Exploration of the Diversity of Vicine and Convicine Derivatives in Faba Bean (<i>Vicia faba</i> L.) Cultivars: Insights from LC-MS/MS Spectra
While numerous <i>Fabaceae</i> seeds are a good nutritional source of high-quality protein, the use of some species is hampered by toxic effects caused by exposure to metabolites that accumulate in the seeds. One such species is the faba or broad bean (<i>Vicia faba</i> L.),...
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| Format: | Article |
| Language: | English |
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MDPI AG
2024-02-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/29/5/1065 |
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| author | Kjell Sergeant Simon Goertz Salma Halime Hanna Tietgen Hanna Heidt Martina Minestrini Cédric Jacquard Stephanie Zimmer Jenny Renaut |
| author_facet | Kjell Sergeant Simon Goertz Salma Halime Hanna Tietgen Hanna Heidt Martina Minestrini Cédric Jacquard Stephanie Zimmer Jenny Renaut |
| author_sort | Kjell Sergeant |
| collection | DOAJ |
| description | While numerous <i>Fabaceae</i> seeds are a good nutritional source of high-quality protein, the use of some species is hampered by toxic effects caused by exposure to metabolites that accumulate in the seeds. One such species is the faba or broad bean (<i>Vicia faba</i> L.), which accumulates vicine and convicine. These two glycoalkaloids cause favism, the breakdown of red blood cells in persons with a glucose-6-phosphate dehydrogenase deficiency. Because this is the most common enzyme deficiency worldwide, faba bean breeding efforts have focused on developing cultivars with low levels of these alkaloids. Consequently, quantification methods have been developed; however, they quantify vicine and convicine only and not the derivatives of these compounds that potentially generate the same bio-active molecules. Based on the recognition of previously unknown (con)vicine-containing compounds, we screened the fragmentation spectra of LC-MS/MS data from five faba bean cultivars using the characteristic fragments generated by (con)vicine. This resulted in the recognition of more than a hundred derivatives, of which 89 were tentatively identified. (Con)vicine was mainly derivatized through the addition of sugars, hydroxycinnamic acids, and dicarboxylic acids, with a group of compounds composed of two (con)vicine residues linked by dicarboxyl fatty acids. In general, the abundance profiles of the different derivatives in the five cultivars mimicked that of vicine and convicine, but some showed a derivative-specific profile. The description of the (con)vicine diversity will impact the interpretation of future studies on the biosynthesis of (con)vicine, and the content in potentially bio-active alkaloids in faba beans may be higher than that represented by the quantification of vicine and convicine alone. |
| first_indexed | 2024-04-25T00:24:38Z |
| format | Article |
| id | doaj.art-a5053c146c4a476fa6eec92b6a3f5008 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-25T00:24:38Z |
| publishDate | 2024-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a5053c146c4a476fa6eec92b6a3f50082024-03-12T16:50:56ZengMDPI AGMolecules1420-30492024-02-01295106510.3390/molecules29051065Exploration of the Diversity of Vicine and Convicine Derivatives in Faba Bean (<i>Vicia faba</i> L.) Cultivars: Insights from LC-MS/MS SpectraKjell Sergeant0Simon Goertz1Salma Halime2Hanna Tietgen3Hanna Heidt4Martina Minestrini5Cédric Jacquard6Stephanie Zimmer7Jenny Renaut8Biotechnologies and Environmental Analytics Platform (BEAP), Environmental Research and Innovation Department (ERIN), Luxembourg Institute of Science and Technology (LIST), 5, Rue Bommel, L-4940 Hautcharage, LuxembourgNPZ Innovation GmbH, Hohenlieth-Hof 1, 24363 Holtsee, GermanyBiotechnologies and Environmental Analytics Platform (BEAP), Environmental Research and Innovation Department (ERIN), Luxembourg Institute of Science and Technology (LIST), 5, Rue Bommel, L-4940 Hautcharage, LuxembourgNPZ Innovation GmbH, Hohenlieth-Hof 1, 24363 Holtsee, GermanyInstitut fir Biologësch Landwirtschaft an Agrarkultur Luxemburg a.s.b.l (IBLA), 1 Wantergaass, L-7664 Medernach, LuxembourgBiotechnologies and Environmental Analytics Platform (BEAP), Environmental Research and Innovation Department (ERIN), Luxembourg Institute of Science and Technology (LIST), 5, Rue Bommel, L-4940 Hautcharage, LuxembourgUniversité de Reims Champagne-Ardenne, INRAE, RIBP USC 1488, 51100 Reims, FranceInstitut fir Biologësch Landwirtschaft an Agrarkultur Luxemburg a.s.b.l (IBLA), 1 Wantergaass, L-7664 Medernach, LuxembourgBiotechnologies and Environmental Analytics Platform (BEAP), Environmental Research and Innovation Department (ERIN), Luxembourg Institute of Science and Technology (LIST), 5, Rue Bommel, L-4940 Hautcharage, LuxembourgWhile numerous <i>Fabaceae</i> seeds are a good nutritional source of high-quality protein, the use of some species is hampered by toxic effects caused by exposure to metabolites that accumulate in the seeds. One such species is the faba or broad bean (<i>Vicia faba</i> L.), which accumulates vicine and convicine. These two glycoalkaloids cause favism, the breakdown of red blood cells in persons with a glucose-6-phosphate dehydrogenase deficiency. Because this is the most common enzyme deficiency worldwide, faba bean breeding efforts have focused on developing cultivars with low levels of these alkaloids. Consequently, quantification methods have been developed; however, they quantify vicine and convicine only and not the derivatives of these compounds that potentially generate the same bio-active molecules. Based on the recognition of previously unknown (con)vicine-containing compounds, we screened the fragmentation spectra of LC-MS/MS data from five faba bean cultivars using the characteristic fragments generated by (con)vicine. This resulted in the recognition of more than a hundred derivatives, of which 89 were tentatively identified. (Con)vicine was mainly derivatized through the addition of sugars, hydroxycinnamic acids, and dicarboxylic acids, with a group of compounds composed of two (con)vicine residues linked by dicarboxyl fatty acids. In general, the abundance profiles of the different derivatives in the five cultivars mimicked that of vicine and convicine, but some showed a derivative-specific profile. The description of the (con)vicine diversity will impact the interpretation of future studies on the biosynthesis of (con)vicine, and the content in potentially bio-active alkaloids in faba beans may be higher than that represented by the quantification of vicine and convicine alone.https://www.mdpi.com/1420-3049/29/5/1065<i>Fabaceae</i>alkaloidsconvicinevicinefragment ion screeningdicarboxylic fatty acid |
| spellingShingle | Kjell Sergeant Simon Goertz Salma Halime Hanna Tietgen Hanna Heidt Martina Minestrini Cédric Jacquard Stephanie Zimmer Jenny Renaut Exploration of the Diversity of Vicine and Convicine Derivatives in Faba Bean (<i>Vicia faba</i> L.) Cultivars: Insights from LC-MS/MS Spectra Molecules <i>Fabaceae</i> alkaloids convicine vicine fragment ion screening dicarboxylic fatty acid |
| title | Exploration of the Diversity of Vicine and Convicine Derivatives in Faba Bean (<i>Vicia faba</i> L.) Cultivars: Insights from LC-MS/MS Spectra |
| title_full | Exploration of the Diversity of Vicine and Convicine Derivatives in Faba Bean (<i>Vicia faba</i> L.) Cultivars: Insights from LC-MS/MS Spectra |
| title_fullStr | Exploration of the Diversity of Vicine and Convicine Derivatives in Faba Bean (<i>Vicia faba</i> L.) Cultivars: Insights from LC-MS/MS Spectra |
| title_full_unstemmed | Exploration of the Diversity of Vicine and Convicine Derivatives in Faba Bean (<i>Vicia faba</i> L.) Cultivars: Insights from LC-MS/MS Spectra |
| title_short | Exploration of the Diversity of Vicine and Convicine Derivatives in Faba Bean (<i>Vicia faba</i> L.) Cultivars: Insights from LC-MS/MS Spectra |
| title_sort | exploration of the diversity of vicine and convicine derivatives in faba bean i vicia faba i l cultivars insights from lc ms ms spectra |
| topic | <i>Fabaceae</i> alkaloids convicine vicine fragment ion screening dicarboxylic fatty acid |
| url | https://www.mdpi.com/1420-3049/29/5/1065 |
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