十七哌啶生物碱,包括15种先前未描述的2-取代的-6-(9-苯基壬基)-哌啶-3,4-二醇生物碱和先前未描述的2-取代的-6-(9-苯基壬基)-哌啶-3-醇生物碱,从刺槐的叶子中分离出来(L.)肖特。基于HR-ESI-MS阐明了它们的平面结构和构型,1D和2DNMR,Snatzke\的方法,改良的Mosher方法,单晶X射线晶体学,以及量子化学计算。发现ΔδH5b-H5a可用于阐明2,3,4,6-四取代哌啶的相对构型,通过分析2-取代的-6-(9-苯基壬基)-哌啶-3,4-二醇的NMR数据。对所有生物碱的抗增殖活性进行了评估,化合物6-8对K562细胞株有相当的抑制活性,IC50值为17.24±1.62、19.31±0.9和18.77±1.09μM,分别。此外,化合物6和7通过诱导细胞凋亡发挥抗增殖作用。
Seventeen piperidine alkaloids, including 15 previously undescribed 2-substituted-6-(9-phenylnonyl)-piperidine-3,4-diol alkaloids and a previously undescribed 2-substituted-6-(9-phenylnonyl)-piperidine-3-ol alkaloid, were isolated from the leaves of Alocasia macrorrhiza (L.) Schott. Their planar structures and configurations were elucidated based on HR-ESI-MS, 1D and 2D NMR, Snatzke\'s method, modified Mosher method, single-crystal X-ray crystallography, as well as quantum chemical calculation. It was found that ΔδH5b-H5a can be used to elucidate the relative configuration of 2,3,4,6-tetrasubstituted piperidine, by analyzing the NMR data of 2-substituted-6-(9-phenylnonyl)-piperidine-3,4-diol. Antiproliferative activity was evaluated for all of the alkaloids, and compounds 6-8 showed considerable inhibitory activity against K562 cell line, with the IC50 values of 17.24 ± 1.62, 19.31 ± 0.9 and 18.77 ± 1.09μM, respectively. Furthermore, compounds 6 and 7 exerted an antiproliferative effect by inducing apoptosis.