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

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

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
Volume1472
Issue number1-2
DOIs
Publication statusPublished - 1999 Oct 18

Keywords

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

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Molecular Biology

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