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
| Molecular Formula | C18H39NO3 |
| Molecular Weight | 317.5072 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Induction of apoptosis and expression of cell cycle regulatory proteins in response to a phytosphingosine derivative in HaCaT human keratinocyte cells. | 2003 Dec 31 |
|
| Tetraacetyl phytosphingosine-induced caspase activation and apoptosis occur through G2 arrest in human keratinocyte HaCaT cells. | 2003 Nov |
|
| Differential regulation of cyclooxygenase-2 expression by phytosphingosine derivatives, NAPS and TAPS, and its role in the NAPS or TAPS-mediated apoptosis. | 2003 Nov |
|
| Alteration of the 4-sphingenine scaffolds of ceramides in keratinocyte-specific Arnt-deficient mice affects skin barrier function. | 2003 Nov |
|
| Cloning and functional characterization of the SUR2/SYR2 gene encoding sphinganine hydroxylase in Pichia ciferrii. | 2004 Apr 15 |
|
| Isolation and structure of a GD3-Type ganglioside molecular species possessing neuritogenic activity from the starfish Luidia maculata. | 2004 Aug |
|
| Effective, high-yielding, and stereospecific total synthesis of D-erythro-(2R,3S)-sphingosine from D-ribo-(2S,3S,4R)-phytosphingosine. | 2004 Aug 20 |
|
| Genetic, biochemical, and transcriptional responses of Saccharomyces cerevisiae to the novel immunomodulator FTY720 largely mimic those of the natural sphingolipid phytosphingosine. | 2004 Aug 27 |
|
| Synthesis of l-lyxo-phytosphingosine and its 1-phosphonate analogue using a threitol acetal synthon. | 2004 Aug 6 |
|
| Carbohydrate recognition by enterohemorrhagic Escherichia coli: characterization of a novel glycosphingolipid from cat small intestine. | 2004 Feb |
|
| Potentiation of UVB-induced apoptosis by novel phytosphingosine derivative, tetraacetyl phytosphingosine in HaCaT cell and mouse skin. | 2004 Jul |
|
| 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 |
|
| Structure and biological functions of fungal cerebrosides. | 2004 Mar |
|
| Sphingolipids as bioactive regulators of thrombin generation. | 2004 Mar 26 |
|
| Acylceramide head group architecture affects lipid organization in synthetic ceramide mixtures. | 2004 Nov |
|
| Effects of lipid chain lengths in alpha-galactosylceramides on cytokine release by natural killer T cells. | 2004 Oct 27 |
|
| Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis. | 2004 Oct 28 |
|
| Molecular species of ceramides from the ascomycete truffle Tuber indicum. | 2004 Sep |
|
| Anti-ulcer actions of phytosphingosine hydrochloride in different experimental rat ulcer models. | 2005 |
|
| A novel coaxial electrospray ionization method for characterizing hexacosanoylceramides by Fourier transform ion cyclotron resonance mass spectrometry. | 2005 |
|
| Influence of phytosphingosine-type ceramides on the structure of DMPC membrane. | 2005 Dec |
|
| Lipid mixtures prepared with well-defined synthetic ceramides closely mimic the unique stratum corneum lipid phase behavior. | 2005 Dec |
|
| Phytosphingosine induced mitochondria-involved apoptosis. | 2005 Feb |
|
| Phosphorylation of sphingoid long-chain bases in Arabidopsis: functional characterization and expression of the first sphingoid long-chain base Kinase gene in plants. | 2005 Feb |
|
| Arabidopsis sphingosine kinase and the effects of phytosphingosine-1-phosphate on stomatal aperture. | 2005 Feb |
|
| Phytosphingosine in combination with ionizing radiation enhances apoptotic cell death in radiation-resistant cancer cells through ROS-dependent and -independent AIF release. | 2005 Feb 15 |
|
| Polymorphism of ceramide 6: a vibrational spectroscopic and X-ray powder diffraction investigation of the diastereomers of N-(alpha-hydroxyoctadecanoyl)-phytosphingosine. | 2005 Jan |
|
| The sphingoid long chain base phytosphingosine activates AGC-type protein kinases in Saccharomyces cerevisiae including Ypk1, Ypk2, and Sch9. | 2005 Jun 17 |
|
| FTIR spectroscopic studies of lipid dynamics in phytosphingosine ceramide models of the stratum corneum lipid matrix. | 2005 Mar |
|
| Design of a phytosphingosine-containing, positively-charged nanoemulsion as a colloidal carrier system for dermal application of ceramides. | 2005 May |
|
| Inositol phosphoceramide synthase is a regulator of intracellular levels of diacylglycerol and ceramide during the G1 to S transition in Saccharomyces cerevisiae. | 2005 May 15 |
|
| Signalling functions for sphingolipid long-chain bases in Saccharomyces cerevisiae. | 2005 Nov |
|
| Regulation of the sphingoid long-chain base kinase Lcb4p by ergosterol and heme: studies in phytosphingosine-resistant mutants. | 2005 Nov 4 |
|
| APP1 transcription is regulated by inositol-phosphorylceramide synthase 1-diacylglycerol pathway and is controlled by ATF2 transcription factor in Cryptococcus neoformans. | 2005 Oct 28 |
|
| Structure-activity relationships of dimethylsphingosine (DMS) derivatives and their effects on intracellular pH and Ca2+ in the U937 monocyte cell line. | 2006 Aug |
|
| Identification of mouse sphingomyelin synthase 1 as a suppressor of Bax-mediated cell death in yeast. | 2006 Aug |
|
| Rapid demonstration of diversity of sulfatide molecular species from biological materials by MALDI-TOF MS. | 2006 Aug |
|
| Biophysics of sphingolipids I. Membrane properties of sphingosine, ceramides and other simple sphingolipids. | 2006 Dec |
|
| Phytosphingosine stimulates the differentiation of human keratinocytes and inhibits TPA-induced inflammatory epidermal hyperplasia in hairless mouse skin. | 2006 Jan-Mar |
|
| Constituents of Holothuroidea, 17. Isolation and structure of biologically active monosialo-gangliosides from the sea cucumber Cucumaria echinata. | 2006 Jul |
|
| An efficient high-yield synthesis of D-ribo-phytosphingosine. | 2006 Jul 20 |
|
| A general, efficient and stereospecific route to sphingosine, sphinganines, phytosphingosines and their analogs. | 2006 Mar 21 |
|
| Structural organisation and phase behaviour of a stratum corneum lipid analogue: ceramide 3A. | 2006 May 21 |
|
| [New ceramides from sea sponge Oceanapia sp]. | 2006 May-Jun |
|
| Efficient synthesis of D-erythro-sphingosine and D-erythro-azidosphingosine from D-ribo-phytosphingosine via a cyclic sulfate intermediate. | 2006 Oct 27 |
|
| Constituents of Holothuroidea, 18. Isolation and structure of biologically active disialo- and trisialo-gangliosides from the sea cucumber Cucumaria echinata. | 2006 Sep |
|
| Characterization of Ca2+ influx induced by dimethylphytosphingosine and lysophosphatidylcholine in U937 monocytes. | 2006 Sep 29 |
|
| Combination treatment with arsenic trioxide and phytosphingosine enhances apoptotic cell death in arsenic trioxide-resistant cancer cells. | 2007 Jan |
|
| Phytosphingosine in combination with TRAIL sensitizes cancer cells to TRAIL through synergistic up-regulation of DR4 and DR5. | 2007 Jan |
|
| SVF1 regulates cell survival by affecting sphingolipid metabolism in Saccharomyces cerevisiae. | 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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 01:52:38 GMT 2023
by
admin
on
Sat Dec 16 01:52:38 GMT 2023
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| Record UNII |
TT871XV7TU
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| Record Status |
Validated (UNII)
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| Record Version |
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