p-hydroxyphenylacetaldoxime

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p-hydroxyphenylacetaldoxime 1.2 1.8 2.4 3.0 3.6 2.0e5 4.0e5 6.0e5 8.0e5 1.0e6 Intensity (cps) Retention time (min) (Z) CYP79A118-M39 (with NADPH) (E) 1.2 1.8 2.4 3.0 3.6 2.0e5 4.0e5 6.0e5 8.0e5 1.0e6 Intensity (cps) Retention time (min) CYP79A118-M39 (without NADPH) (Z) (E) 1.2 1.8 2.4 3.0 3.6 0.8e4 1.6e4 2.4e4 3.2e4 4.0e4 Intensity (cps) Retention time (min) empty vector control (with NADPH) Figure S1. Catalytic activity of CYP79A118-M39. Microsomes prepared from yeast expressing either CYP79A118-M39 or an empty vector were incubated with the amino acid substrate L-tyrosine in the presence or absence of NADPH. LC-MS/MS was used to detect the aldoxime products.

p-hydroxyphenylacetaldoxime indole-3-acetaldoxime 2.0 2.6 3.2 3.8 4.4 1.0e3 2.0e3 3.0e3 4.0e3 Retention time (min) Intensity (cps) 1.0e4 2.0e4 3.0e4 (E) (Z) 4.0e4 5.0e4 p-hydroxyphenylacetaldoxime phenylacetaldoxime indole-3-acetaldoxime CYP79A118-M39 CYP79A118 eGFP Figure S2. Heterologous expression of N-terminal truncated CYP79A118-M39 and full-length CYP79A118 in Nicotiana benthamiana. The genes were transiently expressed under control of a 35S promoter in leaves of N. benthamiana. eGFP was used as negative control. Aldoximes were extracted with methanol from grinded leaves and analyzed using LC-MS/MS.

Ct value Figure S3. Comparison of gene expression of potential housekeeping genes in different organs of Taxus baccata. Gene expression was measured using qRT-PCR. Shown are means and SE (n = 7 biological replicates). GAPDH, glyceraldehyde-3-phosphate dehydrogenase.

dhurrin (2S) dhurrin taxiphyllin taxiphyllin (2R) (Taxus baccata leaf 1.8 2.4 3.0 3.6 4.2 0.8e4 1.6e4 2.4e4 3.2e4 dhurrin Intensity (cps) 2S Retention time (min) taxiphyllin (Taxus baccata leaf methanol extract) taxiphyllin (2R) 0.6e4 1.2e4 1.8e4 2.4e4 1.8 2.4 3.0 3.6 4.2 Intensity (cps) 2R Retention time (min) Figure S4. Identification of taxiphyllin in methanol extracts made from Taxus baccata leaves. The cyanogenic glycosides were measured using LC-MS/MS. Dhurrin was used as authentic standard to identify the enantiomer taxiphyllin.