Four new triterpenoid saponins, vaccarosides E, F, G and H were isolated from the seeds of Vaccaria segetalis and were respectively defined to be 3- O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl] quillaic acid 28- O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L- arabinofuranosyl-(1 → 3)]-β-D-4-O-acetylfucopyranoside; 3-O-[β-D- galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl] 3β,4α,16α-trihydroxy- 23-norolean-12-en-28-oic acid 28-O-β-D-xylopyranosyl-(1 → 4)-α-L- rhamnopyranosyl-(1 → 2)-[α-L-arabinofuranosyl-(1 → 3)]-β-D-4-O- acetylfucopyranoside; 3-O-[β-D-galactopyranosyl-(1 → 2)-β-D- glucuronopyranosyl] gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L- rhamnopyranosyl-(1 → 2)-[α-L-arabinofuranosyl-(1 → 3)]-β-D-4-O- acetylfucopyranoside; and 3-O-[β-D-galactopyranosyl-(1 → 2)-β-D- glucuronopyranosyl] 3β,4α-dihydroxy-23-norolean-12-en-28-oic acid 28-O-β- D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L- arabinofuranosyl-(1 → 3)]-β-D-4-O-acetylfucopyranoside. Their structures were established on the basis of extensive NMR (DEPT, COSY, HOHAHA, HETCOR, HMBC AND NOESY), FAB-MS and ESI-MS studies as well as chemical strategies and enzymatic degradation. The new aglycones of two of the saponins have been designated as segetalic acid and vaccaric acid, respectively.
triterpene, quillaic acid, triterpenoid saponin, seeds, gypsogenin, F, Caryophyllaceae, Vaccaria segetalis, nortriterpene, segetalic acid, vaccaric acid, vaccarosides E, G and H
NCBI PubMed ID: 9654779Publication DOI: 10.1016/S0031-9422(97)01128-XJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Pharmacognosy, School of Pharmaceutical Sciences, Funabashi, Chiba, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, enzymatic hydrolysis, ESI-MS, acid hydrolysis, GLC, HPLC, alkaline hydrolysis, extraction, optical rotation measurement, melting point determination, HMBC, DEPT, COSY, NOESY, MPLC, HOHAHA, HETCOR
Found