Screening of Indanoyl-Type Compounds as Elicitors of Isoflavonoid Phytoalexins in Colombian Common Bean Cultivars
Eleven indanoyl derivatives were synthesized and, along with methyl jasmonate, evaluated as isoflavonoid-phytoalexin elicitors in two cultivars of common bean (<i>Phaseolus vulgaris</i> L. cvs. ICA-Cerinza and Uribe Rosado, tolerant and susceptible to anthracnose, respectively). Indanoyl...
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MDPI AG
2022-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/11/3500 |
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| author | Diego Aristizábal Jesús Gil Winston Quiñones Diego Durango |
| author_facet | Diego Aristizábal Jesús Gil Winston Quiñones Diego Durango |
| author_sort | Diego Aristizábal |
| collection | DOAJ |
| description | Eleven indanoyl derivatives were synthesized and, along with methyl jasmonate, evaluated as isoflavonoid-phytoalexin elicitors in two cultivars of common bean (<i>Phaseolus vulgaris</i> L. cvs. ICA-Cerinza and Uribe Rosado, tolerant and susceptible to anthracnose, respectively). Indanoyl derivatives (an ester, two amides, and eight indanoyl-amino acid conjugates) were obtained from 1-oxo-indane-4-carboxylic acid. In general, the accumulation of isoflavonoid-type phytoalexins, such as isoflavones (genistein, daidzein, and 2′-hydroxygenistein), isoflavanones (dalbergioidin and kievitone), isoflavan (phaseollinisoflavan), coumestrol, and pterocarpans (phaseollidin and phaseollin), was dependent on the common bean cultivar, the post-induction time, and the elicitor structure. Isoflavones, dalbergioidin, and coumestrol reached their highest amounts during the first 48 to 72 h, whereas kievitone, phaseollinisoflavano, and the pterocarpans reached maximum levels between 72 and 96 h. The 1-oxo-indanoyl-L-isoleucine methyl ester elicited the highest levels of phytoalexins (similar to those elicited by the methyl jasmonate) and showed no significant phytotoxic effects on common bean seedlings. The indanoyl-type synthetic elicitor, 1-oxo-indanoyl-L-isoleucine methyl ester, may represent a promising agronomic alternative for disease control in common bean by enhancing the accumulation of antimicrobial isoflavonoid phytoalexins. |
| first_indexed | 2024-03-10T01:04:16Z |
| format | Article |
| id | doaj.art-277c8ca6cba342e099982a6832454c57 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T01:04:16Z |
| publishDate | 2022-05-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-277c8ca6cba342e099982a6832454c572023-11-23T14:29:45ZengMDPI AGMolecules1420-30492022-05-012711350010.3390/molecules27113500Screening of Indanoyl-Type Compounds as Elicitors of Isoflavonoid Phytoalexins in Colombian Common Bean CultivarsDiego Aristizábal0Jesús Gil1Winston Quiñones2Diego Durango3Escuela de Química, Facultad de Ciencias, Universidad Nacional de Colombia-Sede Medellín, Carrera 65, Medellín P.O. Box 3840, ColombiaDepartamento de Ingeniería Agrícola y Alimentos, Facultad de Ciencias Agrarias, Universidad Nacional de Colombia-Sede Medellín, Carrera 65, Medellín P.O. Box 3840, ColombiaGrupo de Química Orgánica de Productos Naturales, Instituto de Química, Universidad de Antioquia, Calle 70, Medellín P.O. Box 1226, ColombiaEscuela de Química, Facultad de Ciencias, Universidad Nacional de Colombia-Sede Medellín, Carrera 65, Medellín P.O. Box 3840, ColombiaEleven indanoyl derivatives were synthesized and, along with methyl jasmonate, evaluated as isoflavonoid-phytoalexin elicitors in two cultivars of common bean (<i>Phaseolus vulgaris</i> L. cvs. ICA-Cerinza and Uribe Rosado, tolerant and susceptible to anthracnose, respectively). Indanoyl derivatives (an ester, two amides, and eight indanoyl-amino acid conjugates) were obtained from 1-oxo-indane-4-carboxylic acid. In general, the accumulation of isoflavonoid-type phytoalexins, such as isoflavones (genistein, daidzein, and 2′-hydroxygenistein), isoflavanones (dalbergioidin and kievitone), isoflavan (phaseollinisoflavan), coumestrol, and pterocarpans (phaseollidin and phaseollin), was dependent on the common bean cultivar, the post-induction time, and the elicitor structure. Isoflavones, dalbergioidin, and coumestrol reached their highest amounts during the first 48 to 72 h, whereas kievitone, phaseollinisoflavano, and the pterocarpans reached maximum levels between 72 and 96 h. The 1-oxo-indanoyl-L-isoleucine methyl ester elicited the highest levels of phytoalexins (similar to those elicited by the methyl jasmonate) and showed no significant phytotoxic effects on common bean seedlings. The indanoyl-type synthetic elicitor, 1-oxo-indanoyl-L-isoleucine methyl ester, may represent a promising agronomic alternative for disease control in common bean by enhancing the accumulation of antimicrobial isoflavonoid phytoalexins.https://www.mdpi.com/1420-3049/27/11/3500<i>Phaseolus vulgaris</i> L.elicitorphytoalexinphaseollinphytotoxicityanthracnose |
| spellingShingle | Diego Aristizábal Jesús Gil Winston Quiñones Diego Durango Screening of Indanoyl-Type Compounds as Elicitors of Isoflavonoid Phytoalexins in Colombian Common Bean Cultivars Molecules <i>Phaseolus vulgaris</i> L. elicitor phytoalexin phaseollin phytotoxicity anthracnose |
| title | Screening of Indanoyl-Type Compounds as Elicitors of Isoflavonoid Phytoalexins in Colombian Common Bean Cultivars |
| title_full | Screening of Indanoyl-Type Compounds as Elicitors of Isoflavonoid Phytoalexins in Colombian Common Bean Cultivars |
| title_fullStr | Screening of Indanoyl-Type Compounds as Elicitors of Isoflavonoid Phytoalexins in Colombian Common Bean Cultivars |
| title_full_unstemmed | Screening of Indanoyl-Type Compounds as Elicitors of Isoflavonoid Phytoalexins in Colombian Common Bean Cultivars |
| title_short | Screening of Indanoyl-Type Compounds as Elicitors of Isoflavonoid Phytoalexins in Colombian Common Bean Cultivars |
| title_sort | screening of indanoyl type compounds as elicitors of isoflavonoid phytoalexins in colombian common bean cultivars |
| topic | <i>Phaseolus vulgaris</i> L. elicitor phytoalexin phaseollin phytotoxicity anthracnose |
| url | https://www.mdpi.com/1420-3049/27/11/3500 |
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