title: Bioactive dihydronaphthoquinone derivatives from Fusarium solani.
abstract: New dihydronaphthoquinone derivatives, karuquinone A (1), karuquinone B (2), and karuquinone C (3), were isolated from a fungal culture broth of Fusarium solani. The structures were determined by interpretation of spectroscopic data (1D/2D NMR, MS, and IR). Three known compounds, javanicin (4), 2,3-dihydro-5-hydroxy-8-methoxy-2,4-dimethylnaphtho[1,2-b]furan-6,9-dione (5), and 5-hydroxydihydrofusarubin C (6), were also isolated. The six isolated compounds were tested for cytotoxicity against three human cancer cell lines and a human umbilical vein endothelial cell (HUVEC) line. Of these, karuquinone A exhibited the strongest cytotoxic activity. Karuquinone B did not affect the proliferation of the cancer cell lines but did inhibit the proliferation of HUVEC. Additionally, we demonstrated that karuquinone A induces apoptosis in cancer cells through the generation of reactive oxygen species (ROS).
authors.affiliation: Department of Applied Biological Science, Tokyo University of Science , Noda, Chiba 278-8510, Japan.
authors.forename: Kenji
authors.initials: K
authors.lastname: Takemoto
authors.forename: Shinji
authors.initials: S
authors.lastname: Kamisuki
authors.forename: Pei Thing
authors.initials: PT
authors.lastname: Chia
authors.forename: Isoko
authors.initials: I
authors.lastname: Kuriyama
authors.forename: Yoshiyuki
authors.initials: Y
authors.lastname: Mizushina
authors.forename: Fumio
authors.initials: F
authors.lastname: Sugawara
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D005670:Fusarium / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D017382:Reactive Oxygen Species / Q000378:metabolism
chemical_list: D000970:Antineoplastic Agents; D009285:Naphthoquinones; D017382:Reactive Oxygen Species; C000594551:karuquinone A; C000594552:karuquinone B; C000594553:karuquinone C; C024503:hydroxydihydrofusarubin