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
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
Cloning and functional characterization of the SUR2/SYR2 gene encoding sphinganine hydroxylase in Pichia ciferrii.	2004 Apr 15	15116344
Isolation and structure of a GD3-Type ganglioside molecular species possessing neuritogenic activity from the starfish Luidia maculata.	2004 Aug	15305002
Effective, high-yielding, and stereospecific total synthesis of D-erythro-(2R,3S)-sphingosine from D-ribo-(2S,3S,4R)-phytosphingosine.	2004 Aug 20	15307742
Genetic, biochemical, and transcriptional responses of Saccharomyces cerevisiae to the novel immunomodulator FTY720 largely mimic those of the natural sphingolipid phytosphingosine.	2004 Aug 27	15190065
Synthesis of l-lyxo-phytosphingosine and its 1-phosphonate analogue using a threitol acetal synthon.	2004 Aug 6	15287793
Potentiation of UVB-induced apoptosis by novel phytosphingosine derivative, tetraacetyl phytosphingosine in HaCaT cell and mouse skin.	2004 Jul	15192327
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	15155728
Structure and biological functions of fungal cerebrosides.	2004 Mar	15048196
Sphingolipids as bioactive regulators of thrombin generation.	2004 Mar 26	14722105
Acylceramide head group architecture affects lipid organization in synthetic ceramide mixtures.	2004 Nov	15482479
Effects of lipid chain lengths in alpha-galactosylceramides on cytokine release by natural killer T cells.	2004 Oct 27	15493902
Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis.	2004 Oct 28	15496103
Molecular species of ceramides from the ascomycete truffle Tuber indicum.	2004 Sep	15351272
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
Influence of phytosphingosine-type ceramides on the structure of DMPC membrane.	2005 Dec	16202987
Lipid mixtures prepared with well-defined synthetic ceramides closely mimic the unique stratum corneum lipid phase behavior.	2005 Dec	16150830
Phytosphingosine induced mitochondria-involved apoptosis.	2005 Feb	15723652
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
Polymorphism of ceramide 6: a vibrational spectroscopic and X-ray powder diffraction investigation of the diastereomers of N-(alpha-hydroxyoctadecanoyl)-phytosphingosine.	2005 Jan	15589229
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
Signalling functions for sphingolipid long-chain bases in Saccharomyces cerevisiae.	2005 Nov	16246074
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
Identification of mouse sphingomyelin synthase 1 as a suppressor of Bax-mediated cell death in yeast.	2006 Aug	16879426
Rapid demonstration of diversity of sulfatide molecular species from biological materials by MALDI-TOF MS.	2006 Aug	16670104
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
An efficient synthesis of the natural tetrahydrofuran pachastrissamine starting from D-ribo-phytosphingosine.	2006 Jan 20	16409007
Phytosphingosine stimulates the differentiation of human keratinocytes and inhibits TPA-induced inflammatory epidermal hyperplasia in hairless mouse skin.	2006 Jan-Mar	16838068
Constituents of Holothuroidea, 17. Isolation and structure of biologically active monosialo-gangliosides from the sea cucumber Cucumaria echinata.	2006 Jul	16819216
An efficient high-yield synthesis of D-ribo-phytosphingosine.	2006 Jul 20	16836391
Long chain base tolerance in Saccharomyces cerevisiae is induced by retrograde signals from the mitochondria.	2006 Mar 10	16407254
A general, efficient and stereospecific route to sphingosine, sphinganines, phytosphingosines and their analogs.	2006 Mar 21	16525559
Structural organisation and phase behaviour of a stratum corneum lipid analogue: ceramide 3A.	2006 May 21	16688309
[New ceramides from sea sponge Oceanapia sp].	2006 May-Jun	16808175
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
Characterization of Ca2+ influx induced by dimethylphytosphingosine and lysophosphatidylcholine in U937 monocytes.	2006 Sep 29	16904073
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
SVF1 regulates cell survival by affecting sphingolipid metabolism in Saccharomyces cerevisiae.	2007 Jan	17057230

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