神经保护
神经炎症
糖基化
化学
药理学
哇巴因
糖苷
炎症
生物化学
医学
立体化学
免疫学
有机化学
钠
作者
Ryan Rutkoski,Lucas Kniess Debarba,Lukas Stilgenbauer,Tay Rosenthal,Marianna Sadagurski,Pavel Nagorny
标识
DOI:10.1021/acsmedchemlett.3c00517
摘要
This work describes the studies on the direct C3-glycosylation of the C19-hydroxylated cardiotonic steroids strophanthidol, anhydro-ouabagenin, and ouabagenin using a strategy based on in situ protection of the C5 and C19 hydroxyl groups with boronic acids. While this strategy resulted in a successful one-pot C3-selective glycosylation of strophanthidol and anhydro-ouabegenin, it failed to provide ouabain from ouabagenin. The neuroprotective activity of the synthetic and natural glycosides against LPS-induced neuroinflammation was explored in neonatal mouse primary glia cells. Co-administration of natural and synthetic C3-glycosides at 200 nM concentrations resulted in the significant reduction of the LPS-induced neuroinflammatory markers IL-6, IL-1, TNFα, and IKBKE, with the anhydro-ouabagenin-3-(α)-l-rhamnoside (anhydro-ouabain) showing the most significant effect. At the same time, unglycosylated anhydro-ouabagenin enhanced rather than suppressed LPS-induced neuroinflammation.
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