Enzymatic Hydrolysis of the Cytotoxic Triterpenoid Glycoside Virgaureasaponin 1

Add time:07/23/2019    Source:sciencedirect.com

The cytotoxic compound, virgaureasaponin 1, was converted using several optimized enzyme-catalysed hydrolyses to the 28-O-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-β-d-fucopyranoside (2), and the 28-O-α-l-rhamnopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-β-d-fucopyranoside (3) and 28-O-β-d-xylyopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-β-d-fucopyranoside (4) both lacking the glucose moiety at C-3 of the aglycone. The terminal rhamnose of the acylglycosidic bonded tetrasaccharide was cleaved by naringinase to give compound 2. The new acylglycosides 3 and 4 were obtained with the help of a relatively crude β-glucuronidase preparation, but the cleavage of the sapogenin bonded glucose was impossible using several β-glucosidase preparations directly. These derivatives were used for the investigation of the relationship between the saponin carbohydrate structure and their cytotoxic activity.

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