TY - JOUR
T1 - Chemical characterization of milk oligosaccharides of the Japanese black bear, Ursus thibetanus japonicus
AU - Urashima, Tadasu
AU - Sumiyoshi, Wataru
AU - Nakamura, Tadashi
AU - Arai, Ikichi
AU - Saito, Tadao
AU - Komatsu, Takeshi
AU - Tsubota, Toshio
PY - 1999/10/18
Y1 - 1999/10/18
N2 - 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.
AB - 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.
KW - B- pentasaccharide
KW - B-tetrasaccharide
KW - Chemical structure
KW - Japanese black bear
KW - Milk
KW - NMR
KW - Oligosaccharide
UR - http://www.scopus.com/inward/record.url?scp=0032876328&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0032876328&partnerID=8YFLogxK
U2 - 10.1016/S0304-4165(99)00134-8
DO - 10.1016/S0304-4165(99)00134-8
M3 - Article
C2 - 10572951
AN - SCOPUS:0032876328
SN - 0006-3002
VL - 1472
SP - 290
EP - 306
JO - Biochimica et Biophysica Acta - General Subjects
JF - Biochimica et Biophysica Acta - General Subjects
IS - 1-2
ER -