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Platycodon grandiflorum root (Platycodi radix) saponins, platycosides, have been used as health supplements and food items for the treatment of respiratory disorders and pulmonary diseases. Deglycosylated saponins have been known to exert stronger biological effects than their glycosylated forms. In the present study, glycosylated platycosides in Platycodi radix extract were biotransformed into deglycosylated 3-O-β-D-glucopyranosyl platycosides, including 3-O-β-Dglucopyranosyl platycodigenin, 3-O-β-D-glucopyranosyl polygalacic acid, and 3-O-β-Dglucopyranosyl platyconic acid, by pectinase from Aspergillus aculeatus. This is the first report on the quantitative enzymatic production of 3-O-β-D-glucopyranosyl platycosides. The chemical structures of 3-O-β-D-glucopyranosyl platycosides were identified with LC/MS. Moreover, the biotransformation pathways of the three types of platycosides in Platycodi radix into 3-O-β-Dglucopyranosyl platycosides were established.