title: Characterization of isobutylhydroxyamides with NGF-potentiating activity from Zanthoxylum bungeanum.
abstract: 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 50μM.
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: Jun-Mian
authors.initials: JM
authors.lastname: Tian
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: Yuan
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: Yuan-Zhen
authors.initials: YZ
authors.lastname: Xu
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: Zhao-Cheng
authors.initials: ZC
authors.lastname: Yu
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: An-Zhi
authors.initials: AZ
authors.lastname: Wei
authors.affiliation: Institute for the Comprehensive Utilization of Wild Plants, China COOP, Nanjing 210042, People's Republic of China. Electronic address: zhangwm@nj.ac.cn.
authors.forename: Wei-Ming
authors.initials: WM
authors.lastname: Zhang
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China. Electronic address: jinminggao@nwsuaf.edu.cn.
authors.forename: Jin-Ming
authors.initials: JM
authors.lastname: Gao
mesh_terms: D000577:Amides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D005231:Fatty Acids, Unsaturated / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D045325:HCT116 Cells; D006801:Humans; D051379:Mice; D020932:Nerve Growth Factor / Q000378:metabolism*; D016716:PC12 Cells; D051381:Rats; D032106:Zanthoxylum / Q000737:chemistry*
chemical_list: D000577:Amides; D000894:Anti-Inflammatory Agents, Non-Steroidal; D005231:Fatty Acids, Unsaturated; D020932:Nerve Growth Factor
keywords: Alkylamides; Huajiao; NGF-mediated PC12 cells; Neurite outgrowth-promoting activity; Neurotrophic activity; Sanshools; Zanthoxylum bungeanum