title: Topical anti-inflammatory activity of quillaic acid from Quillaja saponaria Mol. and some derivatives.
abstract: OBJECTIVE
  Quillaic acid is the major aglycone of the widely studied saponins of the Chilean indigenous tree Quillaja saponaria Mol. The industrial availability of quillaja saponins and the extensive functionalization of this triterpenoid provide unique opportunities for structural modification and pose a challenge from the standpoint of selectivity in regard to one or the other secondary alcohol group, the aldehyde, and the carboxylic acid functions. The anti-inflammatory activity of this sapogenin has not been studied previously and it has never been used to obtain potential anti-inflammatory derivatives.
  
  
  METHODS
  A series of quillaic acid derivatives were prepared and subjected to topical assays for the inhibition of inflammation induced by arachidonic acid or phorbol ester.
  
  
  RESULTS
  Quillaic acid exhibited strong topical anti-inflammatory activity in both models. Most of its derivatives were less potent, but the hydrazone 8 showed similar potency to quillaic acid in the TPA assay.
  
  
  CONCLUSIONS
  The structural modifications performed and the biological results suggest that the aldehyde and carboxyl groups are relevant to the anti-inflammatory activity in these models.
authors.affiliation: Department of Pharmacological and Toxicological Chemistry, Faculty of Chemical and Pharmaceutical Sciences, University of Chile, Santiago, Chile.
authors.forename: Maité
authors.initials: M
authors.lastname: Rodríguez-Díaz
authors.forename: Carla
authors.initials: C
authors.lastname: Delporte
authors.forename: Carlos
authors.initials: C
authors.lastname: Cartagena
authors.forename: Bruce K
authors.initials: BK
authors.lastname: Cassels
authors.forename: Patricia
authors.initials: P
authors.lastname: González
authors.forename: Ximena
authors.initials: X
authors.lastname: Silva
authors.forename: Fredy
authors.initials: F
authors.lastname: León
authors.forename: Ludger A
authors.initials: LA
authors.lastname: Wessjohann
mesh_terms: D000287:Administration, Topical; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000008:administration & dosage / Q000494:pharmacology*; D016718:Arachidonic Acid; D007249:Inflammation / Q000139:chemically induced / Q000188:drug therapy*; D008297:Male; D051379:Mice; D008815:Mice, Inbred Strains; D009828:Oleanolic Acid / Q000008:administration & dosage / Q000031:analogs & derivatives* / Q000494:pharmacology; D010703:Phorbol Esters; D008517:Phytotherapy; D010936:Plant Extracts / Q000008:administration & dosage / Q000494:pharmacology*; D031990:Quillaja / Q000737:chemistry*
chemical_list: D000893:Anti-Inflammatory Agents; D010703:Phorbol Esters; D010936:Plant Extracts; D016718:Arachidonic Acid; C005564:quillaic acid; D009828:Oleanolic Acid