Evaluation of the Cytotoxicity of Structurally Correlated p-Menthane Derivatives
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...
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MDPI AG
2015-07-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/7/13264 |
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| author | Luciana Nalone Andrade Tamires Cardoso Lima Ricardo Guimarães Amaral Cláudia do Ó Pessoa Manoel Odorico de Moraes Filho Bruno Marques Soares Lázaro Gomes do Nascimento Adriana Andrade Carvalho Damião Pergentino de Sousa |
| author_facet | Luciana Nalone Andrade Tamires Cardoso Lima Ricardo Guimarães Amaral Cláudia do Ó Pessoa Manoel Odorico de Moraes Filho Bruno Marques Soares Lázaro Gomes do Nascimento Adriana Andrade Carvalho Damião Pergentino de Sousa |
| author_sort | Luciana Nalone Andrade |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-11T11:24:40Z |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T11:24:40Z |
| publishDate | 2015-07-01 |
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| series | Molecules |
| spelling | doaj.art-dcd0754554fa4a63b531df0bbc769cdb2022-12-22T01:09:02ZengMDPI AGMolecules1420-30492015-07-01207132641328010.3390/molecules200713264molecules200713264Evaluation of the Cytotoxicity of Structurally Correlated p-Menthane DerivativesLuciana Nalone Andrade0Tamires Cardoso Lima1Ricardo Guimarães Amaral2Cláudia do Ó Pessoa3Manoel Odorico de Moraes Filho4Bruno Marques Soares5Lázaro Gomes do Nascimento6Adriana Andrade Carvalho7Damião Pergentino de Sousa8Departamento de Fisiologia, Universidade Federal de Sergipe, CEP 49100-000, São Cristóvão-SE, BrazilDepartamento de Fisiologia, Universidade Federal de Sergipe, CEP 49100-000, São Cristóvão-SE, BrazilDepartamento de Fisiologia, Universidade Federal de Sergipe, CEP 49100-000, São Cristóvão-SE, BrazilDepartamento de Fisiologia e Farmacologia, Universidade Federal do Ceará, CEP 60430-270, Fortaleza-SE, BrazilDepartamento de Fisiologia e Farmacologia, Universidade Federal do Ceará, CEP 60430-270, Fortaleza-SE, BrazilDepartamento de Fisiologia e Farmacologia, Universidade Federal do Ceará, CEP 60430-270, Fortaleza-SE, BrazilDepartamento de Ciências Farmacêuticas, Universidade Federal da Paraíba, CP 5009, CEP 58051-970, João Pessoa-PB, BrazilFarmácia, Universidade Federal de Sergipe, CEP 58051-970, Lagarto-SE, BrazilDepartamento de Ciências Farmacêuticas, Universidade Federal da Paraíba, CP 5009, CEP 58051-970, João Pessoa-PB, BrazilCompounds 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.http://www.mdpi.com/1420-3049/20/7/13264cytotoxic activitycytotoxicityessential oilsmonoterpenesp-menthanenatural productsanticancerantitumoralperillyl alcohol |
| spellingShingle | Luciana Nalone Andrade Tamires Cardoso Lima Ricardo Guimarães Amaral Cláudia do Ó Pessoa Manoel Odorico de Moraes Filho Bruno Marques Soares Lázaro Gomes do Nascimento Adriana Andrade Carvalho Damião Pergentino de Sousa Evaluation of the Cytotoxicity of Structurally Correlated p-Menthane Derivatives Molecules cytotoxic activity cytotoxicity essential oils monoterpenes p-menthane natural products anticancer antitumoral perillyl alcohol |
| title | Evaluation of the Cytotoxicity of Structurally Correlated p-Menthane Derivatives |
| title_full | Evaluation of the Cytotoxicity of Structurally Correlated p-Menthane Derivatives |
| title_fullStr | Evaluation of the Cytotoxicity of Structurally Correlated p-Menthane Derivatives |
| title_full_unstemmed | Evaluation of the Cytotoxicity of Structurally Correlated p-Menthane Derivatives |
| title_short | Evaluation of the Cytotoxicity of Structurally Correlated p-Menthane Derivatives |
| title_sort | evaluation of the cytotoxicity of structurally correlated p menthane derivatives |
| topic | cytotoxic activity cytotoxicity essential oils monoterpenes p-menthane natural products anticancer antitumoral perillyl alcohol |
| url | http://www.mdpi.com/1420-3049/20/7/13264 |
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