Our laboratory has engaged in the exploration of active antimicrobial principles present in chewing sticks commonly used by the African and Middle Eastern countries as a mechanical oral hygiene aid in place of tooth brushing. During this investigation, a methanol extract from the twigs of Diospyros lycioides, a Namibia tooth cleaning stick, demonstrated antimicrobial activity against common oral pathogens including Streptococcus mutans and Porphyromonas gingivalis (MICs 2.5 and 0.156 mg/mL). Subsequent fractionation and purification of this extract led to the identification of two novel binaphathalenone glycosides: 1',2-binaphthalen-4-one-2',3- dimethyl-1,8'-epoxy-1,4'5,5,8,8'-hexahydroxy-8-O-β-gloucopyranosyl-5'-O-β- xylopy- ranosyl(1→6)-β-glucopyranoside (1) and 1',2-binaphthalen-4-one- 2',3-dimethyl-1,8'-epoxy-1,4',5,5',8,8'-hexahydroxy-5',8-di-O-β- xylopyranosyl(1→6)-β-glucopyranoside (2). Their structures were established using spectroscopic techniques. Examination of the antimicrobial activity of these two compounds revealed positive but only marginal growth inhibition against the test cariogenic pathogens, S. sanguis and Streptococcus routans.
mass spectrometry, Magnetic Resonance Spectroscopy, glycosides, Molecular Conformation, Streptococcus mutans, anti-bacterial agents, Dentifrices, microbial sensitivity tests, naphthalenes, spectrophotometry, Streptococcus sanguis
NCBI PubMed ID: 9644074Publication DOI: 10.1021/np970524lJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: Wu C
Institutions: Department of Periodontics, University of Illinois, College of Dentistry, Chicago, US
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, acid hydrolysis, extraction, CC, HMBC, HMQC, antimicrobial assay, COSY, optical rotaion measurement
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