One atypical thiolane-type sulfide, garlicnin I2 (11), two 3,4-dimethylthiolane-type sulfides, garlicnins M (22) and N (33), and one thiabicyclic-type sulfide, garlicnin O (44), were isolated from the acetone exts. of Chinese garlic bulbs, Allium sativum and their structures were characterized. Hypothetical pathways for the prodn. of the resp. sulfides were discussed. Rapid bactericidal action of propolis against Porphyromonas gingivalis J. Dent. Res.Vol. 97, pp. 928-936201830 DOI: 10.1177/0022034518758034 Propolis, a resinous substance produced by bees, is used as a folk medicine for treatment of periodontal diseases. However, its mode of the action and the compounds responsible for its activities remain obscure. In the present study, we comprehensively investigated the antibacterial activities of ethanol-extracted propolis (EEP) and EEP-derived compounds toward Porphyromonas gingivalis, a keystone pathogen for periodontal diseases. Broth microdilution and agar dilution assays were used to determine the minimum inhibitory concentrations of EEP against a range of oral bacterial species, of which P. gingivalis showed a higher level of sensitivity than oral commensals such as streptococci. Its antibacterial activity toward P. gingivalis was maintained even after extensive heat treatment, demonstrating a high level of thermostability. EEP also induced death of P. gingivalis cells by increasing membrane permeability within 30 min. Spatiotemporal analysis based on high-speed atomic force microscopy revealed that EEP immediately triggered development of aberrant membrane blebs, followed by bleb fusion events on the bacterial surface. Furthermore, we isolated artepillin C, baccharin, and ursolic acid from EEP as antibacterial compounds against P. gingivalis. Of those, artepillin C and baccharin showed
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