Chemical characterization of milk oligosaccharides of the Japanese black bear, Ursus thibetanus japonicus

Tadasu Urashima, Wataru Sumiyoshi, Tadashi Nakamura, Ikichi Arai, Tadao Saito, Takeshi Komatsu, Toshio Tsubota

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    30 Citations (Scopus)


    Two trisaccharides, two tetrasaccharides, one penta-, one hexa-, two hepta-, one deca- and two undeca-saccharides were isolated from several Japanese black bear milk samples by chloroform/methanol extraction, gel filtration and preparative thin-layer chromatography. The oligosaccharides were characterized by 1H-NMR as follows: Gal(α 1-3)Gal(β 1-4)Glc (α 3'- galactosyllactose), Fuc(α 1-2)Gal(β 1-4)Glc (2'-fucosyllactose), Gal(α 1- 3)(Fuc(α 1-2))Gal(β 1-4)Glc (B-tetrasaccharide), Gal(α 1-3)Gal(β 1- 4)(Fuc(α 1-3))Glc, Gal(α 1-3)[Fuc(α 1-2)]Gal(β 1-4)[Fuc(α 1-3)]Glc (B- pentasaccharide), Gal(α 1-3)Gal(β 1-4)[Fuc(α 1-3)]GlcNAc(β 1-3)Gal(β 1- 4)Glc (monofucosylhexasaccharide), Gal(α 1-3)[Fuc(α 1-2)]Gal(β 1-4)[Fuc(α 1-3)]GlcNAc(β 1-3)Gal(β 1-4)Glc (difucosylheptasaccharide), Gal(α 1- 3)Gal(β 1-4)[Fuc(α 1-3)]GlcNAc(β 1-3)Gal(β 1-4)[Fuc(α 1-3)]Glc (difucosylheptasaccharide), Gal(α 1-3)Gal(β 1-4)[Fuc(α 1-3)]GlcNAc(β 1- 3){Gal(α 1-3)Gal(β 1-4)[Fuc(α 1-3)]GlcNAc(β 1-6)}Gal(β 1-4)Glc (difucosyldecasaccharide), Gal(α 1-3)[Fuc(α 1-2)]Gal(β 1-4)[Fuc(α 1- 3)]GlcNAc(β 1-3){Gal(α 1-3) Gal(β 1-4)[Fuc(α 1-3)]GlcNAc(β 1-6)}Gal(β 1-4)Glc (trifucosylundecasaccharide), Gal(α 1-3)Gal(β 1-4)[Fuc(α 1- 3)]GlcNAc(β 1-3){Gal(α 1-3)[Fuc(α 1-2)]Gal(β 1-4)[Fuc(α 1-3)]GlcNAc(β 1-6)}Gal(β 1-4)Glc (trifucosylundecasaccharide). Lactose was present only in trace amounts. B-pentasaccharide was a dominant saccharide in early lactation milk, while α 3'-galactosyllactose was dominant in milk, later. The milk oligosaccharides of the Japanese black bear were compared with those of the Ezo brown bear.

    Original languageEnglish
    Pages (from-to)290-306
    Number of pages17
    JournalBiochimica et Biophysica Acta - General Subjects
    Issue number1-2
    Publication statusPublished - 1999 Oct 18


    • B- pentasaccharide
    • B-tetrasaccharide
    • Chemical structure
    • Japanese black bear
    • Milk
    • NMR
    • Oligosaccharide

    ASJC Scopus subject areas

    • Biophysics
    • Biochemistry
    • Molecular Biology


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