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Isotopic labeling of milk disialogangliosides (GD3)

journal contribution
posted on 2023-05-03, 16:54 authored by Mariza Gomes Reis, Rodrigo Bibiloni, Paul McJarrow, Alastair MacGibbon, Bertram Fong, Shalome Bassett, Nicole Roy, Marlon M.Reis
The most abundant ganglioside group in both human milk and bovine milk during the first postnatal week is ganglioside GD3. This group of disialogangliosides forms up to 80% of the total ganglioside content of colostrum. Although dietary gangliosides have shown biological activity such as improvement of cognitive development, gastrointestinal health, and immune function, there is still a gap in our understanding of the molecular mechanisms governing its uptake and the metabolic processes affecting its bioavailability. The use of isotopically labeled ganglioside to track the bioavailability, absorption, distribution, and metabolism of gangliosides may provide key information to bridge this gap. However, isotope labeled GD3 is not commercially available and its preparation has not been described. We report for the first time the preparation of labeled GD3 with stable isotopes. Using alkaline hydrolysis, we were able to selectively remove both acetyl groups from the tetrasaccharide portion of GD3 without promoting significant hydrolysis of the ceramide portion of the molecule to generate N-deacetyl-GD3 (Neu5a2- 8Neu5-GD3). The N-deacetyl-GD3 was then chemoselectively re-acetylated in aqueous medium using deuterated acetic anhydride in the presence of Triton X 100 to produce 2H6-GD3 {GD3[(Neu5Ac-11-2H3)- (Neu5Ac-11-2H3)]}. This method provided 2H6-GD3 with approximately 60% yield. This compound was characterized by proton nuclear magnetic resonance (1H NMR) and liquid chromatography mass spectrometry (LC–MS). The oral absorption of the 2H6-GD3 was demonstrated using a Sprague-Dawley weaning rats. Our results indicate that some ingested labeled milk gangliosides are absorbed and transported into the bloodstream without modification.

History

Rights statement

© 2016 Elsevier Ireland Ltd. All rights reserved.

Language

  • English

Does this contain Māori information or data?

  • No

Publisher

Elsevier

Journal title

Chemistry and Physics of Lipids

ISSN

0009-3084

Citation

Gomes Reis, M., Bibiloni, R., McJarrow, P., MacGibbon, A., Fong, B., Bassett, S., Roy, N., & M.Reis, M. (2016). Isotopic labeling of milk disialogangliosides (GD3). Chemistry and Physics of Lipids, 200, 104–112. doi:10.1016/j.chemphyslip.2016.08.003

Funder

AgResearch (Internal)

Contract number

A15358

Job code

13981

Report number

FBP 67112

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