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.
Common vetch (Vicia sativa L.) is an important annual forage legume. It is used as a cover crop, green manure, pasture legume and for silage and hay production. Its seeds can be used as a source of highly digestible protein and minerals in animal diets. However, their utilization as a feedstuff for monogastric animals is hindered by the fact that the seeds contain cyanogenic antinutritional factors that reduce their palatability. An effective utilization of V. sativa seeds as a successful monogastric feed stuff requires selection for higher protein availability and minimization of the cyanogenic antinutritional factors content. In this study, we selected one natural accession named Mjez Ibeb, from a collection of 25 accessions and cultivars, based on its superior agronomic performance and its naturally occurring genetic variation for cyanogenic traits. We investigated the genetic variation that exists for the cyanogenesis trait in more detail and analysed the seeds of 133 lines derived from accession Mjez lbeb. Of these, 40 naturally polymorphic lines that showed deficiencies in cyanogenesis and cyano‐amino acid content, were subsequently selected for detailed chemical analysis. Cyanogenic glucosides and cyano‐amino acid concentrations varied widely in the 40 lines. Multivariate analysis was performed and three lines (L16, L21, L18) with low content of cyanogenic compounds were identified.
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