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Abstract:

Four new triterpenoid glycosides were isolated from the root bark of M. macrophylla , collected in Nepal. Their structures were determined as 3- O -β-<smallcap>D-glucopyranosyl- 28- O -α-<smallcap>L-rhamnopyranosyl-16α-hydroxy- 23-deoxyprotobassic acid, 28- O -β-<smallcap>D- glucopyranosyl-16α-hydroxy-23-deoxyprotobassic acid, 3- O -β-<smallcap>D-glucopyranosyl-28- O -α- <smallcap>L -rhamnopyranosyl-16α-hydroxyprotobassic acid, and 3- O -{[β-<smallcap>D-glucopyranosyl-(1 right arrow 6)]- O -α-<smallcap>L-rhamnopyranosyl-(1 right arrow 2)- O -β-<smallcap>D-glucopyranosyl-(1 right arrow 2)}- O -β-<smallcap>D-glucopyranosyl-(1 right arrow 3)- O -β-<smallcap>D-glucopyranosyl-cycloarta-22,24-dien- 27-oic acid (mussaendoside W). Four known triterpenoids, 3- O -acetyloleanolic acid, 3- O -acetyldaturadiol, rotundic acid and 16α-hydroxyprotobassic acid were also isolated. The structures of the new compounds were determined by several spectroscopic techniques including 2D NMR methods. Six compounds showed inhibitory activity against a periodontopathic bacterium, Porphyromonas gingivalis , but were inactive against the cariogenic organism, Streptococcus mutans .