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Article

Topical Anti-inflammatory Activity of New Hybrid Molecules of Terpenes and Synthetic Drugs

1
Laboratorio de Cultivo Celular, Facultad de Ciencias de la Salud, Universidad de Talca, Casilla 747, Talca 3460000, Chile
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Laboratorio de Productos Naturales, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Santos Dumont 964, Independencia, Santiago 8380000, Chile
3
Instituto de Salud Pública de Chile, Marathon 1000, Santiago 7750000, Chile
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Laboratorio de Química de Productos Naturales, Instituto de Química de Recursos Naturales, Universidad de Talca, Casilla 747, Talca 3460000, Chile
*
Author to whom correspondence should be addressed.
Academic Editor: Thomas J. Schmidt
Molecules 2015, 20(6), 11219-11235; https://doi.org/10.3390/molecules200611219
Received: 8 April 2015 / Revised: 28 May 2015 / Accepted: 11 June 2015 / Published: 18 June 2015
(This article belongs to the Section Molecular Diversity)
The aim of the study was to assess changes in the activity of anti-inflammatory terpenes from Chilean medicinal plants after the formation of derivatives incorporating synthetic anti-inflammatory agents. Ten new hybrid molecules were synthesized combining terpenes (ferruginol (1), imbricatolic acid (2) and oleanolic acid (3)) with ibuprofen (4) or naproxen (5). The topical anti-inflammatory activity of the compounds was assessed in mice by the arachidonic acid (AA) and 12-O-tetradecanoyl phorbol 13-acetate (TPA) induced ear edema assays. Basal cytotoxicity was determined towards human lung fibroblasts, gastric epithelial cells and hepatocytes. At 1.4 µmol/mouse, a strong anti-inflammatory effect in the TPA assay was observed for oleanoyl ibuprofenate 12 (79.9%) and oleanoyl ibuprofenate methyl ester 15 (80.0%). In the AA assay, the best activity was observed for 12 at 3.2 µmol/mouse, with 56.8% reduction of inflammation, in the same range as nimesulide (48.9%). All the terpenyl-synthetic anti-inflammatory hybrids showed better effects in the TPA assay, with best activity for 6, 12 and 15. The cytotoxicity of the compounds 8 and 10 with a free COOH, was higher than that of 2. The derivatives from 3 were less toxic than the triterpene. Several of the new compounds presented better anti-inflammatory effect and lower cytotoxicity than the parent terpenes. View Full-Text
Keywords: terpenes; ibuprofen; naproxen; anti-inflammatory activity; basal cytotoxicity terpenes; ibuprofen; naproxen; anti-inflammatory activity; basal cytotoxicity
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MDPI and ACS Style

Theoduloz, C.; Delporte, C.; Valenzuela-Barra, G.; Silva, X.; Cádiz, S.; Bustamante, F.; Pertino, M.W.; Schmeda-Hirschmann, G. Topical Anti-inflammatory Activity of New Hybrid Molecules of Terpenes and Synthetic Drugs. Molecules 2015, 20, 11219-11235. https://doi.org/10.3390/molecules200611219

AMA Style

Theoduloz C, Delporte C, Valenzuela-Barra G, Silva X, Cádiz S, Bustamante F, Pertino MW, Schmeda-Hirschmann G. Topical Anti-inflammatory Activity of New Hybrid Molecules of Terpenes and Synthetic Drugs. Molecules. 2015; 20(6):11219-11235. https://doi.org/10.3390/molecules200611219

Chicago/Turabian Style

Theoduloz, Cristina, Carla Delporte, Gabriela Valenzuela-Barra, Ximena Silva, Solange Cádiz, Fernanda Bustamante, Mariano W. Pertino, and Guillermo Schmeda-Hirschmann. 2015. "Topical Anti-inflammatory Activity of New Hybrid Molecules of Terpenes and Synthetic Drugs" Molecules 20, no. 6: 11219-11235. https://doi.org/10.3390/molecules200611219

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