C24-Phytoceramide

Description

C24 Phytoceramide (t18:0/24:0) is a phytoceramide, which is a family of sphingolipids found in the intestine, kidney, and extracellular spaces of the stratum corneum of the mammalian epidermis.^1,2,3 C24 Phytoceramide (t18:0/24:0) is composed of a phytosphingosine backbone amine-linked to a C24 fatty acid chain. It has been used with other ceramides to create stratum corneum substitutes to study percutaneous penetration and psoriasis in vitro.^4,5 In a stratum corneum model of healthy skin, the incorporation of long-chain-containing phytoceramides, such as C24 phytoceramide (t18:0/24:0), increases permeability of the membrane in comparison with incorporation of dihydroceramides.⁶

Uses

N-Tetracosanoyl-phytosphingosine is an ester product.

Definition

ChEBI: N-tetracosanoylphytosphingosine is a phytoceramide compound having a tetracosanoyl group attached to the nitrogen atom. It has a role as a Saccharomyces cerevisiae metabolite. It is a N-(very-long-chain fatty acyl)-sphingoid base and a N-acylphytosphingosine.

References

1. Crossman, M.W., and Hirschberg, C.B. Biosynthesis of phytosphingosine by the rat J. Biol. Chem. 252(16),5815-5819(1977).
2. Omae, F., Miyazaki, M., Enomoto, A., et al. DES2 protein is responsible for phytoceramide biosynthesis in the mouse small intestine Biochem J. 379(Pt. 3),687-695(2004).
3. Mizutani, Y., Kihara, A., and Igarashi, Y. Identification of the human sphingolipid C₄-hydroxylase, hDES2, and its up-regulation during keratinocyte differentiation FEBS Lett. 563(1-3),93-97(2004).
4. de Jager, M., Groenink, W., van der Spek, J., et al. Preparation and characterization of a stratum corneum substitute for in vitro percutaneous penetration studies Biochim. Biophys. Acta 1758(5),636-644(2006).
5. Basse, L.H., Groen, D., and Bouwstra, J.A. Permeability and lipid organization of a novel psoriasis stratum corneum substitute Int. J. Pharm. 457(1),275-282(2013).
6. kolová, B., Kováik, A., Tesa, O., et al. Phytosphingosine, sphingosine and dihydrosphingosine ceramides in model skin lipid membranes: Permeability and biophysics Biochim. Biophys. Acta 1859(5),824-834(2017).