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Document Type:	Artigo
Title:	Evaluation of the cytotoxicity of structurally correlated p-menthane derivatives
Authors:	Andrade, Luciana Nalone Lima, Tamires Cardoso Amaral, Ricardo Guimarães Cláudia do Ó, Pessoa Moraes Filho, Manoel Odorico de Soares, Bruno Marques Nascimento, Lázaro Gomes do Carvalho, Adriana Andrade Sousa, Damião Pergentino de
Issue Date:	2015
Resumo :	Compounds isolated from essential oils play an important role in the prevention and treatment of cancer. Monoterpenes are natural products, and the principal constituents of many essential oils. The aim of this study was to investigate the cytotoxic potential of p-menthane derivatives. Additionally, analogues of perillyl alcohol, a monoterpene with known anticancer activity, were evaluated to identify the molecular characteristics which contribute to their cytotoxicity, which was tested against OVCAR-8, HCT-116, and SF-295 human tumor cell lines, using the MTT assay. The results of this study showed that (−)-perillaldehyde 8,9-epoxide exhibited the highest percentage inhibition of cell proliferation (GI = 96.32%–99.89%). Perillyl alcohol exhibited high cytotoxic activity (90.92%–95.82%), while (+)-limonene 1,2-epoxide (GI = 58.48%–93.10%), (−)-perillaldehyde (GI = 59.28%– 83.03%), and (−)-8-hydroxycarvotanacetone (GI = 61.59%–94.01%) showed intermediate activity. All of the compounds tested were less cytotoxic than perillyl alcohol, except (−)-perillaldehyde 8,9-epoxide (IC50 = 1.75–1.03 µL/mg). In general, replacement of C-C double bonds by epoxide groups in addition to the aldehyde group increases cytotoxicity. Furthermore, stereochemistry seems to play an important role in cytotoxicity. We have demonstrated the cytotoxic influence of chemical substituents on the p-menthane structure, and analogues of perillyl alcohol.
Keywords:	Cytotoxic activity Cytotoxicity Essential oils Monoterpenes P-menthane Natural products Anticancer Antitumoral Perillyl alcohol
ISSN:	1420-3049
Is part of:	Molecules
Language:	eng
Publisher / Institution :	MDPI
Citation:	ANDRADE, L. N. et al. Evaluation of the cytotoxicity of structurally correlated p-menthane derivatives. Molecules, Basel, v. 20, n. 7, p. 13264-13280, 2015. Disponível em: https://www.mdpi.com/1420-3049/20/7/13264. Acesso em: 24 fev. 2025.
License:	Creative Commons Atribuição 4.0 Internacional (CC BY 4.0)
Identifier:	https://doi.org/10.3390/molecules200713264
URI:	https://ri.ufs.br/jspui/handle/riufs/24638
Appears in Collections:	DFAL - Artigos de periódicos DFS - Artigos de periódicos

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