N-Stearoyl Phytosphingosine

• CAT Number: R046418
• CAS Number: 34354-88-6
• Molecular Formula: C36H73NO4
• Molecular Weight: 583.983
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]octadecanamide
• InChI: InChI=1S/C36H73NO4/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-35(40)37-33(32-38)36(41)34(39)30-28-26-24-22-20-16-14-12-10-8-6-4-2/h33-34,36,38-39,41H,3-32H2,1-2H3,(H,37,40)/t33-,34+,36-/m0/s1
• InChIKey: IEZRNEGTKRQRFV-LFBNJJMOSA-N
• SMILES: CCCCCCCCCCCCCCCCCC(=O)NC(CO)C(C(CCCCCCCCCCCCCC)O)O

N-Stearoyl phytosphingosine (SPS)(CAS: 34354-88-6) is a bioactive sphingolipid found in S. cerevisiae, wheat grains, and the stratum corneum layer of mammalian epidermis. SPS is composed of a phytosphingosine (Item No. 20217) backbone amine-linked to a C18 fatty acid chain. SPS has a role in regulation of apoptosis, cell differentiation, proliferation of smooth muscle cells, and inhibition of the mitochondrial respiratory chain. It is used in cosmetics as a skin protectant as it reduces water loss to prevent epidermal dehydration and irritation. SPS also inhibits expression of allergic cytokines IL-4, TNF-α, and transcription factors c-jun and NF-κB in histone stimulated murine skin tissue.

Reference

[1]. Clin Cosmet Investig Dermatol. 2017 Sep 13;10:363-371. doi: 10.2147/CCID.S143591. eCollection 2017.
Novel phytoceramides containing fatty acids of diverse chain lengths are better than a single C18-ceramide N-stearoyl phytosphingosine to improve the physiological properties of human stratum corneum.
Oh MJ(1), Cho YH(1), Cha SY(1), Lee EO(2), Kim JW(2), Kim SK(2), Park CS(1).
Author information: (1)Department of Chemical and Biochemical Engineering, Dongguk University, Chung-gu, Seoul. (2)LCS Biotech, Gwonseon-gu, Suwon-si, Gyeonggi-do, Republic of Korea.
Ceramides in the human stratum corneum (SC) are a mixture of diverse N-acylated fatty acids (FAs) with different chain lengths. C24 is the major class of FAs of ceramides. However, there are also other classes of ceramides with diverse chain lengths of FAs, and these lengths generally range from C16 to C26. This study aimed to prepare several types of phytoceramide containing diverse chain lengths of N-acylated FAs and compare them with C18-ceramide N-stearoyl phytosphingosine (NP) in terms of their effects on the physiological properties of the SC. We chose natural oils, such as horse fat oil, shea butter, sunflower oil, and a mixture of macadamia nut, shea butter, moringa, and meadowfoam seed oil, as sources of FAs and phytosphingosine as a sphingoid backbone to synthesize diverse phytoceramides. Each phytoceramide exhibited a distinctive formation of the lamellar structure, and their FA profiles were similar to those of their respective natural oil. The skin barrier properties, as analyzed in human skin, clearly demonstrated that all the phytoceramides improved the recovery rate of the damaged SC and enhanced hydration better than C18-ceramide NP did. In conclusion, natural oil-derived phytoceramides could represent a novel class of ceramides for cosmetic applications in the development of an ideal skin barrier moisturizer.
DOI: 10.2147/CCID.S143591 PMCID: PMC5602416 PMID: 28979153

[2]. Lipids. 2010 Jul;45(7):613-8. doi: 10.1007/s11745-010-3441-0. Epub 2010 Jun 29.
Anti-scratching behavioral effects of N-stearoyl-phytosphingosine and 4-hydroxysphinganine in mice.
Ryu KR(1), Lee B, Lee IA, Oh S, Kim DH.
Author information: (1)Department of Life and Nanopharmaceutical Sciences, Kyung Hee University, 1, Hoegi, Dongdaemun-ku, Seoul, 130-701, Korea.
N-Stearoyl-phytosphingosine (SPS) and 4-hydroxysphinganine (phytosphingosine, PS), which are sphingolipids frequently found in mammalian skin, plants, and yeast, have been used as ingredients in cosmetics. In mice, treatment with SPS and PS inhibited histamine-induced scratching behavior and vascular permeability. These agents inhibited the expression of the allergic cytokines, IL-4 and TNF-alpha, and the activation of the transcription factors, NF-kappaB and c-jun, in histamine-stimulated skin tissues. These agents also showed potent anti-histamine effects in the Magnus test using guinea pig ileum. Based on these results, SPS and PS may improve scratching behavioral reactions in skin by regulating the action of histamine and the activation of the transcription factors NF-kappaB and c-jun.
DOI: 10.1007/s11745-010-3441-0 PMID: 20585891 [Indexed for MEDLINE]

[3]. Int J Pharm. 2019 May 30;563:384-394. doi: 10.1016/j.ijpharm.2019.04.010. Epub 2019 Apr 5.
Probing the interactions among sphingosine and phytosphingosine ceramides with non- and alpha-hydroxylated acyl chains in skin lipid model membranes.
Čuříková-Kindlová BA(1), Diat O(2), Štěpánek F(3), Vávrová K(4), Zbytovská J(5).
Author information: (1)University of Chemistry and Technology Prague, Faculty of Chemical Technology, Department of Organic Technology, Technická 5, 166 28 Prague, Czech Republic. (2)Institute de Chimie Séparative de Marcoule, ICSM, CEA, CNRS, ENSCM, Univ Montpellier, Bagnols-sur-Cèze, France. (3)University of Chemistry and Technology Prague, Faculty of Chemical Engineering, Department of Chemical Engineering, Technická 5, 166 28 Prague, Czech Republic. (4)Charles University, Faculty of Pharmacy in Hradec Králové, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic. (5)University of Chemistry and Technology Prague, Faculty of Chemical Technology, Department of Organic Technology, Technická 5, 166 28 Prague, Czech Republic; Charles University, Faculty of Pharmacy in Hradec Králové, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic. Electronic address: .
Ceramides (Cers) are significant constituents of the stratum corneum (SC), the uppermost skin layer responsible for skin barrier properties. Cers are a heterogeneous group of lipids whose mutual interactions are still unclear. To better understand these interactions, we characterized model membranes containing stearic acid, cholesterol, cholesterol sulfate and one or more of the following ceramides: N-stearoyl-sphingosine (CerNS), N-stearoyl-phytosphingosine (CerNP) and N-(2-hydroxy)stearoyl-phytosphingosine (CerAP). Small angle X-ray scattering and FTIR spectroscopy were used to study lipid arrangement, phase separation and thermotropic behaviour. In the one-Cer systems, the membranes with CerNP showed strong hydrogen bonding and significant phase separation, even after phase transition, while the systems containing CerAP and CerNS had increased lipid miscibility. The multi-Cer systems exhibited different behaviour. In particular, the membrane containing all three Cers was a highly miscible system with narrow one-step phase transition, which, of all the studied samples, occurred at the lowest temperatures. Our results show that even a small variation in Cer structure results in substantially different phase behaviour, which is further affected by the presence of other Cer subclasses. Interestingly, the phase behaviour of the most complex three-Cer system was simpler than that of the others, highlighting the importance of lipid diversity in real SC.
DOI: 10.1016/j.ijpharm.2019.04.010 PMID: 30959237 [Indexed for MEDLINE]

[4]. Eur Biophys J. 2016 Jan;45(1):91-8. doi: 10.1007/s00249-015-1101-2. Epub 2015 Dec 11.
Two types of syringomycin E channels in sphingomyelin-containing bilayers.
Efimova SS(1), Zakharova AA(2), Schagina LV(2), Ostroumova OS(2).
Author information: (1)Institute of Cytology of the Russian Academy of Sciences, Tikhoretsky Ave. 4, St. Petersburg, Russia, 194064. . (2)Institute of Cytology of the Russian Academy of Sciences, Tikhoretsky Ave. 4, St. Petersburg, Russia, 194064.
The influence of dipole modifiers on the characteristics of single syringomycin E (SRE) channels in bilayers comprising DOPS, DOPE, sphingolipids (sphingomyelin, N-stearoyl-phytosphingosine or N-stearoyl-sphinganine) and sterols (cholesterol or ergosterol) was studied. The effects of dipole modifiers on SRE channel amplitudes were dependent upon the sphingolipid type and were not affected by the membrane sterol content. A decrease in the dipole potential of phytosphingosine- and sphinganine-containing bilayers, which was induced by the adsorption of phloretin, led to a reduction in conductance; however, an increase in this potential, which occurred upon the addition of RH 421, led to an enhancement in the conductance of SRE channels. Two channel populations, one of which is sensitive while the other is insensitive to modifiers, were found in sphingomyelin-containing bilayers. This indicates that SRE channels are distributed in lipid domains with different dipole potentials.
DOI: 10.1007/s00249-015-1101-2 PMID: 26658744 [Indexed for MEDLINE]

[5]. J Phys Chem B. 2017 Nov 2;121(43):10091-10104. doi: 10.1021/acs.jpcb.7b08967. Epub 2017 Oct 20.
Molecular Dynamics Simulations of Ceramide and Ceramide-Phosphatidylcholine Bilayers.
Wang E(1), Klauda JB(1).
Author information: (1)Department of Chemical and Biomolecular Engineering and ‡Biophysics Graduate Program, University of Maryland , College Park, Maryland 20742, United States.
Recent studies in lipid raft formation and stratum corneum permeability have focused on the role of ceramides (CER). In this study, we use the all-atom CHARMM36 (C36) force field to simulate bilayers using N-palmitoylsphingosine (CER16) or α-hydroxy-N-stearoyl phytosphingosine (CER[AP]) in 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) or 1-palmitoyl-2-oleoylphosphatidylcholine (POPC), which serve as general membrane models. Conditions are replicated from experimental studies for comparison purposes, and concentration (XCER) is varied to probe the effect of CER on these systems. Comparisons with experiment based on deuterium order parameters and bilayer thickness demonstrate good agreement, thus supporting further use of the C36 force field. CER concentration is shown to have a profound effect on nearly all membrane properties including surface area per lipid, chain order and tilt, area compressibility moduli, bilayer thickness, hydrogen bonding, and lipid clustering. Hydrogen bonding in particular can significantly affect other membrane properties and can even encourage transition to a gel phase. Despite CER's tendency to condense the membrane, an expansion of CER lipids with increasing XCER is possible depending on how the balance between various hydrogen-bond pairs and lipid clustering is perturbed. Based on gel phase transitions, support is given for phytosphingosine's role as a hydrogen-bond bridge between sphingosine ordered domains in the stratum corneum.
DOI: 10.1021/acs.jpcb.7b08967 PMID: 29017324