1. Antiproliferative piperidine alkaloids from the leaves of Alocasia macrorrhiza.
- Author
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Deng W, Shen L, Zeng J, Gao J, Luo J, Xu J, Wang Y, and He X
- Subjects
- Humans, Molecular Structure, Structure-Activity Relationship, Dose-Response Relationship, Drug, K562 Cells, Crystallography, X-Ray, Plant Leaves chemistry, Alkaloids pharmacology, Alkaloids chemistry, Alkaloids isolation & purification, Antineoplastic Agents, Phytogenic pharmacology, Antineoplastic Agents, Phytogenic chemistry, Antineoplastic Agents, Phytogenic isolation & purification, Cell Proliferation drug effects, Drug Screening Assays, Antitumor, Piperidines pharmacology, Piperidines chemistry, Piperidines isolation & purification, Alocasia chemistry
- Abstract
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 Δδ
H5b - 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., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)- Published
- 2024
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