Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols.
Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols.
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DOI：
10.1194/jlr.r800012-jlr200
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发表时间：
2008-08
影响因子：
6.5
通讯作者：
Merrill AH Jr
中科院分区：
文献类型：
--
作者：
Pruett ST;Bushnev A;Hagedorn K;Adiga M;Haynes CA;Sullards MC;Liotta DC;Merrill AH Jr
“鞘氨醇”由 J. L. W. Thudichum 于 1884 年首次描述，并于 1947 年由 Herb Carter 进行结构表征为 2S,3R,4E-2-aminooctadec-4-ene-1,3-diol，他还提出将“源自鞘氨醇的脂质命名为鞘脂”。目前已知这类氨基醇包括数百种被称为鞘氨醇碱和类鞘氨醇碱化合物的化合物，它们的链长、数量、位置以及双键、羟基和其他官能团的立体化学各不相同。有些具有特别有趣的特征，例如海绵产生的 α,ω-鞘氨醇中两个鞘氨醇碱基的尾对尾组合。这些化合物大多数参与细胞结构和调节，有些（如伏马菌素）会破坏正常的鞘脂代谢并引起植物和动物疾病。许多天然存在和合成的鞘氨醇碱对癌细胞和病原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，它们有望作为药物先导化合物。本专题综述概述了鞘脂骨架的生物多样性以及天然存在和合成的鞘氨醇碱样化合物的更广泛领域。
“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 α,ω-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.