Medium-Chain Fatty Acids from <i>Eugenia winzerlingii</i> Leaves Causing Insect Settling Deterrent, Nematicidal, and Phytotoxic Effects

<i>Eugenia winzerlingii</i> (Myrtaceae) is an endemic plant from the Yucatan peninsula. Its organic extracts and fractions from leaves have been tested on two phloem-feeding insects, <i>Bemisia tabaci</i> and <i>Myzus persicae</i>, on two plant parasitic nematodes...

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Main Authors: Angel Cruz-Estrada, Esaú Ruiz-Sánchez, Jairo Cristóbal-alejo, Azucena González-Coloma, María Fe Andrés, Marcela Gamboa-Angulo
Format: Article
Language:English
Published: MDPI AG 2019-05-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/24/9/1724
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spelling doaj-33c84b971c904ba6b9ecbf2546363ee82020-11-24T22:05:44ZengMDPI AGMolecules1420-30492019-05-01249172410.3390/molecules24091724molecules24091724Medium-Chain Fatty Acids from <i>Eugenia winzerlingii</i> Leaves Causing Insect Settling Deterrent, Nematicidal, and Phytotoxic EffectsAngel Cruz-Estrada0Esaú Ruiz-Sánchez1Jairo Cristóbal-alejo2Azucena González-Coloma3María Fe Andrés4Marcela Gamboa-Angulo5Unidad de Biotecnología, Centro de Investigación Científica de Yucatán, Colonia Chuburná de Hidalgo, Mérida C.P. 97200, Yucatán, MexicoTecnológico Nacional de México, Instituto Tecnológico de Conkal, Conkal C.P. 97345, Yucatán, MexicoTecnológico Nacional de México, Instituto Tecnológico de Conkal, Conkal C.P. 97345, Yucatán, MexicoInstituto de Ciencias Agrarias-CSIC, 115 Dpdo-28006 Madrid, SpainInstituto de Ciencias Agrarias-CSIC, 115 Dpdo-28006 Madrid, SpainUnidad de Biotecnología, Centro de Investigación Científica de Yucatán, Colonia Chuburná de Hidalgo, Mérida C.P. 97200, Yucatán, Mexico<i>Eugenia winzerlingii</i> (Myrtaceae) is an endemic plant from the Yucatan peninsula. Its organic extracts and fractions from leaves have been tested on two phloem-feeding insects, <i>Bemisia tabaci</i> and <i>Myzus persicae</i>, on two plant parasitic nematodes, <i>Meloidogyne incognita</i> and <i>Meloidogyne javanica</i>, and phytotoxicity on <i>Lolium perenne</i> and <i>Solanum lycopersicum</i>. Results showed that both the hexane extract and the ethyl acetate extract, as well as the fractions, have strong antifeedant and nematicidal effects. Gas chromatography-mass spectrometry analyses of methylated active fractions revealed the presence of a mixture of fatty acids. Authentic standards of detected fatty acids and methyl and ethyl derivatives were tested on target organisms. The most active compounds were decanoic, undecanoic, and dodecanoic acids. Methyl and ethyl ester derivatives had lower effects in comparison with free fatty acids. Dose-response experiments showed that undecanoic acid was the most potent compound with EC<sub>50</sub> values of 21 and 6 nmol/cm<sup>2</sup> for <i>M. persicae</i> and <i>B. tabaci</i>, respectively, and 192 and 64 nmol for <i>M. incognita</i> and <i>M. javanica</i>, respectively. In a phytotoxicity assay, medium-chain fatty acids caused a decrease of 38&#8722;52% in root length and 50&#8722;60% in leaf length of <i>L. perenne</i>, but no effects were observed on <i>S.</i> <i>lycopersicum</i>. This study highlights the importance of the genus <i>Eugenia</i> as a source of bioactive metabolites for plant pest management.https://www.mdpi.com/1420-3049/24/9/1724Bemisia tabacidecanoic aciddodecanoic acidEugenia winzerlingiiLolium perenneMeloidogyneMyzus persicaeSolanum lycopersicumundecanoic acid
collection DOAJ
language English
format Article
sources DOAJ
author Angel Cruz-Estrada
Esaú Ruiz-Sánchez
Jairo Cristóbal-alejo
Azucena González-Coloma
María Fe Andrés
Marcela Gamboa-Angulo
spellingShingle Angel Cruz-Estrada
Esaú Ruiz-Sánchez
Jairo Cristóbal-alejo
Azucena González-Coloma
María Fe Andrés
Marcela Gamboa-Angulo
Medium-Chain Fatty Acids from <i>Eugenia winzerlingii</i> Leaves Causing Insect Settling Deterrent, Nematicidal, and Phytotoxic Effects
Molecules
Bemisia tabaci
decanoic acid
dodecanoic acid
Eugenia winzerlingii
Lolium perenne
Meloidogyne
Myzus persicae
Solanum lycopersicum
undecanoic acid
author_facet Angel Cruz-Estrada
Esaú Ruiz-Sánchez
Jairo Cristóbal-alejo
Azucena González-Coloma
María Fe Andrés
Marcela Gamboa-Angulo
author_sort Angel Cruz-Estrada
title Medium-Chain Fatty Acids from <i>Eugenia winzerlingii</i> Leaves Causing Insect Settling Deterrent, Nematicidal, and Phytotoxic Effects
title_short Medium-Chain Fatty Acids from <i>Eugenia winzerlingii</i> Leaves Causing Insect Settling Deterrent, Nematicidal, and Phytotoxic Effects
title_full Medium-Chain Fatty Acids from <i>Eugenia winzerlingii</i> Leaves Causing Insect Settling Deterrent, Nematicidal, and Phytotoxic Effects
title_fullStr Medium-Chain Fatty Acids from <i>Eugenia winzerlingii</i> Leaves Causing Insect Settling Deterrent, Nematicidal, and Phytotoxic Effects
title_full_unstemmed Medium-Chain Fatty Acids from <i>Eugenia winzerlingii</i> Leaves Causing Insect Settling Deterrent, Nematicidal, and Phytotoxic Effects
title_sort medium-chain fatty acids from <i>eugenia winzerlingii</i> leaves causing insect settling deterrent, nematicidal, and phytotoxic effects
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2019-05-01
description <i>Eugenia winzerlingii</i> (Myrtaceae) is an endemic plant from the Yucatan peninsula. Its organic extracts and fractions from leaves have been tested on two phloem-feeding insects, <i>Bemisia tabaci</i> and <i>Myzus persicae</i>, on two plant parasitic nematodes, <i>Meloidogyne incognita</i> and <i>Meloidogyne javanica</i>, and phytotoxicity on <i>Lolium perenne</i> and <i>Solanum lycopersicum</i>. Results showed that both the hexane extract and the ethyl acetate extract, as well as the fractions, have strong antifeedant and nematicidal effects. Gas chromatography-mass spectrometry analyses of methylated active fractions revealed the presence of a mixture of fatty acids. Authentic standards of detected fatty acids and methyl and ethyl derivatives were tested on target organisms. The most active compounds were decanoic, undecanoic, and dodecanoic acids. Methyl and ethyl ester derivatives had lower effects in comparison with free fatty acids. Dose-response experiments showed that undecanoic acid was the most potent compound with EC<sub>50</sub> values of 21 and 6 nmol/cm<sup>2</sup> for <i>M. persicae</i> and <i>B. tabaci</i>, respectively, and 192 and 64 nmol for <i>M. incognita</i> and <i>M. javanica</i>, respectively. In a phytotoxicity assay, medium-chain fatty acids caused a decrease of 38&#8722;52% in root length and 50&#8722;60% in leaf length of <i>L. perenne</i>, but no effects were observed on <i>S.</i> <i>lycopersicum</i>. This study highlights the importance of the genus <i>Eugenia</i> as a source of bioactive metabolites for plant pest management.
topic Bemisia tabaci
decanoic acid
dodecanoic acid
Eugenia winzerlingii
Lolium perenne
Meloidogyne
Myzus persicae
Solanum lycopersicum
undecanoic acid
url https://www.mdpi.com/1420-3049/24/9/1724
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