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Undescribed isoquinolines from Zanthoxylum nitidum and their antiproliferative effects against human cancer cell lines

Cited 11 time in Web of Science Cited 11 time in Scopus
Authors

Qin, Feng; Wang, Cai Yi; Wang, Chun-Gu; Chen, Yao; Li, Jin-Jun; Li, Mei-Shan; Zhu, Yan-Kui; Lee, Sang Kook; Wang, Heng-Shan

Issue Date
2023-01
Publisher
Elsevier BV
Citation
Phytochemistry, Vol.205, p. 113476
Abstract
Eleven previously undescribed alkaloids, including three pairs of enantiomers nitidumalkaloids A-C, a pair of scalemic mixtures nitidumalkaloid D and three optically pure or achiral alkaloids, nitidumalkaloids E-G, along with 20 known alkaloids, were isolated from an ethanolic extract of the whole Zanthoxylum nitidum (Roxb.) DC plant. The chemical structures of the alkaloids were elucidated using a combination of comprehensive nuclear magnetic resonance (NMR) and high-resolution electro-spray ionization mass spectrometry (HR-ESI-MS) ana-lyses. The configuration of the stereogenic centers of all undescribed compounds was precisely established based on single-crystal X-ray diffraction and electronic circular dichroism (ECD) calculations. Racemic mixtures of nitidumalkaloids A-D were purified, and their enantiomers were analyzed via chiral-phase high-performance liquid chromatography with electrochemical detection measurements (HPLC-ECD). Twelve compounds exhibited significant antiproliferative activities against a panel of cancer cell lines. Further studies were designed to investigate the underlying molecular mechanism of (1 ' S, 6R)-nitidumalkaloid B, which was the most active antiproliferative agent against human cancer A549 cells. G2/M cell cycle arrest, induction of apoptosis, and suppression of the Wnt/beta-catenin signaling pathway were in part associated with the antiproliferative activity of (1 ' S, 6R)-nitidumalkaloid B. Moreover, (1 ' S, 6R)-nitidumalkaloid B inhibited cell migration by downregulating the epithelial-mesenchymal transition process in A549 cells. These data suggest that the antiproliferation activity of (1 ' S, 6R)-nitidumalkaloid B was correlated with the stereoselectivity of the stereoisomers, and (1 ' S, 6R)-nitidumalkaloid B was prioritized as a potential leading compound for the management of aggressive human non-small-cell lung cancer (NSCLC) from natural products.
ISSN
0031-9422
URI
https://hdl.handle.net/10371/188822
DOI
https://doi.org/10.1016/j.phytochem.2022.113476
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