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Whey2014 (Urashima) Revised
Whey2014 (Urashima) Revised
Lactose Sialyllactose
1,4 2,3 1,4
Fucosyllactose Lacto-N-neotetraose
1,2 1,4 1,4 1,3 1,4
Lacto-N-hexaose
1,4 1,6 : Galactose
: Glucose
1,4
: Fucose
: Sialic acid
1,4 1,3
: N-acethylglucosamine
Bio functions of human milk oligosaccharides
2. Prebiotics
1.GalNAc(1-4)GlcNAc
2. GalNAc(1-4)Glc
5. GalNAc(1-3)Gal(1-4)Glc
6. GlcNAc(1-3)Gal(1-4)Glc
7. Gal(1-6)Gal(1-4)Glc (6-GL)
8. Gal(1-3)Gal(1-4)Glc (isoglobotriose)
9. Gal(1-3)Gal(1-4)Glc (3-GL)
11. Fuc(1-2)Gal(1-4)Glc
GalNAc(1-3)
13. Gal(1-4)GlcNAc(1-6)
Gal(1-4)Glc
GlcNAc(1-3)
14. Gal(1-4)GlcNAc(1-6)
Gal(1-3) Gal(1-4)Glc (lacto-N-novopentaose 1)
15. Gal(1-4)GlcNAc(1-6)
Gal(1-4)GlcNAc(1-3) Gal(1-4)Glc (lacto-N-neohexaose)
Acidic Bovine Milk Oligosaccharides Characterized by Marino et al.
16.Neu5Ac(2-3)Gal(1-4)GlcNAc(1-3)Gal(1-4)Glc
17. Neu5Ac(2-6)Gal(1-4)GlcNAc(1-3)Gal(1-4)Glc
18. Neu5Ac(2-3)Gal(1-4)GlcNAc(1-6)
Gal(1-4)Glc
GlcNAc(1-3)
19.
Gal(1-4)GlcNAc(1-6)
Neu5Ac(2-3) Gal(1-3)
Gal(1-4)Glc
20. Neu5Ac(2-6)Gal(1-4)GlcNAc(1-6)
Gal(1-4)Glc
GlcNAc(1-3)
21. Neu5Ac(2-6)Gal(1-4)GlcNAc(1-6)
Gal(1-3) Gal(1-4)Glc
22.
Gal(1-4)GlcNAc(1-6)
Neu5Ac(2-3) Gal(1-4)Glc
Gal(1-4)GlcNAc(1-3)
23.
Gal(1-4)GlcNAc(1-6)
Neu5Ac(2-6)
Gal(1-4)GlcNAc(1-3)
Gal(1-4)Glc
28. Neu5Gc(2-6)Gal(1-4)GlcNAc
30. Neu5Gc(2-6)Gal(1-4)Glc
31. Neu5Ac(2-6)Gal(1-4)Glc
GlcNAc(1-3)
32. Neu5Ac(2-3)Gal(1-4)Gal(1-4)Glc
33. Neu5Ac(2-6)Gal(1-4)Glc
Gal(1-3)
35. Neu5Gc(2-8)Neu5Ac(2-3)Gal(1-4)Glc
36. Neu5Ac(2-8)Neu5Gc(2-3)Gal(1-4)Glc
37. Neu5Ac(2-8)Neu5Ac(2-3)Gal(1-4)GlcNAc
Differences between the milk oligosaccharides of human and cows
HMOs
2224 g/L in colostrum
1213 g/L in mature milk
more than 200 varieties
Gal(1-3)GlcNAc containing HMO (type) >Gal(1-4)GlcNAc containing HMO (type)
neutral HMO >acidic HMO
BMOs
more than 1 g/L in colostrum
small concentration in mature milk
around 40 varieties
typeBMOs, typeBMOs
acidic BMO > neutral BMO,70% ; Neu5Ac(2-3)Gal(1-4)Glc
The concentration of fucosyl oligosaccharides is very low
Gal(1-3)Gal(1-4)Glc, GalNAc(1-3)Gal(1-4)Glc
Neu5Gc containing BMO
Sialyl galactosyllactose
Minor fucosyl BMOs characterizaed in recent study
Annotation and structural elucidation of bovine milk oligosaccharides and determination
of novel fucosylated structures
D.L.Aldredge, M.R.Geronimo, S.Hua, C.C.Nwosu, C.B.Lebrilla, D.Barile
Glycobiology 23,664,2013
Fuc
Fuc
0.8
0.6 0.1
0.4
0.2
0 0
24 48 72 96 120 144 168 0 24 48 72 96 120 144 168
0
Time post partum (h) Time post partum (h)
0.2
6'SLN concentration (g/L)
0.1
0
0 24 48 72 96 120 144 168
Time post partum (h)
3SL ( mg/L) 6SL (mg/L) 6SLN ( mg/L) DSL ( mg/L) GNL ( mg/L)
a a
Skim milk 1 51 4 (30,9%) 6.3 0.4 (8,6%) 0.13 0.02 (2,14%) 1.5 0.1 (2,6%) 2.6 0.3 (2,10%)
Skim milk 2 a a
55 4 (2, 6%) 9 0.2 (2, 2%) 0.10 0.02 (2, 17%) 2.1 0.3 (2, 14%) 3.4 0.4 (2, 13%)
Homogenized milk a a
48 4 (6, 8%) 9.6 0.8 (3, 8%) 0.1 0.03 (3, 14%) 3.1 0.2 (3, 6%) 2.4 0.1 (3, 2%)
Unpasteurized milk a
47 4 (6, 9%) 3.6 0.3 (2, 9%) <LOD (2) 0.54 0.01 (2,14%) <LOD (2%)
Mature milk
94-119 67-88 145-176 41-77
(Martin-Sosa et al.)
Mature milk
35-50 14-25 9-12 2-7 3-4
(?g/mL, McJarrow and van
Amelsfort-Schoonbeek)
Mature milk
30 25 12 ND
(7 d post partum, Nakamura et al.)
Colostrum (second milking) a
1245 82 (7, 85 6 (7, 7%) 119 7 (7, 6%) 126 8 (2, 8%) 1 0.1 (2, 12%)
7%)
Colostrum
354 147 210 135
(Martin-Sosa et al.)
Development of the innovative utilizations
of bovine colostrum components
1. Obihiro University of Agriculture & Veterinary Medicine, Graduate course of Food Hygiene
3. Kitasato University
Hemagglunitin
(HA) Neu5Ac-Gal-
OH COOH
HO OH OH
OH
HO O O HO OH
O O O
AcHN OH OH O
HN
OH n
O
Neu5Aca2-3Gal1-4Glc1-Cer
Ganglioside GM3
OH COOH
HO OH OH
OH
HO O O HO NH2
O O removal of NH4HCO3 by rotary evaporation
AcHN OH OH O
OH
3 -sialyllactosylamine (3 SL-NH2)
6'-SL-N-C14
3'-SL-N-C18
50
6'-SLN-N-C14
0 1 2 3 4 5 6 7 8 9
Days after infection
10000
5000
0
Potential utilization of bovine milk oligosaccharides