Garcinoic Acids and a Benzophenone Derivative from the Seeds of and Their Antibacterial Activities against Oral Bacterial Pathogenic Organisms.

In this study, three new garcinoic acid dimers, δ,δ-bigarcinoic acid (), δ,δ-bi--garcinoic acid (), and γ,δ-bi--garcinoic acid (), and a new benzophenone derivative, (8)-4-geranyl-3,5-dihydroxybenzophenone (), as well as seven known compounds (-) were isolated from the seeds of . The structures of the new compounds were elucidated using MALDI-TOF-MS and spectroscopic data, including 1D and 2D NMR and electronic circular dichroism spectra. All of the isolated compounds were evaluated for their antimicrobial activity against two oral pathogens, and . Among them, and δ-garcinoic acid () exhibited antimicrobial activity against both of these microorganisms (MICs of 31.3-62.5 μM for and 15.6-31.3 μM for ). These results indicate that some chemical constituents in seeds have potential application in the prevention of oral diseases.