Characterization of isobutylhydroxyamides with NGF-potentiating activity from Zanthoxylum bungeanum

Bioorg Med Chem Lett. 2016 Jan 15;26(2):338-342. doi: 10.1016/j.bmcl.2015.12.015. Epub 2015 Dec 10.

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.

Keywords: Alkylamides; Huajiao; NGF-mediated PC12 cells; Neurite outgrowth-promoting activity; Neurotrophic activity; Sanshools; Zanthoxylum bungeanum.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Amides / isolation & purification
  • Amides / pharmacology*
  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Fatty Acids, Unsaturated / chemistry
  • Fatty Acids, Unsaturated / isolation & purification
  • Fatty Acids, Unsaturated / pharmacology*
  • HCT116 Cells
  • Humans
  • Mice
  • Nerve Growth Factor / metabolism*
  • PC12 Cells
  • Rats
  • Zanthoxylum / chemistry*

Substances

  • Amides
  • Anti-Inflammatory Agents, Non-Steroidal
  • Fatty Acids, Unsaturated
  • Nerve Growth Factor