Abstract
Phytosphingosines constitute a group of functionally related, long-chain aliphatic 2-amino-1,3,4-triols of which D-ribo-C18-phytosphingosine ((2S,3S,4R)-2-aminooctadecane-1,3,4-triol) is the most prevalent. D-ribo-Phytosphingosine is a bioactive lipid and is reported to be a potential heat stress signal in yeast cells. Phytosphingosines are widely distributed as structural components of sphingolipids in yeast, fungi, mammalian tissues and marine organisms. The long-chain base (phytosphingosine component) of the majority of the phytosphingolipids has 18-carbons minor amounts of other chain lengths, especially C20, are also found, depending on their origin. Some of these phytosphingolipids exhibit important physiological activities. For example, there are α-and β-galactosyl- and glucosylphytoceramides that possess high tumor inhibitory potency. Due to the variety and significance of their biological activities and their scarcity in nature, phytosphingosines have become important synthetic targe ts. In general, approaches can be placed into three main categories. The first two rely on the chiral pool of amino acids and carbohydrates as the foundation for the asymmetric centers. Most amino acid strategies utilize (L)-serine. The carbohydrate-based approaches are the most abundant and employ a variety of common sugars and amino sugars. The third category of syntheses is based on asymmetric transformations. In this review the biological importance of phytosphingosines will be highlighted and approaches to their synthesis will be reviewed.
Keywords: Phytosphingosines
Current Organic Chemistry
Title: The Preparation and Biological Significance of Phytosphingosines
Volume: 6 Issue: 4
Author(s): Amy R. Howell and Albert J. Ndakala
Affiliation:
Keywords: Phytosphingosines
Abstract: Phytosphingosines constitute a group of functionally related, long-chain aliphatic 2-amino-1,3,4-triols of which D-ribo-C18-phytosphingosine ((2S,3S,4R)-2-aminooctadecane-1,3,4-triol) is the most prevalent. D-ribo-Phytosphingosine is a bioactive lipid and is reported to be a potential heat stress signal in yeast cells. Phytosphingosines are widely distributed as structural components of sphingolipids in yeast, fungi, mammalian tissues and marine organisms. The long-chain base (phytosphingosine component) of the majority of the phytosphingolipids has 18-carbons minor amounts of other chain lengths, especially C20, are also found, depending on their origin. Some of these phytosphingolipids exhibit important physiological activities. For example, there are α-and β-galactosyl- and glucosylphytoceramides that possess high tumor inhibitory potency. Due to the variety and significance of their biological activities and their scarcity in nature, phytosphingosines have become important synthetic targe ts. In general, approaches can be placed into three main categories. The first two rely on the chiral pool of amino acids and carbohydrates as the foundation for the asymmetric centers. Most amino acid strategies utilize (L)-serine. The carbohydrate-based approaches are the most abundant and employ a variety of common sugars and amino sugars. The third category of syntheses is based on asymmetric transformations. In this review the biological importance of phytosphingosines will be highlighted and approaches to their synthesis will be reviewed.
Export Options
About this article
Cite this article as:
Howell R. Amy and Ndakala J. Albert, The Preparation and Biological Significance of Phytosphingosines, Current Organic Chemistry 2002; 6 (4) . https://dx.doi.org/10.2174/1385272024604998
DOI https://dx.doi.org/10.2174/1385272024604998 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |

- Author Guidelines
- Bentham Author Support Services (BASS)
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
- Announcements
Related Articles
-
Molecular Mechanisms of Thymoquinone as Anticancer Agent
Combinatorial Chemistry & High Throughput Screening Chlamydia-Secreted Proteins in Chlamydial Interactions with Host Cells
Current Chemical Biology Enhanced Expression of miR-199b-5p Promotes Proliferation of Pancreatic β-Cells by Down-Regulation of MLK3
MicroRNA Reconstruction of the 1918 Pandemic Influenza Virus: How Revealing the Molecular Secrets of the Virus Responsible for the Worst Pandemic in Recorded History Can Guide Our Response to Future Influenza Pandemics
Infectious Disorders - Drug Targets Metabotropic Glutamate Receptor 5 in Down's Syndrome Hippocampus During Development: Increased Expression in Astrocytes
Current Alzheimer Research Development of a STAT5 Phosphorylation Assay as a Rapid Bioassay to Assess Interleukin-7 Potency
Current Pharmaceutical Biotechnology Knockdown of C-C Chemokine Receptor 5 (CCR5) is Protective Against Cerebral Ischemia and Reperfusion Injury
Current Neurovascular Research Hypoxia-Inducible Factors and Sphingosine 1-Phosphate Signaling
Anti-Cancer Agents in Medicinal Chemistry The Role of Nitric Oxide (NO) in Control of LHRH Release that Mediates Gonadotropin Release and Sexual Behavior
Current Pharmaceutical Design Role of Cathepsin K in Normal Joints and in the Development of Arthritis
Current Drug Targets Small Molecules for Immunomodulation in Cancer: A Review
Anti-Cancer Agents in Medicinal Chemistry Preface
Current Pharmaceutical Design A Progressive Review of V600E-B-RAF-Dependent Melanoma and Drugs Inhibiting It
Mini-Reviews in Medicinal Chemistry Many Drugs and Phytochemicals Can Be Activated to Biological Reactive Intermediates
Current Drug Metabolism A Review of <i>Aristolochia indica</i>: Ethnomedicinal Uses, Phytochemistry, Pharmacological and Toxicological Effects
Current Traditional Medicine Strong Association of Serum GSK-3β/BDNF Ratio with Mild Cognitive Impairment in Elderly Type 2 Diabetic Patients
Current Alzheimer Research Target Fishing of Calactin, Calotropin and Calotoxin Using Reverse Pharmacophore Screening and Consensus Inverse Docking Approach
Current Drug Discovery Technologies Vaccines and Vaccine Strategies Against HIV
Current Drug Targets Central Nervous System Agents for Ischemic Stroke: Neuroprotection Mechanisms
Central Nervous System Agents in Medicinal Chemistry Kavalactone Pharmacophores for Major Cellular Drug Targets
Mini-Reviews in Medicinal Chemistry