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  • Analysis of 1-Deoxysphingoid Bases and Their N-Acyl Metabolites and Exploration of Their Occurrence in Some Food Materials.

Analysis of 1-Deoxysphingoid Bases and Their N-Acyl Metabolites and Exploration of Their Occurrence in Some Food Materials.

Journal of agricultural and food chemistry (2019-10-23)
Junliang Wan, Jian Li, Sibali Bandyopadhyay, Samuel L Kelly, Yang Xiang, Jin Zhang, Alfred H Merrill, Jingjing Duan
ABSTRACT

Most common sphingolipids are comprised of "typical" sphingoid bases (sphinganine, sphingosine, and structurally related compounds) and are produced via the condensation of l-serine with a fatty acyl-CoA by serine palmitoyltransferase. Some organisms, including mammals, also produce "atypical" sphingoid bases that lack a 1-hydroxyl group as a result of the utilization of l-alanine or glycine instead of l-serine, resulting in the formation of 1-deoxy- or 1-desoxymethylsphingoid bases, respectively. Elevated production of "atypical" sphingolipids has been associated with human disease, but 1-deoxysphingoid bases have also been found to have potential as anticancer compounds, hence, the importance of knowing more about the occurrence of these compounds in food. Most of the "typical" and "atypical" sphingoid bases are found as the N-acyl metabolites (e.g., ceramides and 1-deoxyceramides) in mammals, but this has not been uniformly assessed in previous studies nor determined in consumed food. Therefore, we developed a method for the quantitative analysis of "typical" and "atypical" sphingoid bases and their N-acyl derivatives by reverse-phase liquid chromatography coupled to electrospray ionization tandem mass spectrometry. On the basis of these analyses, there was considerable variability in the amounts and molecular subspecies of atypical sphingoid bases and their N-acyl metabolites found in different edible sources. These findings demonstrate that a broader assessment of the types of sphingolipids in foods is needed because some diets might contain sufficient amounts of atypical as well as typical sphingolipids that could have beneficial or possibly deleterious effects on human health.

MATERIALS
Product Number
Brand
Product Description

Avanti
18:1 Lyso PA, Avanti Research - A Croda Brand
Avanti
N-C24:1-desoxymethylsphingosine, Avanti Research - A Croda Brand 860468P, powder
Avanti
N-C12-deoxysphingosine, N-lauroyl-1-deoxysphingosine (m18:1/12:0), powder
Avanti
N-C16-desoxymethylsphingosine, Avanti Research - A Croda Brand 860467P, powder
Avanti
N-C12-desoxymethylsphingosine, Avanti Research - A Croda Brand 860466P, powder
Avanti
N-C24:1-deoxysphinganine, Avanti Research - A Croda Brand 860464P, powder
Avanti
1-deoxysphinganine-d3, Avanti Research - A Croda Brand 860474P, powder
Avanti
16:0-17:0 cyclo PC, Avanti Research - A Croda Brand 857501P, powder
Avanti
NBD Sphinganine, omega(7-nitro-2-1,3-benzoxadiazol-4-yl)(2S,3R)-2-aminooctadecane-1,3-diol, powder