Prenylated Benzophenones from Triadenum japonicum

Six new prenylated benzophenones, (−)-nemorosonol (1) and trijapins A–E (2–6), were isolated from the aerial parts of Triadenum japonicum. (−)-Nemorosonol (1) and trijapins A–C (2–4) have a common tricyclo[4.3.1.03,7]decane skeleton, while 1 is an enantiomer of (+)-nemorosonol previously isolated from Clusia nemorosa. The absolute configuration of (−)-nemorosonol (1) was assigned by ECD spectroscopy. Trijapins A–C (2–4) are analogues of 1 possessing an additional tetrahydrofuran ring. Trijapins D (5) and E (6) are prenylated benzophenones with a 1,2-dioxane moiety and a hydroperoxy group, respectively. (−)-Nemorosonol (1) exhibited antimicrobial activity against Escherichia coli (MIC, 8 μg/mL), Staphylococcus aureus (MIC, 16 μg/mL), Bacillus subtilis (MIC, 16 μg/mL), Micrococcus luteus (MIC, 32 μg/mL), Aspergillus niger (IC50, 16 μg/mL), Trichophyton mentagrophytes (IC50, 8 μg/mL), and Candida albicans (IC50, 32 μg/mL), while trijapin D (5) showed antimicrobial activity against C. albicans (IC50, 8 μg/mL).