Supplementary Material

Figure S1. Chromatograms obtained after enzymatic hydrolysis of U-SFM with 30 nkat AnFaeB/g DDM (A) and 10 nkat ChlE/g DDM (B) at t = 0 min (red) and t = 240 min (black) at 326 nm. 3-O-caffeoylquinic acid (3-CQA) (1), 4-O-caffeoylquinic acid (4-CQA) (2), 5-O-caffeoylquinic acid (5-CQA) (3), caffeic acid (4), 5-O-coumaroylquinic acid (5-CoQA) (5), 5-O-feruloylquinic acid (5-FQA) (6), 3,5-Di-O-caffeoylquinic (3,5-diCQA) (7) and 4,5-Di-O-caffeoylquinic (3,5-diCQA) (4,5-diCQA) (8). From Laguna (2019).

Figure S2. Chromatograms obtained after enzymatic hydrolysis of U-RSM (A) and U-RSM dry methanolic extract (B) with 39 nkat AnFaeA/g DDM at t = 0 min (red) and t = 240 min (black) at 323 nm. Sinapoyl-kaempferol derivatives (1), sinapine (SNP) (2), trans-sinapic acid (SA) (3), cis-sinapic acid (SA) (4), di-sinapoyl derivatives (5), Tri-sinapoyl derivatives (6), sinapoyl glucose (7) and 1,2-di-O-sinapoyl-β-D-glucose (8). From Laguna (2019).

Figure S3. Chemical structure and NMR ¹H and ¹³C data of 1,2-di-O-sinapoyl-b-D-glucose. From Laguna et al. (2019).

Figure S4. Chemical structure and LC-MS data of 1,2-di-O-sinapoyl-b-D-glucose. From Laguna et al. (2019).

Figure S5. Possible mechanism for the formation of 1,2-di-O-sinapoyl-b-D-glucose by transesterification of sinapine with 1-O-sinapoyl-b-D-glucose catalyzed by AnFaeA. Note: Mechanism adapted from Dilokpimol et al. (2016).

© O. Laguna et al., Hosted by EDP Sciences, 2020