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Molecules 2015, 20(6), 11219-11235; doi:10.3390/molecules200611219

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
2
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
4
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
Received: 8 April 2015 / Revised: 28 May 2015 / Accepted: 11 June 2015 / Published: 18 June 2015
(This article belongs to the Section Molecular Diversity)
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Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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.

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