Insect‐resistant soybean genotypes accumulate rutin and its O ‐methylated derivative narcissin, a more potent flavonol targeting Anticarsia gemmatalis digestive and detoxification enzymes and reducing larval survival
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| Format: | Artículo Open Access |
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2026
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| author | Jessica Nunes de Assis Valquira Joana Medina Pinheiro Jodieh Oliveira Santana Varejão Ian de Paula Alves Pinto André Luiz Lourenção Nathália Silva Oliveira Giovanna Cassia Mendes Moraes Eduardo Vinícius Vieira Varejão Maria Goreti de Almeida Oliveira Humberto Josué de Oliveira Ramos |
| author_facet | Jessica Nunes de Assis Valquira Joana Medina Pinheiro Jodieh Oliveira Santana Varejão Ian de Paula Alves Pinto André Luiz Lourenção Nathália Silva Oliveira Giovanna Cassia Mendes Moraes Eduardo Vinícius Vieira Varejão Maria Goreti de Almeida Oliveira Humberto Josué de Oliveira Ramos Jessica Nunes de Assis Valquira Joana Medina Pinheiro Jodieh Oliveira Santana Varejão Ian de Paula Alves Pinto André Luiz Lourenção Nathália Silva Oliveira Giovanna Cassia Mendes Moraes Eduardo Vinícius Vieira Varejão Maria Goreti de Almeida Oliveira Humberto Josué de Oliveira Ramos |
| collection | Wiley Open Access |
| contents | Insect‐resistant soybean genotypes accumulate rutin and its O ‐methylated derivative narcissin, a more potent flavonol targeting Anticarsia gemmatalis digestive and detoxification enzymes and reducing larval survival Jessica Nunes de Assis Valquira Joana Medina Pinheiro Jodieh Oliveira Santana Varejão Ian de Paula Alves Pinto André Luiz Lourenção Nathália Silva Oliveira Giovanna Cassia Mendes Moraes Eduardo Vinícius Vieira Varejão Maria Goreti de Almeida Oliveira Humberto Josué de Oliveira Ramos Journal of the Science of Food and Agriculture Abstract BACKGROUND Soybean underpins Brazil's agricultural, yet its sustainability is threatened by lepidopteran pests such as Anticarsia gemmatalis . Although insect‐resistant cultivars have long been associated with the constitutive accumulation of quercetin‐derived flavonols, the biochemical mechanisms underlying this resistance remain poorly understood. In particular, the role of flavonol O ‐methylation in enhancing plant defense has not been demonstrated. RESULTS Here we combined metabolite identification, biological assays, and structure‐based modeling to investigate flavonol‐mediated resistance in soybean. The resistant genotype IAC 17 was found to accumulate not only rutin (quercetin 3‐ O ‐rutinoside; [M + H] + = 611 Da) but also its O ‐methylated derivative isorhamnetin 3‐ O ‐rutinoside (narcissin; [M + H] + = 625 Da). The 625 Da compound was purified by reversed‐phase high‐performance liquid chromatography and structurally confirmed by liquid chromatography–tandem mass spectrometry and nuclear magnetic resonance analyses. Chemical methylation of rutin using methyl iodide generated methylated derivatives that were evaluated in dietary bioassays with A. gemmatalis larvae. Both rutin and its methylated derivatives reduced survival, but O ‐methylation markedly enhanced toxicity: methylated rutin caused approximately 95% mortality within 5 days, whereas non‐methylated rutin required about 17 days to reach comparable lethality. Molecular docking against the 70 most abundant larval midgut proteins revealed strong binding of both flavonols to proteases, cytochrome P450 enzymes, glutathione S ‐transferases, and membrane‐associated proteins. CONCLUSION These findings support a dual‐ligand model in which rutin and narcissin cooperatively disrupt digestive and detoxification pathways in the insect midgut. The discovery of a constitutive flavonol O ‐methylation branch identifies narcissin as a potent defensive metabolite and provides mechanistic targets for breeding and metabolic engineering strategies aimed at developing soybean cultivars with improved resistance. © 2026 The Author(s). Journal of the Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry. 10.1002/jsfa.70640 http://creativecommons.org/licenses/by/4.0/ |
| doi_str_mv | 10.1002/jsfa.70640 |
| format | Artículo Open Access |
| id | wiley_oa_10_1002_jsfa_70640 |
| institution | Wiley Open Access |
| license_str_mv | http://creativecommons.org/licenses/by/4.0/ |
| publishDate | 2026 |
| publisher | Wiley |
| record_format | wiley_oa |
| spellingShingle | Insect‐resistant soybean genotypes accumulate rutin and its O ‐methylated derivative narcissin, a more potent flavonol targeting Anticarsia gemmatalis digestive and detoxification enzymes and reducing larval survival Jessica Nunes de Assis Valquira Joana Medina Pinheiro Jodieh Oliveira Santana Varejão Ian de Paula Alves Pinto André Luiz Lourenção Nathália Silva Oliveira Giovanna Cassia Mendes Moraes Eduardo Vinícius Vieira Varejão Maria Goreti de Almeida Oliveira Humberto Josué de Oliveira Ramos Journal of the Science of Food and Agriculture Insect‐resistant soybean genotypes accumulate rutin and its O ‐methylated derivative narcissin, a more potent flavonol targeting Anticarsia gemmatalis digestive and detoxification enzymes and reducing larval survival Jessica Nunes de Assis Valquira Joana Medina Pinheiro Jodieh Oliveira Santana Varejão Ian de Paula Alves Pinto André Luiz Lourenção Nathália Silva Oliveira Giovanna Cassia Mendes Moraes Eduardo Vinícius Vieira Varejão Maria Goreti de Almeida Oliveira Humberto Josué de Oliveira Ramos Journal of the Science of Food and Agriculture Abstract BACKGROUND Soybean underpins Brazil's agricultural, yet its sustainability is threatened by lepidopteran pests such as Anticarsia gemmatalis . Although insect‐resistant cultivars have long been associated with the constitutive accumulation of quercetin‐derived flavonols, the biochemical mechanisms underlying this resistance remain poorly understood. In particular, the role of flavonol O ‐methylation in enhancing plant defense has not been demonstrated. RESULTS Here we combined metabolite identification, biological assays, and structure‐based modeling to investigate flavonol‐mediated resistance in soybean. The resistant genotype IAC 17 was found to accumulate not only rutin (quercetin 3‐ O ‐rutinoside; [M + H] + = 611 Da) but also its O ‐methylated derivative isorhamnetin 3‐ O ‐rutinoside (narcissin; [M + H] + = 625 Da). The 625 Da compound was purified by reversed‐phase high‐performance liquid chromatography and structurally confirmed by liquid chromatography–tandem mass spectrometry and nuclear magnetic resonance analyses. Chemical methylation of rutin using methyl iodide generated methylated derivatives that were evaluated in dietary bioassays with A. gemmatalis larvae. Both rutin and its methylated derivatives reduced survival, but O ‐methylation markedly enhanced toxicity: methylated rutin caused approximately 95% mortality within 5 days, whereas non‐methylated rutin required about 17 days to reach comparable lethality. Molecular docking against the 70 most abundant larval midgut proteins revealed strong binding of both flavonols to proteases, cytochrome P450 enzymes, glutathione S ‐transferases, and membrane‐associated proteins. CONCLUSION These findings support a dual‐ligand model in which rutin and narcissin cooperatively disrupt digestive and detoxification pathways in the insect midgut. The discovery of a constitutive flavonol O ‐methylation branch identifies narcissin as a potent defensive metabolite and provides mechanistic targets for breeding and metabolic engineering strategies aimed at developing soybean cultivars with improved resistance. © 2026 The Author(s). Journal of the Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry. 10.1002/jsfa.70640 http://creativecommons.org/licenses/by/4.0/ |
| title | Insect‐resistant soybean genotypes accumulate rutin and its O ‐methylated derivative narcissin, a more potent flavonol targeting Anticarsia gemmatalis digestive and detoxification enzymes and reducing larval survival |
| topic | Journal of the Science of Food and Agriculture |
| url | https://scijournals.onlinelibrary.wiley.com/doi/10.1002/jsfa.70640 |