Glucosylceramide (Soy) | 131304
Glucocerebrosides (Soy, 98%)
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- Glucosylceramide (GluCer) is a major sphingolipid of plant tissue and, thus, abundant in nature and in dietary food sources. The lipid backbones of mammalian GluCer (sphingosine, d18:1(delta4), and ceramide) induce cell death (apoptosis) and inhibit colon carcinogenesis, it is critical to know the structures of GluCer present in plants as a first step toward understanding this potential link between diet and cancer. This study characterized the molecular species of GluCer from soybean and wheat by low-resolution, high-resolution and tandem mass spectrometry. Soybean GluCer was comprised primarily (>98%) of ceramide with 4,8-sphingadiene (d18:2(delta4,delta8)) and alpha- hydroxypalmitic acid (h16:0); the remainder had the same backbone with h18:0, h20:0, h22:0 and h24:0 fatty acids. Wheat GluCer had three major ceramide, d18:2(delta4,delta8) with h16:0, d18:1(delta8) with h16:0 and d18: 2(delta4,delta8) with h20:0, and smaller amounts of other homologs. These backbones differ from those of mammalian sphingolipids, which often have a delta4-double bond (but rarely a delta8-double bond), and have alpha-hydroxy fatty acids in only some cases. Previously unexplained fragmentations that were diagnostic for the type of sphingoid base backbone (i.e. by homolytic cleavage of the doubly allylic C-6-C-7 bond to yield a stable distonic allylic radical cation and an allylic radical neutral) were also identified. Hence this method should be useful in the identification of double bonds in sphingolipids, and structure-function relationships between sphingolipids and colon carcinogenesis.
Sullards, M.C., D.V. Lynch, A.H. Merrill Jr, and J. Adams. (2000). Structure determination of soybean and wheat glucosylceramides by tandem mass spectrometry. J Mass Spectrom 35:347-53.
- 1 Years
- CAS Number
CAS Registry Number is a Registered Trademark of the American Chemical Society
- Molecular Weight
- 714.025 (based on representative structure; may not reflect exact MW of compound)
- Cerebroside (Soy)
Production of Rare Phyto-Ceramides from Abundant Food Plant Residues Mathias Reisberg, Norbert Arnold, Andrea Porzel, Reinhard H. H. Neubert and Birgit Dräger J. Agric. Food Chem., Article ASAP DOI: 10.1021/acs.jafc.6b04275 Publication Date (Web): February 13, 2017 Copyright © 2017, American Chemical Society [PubMed]