title: Seed dormancy breaking diterpenoids, including novel brassicicenes J and K, from fungus Alternaria brassicicola, and their necrotic/apoptotic activities in HL-60 cells.
abstract: To find new metabolites similar to cotylenins and fusicoccins from the fungus Alternaria brassicicola, screening tests were carried out using the lettuce seed dormancy breaking assay. Activity-guided fractionation of the EtOAc extract from the culture using the assay afforded the isolation of two novel fusicoccane diterpenoids named brassicicenes J (1) and K (2), along with three known brassicicenes A (3), B (4), and F (5). Their structures were elucidated from extensive NMR spectral data and by comparison of these with those reported in the literature. Brassicicenes (1-5) exhibited weak to moderate seed dormancy breaking activities against lettuce seeds in the presence of abscisic acid. In addition, the necrotic/apoptotic activities of the brassicicenes (1-5), fusicoccin A (6) and cotylenin A (7) were evaluated by determining their cytotoxicity, cell viability and caspase-3/7 activation on the HL-60 cell line. Brassicicene K (2) exhibited similar cytostatic profiles to that of cotylenin A (7), and brassicicenes J (1), A (3), B (4), and F (5) exhibited necrotic activity. This is the first report of the seed dormancy breaking activity of brassicicenes in plants, and of necrotic/apoptotic activity in mammalian cells.
authors.forename: Hiromichi
authors.initials: H
authors.lastname: Kenmoku
authors.forename: Sayaka
authors.initials: S
authors.lastname: Takeue
authors.forename: Megumi
authors.initials: M
authors.lastname: Oogushi
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Yagi
authors.forename: Takeshi
authors.initials: T
authors.lastname: Sassa
authors.forename: Masao
authors.initials: M
authors.lastname: Toyota
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Asakawa
mesh_terms: D000528:Alternaria / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000302:isolation & purification* / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006801:Humans; D018545:Lactuca; D057445:Plant Dormancy / Q000187:drug effects*
chemical_list: D000970:Antineoplastic Agents; D004224:Diterpenes; C588196:brassicicene J