Biosynthesis of cyanogenic glucosides in Phaseolus lunatus and the evolution of oxime-based defense
Lima bean, Phaseolus lunatus, is a crop legume that produces the cyanogenic glucosides linamarin and lotaustralin. In the legumes Lotus japonicus and Trifolium repens, the biosynthesis of these two α‐hydroxynitrile glucosides involves cytochrome P450 enzymes of the CYP79 and CYP736 families and a UD...
| Autores principales: | , , , , , , , , , , , |
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| Formato: | Journal Article |
| Lenguaje: | Inglés |
| Publicado: |
Wiley
2020
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| Materias: | |
| Acceso en línea: | https://hdl.handle.net/10568/108996 |
| _version_ | 1855540220743647232 |
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| author | Lai, Daniela Maimann, Alexandra B. Macea Choperena, Eliana del Pilar Ocampo Nahar, César H. Cardona, Gustavo Pičmanová, Martina Darbani, Behrooz Olsen, Carl Erik Debouck, Daniel G. Raatz, Bodo Møller, Birger Lindberg Rook, Fred |
| author_browse | Cardona, Gustavo Darbani, Behrooz Debouck, Daniel G. Lai, Daniela Macea Choperena, Eliana del Pilar Maimann, Alexandra B. Møller, Birger Lindberg Ocampo Nahar, César H. Olsen, Carl Erik Pičmanová, Martina Raatz, Bodo Rook, Fred |
| author_facet | Lai, Daniela Maimann, Alexandra B. Macea Choperena, Eliana del Pilar Ocampo Nahar, César H. Cardona, Gustavo Pičmanová, Martina Darbani, Behrooz Olsen, Carl Erik Debouck, Daniel G. Raatz, Bodo Møller, Birger Lindberg Rook, Fred |
| author_sort | Lai, Daniela |
| collection | Repository of Agricultural Research Outputs (CGSpace) |
| description | Lima bean, Phaseolus lunatus, is a crop legume that produces the cyanogenic glucosides linamarin and lotaustralin. In the legumes Lotus japonicus and Trifolium repens, the biosynthesis of these two α‐hydroxynitrile glucosides involves cytochrome P450 enzymes of the CYP79 and CYP736 families and a UDP‐glucosyltransferase. Here, we identify CYP79D71 as the first enzyme of the pathway in P. lunatus, producing oximes from valine and isoleucine. A second CYP79 family member, CYP79D72, was shown to catalyze the formation of leucine‐derived oximes, which act as volatile defense compounds in Phaseolus spp. The organization of the biosynthetic genes for cyanogenic glucosides in a gene cluster aided their identification in L. japonicus. In the available genome sequence of P. vulgaris, the gene orthologous to CYP79D71 is adjacent to a member of the CYP83 family. Although P. vulgaris is not cyanogenic, it does produce oximes as volatile defense compounds. We cloned the genes encoding two CYP83s (CYP83E46 and CYP83E47) and a UDP‐glucosyltransferase (UGT85K31) from P. lunatus, and these genes combined form a complete biosynthetic pathway for linamarin and lotaustralin in Lima bean. Within the genus Phaseolus, the occurrence of linamarin and lotaustralin as functional chemical defense compounds appears restricted to species belonging to the closely related Polystachios and Lunatus groups. A preexisting ability to produce volatile oximes and nitriles likely facilitated evolution of cyanogenesis within the Phaseolus genus. |
| format | Journal Article |
| id | CGSpace108996 |
| institution | CGIAR Consortium |
| language | Inglés |
| publishDate | 2020 |
| publishDateRange | 2020 |
| publishDateSort | 2020 |
| publisher | Wiley |
| publisherStr | Wiley |
| record_format | dspace |
| spelling | CGSpace1089962025-11-11T19:06:52Z Biosynthesis of cyanogenic glucosides in Phaseolus lunatus and the evolution of oxime-based defense Lai, Daniela Maimann, Alexandra B. Macea Choperena, Eliana del Pilar Ocampo Nahar, César H. Cardona, Gustavo Pičmanová, Martina Darbani, Behrooz Olsen, Carl Erik Debouck, Daniel G. Raatz, Bodo Møller, Birger Lindberg Rook, Fred phaseolus composicion quimica chemical composition glicosidos cianogenicos cyanogenic glycosides citocromo p450 cytochrome p450 Lima bean, Phaseolus lunatus, is a crop legume that produces the cyanogenic glucosides linamarin and lotaustralin. In the legumes Lotus japonicus and Trifolium repens, the biosynthesis of these two α‐hydroxynitrile glucosides involves cytochrome P450 enzymes of the CYP79 and CYP736 families and a UDP‐glucosyltransferase. Here, we identify CYP79D71 as the first enzyme of the pathway in P. lunatus, producing oximes from valine and isoleucine. A second CYP79 family member, CYP79D72, was shown to catalyze the formation of leucine‐derived oximes, which act as volatile defense compounds in Phaseolus spp. The organization of the biosynthetic genes for cyanogenic glucosides in a gene cluster aided their identification in L. japonicus. In the available genome sequence of P. vulgaris, the gene orthologous to CYP79D71 is adjacent to a member of the CYP83 family. Although P. vulgaris is not cyanogenic, it does produce oximes as volatile defense compounds. We cloned the genes encoding two CYP83s (CYP83E46 and CYP83E47) and a UDP‐glucosyltransferase (UGT85K31) from P. lunatus, and these genes combined form a complete biosynthetic pathway for linamarin and lotaustralin in Lima bean. Within the genus Phaseolus, the occurrence of linamarin and lotaustralin as functional chemical defense compounds appears restricted to species belonging to the closely related Polystachios and Lunatus groups. A preexisting ability to produce volatile oximes and nitriles likely facilitated evolution of cyanogenesis within the Phaseolus genus. 2020-08 2020-08-11T15:00:00Z 2020-08-11T15:00:00Z Journal Article https://hdl.handle.net/10568/108996 en Open Access application/pdf application/pdf Wiley Lai, D.; Maimann, A.B.; Macea, E.; Ocampo, C.H.; Cardona, G.; Picmanová, M.; Darbani, B.; Olsen, C.E.; Debouck, D.G.; Raatz, B.; Møller, B.L.; Rook, F. (2020) Biosynthesis of cyanogenic glucosides in Phaseolus lunatus and the evolution of oxime-based defenses. Plant Direct 4 (8): 1-13. ISSN: 2475-4455 |
| spellingShingle | phaseolus composicion quimica chemical composition glicosidos cianogenicos cyanogenic glycosides citocromo p450 cytochrome p450 Lai, Daniela Maimann, Alexandra B. Macea Choperena, Eliana del Pilar Ocampo Nahar, César H. Cardona, Gustavo Pičmanová, Martina Darbani, Behrooz Olsen, Carl Erik Debouck, Daniel G. Raatz, Bodo Møller, Birger Lindberg Rook, Fred Biosynthesis of cyanogenic glucosides in Phaseolus lunatus and the evolution of oxime-based defense |
| title | Biosynthesis of cyanogenic glucosides in Phaseolus lunatus and the evolution of oxime-based defense |
| title_full | Biosynthesis of cyanogenic glucosides in Phaseolus lunatus and the evolution of oxime-based defense |
| title_fullStr | Biosynthesis of cyanogenic glucosides in Phaseolus lunatus and the evolution of oxime-based defense |
| title_full_unstemmed | Biosynthesis of cyanogenic glucosides in Phaseolus lunatus and the evolution of oxime-based defense |
| title_short | Biosynthesis of cyanogenic glucosides in Phaseolus lunatus and the evolution of oxime-based defense |
| title_sort | biosynthesis of cyanogenic glucosides in phaseolus lunatus and the evolution of oxime based defense |
| topic | phaseolus composicion quimica chemical composition glicosidos cianogenicos cyanogenic glycosides citocromo p450 cytochrome p450 |
| url | https://hdl.handle.net/10568/108996 |
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