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Molecules 2015, 20(4), 6194-6210; doi:10.3390/molecules20046194

Biological Activities and Cytotoxicity of Diterpenes from Copaifera spp. Oleoresins

1
Chemistry Department, Federal University of Amazonas, Av. Gal. Rodrigo Octávio, 6.200, Japiim, Manaus-AM 69080-900, Brazil
2
Faculty of Pharmaceutical Sciences, Federal University of Amazonas, Manaus, Av. Gal. Rodrigo Octávio, 6.200, Japiim, Manaus-AM 69080-900, Brazil
3
Environmental Studies Program, University of Colorado, Boulder, CO 80309, USA
4
School of Environmental Sciences, University of East Anglia, Norwich NR4 7TJ, UK
*
Author to whom correspondence should be addressed.
Academic Editor: Isabel C. F. R. Ferreira
Received: 14 January 2015 / Revised: 1 April 2015 / Accepted: 2 April 2015 / Published: 9 April 2015
(This article belongs to the Collection Bioactive Compounds)
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Abstract

Copaifera spp. are Amazonian species widely studied and whose oleoresins are used by local people for various medicinal purposes. However, a detailed study of the activity of the main phytochemical components of these oleoresins remains to be done. Here, we studied the cytotoxicity and in vitro anti-inflammatory effects of six diterpene acids: copalic, 3-hydroxy-copalic, 3-acetoxy-copalic, hardwickiic, kolavic-15-metyl ester, and kaurenoic, isolated from the oleoresins of Copaifera spp. The diterpenes did not show cytotoxicity in normal cell lines, nor did they show significant changes in viability of tumoral line cells. The 3-hydroxy-copalic was able to inhibit the enzyme tyrosinase (64% ± 1.5%) at 250 µM. The kolavic-15-metyl ester at 200 µM showed high inhibitory effect on lipoxygenase (89.5% ± 1.2%). Among the diterpenes tested, only kaurenoic and copalic acids showed significant hemolytic activities with 61.7% and 38.4% at 100 µM, respectively. In addition, it was observed that only the copalic acid (98.5% ± 1.3%) and hardwickiic acid (92.7% ± 4.9%) at 100 mM inhibited nitric oxide production in macrophages activated by lipopolysaccharide. In this assay, the diterpenes did not inhibit tumor necrosis factor-α production. The acids inhibited the production of IL-6, 3-acetoxy-copalic (23.8% ± 8.2%), kaurenoic (11.2% ± 5.7%), kolavic-15-methyl ester (17.3% ± 4.2%), and copalic (4.2% ± 1.8%), respectively, at 25 µM. The kaurenoic, 3-acetoxy-copalic and copalic acids increased IL-10 production. This study may provide a basis for future studies on the therapeutic role of diterpenic acids in treating acute injuries such as inflammation or skin disorders. View Full-Text
Keywords: Copaifera L.; diterpenic acids; anti-inflammatory; antitumoral Copaifera L.; diterpenic acids; anti-inflammatory; antitumoral
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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

de S. Vargas, F.; D. O. de Almeida, P.; Aranha, E.S.P.; de A. Boleti, A.P.; Newton, P.; de Vasconcellos, M.C.; Junior, V.F.V.; Lima, E.S. Biological Activities and Cytotoxicity of Diterpenes from Copaifera spp. Oleoresins. Molecules 2015, 20, 6194-6210.

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