(β1- 4)GlcNAc(β1-6)]Gal(β1-4)Glc (sialyl lacto-N-novopentaose b), Gal(β1-3)[Neu5Ac(α2-3)Gal(β1-4)GlcNAc(β1-6)]Gal(β1- 4)Glc (sialyl lacto-N-novopentaose c), and Neu5Ac(α2- 3)Gal(β1-3){Gal(β1-4)[Fuc(α1-3)]GlcNAc(β1-6)}Gal(β1- 4)Glc (fucosyl sialyl lacto-N-novopentaose a). The neutral oligosaccharides, other than fucosyl lacto-N-novopentaose I, a novel hexasaccharide, had been found in milk of the tammar wallaby, a macropod marsupial, while the acidic oligosaccharides, other than fucosyl sialyl lacto-N-novopentaose a had been identified in milk carbohydrate of the red kangaroo. The presence of fucosyl oligosaccharides is a significant feature of koala milk, in which it differs from milk of the tammar wallaby and the red kangaroo.

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