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Fig. S1 Phylogenetic trees of OSCs, cytochrome P450s and SDR-like proteins constructed by the maximum likelihood method with 1000 bootstrap replicates.

Fig. S2 Gene transcript levels of AMY2, LjCYP88D5 and LjCYP71D353, constituting the AMY2 gene cluster, expressed relative to the level of each gene expression in 7-d-old root tissues.

Fig. S3 In situ hybridization of AMY2, LjCYP71D353 and LjCYP88D5 gene transcripts in mature 28 dpi and developing 14 dpi L. japonicus nodules.

Fig. S4 Gene transcript levels of LjSDRt, present in the AMY2 gene cluster, detected in both uninoculated and inoculated with M. loti.

Fig. S5 AMY2 cluster gene expression in L. japonicus root tissues subjected to salt stress.

Fig. S6 Main fragments in the mass spectrometry fragmentation patterns of the TMS-derivatives of 20-hydroxy-lupeol and 20-hydroxy-betulinic acid.

Fig. S7 GC-MS analysis of N. benthamiana leaf extracts infiltrated with different AsbAS1 construct combinations.

Fig. S8 Syntenic analysis of multiple genomic regions encompassing OSC genes in L. japonicus and A. thaliana.

Table S1 Primers used in experimental procedures