Ribaudo Giovanni, Vendrame Tiziano, Bova Sergio
a Department of Pharmaceutical and Pharmacological Sciences , University of Padova , Padova , Italy.
b Accademia Trevigiana per il Territorio , Treviso , Italy.
Nat Prod Res. 2017 Sep;31(17):1988-1994. doi: 10.1080/14786419.2016.1269101. Epub 2016 Dec 27.
While osajin and pomiferin are known for their anticancer, antibacterial and antidiabetic properties, scandenone and auriculasin have been proposed as anti-inflammatory and antinociceptive agents. Curiously, these two couples of molecules are, from a chemical point of view, structural isomers which can all be extracted from Maclura pomifera. Although previous works described, separately, the isolation in reasonable amounts of the sole osajin/pomiferin couple or of scandenone/auriculasin, we report the extraction and characterization using direct spectral and chromatographical comparison of the four compounds. 2D NMR allowed to unambiguously assign the correct structures to the isomers. The compounds were screened in silico against PDE5 and their interaction pattern with the protein was compared with that of icarisid II, a natural PDE5 inhibitor.
虽然奥沙金和波米菲林以其抗癌、抗菌和抗糖尿病特性而闻名，但 scandione 和耳状素已被提议作为抗炎和抗伤害感受剂。奇怪的是，从化学角度来看，这两对分子是结构异构体，它们都可以从桑橙中提取出来。尽管先前的研究分别描述了仅以合理数量分离出奥沙金/波米菲林对或 scandione/耳状素对，但我们报告了使用四种化合物的直接光谱和色谱比较进行的提取和表征。二维核磁共振允许明确地为异构体指定正确的结构。这些化合物在计算机上针对磷酸二酯酶 5 进行了筛选，并将它们与蛋白质的相互作用模式与天然磷酸二酯酶 5 抑制剂淫羊藿苷 II 的相互作用模式进行了比较。
