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Undescribed isoquinolines from Zanthoxylum nitidum and their antiproliferative effects against human cancer cell lines
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Qin, Feng | - |
dc.contributor.author | Wang, Cai Yi | - |
dc.contributor.author | Wang, Chun-Gu | - |
dc.contributor.author | Chen, Yao | - |
dc.contributor.author | Li, Jin-Jun | - |
dc.contributor.author | Li, Mei-Shan | - |
dc.contributor.author | Zhu, Yan-Kui | - |
dc.contributor.author | Lee, Sang Kook | - |
dc.contributor.author | Wang, Heng-Shan | - |
dc.date.accessioned | 2023-01-02T08:07:45Z | - |
dc.date.available | 2023-01-02T08:07:45Z | - |
dc.date.created | 2022-12-06 | - |
dc.date.issued | 2023-01 | - |
dc.identifier.citation | Phytochemistry, Vol.205, p. 113476 | - |
dc.identifier.issn | 0031-9422 | - |
dc.identifier.uri | https://hdl.handle.net/10371/188822 | - |
dc.description.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. | - |
dc.language | 영어 | - |
dc.publisher | Elsevier BV | - |
dc.title | Undescribed isoquinolines from Zanthoxylum nitidum and their antiproliferative effects against human cancer cell lines | - |
dc.type | Article | - |
dc.identifier.doi | 10.1016/j.phytochem.2022.113476 | - |
dc.citation.journaltitle | Phytochemistry | - |
dc.identifier.wosid | 000877351200002 | - |
dc.identifier.scopusid | 2-s2.0-85140344759 | - |
dc.citation.startpage | 113476 | - |
dc.citation.volume | 205 | - |
dc.description.isOpenAccess | N | - |
dc.contributor.affiliatedAuthor | Lee, Sang Kook | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
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