Activity of triterpenoid glycosides from the root bark of Mussaenda macrophylla against two oral pathogens.
Four new triterpenoid glycosides were isolated from the root bark of Mussaenda macrophylla. Their structures were determined as 3-O-beta-D-glucopyranosyl-28-O-alpha-L-rhamnopyranosyl-16alpha- hydrox y-23-deoxyprotobassic acid (1), 28-O-beta-D-glucopyranosyl-16alpha-hydroxy-23-deoxyprotobassic+ ++ acid (2), 3-O-beta-D-glucopyranosyl-28-O-alpha-L-rhamnopyranosyl-16alpha- hydrox yprotobassic acid (3), and 3-O-¿[beta-D-glucopyranosyl-(1-->6)]-O-alpha-L-rhamnopyranosyl-(1-->2 )-O-beta-D-glucopyranosyl-(1-->2)¿-O-beta-D-glucopyranosyl-(1-->3)-O- beta-D-glucopyranosyl-cycloarta-22,24-dien-27-oic acid (mussaendoside W, 4). Four known triterpenoids [3-O-acetyloleanolic acid (5), 3-O-acetyldaturadiol (6), rotundic acid (7), and 16alpha-hydroxyprotobassic acid (8)] were also isolated. The structures of 1-4 were determined by several spectroscopic techniques including 2D NMR methods. Compounds 1-6 showed inhibitory activity against a periodontopathic bacterium, Porphyromonas gingivalis, but were inactive against the cariogenic organism, Streptococcus mutans.
Kim
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NC
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, USA.
Desjardins
A E
AE
Wu
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CD
Kinghorn
A D
AD
D002240:Carbohydrate Sequence; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013058:Mass Spectrometry / Q000379:methods; D008826:Microbial Sensitivity Tests; D008969:Molecular Sequence Data; D009055:Mouth / Q000382:microbiology*; D018517:Plant Roots / Q000737:chemistry; D016966:Porphyromonas gingivalis / Q000187:drug effects*; D019666:Rubiaceae / Q000737:chemistry*; D013057:Spectrum Analysis; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*
D006027:Glycosides; D014315:Triterpenes