Pruett Sarah T, Bushnev Anatoliy, Hagedorn Kerri, Adiga Madhura, Haynes Christopher A, Sullards M Cameron, Liotta Dennis C, Merrill Alfred H
Department of Chemistry, Emory University, Atlanta, GA 30322, USA.
J Lipid Res. 2008 Aug;49(8):1621-39. doi: 10.1194/jlr.R800012-JLR200. Epub 2008 May 21.
"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 alpha,omega-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.
“鞘氨醇”于1884年由J. L. W. 图迪雄首次描述，并于1947年由赫伯·卡特在结构上表征为2S,3R,4E-2-氨基十八碳-4-烯-1,3-二醇，他还提议将“源自鞘氨醇的脂质称为鞘脂”。现在已知这类氨基醇包含数百种化合物，它们被称为鞘氨醇碱基和类鞘氨醇碱基化合物，其碳链长度、双键数量、位置以及立体化学、羟基和其他官能团各不相同。有些具有特别有趣的特征，比如海绵产生的α,ω-鞘氨醇中两个鞘氨醇碱基的尾对尾组合。这些化合物大多参与细胞结构和调节，有些（如伏马菌素）会扰乱正常的鞘脂代谢并导致动植物疾病。许多天然存在的和合成的鞘氨醇碱基对癌细胞和致病微生物具有细胞毒性，或具有其他潜在有用的生物活性；因此，它们有望成为药物先导物。这篇专题综述概述了鞘脂骨架的生物多样性以及天然存在的和合成的类鞘氨醇碱基化合物这一更广泛的领域。
