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Chemical characterization of milk oligosaccharides of the eastern quoll (Dasyurus viverrinus)

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Abstract

Structural characterizations of marsupial milk oligosaccharides have been performed in four species to date: the tammar wallaby (Macropus eugenii), the red kangaroo (Macropus rufus), the koala (Phascolarctos cinereus) and the common brushtail possum (Trichosurus vulpecula). To clarify the homology and heterogeneity of milk oligosaccharides among marsupials, the oligosaccharides in the carbohydrate fraction of eastern quoll milk were characterized in this study. Neutral and acidic oligosaccharides were separated and characterized by 1H-nuclear magnetic resonance spectroscopy and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. The structures of the neutral oligosaccharides were 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 (lacto-N-novopentaose I), Gal(β1–3)Gal(β1–3)[Gal(β1–4)GlcNAc(β1–6)]Gal(β1–4)Glc (galactosyl lacto-N-novopentaose I), Gal(β1–3)[Gal(β1–4)GlcNAc(β1–6)]Gal(β1–3)Gal(β1–4)Glc (galactosyl lacto-N-novopentaose II), Gal(β1–3)[Gal(β1–3)Gal(β1–4)GlcNAc(β1–6)]Gal(β1–4)Glc (galactosyl lacto-N-novopentaose III) and Gal(β1–3)[Gal(β1–4)GlcNAc(β1–6)]Gal(β1–3)[Gal(β1–4)GlcNAc(β1–6)]Gal(β1–4)Glc (lacto-N-novooctaose). The structures of the acidic oligosaccharides detected are Neu5Ac(α2–3)Gal(β1–4)Glc (3’-sialyllactose), Gal(β1–3)(O-3-sulfate)[Gal(β1–4)GlcNAc(β1–6)]Gal(β1–4)Glc (lacto-N-novopentaose I sulfate a), Gal(β1–3)[Gal(β1–4)(O-3-sulfate)GlcNAc(β1–6)]Gal(β1–4)Glc (lacto-N-novopentaose I sulfate b), 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(α2–3)Gal(β1–4)GlcNAc(β1–6)]Gal(β1–4)Glc (sialyl lacto-N-novopentaose c), Neu5Ac(α2–3) Gal(β1–3)[Gal(β1–4)GlcNAc(β1–6)]Gal(β1–3)[Gal(β1–4)GlcNAc(β1–6)]Gal(β1–4)Glc, and Gal(β1–3)[Gal(β1–4)GlcNAc(β1–6)]Gal(β1–3)[Gal(β1–4)GlcNAc(β1–6)]Gal(β1–4)Glc with an α(2–3) Neu5Ac linked to β(1–4)Gal residue of either branch of Gal(β1–4)GlcNAc(β1–6) units. The most predominant oligosaccharides in the carbohydrate fraction of mid-lactation milk were found to be lacto-N-novopentaose I and lacto-N-novooctaose, i.e., branched oligosaccharides that contain N-acetylglucosamine. The predominance of these branched oligosaccharides, rather than of a series of linear β(1–3) linked galacto oligosaccharides, appears to be the main feature of the eastern quoll milk oligosaccharides that differentiates them from those of the tammar wallaby and the brushtail possum.

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Authors and Affiliations

  1. Graduate School of Animal and Food Hygiene, Obihiro University of Agriculture & Vererinary Medicine, Obihiro, Hokkaido, 080-8555, Japan

    Tadasu Urashima, Yiliang Sun, Kenji Fukuda & Kentaro Hirayama

  2. Department of Food Science, Obihiro University of Agriculture & Veterinary Medicine, Obihiro, Hokkaido, 080-8555, Japan

    Tadashi Nakamura

  3. Faculty of Animal Science, Bogor Agricultural University, Bogor, 16680, Indonesia

    Epi Taufik

  4. Graduate School of Agriculture, Tohoku University, Sendai, 981-8555, Japan

    Tadao Saito

  5. 20 Templeton St., Cook, ACT, 2614, Australia

    Jim Merchant

  6. Institute for Applied Ecology, University of Canberra, Canberra, ACT, 2601, Australia

    Brian Green

  7. School of Molecular Biosciences, The University of Sydney, Sydney, NSW, 2006, Australia

    Michael Messer

Authors
  1. Tadasu Urashima
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  2. Yiliang Sun
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  3. Kenji Fukuda
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  4. Kentaro Hirayama
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  5. Epi Taufik
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  6. Tadashi Nakamura
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  7. Tadao Saito
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  8. Jim Merchant
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  9. Brian Green
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  10. Michael Messer
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Correspondence to Tadasu Urashima.

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Urashima, T., Sun, Y., Fukuda, K. et al. Chemical characterization of milk oligosaccharides of the eastern quoll (Dasyurus viverrinus). Glycoconj J 32, 361–370 (2015). https://doi.org/10.1007/s10719-015-9600-z

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  • DOI: https://doi.org/10.1007/s10719-015-9600-z

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