Topical anti-inflammatory activity of quillaic acid from Quillaja saponaria Mol. and some derivatives

Maité Rodríguez-Díaz, Carla Delporte, Carlos Cartagena, Bruce K. Cassels, Patricia González, Ximena Silva, Fredy Leõn, Ludger A. Wessjohann

Resultado de la investigación: Article

6 Citas (Scopus)

Resumen

Objectives 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 functionalisation 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. Key findings 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.

Idioma originalEnglish
Páginas (desde-hasta)718-724
Número de páginas7
PublicaciónJournal of Pharmacy and Pharmacology
Volumen63
N.º5
DOI
EstadoPublished - 1 may 2011

Huella dactilar

Quillaja
Anti-Inflammatory Agents
Aldehydes
Quillaja Saponins
Sapogenins
Hydrazones
Saponins
Phorbol Esters
Carboxylic Acids
Arachidonic Acid
Alcohols
Inflammation
quillaic acid

ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science

Citar esto

Rodríguez-Díaz, M., Delporte, C., Cartagena, C., Cassels, B. K., González, P., Silva, X., ... Wessjohann, L. A. (2011). Topical anti-inflammatory activity of quillaic acid from Quillaja saponaria Mol. and some derivatives. Journal of Pharmacy and Pharmacology, 63(5), 718-724. https://doi.org/10.1111/j.2042-7158.2011.01263.x
Rodríguez-Díaz, Maité ; Delporte, Carla ; Cartagena, Carlos ; Cassels, Bruce K. ; González, Patricia ; Silva, Ximena ; Leõn, Fredy ; Wessjohann, Ludger A. / Topical anti-inflammatory activity of quillaic acid from Quillaja saponaria Mol. and some derivatives. En: Journal of Pharmacy and Pharmacology. 2011 ; Vol. 63, N.º 5. pp. 718-724.
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Rodríguez-Díaz, M, Delporte, C, Cartagena, C, Cassels, BK, González, P, Silva, X, Leõn, F & Wessjohann, LA 2011, 'Topical anti-inflammatory activity of quillaic acid from Quillaja saponaria Mol. and some derivatives', Journal of Pharmacy and Pharmacology, vol. 63, n.º 5, pp. 718-724. https://doi.org/10.1111/j.2042-7158.2011.01263.x

Topical anti-inflammatory activity of quillaic acid from Quillaja saponaria Mol. and some derivatives. / Rodríguez-Díaz, Maité; Delporte, Carla; Cartagena, Carlos; Cassels, Bruce K.; González, Patricia; Silva, Ximena; Leõn, Fredy; Wessjohann, Ludger A.

En: Journal of Pharmacy and Pharmacology, Vol. 63, N.º 5, 01.05.2011, p. 718-724.

Resultado de la investigación: Article

TY - JOUR

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AU - Rodríguez-Díaz, Maité

AU - Delporte, Carla

AU - Cartagena, Carlos

AU - Cassels, Bruce K.

AU - González, Patricia

AU - Silva, Ximena

AU - Leõn, Fredy

AU - Wessjohann, Ludger A.

PY - 2011/5/1

Y1 - 2011/5/1

N2 - Objectives 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 functionalisation 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. Key findings 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.

AB - Objectives 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 functionalisation 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. Key findings 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.

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