title: Prenylated benzophenones from Triadenum japonicum.
abstract: 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[4.3.1.0(3,7)]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).
authors.affiliation: Graduate School of Pharmaceutical Sciences, Hokkaido University , Sapporo 060-0812, Japan.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Oya
authors.forename: Naonobu
authors.initials: N
authors.lastname: Tanaka
authors.forename: Taishi
authors.initials: T
authors.lastname: Kusama
authors.forename: Sang-Yong
authors.initials: SY
authors.lastname: Kim
authors.forename: Shigeki
authors.initials: S
authors.lastname: Hayashi
authors.forename: Mareshige
authors.initials: M
authors.lastname: Kojoma
authors.forename: Atsuyuki
authors.initials: A
authors.lastname: Hishida
authors.forename: Nobuo
authors.initials: N
authors.lastname: Kawahara
authors.forename: Kanae
authors.initials: K
authors.lastname: Sakai
authors.forename: Tohru
authors.initials: T
authors.lastname: Gonoi
authors.forename: Jun'ichi
authors.initials: J
authors.lastname: Kobayashi
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001234:Aspergillus niger / Q000187:drug effects; D001412:Bacillus subtilis / Q000187:drug effects; D001577:Benzophenones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D020902:Hypericum / Q000737:chemistry*; D007564:Japan; D008826:Microbial Sensitivity Tests; D016982:Micrococcus luteus / Q000187:drug effects; D015394:Molecular Structure; D035261:Plant Components, Aerial / Q000737:chemistry; D054876:Prenylation; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism; D014249:Trichophyton / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; D001577:Benzophenones