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Journal of Lipid Research, Vol. 49, 1621-1639, August 2008
Copyright © 2008 by American Society for Biochemistry and Molecular Biology

Thematic Review

Thematic Review Series: Sphingolipids. Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols^*

Sarah T. Pruett^1,*, Anatoliy Bushnev^*, Kerri Hagedorn, Madhura Adiga, Christopher A. Haynes, M. Cameron Sullards, Dennis C. Liotta^* and Alfred H. Merrill, Jr.^2,

^* Department of Chemistry, Emory University, Atlanta, GA 30322
Schools of Biology, Chemistry, and Biochemistry and the Parker H. Petit Institute for Bioengineering and Bioscience, Georgia Institute of Technology, Atlanta, GA 30332-0230
¹ Present address of S. T. Pruett: Yerkes National Primate Research Center, Emory University, Atlanta, GA 30329.

^* The work from our laboratories on naturally occurring sphingolipids cited in this review was supported by National Institutes of Health Grants GM-076217 and GM-069338 (Lipid Maps Consortium), and work involving sphingolipid analogs was supported by funding from the National Cancer Institute (Grant CA-87525).

Published, JLR Papers in Press, May 21, 2008.

² To whom correspondence should be addressed. e-mail: 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 the 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 ,-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, they 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.

Supplementary key words sphinganine • phytosphingosine • fumonisin • myriocin • long-chain base • anti-tumor • anti-fungal

Abbreviations: SPT, serine palmitoyltransferase

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