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通过快速微波水解增强皂苷的膜裂解活性。

Enhancing the Membranolytic Activity of Saponins by Fast Microwave Hydrolysis.

机构信息

Organic Synthesis and Mass Spectrometry Laboratory (S²MOs), University of Mons-UMONS, 23 Place du Parc, 7000 Mons; Belgium.

Biology of Marine Organisms and Biomimetics Unit (BOMB), University of Mons-UMONS, 23 Place du Parc, 7000 Mons, Belgium.

出版信息

Molecules. 2020 Apr 9;25(7):1731. doi: 10.3390/molecules25071731.

Abstract

Saponins are plant secondary metabolites. There are associated with defensive roles due to their cytotoxicity and are active against microorganisms. Saponins are frequently targeted to develop efficient drugs. Plant biomass containing saponins deserves sustained interest to develop high-added value applications. A key issue when considering the use of saponins for human healthcare is their toxicity that must be modulated before envisaging any biomedical application. This can only go through understanding the saponin-membrane interactions. Quinoa is abundantly consumed worldwide, but the quinoa husk is discarded due to its astringent taste associated with its saponin content. Here, we focus on the saponins of the quinoa husk extract (QE). We qualitatively and quantitively characterized the QE saponins using mass spectrometry. They are bidesmosidic molecules, with two oligosaccharidic chains appended on the aglycone with two different linkages; a glycosidic bond and an ester function. The latter can be hydrolyzed to prepare monodesmosidic molecules. The microwave-assisted hydrolysis reaction was optimized to produce monodesmosidic saponins. The membranolytic activity of the saponins was assayed based on their hemolytic activity that was shown to be drastically increased upon hydrolysis. In silico investigations confirmed that the monodesmosidic saponins interact preferentially with a model phospholipid bilayer, explaining the measured increased hemolytic activity.

摘要

皂苷是植物次生代谢产物。由于其细胞毒性,与防御作用有关,并对微生物有活性。皂苷经常被用于开发有效的药物。含有皂苷的植物生物质值得持续关注,以开发高附加值的应用。考虑将皂苷用于人类健康护理时的一个关键问题是其毒性,在设想任何生物医学应用之前,必须对其进行调节。这只能通过了解皂苷与膜的相互作用来实现。藜麦在全球范围内被大量食用,但由于其含有皂苷而具有涩味,因此藜麦壳被丢弃。在这里,我们专注于藜麦壳提取物(QE)中的皂苷。我们使用质谱法对 QE 皂苷进行了定性和定量分析。它们是双糖基分子,在糖苷配基上附加有两个具有两种不同键的寡糖链;糖苷键和酯基。后者可以水解制备单糖基分子。优化了微波辅助水解反应,以制备单糖基皂苷。根据溶血活性测定了皂苷的溶血活性,结果表明水解后溶血活性大大增加。计算机模拟研究证实,单糖基皂苷优先与模型磷脂双层相互作用,这解释了所测量的溶血活性增加。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1d92/7181122/03985b7d1813/molecules-25-01731-g001.jpg

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