New benzo[c]phenanthridine and benzenoid derivatives, and other constituents from Zanthoxylum ailanthoides: Effects on neutrophil pro-inflammatory responses

Int J Mol Sci. 2013 Nov 13;14(11):22395-408. doi: 10.3390/ijms141122395.

Abstract

A new benzo[c]phenanthridine, oxynorchelerythrine (1), and two new benzenoid derivatives, methyl 4-(2-hydroxy-4-methoxy-3-methyl-4-oxobutoxy)benzoate (2) and (E)-methyl 4-(4-((Z)-3-methoxy-3-oxoprop-1-enyl)phenoxy)-2-methylbut-2-enoate (3), have been isolated from the twigs of Zanthoxylum ailanthoides, together with 11 known compounds (4-14). The structures of these new compounds were determined through spectroscopic and MS analyses. Among the isolated compounds, decarine (4), (-)-syringaresinol (6), (+)-episesamin (8), glaberide I (9), (-)-dihydrocubebin (10), and xanthyletin (11) exhibited potent inhibition (IC50 values ≤ 4.79 µg/mL) of superoxide anion generation by human nutrophils in response to N-formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 4, 8, and 11 also inhibited fMLP/CB-induced elastase release with IC50 values ≤ 5.48 µg/mL.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoates / chemistry*
  • Benzophenanthridines / chemistry
  • Benzophenanthridines / isolation & purification
  • Benzophenanthridines / pharmacology*
  • Cinnamates / chemistry*
  • Humans
  • Hydroxybutyrates / chemistry*
  • Neutrophils / drug effects*
  • Superoxides / antagonists & inhibitors
  • Zanthoxylum / chemistry*

Substances

  • Benzoates
  • Benzophenanthridines
  • Cinnamates
  • Hydroxybutyrates
  • Superoxides