Figure S1. Western blots of CYP99A2, and CYP99A3, as indicated, following expression in Sf21 insect cell cultures as 6xHis tagged proteins, and as detected with an anti-His tag probe.

Figure S2. Optimized gene sequence for CYP99A2.

Figure S3. Optimized gene sequence for CYP99A3.

Figure S4. Summary of NMR structural analyses. (a) Carbon numbering for the syn-pimara-7(8),15(16)-dien-ol, al, or oic acid and syn-stemoden-19-ol,al,or oic acid diterpenoids. (b) Observed HMBC NMR spectra signals for syn-pimara-7(8),15(16)-dien-ol and syn-stemoden-19-ol. These are representative of the aldehydes and acids as well, minus the C19 proton correlations since C19 in the aldehydes and acids is quaternary. (c) Important cross-peak signals from NOESY spectra for the alcohols were used to determine which C4 geminal methyl group, C18 or C19, was the oxidized carbon. There was a strong signal between the alcohol protons and the C20 methyl group (known to be (R) beta from the syn configuration) protons for syn-pimara-7(8),15(16)-dien-ol and syn-stemoden-19-ol, indicating that C19 ((R) or beta on C4) is the oxidized carbon.

Figure S5. Kinetic plots for rCYP99A3 with (a) syn-pimaradiene and (b) syn-stemodene.

Figure S6. Detection of syn-pimaradien-19-oic acid, but not syn-stemoden-19-oic acid, from rice plant metabolites (both analyzed as methyl ester derivatives). Extracted GC-MS chromatogram of authentic standard, methyl jasmonate induced fractionated rice leaf extract (72 h time point), and uninduced (control) fractionated rice leaf extract for (a) syn-pimaradien-19-oic acid (m/z = 241), and (b) syn-stemoden-19-oic acid (m/z = 257).

Table S1.1H and 13C NMR assignments for syn-pimara-7,15-dien-19-ol (500 MHz at 25°C in chloroform-d).

Table S2.1H and 13C NMR assignments for syn-pimara-7,15-dien-19-al (700 MHz at 25°C in chloroform-d).

Table S3.1H and 13C NMR assignments for syn-pimara-7,15-dien-19-oic acid (500 MHz at 25°C in chloroform-d).

Table S4.1H and 13C NMR assignments for syn-stemod-13(17)-en-19-ol (500 MHz at 25°C in methanol-d4).

Table S5.1H and 13C NMR assignments for syn- stemod-13(17)-en-19-al (500 MHz at 25°C in methanol-d4).

Table S6.1H and 13C NMR assignments for syn- stemod-13(17)-en-19-oic acid (500 MHz at 25°C in methanol-d4).

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