PHYTOSPHINGOSINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H39NO3
Molecular Weight	317.5072
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15723652 | https://www.truthinaging.com/ingredients/phytosphingosine | https://www.ncbi.nlm.nih.gov/pubmed/28390782 | https://www.ncbi.nlm.nih.gov/pubmed/18489348 | https://www.ncbi.nlm.nih.gov/pubmed/20179727 | https://www.ncbi.nlm.nih.gov/pubmed/14522966

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
MITF signaling pathway 3 Target ID: MITF signaling pathway Sources: https://www.ncbi.nlm.nih.gov/pubmed/28390782	Modulator 828
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14522966 \| https://www.ncbi.nlm.nih.gov/pubmed/15723652	Activator 1430
apoptotic DNA fragmentation 5 Target ID: GO:0006309 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15723652	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Metabolic syndrome 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20179727	Primary	Phase II 1132	Unknown Approved Use Unknown
Acne vulgaris 34 Sources: https://www.truthinaging.com/ingredients/phytosphingosine https://www.ncbi.nlm.nih.gov/pubmed/18489348	Primary	Phase II 1132	Unknown Approved Use Unknown
Hyperpigmentation 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28390782	Primary	Basic research	Unknown Approved Use Unknown
Skin Care 16 Sources: https://www.drugs.com/otc/130001/white-petrolatum.html	Inactive ingredient	Approved 8429	CheryLee MD TrueLipids Relieve and Protect Ointment Approved Use Uses: 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
Functional characterization of sphingolipid C4-hydroxylase genes from Arabidopsis thaliana.	2001 Apr 6	11297741
C26-CoA-dependent ceramide synthesis of Saccharomyces cerevisiae is operated by Lag1p and Lac1p.	2001 Jun 1	11387200
Role for de novo sphingoid base biosynthesis in the heat-induced transient cell cycle arrest of Saccharomyces cerevisiae.	2001 Mar 16	11056159
Dependence of the sphingoid bases concentration on growth phase and temperature in the yeast Yarrowia lipolytica.	2002	11925759
Simultaneous quantitative analysis of sphingoid base 1-phosphates in biological samples by o-phthalaldehyde precolumn derivatization after dephosphorylation with alkaline phosphatase.	2002 Apr 15	11950216
Human epidermal glucosylceramides are major precursors of stratum corneum ceramides.	2002 Aug	12190865
[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	12244285
Suppression of extracellular signal-related kinase and activation of p38 MAPK are two critical events leading to caspase-8- and mitochondria-mediated cell death in phytosphingosine-treated human cancer cells.	2003 Dec 12	14522966
Induction of apoptosis and expression of cell cycle regulatory proteins in response to a phytosphingosine derivative in HaCaT human keratinocyte cells.	2003 Dec 31	14744023
Metabolomic profiling of sphingolipids in human glioma cell lines by liquid chromatography tandem mass spectrometry.	2003 Jul	14528916
Synthesis of 4-hydroxysphinganine and characterization of sphinganine hydroxylase activity in corn.	2003 Jul 15	12831841
The mitochondria-associated endoplasmic-reticulum subcompartment (MAM fraction) of rat liver contains highly active sphingolipid-specific glycosyltransferases.	2003 May 1	12578562
Tetraacetyl phytosphingosine-induced caspase activation and apoptosis occur through G2 arrest in human keratinocyte HaCaT cells.	2003 Nov	14708616
Alteration of the 4-sphingenine scaffolds of ceramides in keratinocyte-specific Arnt-deficient mice affects skin barrier function.	2003 Nov	14597763
Induction of apoptosis in cultured human proximal tubule cells by fumonisins and fumonisin metabolites.	2003 Oct 15	14550748
Distribution of sphingosine kinase activity in mouse tissues: contribution of SPHK1.	2003 Sep 12	12943676
Carbohydrate recognition by enterohemorrhagic Escherichia coli: characterization of a novel glycosphingolipid from cat small intestine.	2004 Feb	14576169
Structure and biological functions of fungal cerebrosides.	2004 Mar	15048196
Anti-ulcer actions of phytosphingosine hydrochloride in different experimental rat ulcer models.	2005	16149714
A novel coaxial electrospray ionization method for characterizing hexacosanoylceramides by Fourier transform ion cyclotron resonance mass spectrometry.	2005	15838927
Lipid mixtures prepared with well-defined synthetic ceramides closely mimic the unique stratum corneum lipid phase behavior.	2005 Dec	16150830
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	15695468
Arabidopsis sphingosine kinase and the effects of phytosphingosine-1-phosphate on stomatal aperture.	2005 Feb	15665242
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	15486061
The sphingoid long chain base phytosphingosine activates AGC-type protein kinases in Saccharomyces cerevisiae including Ypk1, Ypk2, and Sch9.	2005 Jun 17	15840588
FTIR spectroscopic studies of lipid dynamics in phytosphingosine ceramide models of the stratum corneum lipid matrix.	2005 Mar	15752463
Design of a phytosphingosine-containing, positively-charged nanoemulsion as a colloidal carrier system for dermal application of ceramides.	2005 May	15848061
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	15560753
Candida albicans serotype B strains synthesize a serotype-specific phospholipomannan overexpressing a beta-1,2-linked mannotriose.	2005 Nov	16262785
Regulation of the sphingoid long-chain base kinase Lcb4p by ergosterol and heme: studies in phytosphingosine-resistant mutants.	2005 Nov 4	16141212
APP1 transcription is regulated by inositol-phosphorylceramide synthase 1-diacylglycerol pathway and is controlled by ATF2 transcription factor in Cryptococcus neoformans.	2005 Oct 28	16129666
Structure-activity relationships of dimethylsphingosine (DMS) derivatives and their effects on intracellular pH and Ca2+ in the U937 monocyte cell line.	2006 Aug	16964761
Biophysics of sphingolipids I. Membrane properties of sphingosine, ceramides and other simple sphingolipids.	2006 Dec	17070498
Effect of lipid-containing, positively charged nanoemulsions on skin hydration, elasticity and erythema--an in vivo study.	2006 Jan 13	16289984
Phytosphingosine stimulates the differentiation of human keratinocytes and inhibits TPA-induced inflammatory epidermal hyperplasia in hairless mouse skin.	2006 Jan-Mar	16838068
An efficient high-yield synthesis of D-ribo-phytosphingosine.	2006 Jul 20	16836391
A general, efficient and stereospecific route to sphingosine, sphinganines, phytosphingosines and their analogs.	2006 Mar 21	16525559
Efficient synthesis of D-erythro-sphingosine and D-erythro-azidosphingosine from D-ribo-phytosphingosine via a cyclic sulfate intermediate.	2006 Oct 27	17064054
Constituents of Holothuroidea, 18. Isolation and structure of biologically active disialo- and trisialo-gangliosides from the sea cucumber Cucumaria echinata.	2006 Sep	16946538
Combination treatment with arsenic trioxide and phytosphingosine enhances apoptotic cell death in arsenic trioxide-resistant cancer cells.	2007 Jan	17237268
Phytosphingosine in combination with TRAIL sensitizes cancer cells to TRAIL through synergistic up-regulation of DR4 and DR5.	2007 Jan	17143496

Patents

Sample Use Guides

In Vivo Use Guide

500 mg twice daily for a 4 weeks

Route of Administration: Oral

In Vitro Use Guide

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.

Name

Type

Language

PHYTOSPHINGOSINE

Official Name

English

D-RIBO-1,3,4-TRIHYDROXY-2-AMINOOCTADECANE

Common Name

English

1,3,4-OCTADECANETRIOL, 2-AMINO-, (2S-(2R*,3R*,4S*))-

Common Name

English

1,3,4-OCTADECANETRIOL, 2-AMINO-, D-RIBO-

Common Name

English

D-RIBO-PHYTOSPHINGOSINE

Common Name

English

DS-PHYTOSPHINGOSINE

Brand Name

English

1,3,4-OCTADECANETRIOL, 2-AMINO-, (2S,3S,4R)-

Systematic Name

English

(+)-D-RIBO-PHYTOSPHINGOSINE

Common Name

English

C18-PHYTOSPHINGOSINE

Common Name

English

CYTOMIDE PGS

Brand Name

English

BIOMIDE PS

Brand Name

English

SPHINGANINE, 4-D-HYDROXY

Common Name

English

PHYTOSPHINGOSINE [INCI]

Common Name

English

Phytosphingosine [WHO-DD]

Common Name

English

4-D-HYDROXYSPHINGANINE

Common Name

English

Code System Code Type Description

DRUG BANK

DB14119