Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H39NO3.ClH |
| Molecular Weight | 353.968 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO
InChI
InChIKey=GDKAAHDFPOWGQE-RXQQAGQTSA-N
InChI=1S/C18H39NO3.ClH/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(21)18(22)16(19)15-20;/h16-18,20-22H,2-15,19H2,1H3;1H/t16-,17+,18-;/m0./s1
Phytosphingosine is structural analog of sphingolipids and is classified as long-chain sphingoid base. Phytosphingosine significantly induced chromatin DNA fragmentation. Phytosphingosine caused strong induction of caspase-8 activity and caspase-independent Bax translocation to the mitochondria. It shows excellent clinical results in the context of skin care in acne, based on both anti-inflammatory and anti-microbial activity. Phytosphingosine is currently seen in a variety of products as a skin and hair conditioning agent. Phytosphingosine might serve as an effective melanogenesis inhibitor in melanocytes via the regulation of the MITF signaling pathways. Dietary supplementation of phytosphingosine decreases plasma cholesterol levels and enhances insulin sensitivity in men with the metabolic syndrome.
Originator
Sources: DOI: 10.1007/BF01519846
Curator's Comment: Cerebrin base was iirst isolated from mushrooms by Zellner and later from yeast by Reindel. Carter et al. isolated a long-chain base from corn phosphatide and showed it to be identical to cerebrin base. Its structure was established as 1,3,4-trihydroxy-2-aminooctadecane and it was named phytosphingosine. https://www.ncbi.nlm.nih.gov/pubmed/14018956
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: MITF signaling pathway |
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Target ID: map04210 |
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Target ID: GO:0006309 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Inactive ingredient | CheryLee MD TrueLipids Relieve and Protect Ointment Approved UseUses:
helps relieve, prevent and temporarily protect chafed, chapped, cracked or windburned skin and lips
temporarily protects minor:
cuts
scrapes
burns
helps protect from the drying effects of wind and cold weather |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Natural zeolite clinoptilolite increases the concentrations of sphingoid bases in the yeast Yarrowia lipolytica. | 2001 |
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| Functional characterization of sphingolipid C4-hydroxylase genes from Arabidopsis thaliana. | 2001 Apr 6 |
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| Characterization of cerebrosides from the thermally dimorphic mycopathogen Histoplasma capsulatum: expression of 2-hydroxy fatty N-acyl (E)-Delta(3)-unsaturation correlates with the yeast-mycelium phase transition. | 2001 Feb |
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| Phytosphingosine as a specific inhibitor of growth and nutrient import in Saccharomyces cerevisiae. | 2001 Sep 21 |
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| Dependence of the sphingoid bases concentration on growth phase and temperature in the yeast Yarrowia lipolytica. | 2002 |
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| Isolation and characterization of the genes encoding delta(8)-sphingolipid desaturase from Saccharomyces kluyveri and Kluyveromyces lactis. | 2002 Dec |
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| Sphingosine kinase, sphingosine-1-phosphate, and apoptosis. | 2002 Dec 30 |
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| Repair of acetone- and sodium lauryl sulphate-damaged human skin barrier function using topically applied emulsions containing barrier lipids. | 2002 Nov |
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| [Experimental survey of a new topical anti-oxidant based on furfuryl palmitate in the treatment of child's and baby's dermatitis with eczema: results from a multicenter clinical investigation]. | 2002 Oct |
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| Yeast cells lacking the ARV1 gene harbor defects in sphingolipid metabolism. Complementation by human ARV1. | 2002 Sep 27 |
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| Analysis of ceramides in cosmetics by reversed-phase liquid chromatography/electrospray ionization mass spectrometry with collision-induced dissociation. | 2003 |
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| The emerging role for sphingolipids in the eukaryotic heat shock response. | 2003 Apr |
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| Synthesis of 4-hydroxysphinganine and characterization of sphinganine hydroxylase activity in corn. | 2003 Jul 15 |
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| Induction of apoptosis in cultured human proximal tubule cells by fumonisins and fumonisin metabolites. | 2003 Oct 15 |
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| Newly discovered neutral glycosphingolipids in aureobasidin A-resistant zygomycetes: Identification of a novel family of Gala-series glycolipids with core Gal alpha 1-6Gal beta 1-6Gal beta sequences. | 2004 Jul 30 |
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| Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis. | 2004 Oct 28 |
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| Molecular species of ceramides from the ascomycete truffle Tuber indicum. | 2004 Sep |
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| A novel coaxial electrospray ionization method for characterizing hexacosanoylceramides by Fourier transform ion cyclotron resonance mass spectrometry. | 2005 |
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| Phytosphingosine induced mitochondria-involved apoptosis. | 2005 Feb |
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| Polymorphism of ceramide 6: a vibrational spectroscopic and X-ray powder diffraction investigation of the diastereomers of N-(alpha-hydroxyoctadecanoyl)-phytosphingosine. | 2005 Jan |
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| APP1 transcription is regulated by inositol-phosphorylceramide synthase 1-diacylglycerol pathway and is controlled by ATF2 transcription factor in Cryptococcus neoformans. | 2005 Oct 28 |
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| Biophysics of sphingolipids I. Membrane properties of sphingosine, ceramides and other simple sphingolipids. | 2006 Dec |
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| Efficient synthesis of D-erythro-sphingosine and D-erythro-azidosphingosine from D-ribo-phytosphingosine via a cyclic sulfate intermediate. | 2006 Oct 27 |
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| Characterization of Ca2+ influx induced by dimethylphytosphingosine and lysophosphatidylcholine in U937 monocytes. | 2006 Sep 29 |
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| Combination treatment with arsenic trioxide and phytosphingosine enhances apoptotic cell death in arsenic trioxide-resistant cancer cells. | 2007 Jan |
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| Phytosphingosine in combination with TRAIL sensitizes cancer cells to TRAIL through synergistic up-regulation of DR4 and DR5. | 2007 Jan |
Patents
Sample Use Guides
Jurkat and NCI-H460 cells were treated with 5 or 10 ug/ml phytosphingosine, respectively, for the 2, 5, 10, 30, 60, 120 min. phytosphingosine treatment
led to a dramatic down-regulation of phosphorylated ERK1/2. The phosphorylated ERK started to diminish within 2 min of the phytosphingosine treatment.
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ACTIVE MOIETY
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