Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H39NO3 |
| Molecular Weight | 317.5072 |
| Optical Activity | ( + ) |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO
InChI
InChIKey=AERBNCYCJBRYDG-KSZLIROESA-N
InChI=1S/C18H39NO3/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/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 |
|---|---|---|
| Combination treatment with arsenic trioxide and phytosphingosine enhances apoptotic cell death in arsenic trioxide-resistant cancer cells. | 2007-01 |
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| Phytosphingosine in combination with TRAIL sensitizes cancer cells to TRAIL through synergistic up-regulation of DR4 and DR5. | 2007-01 |
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| SVF1 regulates cell survival by affecting sphingolipid metabolism in Saccharomyces cerevisiae. | 2007-01 |
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| Biophysics of sphingolipids I. Membrane properties of sphingosine, ceramides and other simple sphingolipids. | 2006-12 |
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| Efficient synthesis of D-erythro-sphingosine and D-erythro-azidosphingosine from D-ribo-phytosphingosine via a cyclic sulfate intermediate. | 2006-10-27 |
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| Characterization of Ca2+ influx induced by dimethylphytosphingosine and lysophosphatidylcholine in U937 monocytes. | 2006-09-29 |
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| Constituents of Holothuroidea, 18. Isolation and structure of biologically active disialo- and trisialo-gangliosides from the sea cucumber Cucumaria echinata. | 2006-09 |
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| Structure-activity relationships of dimethylsphingosine (DMS) derivatives and their effects on intracellular pH and Ca2+ in the U937 monocyte cell line. | 2006-08 |
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| Identification of mouse sphingomyelin synthase 1 as a suppressor of Bax-mediated cell death in yeast. | 2006-08 |
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| Rapid demonstration of diversity of sulfatide molecular species from biological materials by MALDI-TOF MS. | 2006-08 |
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| An efficient high-yield synthesis of D-ribo-phytosphingosine. | 2006-07-20 |
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| [New ceramides from sea sponge Oceanapia sp]. | 2006-07-01 |
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| Constituents of Holothuroidea, 17. Isolation and structure of biologically active monosialo-gangliosides from the sea cucumber Cucumaria echinata. | 2006-07 |
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| Structural organisation and phase behaviour of a stratum corneum lipid analogue: ceramide 3A. | 2006-05-21 |
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| A general, efficient and stereospecific route to sphingosine, sphinganines, phytosphingosines and their analogs. | 2006-03-21 |
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| Long chain base tolerance in Saccharomyces cerevisiae is induced by retrograde signals from the mitochondria. | 2006-03-10 |
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| An efficient synthesis of the natural tetrahydrofuran pachastrissamine starting from D-ribo-phytosphingosine. | 2006-01-20 |
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| Effect of lipid-containing, positively charged nanoemulsions on skin hydration, elasticity and erythema--an in vivo study. | 2006-01-13 |
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| Phytosphingosine stimulates the differentiation of human keratinocytes and inhibits TPA-induced inflammatory epidermal hyperplasia in hairless mouse skin. | 2006-01-11 |
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| Influence of phytosphingosine-type ceramides on the structure of DMPC membrane. | 2005-12 |
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| Lipid mixtures prepared with well-defined synthetic ceramides closely mimic the unique stratum corneum lipid phase behavior. | 2005-12 |
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| Regulation of the sphingoid long-chain base kinase Lcb4p by ergosterol and heme: studies in phytosphingosine-resistant mutants. | 2005-11-04 |
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| Candida albicans serotype B strains synthesize a serotype-specific phospholipomannan overexpressing a beta-1,2-linked mannotriose. | 2005-11 |
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| Signalling functions for sphingolipid long-chain bases in Saccharomyces cerevisiae. | 2005-11 |
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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. | 2005-10-28 |
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| The sphingoid long chain base phytosphingosine activates AGC-type protein kinases in Saccharomyces cerevisiae including Ypk1, Ypk2, and Sch9. | 2005-06-17 |
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| Inositol phosphoceramide synthase is a regulator of intracellular levels of diacylglycerol and ceramide during the G1 to S transition in Saccharomyces cerevisiae. | 2005-05-15 |
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| Design of a phytosphingosine-containing, positively-charged nanoemulsion as a colloidal carrier system for dermal application of ceramides. | 2005-05 |
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| FTIR spectroscopic studies of lipid dynamics in phytosphingosine ceramide models of the stratum corneum lipid matrix. | 2005-03 |
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| Phytosphingosine in combination with ionizing radiation enhances apoptotic cell death in radiation-resistant cancer cells through ROS-dependent and -independent AIF release. | 2005-02-15 |
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| Phytosphingosine induced mitochondria-involved apoptosis. | 2005-02 |
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| Phosphorylation of sphingoid long-chain bases in Arabidopsis: functional characterization and expression of the first sphingoid long-chain base Kinase gene in plants. | 2005-02 |
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| Arabidopsis sphingosine kinase and the effects of phytosphingosine-1-phosphate on stomatal aperture. | 2005-02 |
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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. | 2005-01 |
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| Anti-ulcer actions of phytosphingosine hydrochloride in different experimental rat ulcer models. | 2005 |
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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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| Acylceramide head group architecture affects lipid organization in synthetic ceramide mixtures. | 2004-11 |
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| Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis. | 2004-10-28 |
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| Effects of lipid chain lengths in alpha-galactosylceramides on cytokine release by natural killer T cells. | 2004-10-27 |
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| Molecular species of ceramides from the ascomycete truffle Tuber indicum. | 2004-09 |
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| Genetic, biochemical, and transcriptional responses of Saccharomyces cerevisiae to the novel immunomodulator FTY720 largely mimic those of the natural sphingolipid phytosphingosine. | 2004-08-27 |
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| Effective, high-yielding, and stereospecific total synthesis of D-erythro-(2R,3S)-sphingosine from D-ribo-(2S,3S,4R)-phytosphingosine. | 2004-08-20 |
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| Synthesis of l-lyxo-phytosphingosine and its 1-phosphonate analogue using a threitol acetal synthon. | 2004-08-06 |
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| Isolation and structure of a GD3-Type ganglioside molecular species possessing neuritogenic activity from the starfish Luidia maculata. | 2004-08 |
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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. | 2004-07-30 |
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| Potentiation of UVB-induced apoptosis by novel phytosphingosine derivative, tetraacetyl phytosphingosine in HaCaT cell and mouse skin. | 2004-07 |
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| Cloning and functional characterization of the SUR2/SYR2 gene encoding sphinganine hydroxylase in Pichia ciferrii. | 2004-04-15 |
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| Sphingolipids as bioactive regulators of thrombin generation. | 2004-03-26 |
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| Structure and biological functions of fungal cerebrosides. | 2004-03 |
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| Induction of apoptosis and expression of cell cycle regulatory proteins in response to a phytosphingosine derivative in HaCaT human keratinocyte cells. | 2003-12-31 |
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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DB14119
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Phytosphingosine
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554-62-1
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
