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
In vitro activity of phytosphingosines against Malassezia furfur and Candida albicans.	2002	12353705
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
Isolation and characterization of the genes encoding delta(8)-sphingolipid desaturase from Saccharomyces kluyveri and Kluyveromyces lactis.	2002 Dec	12402089
Sphingosine kinase, sphingosine-1-phosphate, and apoptosis.	2002 Dec 30	12531554
Deficiency of epidermal protein-bound omega-hydroxyceramides in atopic dermatitis.	2002 Jul	12164940
Sphingolipid functions in Saccharomyces cerevisiae.	2002 Jun 13	12069845
Mutant analysis reveals complex regulation of sphingolipid long chain base phosphates and long chain bases during heat stress in yeast.	2002 May	11967828
[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
The Saccharomyces cerevisiae YBR159w gene encodes the 3-ketoreductase of the microsomal fatty acid elongase.	2002 Sep 20	12087109
Yeast cells lacking the ARV1 gene harbor defects in sphingolipid metabolism. Complementation by human ARV1.	2002 Sep 27	12145310
New acylceramide in native and reconstructed epidermis.	2003 Apr	12648220
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
Structures of the glycosylphosphatidylinositol membrane anchors from Aspergillus fumigatus membrane proteins.	2003 Mar	12626404
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
Differential regulation of cyclooxygenase-2 expression by phytosphingosine derivatives, NAPS and TAPS, and its role in the NAPS or TAPS-mediated apoptosis.	2003 Nov	14708615
Alteration of the 4-sphingenine scaffolds of ceramides in keratinocyte-specific Arnt-deficient mice affects skin barrier function.	2003 Nov	14597763
Distribution of sphingosine kinase activity in mouse tissues: contribution of SPHK1.	2003 Sep 12	12943676
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
Synthesis of l-lyxo-phytosphingosine and its 1-phosphonate analogue using a threitol acetal synthon.	2004 Aug 6	15287793
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
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 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
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
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
Long chain base tolerance in Saccharomyces cerevisiae is induced by retrograde signals from the mitochondria.	2006 Mar 10	16407254
[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
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