N-[(1S,2R,3E)-1-[(4-O-β-D-Galactopyranosyl-β-D-glucopyranosyl)oxymethyl]-2-hydroxy-3-heptadecenyl]hexadecanamide

Description

C16 Lactosylceramide is an endogenous bioactive sphingolipid.¹ It forms membrane microdomains with Lyn kinase and the α_i subunits of inhibitory G protein-coupled receptors (GPCRs), suggesting a role in cell signaling. Plasma levels of C16 lactosylceramide are elevated in insulin-resistant cattle.² C16 Lactosylceramide is also upregulated in a mouse model of Niemann-Pick type C1 disease, a neurodegenerative cholesterol-sphingolipid lysosomal storage disorder.³

Definition

ChEBI: Beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-N-hexadecanoylsphingosine is a beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1')-N-acylsphingosine in which the acyl group specified is hexadecanoyl. It has a role as a mouse metabolite. It is functionally related to a hexadecanoic acid.

References

1. Iwabuchi, K., Nakayama, H., Oizumi, A., et al. Role of ceramide from glycosphingolipids and its metabolites in immunological and inflammatory responses in humans Mediators Inflamm. 2015,120748(2015).
2. Rico, J.E., Bandaru, V.V., Dorskind, J.M., et al. Plasma ceramides are elevated in overweight Holstein dairy cows experiencing greater lipolysis and insulin resistance during the transition from late pregnancy to early lactation J. Dairy Sci. 98(11),7757-7770(2015).
3. Praggastis, M., Tortelli, B., Zhang, J., et al. A murine Niemann-Pick C1 I1061T knock-in model recapitulates the pathological features of the most prevalent human disease allele J. Neurosci. 35(21),8091-8106(2015).