Detoxification Mechanism of 8,8-Dimethyl-3-[(<i>R</i>-phenyl)amino]-1,4,5(8<i>H</i>)-naphthalentrione Derivatives by <i>Botrytis cinerea</i>
The effect of 8,8-dimethyl-3-[(<i>R</i>-phenyl)amino]-1,4,5(8<i>H</i>)-naphthalentrione derivatives (compounds <b>1</b>⁻<b>13</b>) on the mycelial growth of <i>Botrytis cinerea</i> was evaluated. The fungitoxic effect depended on...
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MDPI AG
2019-02-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/3/544 |
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| author | Leonora Mendoza Marcela Vivanco Ricardo Melo Paulo Castro Ramiro Araya-Maturana Milena Cotoras |
| author_facet | Leonora Mendoza Marcela Vivanco Ricardo Melo Paulo Castro Ramiro Araya-Maturana Milena Cotoras |
| author_sort | Leonora Mendoza |
| collection | DOAJ |
| description | The effect of 8,8-dimethyl-3-[(<i>R</i>-phenyl)amino]-1,4,5(8<i>H</i>)-naphthalentrione derivatives (compounds <b>1</b>⁻<b>13</b>) on the mycelial growth of <i>Botrytis cinerea</i> was evaluated. The fungitoxic effect depended on the substituent and its position in the aromatic ring. Compounds substituted with halogens in meta and/or para positions (compounds <b>3</b>, <b>4</b>, <b>5</b> and <b>7</b>), methyl (compounds <b>8</b> and <b>9</b>), methoxyl (compounds <b>10</b> and <b>11</b>), or ethoxy-carbonyl groups (compound <b>12</b>) presented higher antifungal activity than compound <b>1</b>, which had an unsubstituted aromatic ring. In addition, compounds with halogens in the ortho position, such as compounds <b>2</b> and <b>6</b>, and a substitution with an acetyl group in the para position (compound <b>13</b>) were less active. The role of the ABC efflux pump Bctr B-type as a defense mechanism of <i>B. cinerea</i> against these naphthalentrione derivatives was analyzed. This pump could be involved in the detoxification of compounds <b>2</b>, <b>6</b>, and <b>13</b>. On the contrary, this mechanism would not participate in the detoxification of compounds <b>1</b>, <b>7</b>, <b>9</b> and <b>12</b>. Finally, the biotransformation of compound <b>7</b> by <i>B. cinerea</i> was studied. A mixture of two biotransformed products was obtained. One of them was compound <b>7A</b>, which is reduced at C1 and C4, compared to compound <b>7</b>. The other product of biotransformation, 7B, is oxidized at C7. |
| first_indexed | 2024-12-12T19:16:19Z |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-12T19:16:19Z |
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| spelling | doaj.art-f62b1c8da29d40cbbcd924ca81d050762022-12-22T00:14:44ZengMDPI AGMolecules1420-30492019-02-0124354410.3390/molecules24030544molecules24030544Detoxification Mechanism of 8,8-Dimethyl-3-[(<i>R</i>-phenyl)amino]-1,4,5(8<i>H</i>)-naphthalentrione Derivatives by <i>Botrytis cinerea</i>Leonora Mendoza0Marcela Vivanco1Ricardo Melo2Paulo Castro3Ramiro Araya-Maturana4Milena Cotoras5Laboratorio de Micología, Facultad de Biología y Química, Universidad de Santiago de Chile, Alameda 3363, Estación Central, Santiago 9160000, ChileNúcleo de Química y Bioquímica, Facultad de Estudios Interdisciplinarios, Universidad Mayor, Camino La Pirámide 5750, Huechuraba, Santiago 8580000, ChileNúcleo de Química y Bioquímica, Facultad de Estudios Interdisciplinarios, Universidad Mayor, Camino La Pirámide 5750, Huechuraba, Santiago 8580000, ChileLaboratorio de Micología, Facultad de Biología y Química, Universidad de Santiago de Chile, Alameda 3363, Estación Central, Santiago 9160000, ChileInstituto de Química de Recursos Naturales and Programa de Investigación Asociativa en Cáncer Gástrico, Universidad de Talca, casilla 747, Talca 3460000, ChileLaboratorio de Micología, Facultad de Biología y Química, Universidad de Santiago de Chile, Alameda 3363, Estación Central, Santiago 9160000, ChileThe effect of 8,8-dimethyl-3-[(<i>R</i>-phenyl)amino]-1,4,5(8<i>H</i>)-naphthalentrione derivatives (compounds <b>1</b>⁻<b>13</b>) on the mycelial growth of <i>Botrytis cinerea</i> was evaluated. The fungitoxic effect depended on the substituent and its position in the aromatic ring. Compounds substituted with halogens in meta and/or para positions (compounds <b>3</b>, <b>4</b>, <b>5</b> and <b>7</b>), methyl (compounds <b>8</b> and <b>9</b>), methoxyl (compounds <b>10</b> and <b>11</b>), or ethoxy-carbonyl groups (compound <b>12</b>) presented higher antifungal activity than compound <b>1</b>, which had an unsubstituted aromatic ring. In addition, compounds with halogens in the ortho position, such as compounds <b>2</b> and <b>6</b>, and a substitution with an acetyl group in the para position (compound <b>13</b>) were less active. The role of the ABC efflux pump Bctr B-type as a defense mechanism of <i>B. cinerea</i> against these naphthalentrione derivatives was analyzed. This pump could be involved in the detoxification of compounds <b>2</b>, <b>6</b>, and <b>13</b>. On the contrary, this mechanism would not participate in the detoxification of compounds <b>1</b>, <b>7</b>, <b>9</b> and <b>12</b>. Finally, the biotransformation of compound <b>7</b> by <i>B. cinerea</i> was studied. A mixture of two biotransformed products was obtained. One of them was compound <b>7A</b>, which is reduced at C1 and C4, compared to compound <b>7</b>. The other product of biotransformation, 7B, is oxidized at C7.https://www.mdpi.com/1420-3049/24/3/544naphthalentrione derivatives<i>Botrytis cinerea</i>ABC pump effluxbiotransformation |
| spellingShingle | Leonora Mendoza Marcela Vivanco Ricardo Melo Paulo Castro Ramiro Araya-Maturana Milena Cotoras Detoxification Mechanism of 8,8-Dimethyl-3-[(<i>R</i>-phenyl)amino]-1,4,5(8<i>H</i>)-naphthalentrione Derivatives by <i>Botrytis cinerea</i> Molecules naphthalentrione derivatives <i>Botrytis cinerea</i> ABC pump efflux biotransformation |
| title | Detoxification Mechanism of 8,8-Dimethyl-3-[(<i>R</i>-phenyl)amino]-1,4,5(8<i>H</i>)-naphthalentrione Derivatives by <i>Botrytis cinerea</i> |
| title_full | Detoxification Mechanism of 8,8-Dimethyl-3-[(<i>R</i>-phenyl)amino]-1,4,5(8<i>H</i>)-naphthalentrione Derivatives by <i>Botrytis cinerea</i> |
| title_fullStr | Detoxification Mechanism of 8,8-Dimethyl-3-[(<i>R</i>-phenyl)amino]-1,4,5(8<i>H</i>)-naphthalentrione Derivatives by <i>Botrytis cinerea</i> |
| title_full_unstemmed | Detoxification Mechanism of 8,8-Dimethyl-3-[(<i>R</i>-phenyl)amino]-1,4,5(8<i>H</i>)-naphthalentrione Derivatives by <i>Botrytis cinerea</i> |
| title_short | Detoxification Mechanism of 8,8-Dimethyl-3-[(<i>R</i>-phenyl)amino]-1,4,5(8<i>H</i>)-naphthalentrione Derivatives by <i>Botrytis cinerea</i> |
| title_sort | detoxification mechanism of 8 8 dimethyl 3 i r i phenyl amino 1 4 5 8 i h i naphthalentrione derivatives by i botrytis cinerea i |
| topic | naphthalentrione derivatives <i>Botrytis cinerea</i> ABC pump efflux biotransformation |
| url | https://www.mdpi.com/1420-3049/24/3/544 |
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