Chemical characterization of milk oligosaccharides of the common wombat (Vombatus ursinus)

K Hirayama, E Taufik, Megumi Kikuchi, T Nakamura, K Fukuda, T Saito, Keith Newgrain, Brian Green, M Messer, T Urashima

    Research output: Contribution to journalArticle

    5 Citations (Scopus)

    Abstract

    Previous structural characterizations of marsupial milk oligosaccharides have been performed in the tammar wallaby, red kangaroo, koala, common brushtail possum and the eastern quoll. To clarify the homology and heterogeneity of milk oligosaccharides among marsupial species, which could provide information on their evolution, the oligosaccharides of wombat milk carbohydrate were characterized in this study. Neutral and acidic oligosaccharides were isolated from the carbohydrate fractions of two samples of milk of the common wombat and characterized by 1H-nuclear magnetic resonance spectroscopy. The structures of six 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(β1-3)Gal(β1-3)Gal(β1-4)Glc, Gal(β1-3)Gal(β1-3)[Gal(β1-4)GlcNAc(β1-6)]Gal(β1-4)Glc (galactosyl lacto-N-novopentaose I) 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), while those of six acidic saccharides were Neu5Ac(α2-3)Gal(β1-3)Gal(β1-4)Glc. (sialyl 3'-galactosyllactose), Neu5Ac(α2-3)Gal(β1-3)Gal(β1-3)Gal(β1-4)Glc (sialyl 3',3”-digalactosyllactose), 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(β1-3)Gal(β1-3)Gal(β1-4)Glc,, Neu5Ac(α2-3)Gal(β1-3)Gal(β1-3)[Gal(β1-4)GlcNAc(β1-6)]Gal(β1-4)Glc and Gal(β1-3)Gal(β1-3)[Neu5Ac(α2-3)Gal(β1-4)GlcNAc(β1-6)]Gal(β1-4)Glc. In addition, small amounts of sulfated oligosaccharides but no oligosaccharides containing Neu5Gc or α(2–6) linked Neu5Ac were detected.

    Original languageEnglish
    Pages (from-to)1167-1177
    Number of pages11
    JournalAnimal Science Journal
    Volume87
    Issue number9
    DOIs
    Publication statusPublished - 2016

    Fingerprint

    Oligosaccharides
    oligosaccharides
    Milk
    milk
    carbohydrates
    Metatheria
    Macropus eugenii
    Macropodidae
    lactose
    galactosyl-(1-3)galactose
    nuclear magnetic resonance spectroscopy
    Marsupialia
    glucose tetrasaccharide
    Phascolarctidae
    Carbohydrates
    sampling
    Lactose
    N-acetylglucosamine hexasaccharide 1-4

    Cite this

    Hirayama, K., Taufik, E., Kikuchi, M., Nakamura, T., Fukuda, K., Saito, T., ... Urashima, T. (2016). Chemical characterization of milk oligosaccharides of the common wombat (Vombatus ursinus). Animal Science Journal, 87(9), 1167-1177. https://doi.org/10.1111/asj.12566
    Hirayama, K ; Taufik, E ; Kikuchi, Megumi ; Nakamura, T ; Fukuda, K ; Saito, T ; Newgrain, Keith ; Green, Brian ; Messer, M ; Urashima, T. / Chemical characterization of milk oligosaccharides of the common wombat (Vombatus ursinus). In: Animal Science Journal. 2016 ; Vol. 87, No. 9. pp. 1167-1177.
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    abstract = "Previous structural characterizations of marsupial milk oligosaccharides have been performed in the tammar wallaby, red kangaroo, koala, common brushtail possum and the eastern quoll. To clarify the homology and heterogeneity of milk oligosaccharides among marsupial species, which could provide information on their evolution, the oligosaccharides of wombat milk carbohydrate were characterized in this study. Neutral and acidic oligosaccharides were isolated from the carbohydrate fractions of two samples of milk of the common wombat and characterized by 1H-nuclear magnetic resonance spectroscopy. The structures of six 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(β1-3)Gal(β1-3)Gal(β1-4)Glc, Gal(β1-3)Gal(β1-3)[Gal(β1-4)GlcNAc(β1-6)]Gal(β1-4)Glc (galactosyl lacto-N-novopentaose I) 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), while those of six acidic saccharides were Neu5Ac(α2-3)Gal(β1-3)Gal(β1-4)Glc. (sialyl 3'-galactosyllactose), Neu5Ac(α2-3)Gal(β1-3)Gal(β1-3)Gal(β1-4)Glc (sialyl 3',3”-digalactosyllactose), 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(β1-3)Gal(β1-3)Gal(β1-4)Glc,, Neu5Ac(α2-3)Gal(β1-3)Gal(β1-3)[Gal(β1-4)GlcNAc(β1-6)]Gal(β1-4)Glc and Gal(β1-3)Gal(β1-3)[Neu5Ac(α2-3)Gal(β1-4)GlcNAc(β1-6)]Gal(β1-4)Glc. In addition, small amounts of sulfated oligosaccharides but no oligosaccharides containing Neu5Gc or α(2–6) linked Neu5Ac were detected.",
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    author = "K Hirayama and E Taufik and Megumi Kikuchi and T Nakamura and K Fukuda and T Saito and Keith Newgrain and Brian Green and M Messer and T Urashima",
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    Hirayama, K, Taufik, E, Kikuchi, M, Nakamura, T, Fukuda, K, Saito, T, Newgrain, K, Green, B, Messer, M & Urashima, T 2016, 'Chemical characterization of milk oligosaccharides of the common wombat (Vombatus ursinus)', Animal Science Journal, vol. 87, no. 9, pp. 1167-1177. https://doi.org/10.1111/asj.12566

    Chemical characterization of milk oligosaccharides of the common wombat (Vombatus ursinus). / Hirayama, K; Taufik, E; Kikuchi, Megumi; Nakamura, T; Fukuda, K; Saito, T; Newgrain, Keith; Green, Brian; Messer, M; Urashima, T.

    In: Animal Science Journal, Vol. 87, No. 9, 2016, p. 1167-1177.

    Research output: Contribution to journalArticle

    TY - JOUR

    T1 - Chemical characterization of milk oligosaccharides of the common wombat (Vombatus ursinus)

    AU - Hirayama, K

    AU - Taufik, E

    AU - Kikuchi, Megumi

    AU - Nakamura, T

    AU - Fukuda, K

    AU - Saito, T

    AU - Newgrain, Keith

    AU - Green, Brian

    AU - Messer, M

    AU - Urashima, T

    PY - 2016

    Y1 - 2016

    N2 - Previous structural characterizations of marsupial milk oligosaccharides have been performed in the tammar wallaby, red kangaroo, koala, common brushtail possum and the eastern quoll. To clarify the homology and heterogeneity of milk oligosaccharides among marsupial species, which could provide information on their evolution, the oligosaccharides of wombat milk carbohydrate were characterized in this study. Neutral and acidic oligosaccharides were isolated from the carbohydrate fractions of two samples of milk of the common wombat and characterized by 1H-nuclear magnetic resonance spectroscopy. The structures of six 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(β1-3)Gal(β1-3)Gal(β1-4)Glc, Gal(β1-3)Gal(β1-3)[Gal(β1-4)GlcNAc(β1-6)]Gal(β1-4)Glc (galactosyl lacto-N-novopentaose I) 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), while those of six acidic saccharides were Neu5Ac(α2-3)Gal(β1-3)Gal(β1-4)Glc. (sialyl 3'-galactosyllactose), Neu5Ac(α2-3)Gal(β1-3)Gal(β1-3)Gal(β1-4)Glc (sialyl 3',3”-digalactosyllactose), 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(β1-3)Gal(β1-3)Gal(β1-4)Glc,, Neu5Ac(α2-3)Gal(β1-3)Gal(β1-3)[Gal(β1-4)GlcNAc(β1-6)]Gal(β1-4)Glc and Gal(β1-3)Gal(β1-3)[Neu5Ac(α2-3)Gal(β1-4)GlcNAc(β1-6)]Gal(β1-4)Glc. In addition, small amounts of sulfated oligosaccharides but no oligosaccharides containing Neu5Gc or α(2–6) linked Neu5Ac were detected.

    AB - Previous structural characterizations of marsupial milk oligosaccharides have been performed in the tammar wallaby, red kangaroo, koala, common brushtail possum and the eastern quoll. To clarify the homology and heterogeneity of milk oligosaccharides among marsupial species, which could provide information on their evolution, the oligosaccharides of wombat milk carbohydrate were characterized in this study. Neutral and acidic oligosaccharides were isolated from the carbohydrate fractions of two samples of milk of the common wombat and characterized by 1H-nuclear magnetic resonance spectroscopy. The structures of six 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(β1-3)Gal(β1-3)Gal(β1-4)Glc, Gal(β1-3)Gal(β1-3)[Gal(β1-4)GlcNAc(β1-6)]Gal(β1-4)Glc (galactosyl lacto-N-novopentaose I) 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), while those of six acidic saccharides were Neu5Ac(α2-3)Gal(β1-3)Gal(β1-4)Glc. (sialyl 3'-galactosyllactose), Neu5Ac(α2-3)Gal(β1-3)Gal(β1-3)Gal(β1-4)Glc (sialyl 3',3”-digalactosyllactose), 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(β1-3)Gal(β1-3)Gal(β1-4)Glc,, Neu5Ac(α2-3)Gal(β1-3)Gal(β1-3)[Gal(β1-4)GlcNAc(β1-6)]Gal(β1-4)Glc and Gal(β1-3)Gal(β1-3)[Neu5Ac(α2-3)Gal(β1-4)GlcNAc(β1-6)]Gal(β1-4)Glc. In addition, small amounts of sulfated oligosaccharides but no oligosaccharides containing Neu5Gc or α(2–6) linked Neu5Ac were detected.

    KW - common wombat

    KW - marsupial

    KW - milk oligosaccharide

    KW - Vombatus ursinus

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    UR - http://www.mendeley.com/research/chemical-characterization-milk-oligosaccharides-common-wombat-vombatus-ursinus

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