Binaphthalenone glycosides from African chewing sticks, Diospyros lycioides

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-beta-glucopyranosyl-5'-O-beta-xylopyranosyl(1-- >6) -beta-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-beta-xylopyranosyl(1-->6)-beta-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 mutans.