Enzymatic hydrolysis of the cytotoxic triterpenoid glycoside virgaureasaponin 1.
The cytotoxic compound, virgaureasaponin 1, was converted using several optimized enzymecatalysed hydrolyses to the 28-O-beta-D-xylopyranosyl (1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (2), and the 28-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha- L- rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (3) and 28-O-beta-D-xylyopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2) - beta-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 beta-glucuronidase preparation, but the cleavage of the sapogenin bonded glucose was impossible using several beta-glucosidase preparations directly. These derivatives were used for the investigation of the relationship between the saponin carbohydrate structure and their cytotoxic activity.
Bader
G
G
Institut für Pharmazie, Mathematisch-Naturwissenschaftliche Fakultät I, Humboldt-Universität zu Berlin.
Wray
V
V
Just
U
U
Hiller
K
K
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002470:Cell Survival / Q000187:drug effects; D006026:Glycoside Hydrolases / Q000378:metabolism*; D006868:Hydrolysis; D051379:Mice; D008958:Models, Molecular; D008969:Molecular Sequence Data; D009097:Multienzyme Complexes / Q000378:metabolism*; D010407:Penicillium / Q000201:enzymology; D012503:Saponins / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D014407:Tumor Cells, Cultured; D001617:beta-Glucosidase / Q000378:metabolism*
D000972:Antineoplastic Agents, Phytogenic; D009097:Multienzyme Complexes; D012503:Saponins; D014315:Triterpenes; C114777:virgaureasaponin 1; D006026:Glycoside Hydrolases; C039827:naringinase; D001617:beta-Glucosidase