Characterization of isobutylhydroxyamides with NGF-potentiating activity from Zanthoxylum bungeanum

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• 作者：Jun-Mian Tian^a ; ^&dagger ; ; Yuan Wang^a ; ^&dagger ; ; Yuan-Zhen Xu^a ; Zhao-Cheng Yu^a ; An-Zhi Wei^a ; Wei-Ming Zhang^b ; ^{zhangwm@nj.ac.cn" class="auth_mail" title="E-mail the corresponding author} ; Jin-Ming Gao^a ; ^{jinminggao@nwsuaf.edu.cn" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Huajiao ; Alkylamides ; Sanshools ; Zanthoxylum bungeanum ; Neurotrophic activity ; Neurite outgrowth-promoting activity ; NGF-mediated PC12 cells
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2016
• 出版时间：15 January 2016
• 年：2016
• 卷：26
• 期：2
• 页码：338-342
• 全文大小：683 K

文摘

Eight isobutylhydroxyamides, including three new (1–3), qinbunamides A–C, and five known sanshools (4–8), ZP-amide A (4), ZP-amide B (5), ZP-amide E (6), ZP-amide C (7), and ZP-amide D (8), were isolated from the pericarps of cultivated Zanthoxylum bungeanum Maxim, cultivated in Qinling mountain area, Shaanxi, China. The structures of all compounds were determined on the basis of spectroscopic techniques, including 1D and 2D NMR analysis and comparison with previously reported data. Compounds 1 and 2 are the first example of isobutylhydroxyamides containing an ethoxy group, and compound 3 is a rare C₁₁ fatty acid-containing sanshool existing in genus Zanthoxylum. The tested compounds enhanced nerve growth factor (NGF)-mediated neurite outgrowth (neurotrophic activity) in rat pheochromocytoma (PC12) cells, but were inactive in the inhibitory effects on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and growth of HCT116 cells at concentrations of 50 μM.