Evaluation of the Cytotoxicity of Structurally Correlated p-Menthane Derivatives

Molecules

Luciana Nalone Andrade¹  Tamires Cardoso Lima¹  Ricardo Guimar฾s Amaral¹  Cláudia do Ó Pessoa²  Manoel Odorico de Moraes Filho²  Bruno Marques Soares²  Lázaro Gomesdo Nascimento³  Adriana Andrade Carvalho⁴  Damião Pergentino de Sousa³ 

[1] Departamento de Fisiologia, Universidade Federal de Sergipe, CEP 49100-000, São Cristóvão-SE, Brazil; E-Mails:;Departamento de Fisiologia e Farmacologia, Universidade Federal do Ceará, CEP 60430-270, Fortaleza-SE, Brazil; E-Mails:;Universidade Federal da Paraíba, CP 5009, CEP 58051-970, João Pessoa-PB, Brazil; E-Mail:;Universidade Federal de Sergipe, CEP 58051-970, Lagarto-SE, Brazil; E-Mail:

关键词: cytotoxic activity;    cytotoxicity;    essential oils;    monoterpenes;    p-menthane;    natural products;    anticancer;    antitumoral;    perillyl alcohol;   

DOI  :  10.3390/molecules200713264

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.