Submitted on May 15, 2008
Accepted on May 21, 2008
Sphingolipids. Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols
Sarah T. Pruett, Anatoliy Bushnev, Kerri Hagedorn, Madhura Adiga, Christopher A. Haynes, M. Cameron Sullards, Dennis C. Liotta, and Alfred H. Merrill . Jr
School of Biology, Georgia Tech, Atlanta, GA 30332-0230
Corresponding Author: al.merrill{at}biology.gatech.edu
“Sphingosin” was first described by J. L. W. Thudichum in 1884, and structurally characterized as 2S,3R,4E-2-aminooctadec-4-ene-1,3-diol in 1947 by Herb Carter, who also proposed designation of “lipides derived from sphingosine as sphingolipides.” This category of amino alcohols is now known to encompass hundreds of compounds that are referred to as sphingoid bases and sphingoid base-like compounds, which vary in chain length, number, position and stereochemistry of double bonds, hydroxyl groups and other functionalities. Some have especially intriguing features such as the tail-to-tail combination of two sphingoid bases in the a,-sphingoids produced by sponges. Most of these compounds participate in cell structure and regulation, and some (such as the fumonisins) disrupt normal sphingolipid metabolism and cause plant and animal disease. Many of the naturally occurring and synthetic sphingoid bases are cytotoxic for cancer cells and pathogenic microorganisms, or have other potentially useful bioactivities, hence, offer promise as pharmaceutical leads. This thematic review gives an overview of the biodiversity of the backbones of sphingolipids and the broader field of naturally occurring and synthetic sphingoid base-like compounds.
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