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1tables and figures Supplementary Table 1 Genes potentially implicated in Medicago truncatula triterpenoid biosynthesis correlated with bAS NameProbeset.

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Presentation on theme: "1tables and figures Supplementary Table 1 Genes potentially implicated in Medicago truncatula triterpenoid biosynthesis correlated with bAS NameProbeset."— Presentation transcript:

1 1tables and figures Supplementary Table 1 Genes potentially implicated in Medicago truncatula triterpenoid biosynthesis correlated with bAS NameProbeset IDCorrelation bAS Mtr.32384.1.S1_s_a t 0.9929 CYP72A68Mtr.37298.1.S1_at0.9036 CYP72A67Mtr.37299.1.S1_at0.9027 Anthocyanidin 3-O- glucosyltransferase Mtr.40639.1.S1_at0.847 CYP72A67Mtr.28860.1.S1_at0.827 bASMtr.32384.1.S1_at0.8215 CYP72A65Mtr.24379.1.S1_at0.7903 Cytokinin-O-glucosyltransferaseMtr.13275.1.S1_at0.7838 CYP716A12 Mtr.31199.1.S1_s_a t 0.7525 Anthocyanidin 3-O- glucosyltransferase Mtr.41162.1.S1_at0.7504 Cytokinin-O-glucosyltransferaseMtr.43628.1.S1_at0.7391 CYP716A12Mtr.43018.1.S1_at0.6951 CYP89A2 Mtr.51061.1.S1_x_a t 0.6693 CYP89A2Mtr.51061.1.S1_at0.6693 UGT73K1Mtr.37228.1.S1_at0.5747 CYP72A61Mtr.43117.1.S1_at0.5452 CYP93E2Mtr.8618.1.S1_at0.4834 P450s correlated with bAS (Mtr.18630.1.S1_at) based on a Pearson correlation coefficient cut-off 0.4.

2 2tables and figures Supplementary Table 2 Estimated product yields of bAS/CPR/CYP716A12/CYP72A68v2- and bAS/CPR/CYP93E2/CYP72A61v2-expressing yeast Compound (peak no.)Estimated yield (mg/L) bAS/CPR/CYP93E2/CYP72A61-expressing yeast β-Amyrin (1)1.07 24-OH-β-Amyrin (2)0.27 Soyasapogenol B (3)1.35 bAS/CPR/CYP716A12/CYP72A68-expressing yeast β-Amyrin (1)0.55 Erythrodiol (4)0.09 Gypsogenic acid (8)0.96 Estimation was performed based on peak areas from the mass chromatograms shown in Figs. 2 and 3, by comparing the areas of internal standard and authentic compounds with known concentrations.

3 3 Supplementary Fig. S1 Expression profiles of P450 genes potentially involved in soyasapogenol B biosynthesis. Co-expression analysis was performed using the gene co-expression tool for Medicago truncatula (http://mtgea.noble.org/v2/correlation_search_form.php). Expression profiles for bAS, CYP93E2, CYP72A61, and UGT73K1 are shown. Corresponding probe IDs and correlation values are indicated in Table 1. CYP93E2bASCYP72A61UGT73K 1

4 4 Supplementary Fig. S2 Expression profiles of P450 genes potentially involved in gypsogenic acid biosynthesis. Co-expression analysis was performed using the gene co-expression tool for Medicago truncatula (http://mtgea.noble.org/v2/correlation_search_form.php). Expressions of bAS, CYP716A12, CYP72A68, and UGT73F3 are shown. Corresponding probe IDs are indicated in Table 2. CYP716A12bASCYP72A68UGT73F3

5 5tables and figures Supplementary Fig. S4 Mass spectrum of product resulting from transgenic yeast co- expressing bAS, CPR, CYP716A12, and CYP72A68. The mass spectrum of peak 4 shown in Fig. 3A matches up with that of authentic erythrodiol (4). Peak 4 in Fig. 3A Authentic erythrodiol (4) Supplementary Fig. S3 Mass spectrum of product resulting from transgenic yeast co- expressing bAS, CPR, CYP93E2, and CYP72A61. The mass spectrum of peak 2 shown in Fig. 2A matches up with that of authentic 24-OH-β- amyrin (2). Peak 2 in Fig. 2A Authentic 24-OH-β-amyrin (2)

6 6tables and figures Peak 4 in Fig. 4A Peak 5 in Fig. 4A Authentic erythrodiol (4) Authentic oleanolic acid (5) Supplementary Fig. S5 Mass spectra of products resulting from transgenic yeast co- expressing bAS, CPR, CYP93E2, and CYP716A12. The mass spectra of peaks 2, 4, and 5 shown in Fig. 4A match up with those of authentic 24-OH-β-amyrin (2), erythrodiol (4), and oleanolic acid (5), respectively. Authentic 24-OH-β-amyrin (2) Peak 2 in Fig. 4A

7 7tables and figures Supplementary Fig. S6 In vivo production of queretaroic acid and other β-amyrin derivatives in transgenic yeast co-expressing bAS, CPR, CYP716A12, and CYP72A63. (A) and (B) show GC-MS analysis (TIC) of ethyl acetate extracts (using DB-1 MS column) from yeast cultures. (A) The yeast strains were engineered to express bAS, CPR, CYP716A12, and CYP72A63; (B) bAS, CPR, and CYP716A12 as controls. (C) The structures were deduced from mass spectra because authentic standards were not available. Queretaroic acid was identified by comparison with bibliographic data (Burnouf- Radosevich et al. 1985). bAS/CPR/CYP716A12 Relative ion intensity (%) Retention time (min) bAS/CPR/CYP716A12/CYP72A63 A B 141516 1817 1920212324222518 26 5 4

8 8tables and figures Peak 14 in (A) Peak 15 in (A) Authentic 30-OH-β-amyrin Peak 18 in (A) Peak 16 in (A) Peak 17 in (A) Queretaroic acid C Peak 4 in (A) Peak 5 in (A) Authentic erythrodiol (4) Authentic oleanolic acid (5) Supplementary Fig. S6 (Cont.)

9 9tables and figures Supplementary Fig. S7 In vivo production of rare triterpenoids in transgenic yeast co- expressing bAS, CPR, CYP93E2, and CYP72A63. (A) and (B) show GC-MS analysis (TIC) of ethyl acetate extracts (using DB-1 MS column) from yeast cultures. (A) The yeast strains were engineered to express bAS, CPR, CYP93E2, and CYP72A63; (B) bAS, CPR, and CYP93E2 as controls. (C) The structures were deduced from mass spectra. bAS/CPR/CYP93E2 Relative ion intensity (%) Retention time (min) 20 β-Amyrin (1) bAS/CPR/CYP93E2/CYP72A63 A B 21 22 1920212324222518 214 1726 15 2728 19

10 10tables and figures Peak 2 in (A) Authentic 24-OH-β-amyrin (6) Peak 19 in (A) C Peak 20 in (A) Peak 14 in (A) Peak 15 in (A) Authentic 30-OH-β-amyrin (14) Authentic 11-deoxo-glycyrrhetinic acid(15) Peak 21 in (A) Peak 22 in (A) Supplementary Fig. S7 (Cont.)

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