Four novel triterpenoid saponins were isolated from the seeds of Vaccaria segetalis. Their structures were established as vaccaroside A, gypsogenic acid-28-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosyl-(1 → 6)-[β-D-glucopyranosyl-(1 → 3)]-β-D-glucopyranoside; vaccaroside B, gypsogenic acid-28-O-β-D-glucopyranosyl-(1 → 2)-[3-hydroxyl-3- methylglutaroyl-(1 → 6)]-β-D-glucopyranosyl-(1 → 6)-[β-D-glucopyranosyl- (1 → 3)]-β-D-glucopyranoside; vaccaroside C, 23-O-β-D-glucopyranosyl- gypsogenic acid-28-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosyl-(1 → 6)-[β-D-glucopyranosyl-(1 → 3)]-β-D-glucopyranoside and vaccaroside D, 3,4-secogypsogenic acid-28-O-β-D-glucopyranosyl-(1 → 3)-[β-D- glucopyranosyl-(1 → 6)]-β-D-glucopyranoside by a combination of extensive NMR (DEPT, COSY, HOHAHA, HETCOR, HMBC and NOESY) studies and chemical degradation.
3, D, C, triterpenoid saponin, seeds, B, Caryophyllaceae, Vaccaria segetalis, 4-secogypsogenic acid, gypsogenic acid, vaccarosides A
Publication DOI: 10.1016/S0031-9422(97)00707-3Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Pharmacognosy, School of Pharmaceutical Sciences, Funabashi, Chiba, Japan
Methods: IR, FAB-MS, HPLC, extraction, optical rotation measurement, melting point determination, HMBC, HMQC, DEPT, COSY, NOESY, MPLC, HOHAHA, HETCOR
Found