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高效液相色谱-电喷雾-串联质谱分析及哥伦比亚产海洋海绵 Ectyoplasia ferox 中三萜糖苷的生物活性

HPLC-ESI-IT-MS/MS analysis and biological activity of triterpene glycosides from the Colombian marine sponge Ectyoplasia ferox.

机构信息

Grupo de Investigación Productos Naturales Marinos, Facultad de Química Farmacéutica, Universidad de Antioquia, Calle 70 N° 52-21, Medellín, Colombia.

出版信息

Mar Drugs. 2013 Dec 2;11(12):4815-33. doi: 10.3390/md11124815.

Abstract

The marine sponge Ectyoplasia ferox produces antipredatory and allelopathic triterpenoid glycosides as part of its chemical defense repertoire against predators, competitors, and fouling organisms. These molecules are responsible for the pharmacological potential found in the glycosides present in this species. In order to observe the glycochemical diversity present in E. ferox, a liquid chromatography coupled to a tandem mass spectrometry approach to analyse a complex polar fraction of this marine sponge was performed. This gave valuable information for about twenty-five compounds three of which have been previously reported and another three which were found to be composed of known aglycones. Furthermore, a group of four urabosides, sharing two uncommon substitutions with carboxyl groups at C-4 on the terpenoid core, were identified by a characteristic fragmentation pattern. The oxidized aglycones present in this group of saponins can promote instability, making the purification process difficult. Cytotoxicity, cell cycle modulation, a cell cloning efficiency assay, as well as its hemolytic activity were evaluated. The cytotoxic activity was about IC₅₀ 40 µg/mL on Jurkat and CHO-k₁ cell lines without exhibiting hemolysis. Discussion on this bioactivity suggests the scanning of other biological models would be worthwhile.

摘要

海洋海绵 Ectyoplasia ferox 产生抗捕食和化感三萜糖苷作为其化学防御 repertoire 的一部分,以抵御捕食者、竞争者和污损生物。这些分子是该物种中存在糖苷的药理学潜力的原因。为了观察 E. ferox 中存在的糖化学多样性,对这种海洋海绵的复杂极性部分进行了液相色谱与串联质谱联用的分析。这为大约二十五种化合物提供了有价值的信息,其中三种以前有报道,另外三种被发现由已知的糖苷配基组成。此外,通过特征性的碎裂模式,鉴定了一组具有四个 urabosides,它们在萜类核心的 C-4 上具有两个不常见的取代基,即羧基。该组皂苷中存在的氧化糖苷配基可能会导致不稳定,从而使纯化过程变得困难。评估了细胞毒性、细胞周期调节、细胞克隆效率测定以及溶血活性。在 Jurkat 和 CHO-k₁ 细胞系上,细胞毒性约为 IC₅₀ 40 µg/mL,而没有表现出溶血。关于这种生物活性的讨论表明,扫描其他生物模型将是值得的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5564/3877889/23942ab4701e/marinedrugs-11-04815-g001.jpg

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