From the herb of Anagallis arvensis L., we have isolated five novel oleanane glycosides, anagallosaponins I-V and the artifact, methyl anagallosaponin I, besides anagallosides A, B, C, and desglucoanagallosides A and B. The structures of isolates were identified by the use of 2D-NMR techniques (1H-1H correlation spectroscopy (COSY), 1H-detected heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple quantum coherence (HMBC), rotating frame Overhauser enhancement spectroscopy (ROESY), total correlation spectroscopy (TOCSY). The structures of anagallosaponins I and II were characterized as anagallogenin A. 3-O-(β-D-glucopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→2)-]-β-D-glucopyranosyl-(1→4)- [β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranoside) and anagallogenin A 22-acetate 3-O-(β-D-xylopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranoside), respectively. The structures of anagallosaponins III, IV and V were characterized as priverogenin B 22-acetate 3-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranoside, 3-O-(β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl (1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranoside), 3-O-(β-D-glucopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→2)]-β-D-glucopyranosyl (1→4)-α-L-arabinopyranoside), respectively. Methyl anagallosaponin I, the methylacetal of anagallosaponin I might be derived from anagallosaponin I during the isolation procedure.
Anagallis arvensis, Primulaceae, oleanane glycoside, anagallosaponin, anagalloside, 23-hydroxyanagalligenin
NCBI PubMed ID: 7954927Publication DOI: 10.1248/cpb.42.1750Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, TLC, extraction, optical rotation measurement, CC, melting point determination, derivatization, RP-MPLC
Found