Citation: WANG Hai-Yan, ZHANG Xi-Mei, CUI Xiu-Xiu, KANG Peng, ZHANG Yan, ZHANG Jia-Ying, GE Wu-Peng. Structural Analysis of Human Milk Oligosaccharides via High Resolution Mass Spectrometry and Optimization of Chromatographic Separation Conditions[J]. Chinese Journal of Analytical Chemistry, ;2022, 50(2): 278-289. doi: 10.19756/j.issn.0253-3820.210603 shu

Structural Analysis of Human Milk Oligosaccharides via High Resolution Mass Spectrometry and Optimization of Chromatographic Separation Conditions

1.
College of Food Science and Engineering, Northwest A&F University, Yangling 712100, China;
2.
Xi'an Baiyue Goat Group Co. Ltd., Xi'an 710000, China;
3.
Shaanxi Goat Milk Product Quality Supervision and Inspection Center, Fuping 711700, China

Corresponding author: GE Wu-Peng, josephge@nwafu.edu.cn
Received Date: 1 July 2021
Revised Date: 25 November 2021

Fund Project: Supported by the School-Enterprise Cooperation Project (No.K4030220076)

Human milk oligosaccharides (HMOs) are closely related to the growth and development of infants in early life. In this study, the structures of 19 HMOs (16 neutral HMOs and 3 sialylated HMOs) were analyzed by ultra-high performance liquid chromatography-high resolution mass spectrometry (UHPLC-HRMS). Based on the cleavage rules of oligosaccharide isomers, the differences of fragment ions among the four groups of isomers were discussed. The separation effects of HMOs isomers under three different UHPLC conditions were compared, which provided scientific basis for the structural analysis of complex HMOs isomers and the selection of UHPLC conditions.
1. [1]
  STAHL B, THURL S, ZENG J, KARAS M, HILLENKAMP F, STEUP M, SAWATZKIT G. Anal. Biochem., 1994, 223(2): 218-226.
2. [2]
  SOUSA Y R F, MEDEIROS L B, PINTADO M M E, QUEIROGA R C R E. Trends Food Sci. Technol., 2019, 92: 152-161.
3. [3]
  ZIVKOVIC A M, GERMAN J B, LEBRILLA C B, MILLS D A. Proc. Natl. Acad. Sci. U. S. A., 2011,108(Suppl 1): 4653-4658.
4. [4]
  THURL S, MUNZERT M, HENKER J, BOEHM G, MULLER-WERNER B, JELINEK J, STAHL B. Br. J. Nutr., 2010, 104(9): 1261-1271.
5. [5]
  MEHRA R, KELLY P. Int. Dairy J., 2006, 16(11): 1334-1340.
6. [6]
7. [7]
  ALDREDGE D L, GERONIMO M R, HUA S, NWOSU C C, LEBRILLA C B, BARILE D. Glycobiology, 2013, 23(6): 664-676.
8. [8]
  CHAI W, PISKAREV V E, ZHANG Y, LAWSON A M, KOGELBERG H. Arch. Biochem. Biophys., 2005,434(1): 116-127.
9. [9]
  KAILEMIA M J, RUHAAK L R, LEBRILLA C B, AMSTER I J. Anal. Chem., 2014, 86(1): 196-212.
10. [10]
  ELWAKIEL M, HAGEMAN J A, WANG W, SZETO I M, VAN GOUDOEVER J B, HETTINGA K A,SCHOLS H A. J. Agric. Food Chem., 2018, 66(27): 7036-7043.
11. [11]
  MARTIN-ORTIZ A, BARILE D, SALCEDO J, MORENO F J, CLEMENTE A, RUIZ-MATUTE A I, SANZ M L. J. Agric. Food Chem., 2017, 65(17): 3523-3531.
12. [12]
13. [13]
14. [14]
15. [15]
16. [16]
17. [17]
  WEI J, WANG Z A, WANG B, JAHAN M, WANG Z F, WYNN P C, DU Y G. Sci. Rep., 2018, 8: 4688.
18. [18]
  LU J, ZHANG Y, SONG B, ZHANG S W, PANG X Y, SARI R N, LIU L, WANG J H, LV J P. Carbohydr. Polym., 2020, 235: 115965.
19. [19]
  XU G, DAVIS J C, GOONATILLEKE E, SMILOWITZ J T, GERMAN J B, LEBRILLA C B. J. Nutr., 2017,147(1): 117-124.
20. [20]
  RAMAKRISHNAN B, BOEGGEMAN E, QASBA P K. Biochem. Biophys. Res. Commun., 2002, 291(5): 1113-1118.
21. [21]
  KOBATA A. Chang Gung Med. J., 2003, 26(9): 621-636.
22. [22]
  MCGUIRE M, MCGUIRE M A, BODE L. Prebiotics and Probiotics in Human Milk: Origins and Functions of Milk-Borne Oligosaccharides and Bacteria. USA: Academic Press, 2016: 24-39.
23. [23]
  WU S, TAO N, GERMAN J B, GRIMM R, LEBRILLA C B. J. Proteome Res., 2010, 9: 4138-4151.
24. [24]
  BODE L. Glycobiology, 2012, 22(9): 1147-1162.
25. [25]
  AYECHU-MURUZABAL V, VAN STIGT A H, MANK M, WILLEMSEN L E M, STAHL B, GARSSEN J,VAN'T LAND B. Front. Pediatr., 2018, 6: 239.
26. [26]
  DOMON B, COSTELLO C E. Glycoconjugate J., 1988, 5(4): 397-405.
27. [27]
  CHAI W, PISKAREV V, LAWSON A M. Anal. Chem., 2001, 73(3): 651-657.
28. [28]
  WU S, GRIMM R, GERMAN J B, LEBRILLA C B. J. Proteome Res., 2011, 10: 856-868.
29. [29]
  ZHANG H, ZHANG S, TAO G, ZHANG Y, MULLOY B, ZHAN X, CHAI W. Anal. Chem., 2013, 85(12): 5940-5949.
30. [30]
  BLACK B A, LEE V S, ZHAO Y Y, HU Y, CURTIS J M, GANZLE M G. J. Agric. Food Chem., 2012,60(19): 4886-4894.
31. [31]
  CHAI W, LAWSON A M, PISKAREV V. J. Am. Soc. Mass Spectrom., 2002, 13: 670-679.
32. [32]
  WHEELER S F, HARVEY D J. Anal. Chem., 2000, 70(20): 5027-5039.
33. [33]
  VAZQUEZ E, SANTOS-FANDILA A, BUCK R, RUEDA R, RAMIREZ M. Br. J. Nutr., 2017, 117(2): 237-247.
34. [34]
  JANTSCHER-KRENN E, TREICHLER C, BRANDL W, SCHONBACHER L, KOFELER H, VAN POPPEL M N. Am. J. Clin. Nutr., 2019, 110(6): 1335-1343.
35. [35]
  JAMES K, BOTTACINI F, CONTRERAS J I S, VIGOUREUX M, EGAN M, MOTHERWAY M O C, HOLMES E, VAN SINDEREN D. Sci. Rep., 2019, 9: 15427.
36. [36]
  LIU Z, AULDIST M, WRIGHT M, COCKS B, ROCHFORT S. J. Agric. Food Chem., 2017, 65(7): 1307-1313.
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