Ustilipids, acylated β-D-mannopyranosyl D-erythritols from Ustilago maydis and Geotrichum candidum
Ustilipids, acylated β-D-mannopyranosyl D-erythritols from Ustilago maydis and Geotrichum candidum
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DOI：
10.7164/antibiotics.56.91
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发表时间：
2003-02-01
影响因子：
3.3
通讯作者：
Seibert, G
中科院分区：
文献类型：
--
作者：
Kurz, M;Eder, C;Seibert, G
黑粉菌属物种产生在各种药物测定中显示活性的细胞外油。我们从玉米黑粉菌DSM 11494和白地霉ST 002515的培养物中分离出了这种异质糖脂的几种复合物，并根据NMR实验、质谱和脂肪酸分析确定了这些新化合物的化学结构，称为ustilipids。它们都具有4-O-β-D-甘露吡喃糖基D-吡喃基本框架，其构型在初始溶剂分解后通过单晶X-射线结构分析确认。所有研究的ustilipids和相关化合物的结构类似：在所有情况下，β-侧链的三个羟基都是游离的，而甘露糖残基的羟基大部分是酰化的。中链脂肪酸首次被检测到作为由黑粉菌目产生的糖脂的组分。虽然甘露糖残基的2-羟基被C-2-C-8羧酸酯侧链酯化，但3-羟基在所有情况下都被较长的C-12-C-20脂肪酸残基酯化。在4和6位的氧官能团是乙酰化的或作为游离羟基存在。Ustipids拮抗多巴胺D3受体的微摩尔量，这类化合物的其他成员已被发现具有抑制作用的神经降压素受体。溶血活性低。
Ustilago species produce an extracellular oil that shows activity in various pharmaceutical assays. We isolated several complexes of this heterogeneous glycolipid from cultures of Ustilago maydis DSM 11494 and Geotrichum candidum ST 002515, and determined the chemical structures of these new compounds, termed ustilipids, on the basis of NMR experiments, mass spectra, and fatty acid analyses. They all possess a 4-O-beta-D-mannopyranosyl D-erythritol basic framework, the configuration of which was confirmed, after initial solvolysis, by a single-crystal X-ray structure analysis. All the investigated ustilipids and related compounds are similarly constructed: the three hydroxy groups of the erythritol side chain are free in all cases, whereas the hydroxy groups of the mannose residue are for the most part acylated. Medium-chain fatty acids have for the first time been detected as components of glycolipids produced by Ustilaginales. While the 2-hydroxy group of the mannose residue is esterified with a C-2-C-8, carboxylate side chain, the 3-hydroxy group is in all cases esterified by a longer, C-12-C-20 fatty acid,residue. The oxygen functionalities at the 4 and 6 positions are either acetylated or present as free hydroxy groups.Ustilipids antagonize dopamine D3 receptors in micromolar quantities; other members of this class of compounds have been found to possess an inhibitory action on the neurotensin receptor. The hemolytic activity of ustilipids is low.