Natural Products

Glucosylceramide

Purity > 98%

Glcß1Cer

Glucosylcerebroside

1R, 2S, 3R, 4R, 5S glycosyl-2S, 3R, 4E, 8E-sphingadiene d18:2

Glucosyl (E,E)N(2-hydroxyhexadecanoyl)sphing4,8dienine.

MW	Stability	Product Number
714.04	1 year Storage -20oC	131304	Product Data

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.

Source: Soybean Physical State: Powder. Chemical Purity: >98%, by TLC. Molecular Species : Composed primarily (>98%) of ceramide with 4,8-sphingadiene (d18:2(delta4,delta8) and alpha-hydroxypalmitic acid (h16:0); the remainder has the same backbone with h18:0, h20:0, h22:0, h24:0 fatty acids.

Reference: 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.