New triterpenoid saponins and sapogenins from Saponaria officinalis

Five new triterpenoid saponins, named saponariosides I-M, were isolated from the whole plants of Saponario officinalis. Their structures were established as saponarioside I (1) 3-O-beta-D-xylopyranosyl-16 alpha-hydroxygypsogenic acid 28-O-alpha-D-galactopyranosyl-(1-->6)-beta-D- glucopyranosyl-(1-->3)[-beta-D-glucopyranoside[, saponarioside J (3) 3-O-beta-D-xylopyranosylolean-11,13(18)-diene-23,28-dioic acid 28-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->6)[- beta-D-glucopyranoside[, saponarioside K (4) 3,4-seco-16 alpha-hydroxygypsogenic acid 28-O-beta-D-glucopyranosyl- (1-->3)-beta-D-glucopyranosyl-(1-->6)[-beta-D-glucopyranoside[, saponarioside L (5) 3-O-beta-D-xylopyranosylgypsogenic acid 28-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->6)[-beta- D- glucopyranoside[, and saponarioside M (6) 3-O-beta-D-glucopyrano-sylgypsogenic acid 28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1--6)-beta-D- glucopyranoside[ by NMR studies and chemical degradations. The aglycons of saponariosides J (3) and K (4) are new sapogenins.