title: Antitumor-promoting naphthoquinones from Catalpa ovata.
abstract: Bioassay-directed fractionation of an extract of the stem-bark of Catalpa ovata led to the isolation of three new naphthoquinones: 8-methoxydehydroiso-alpha-lapachone (1), 9-methoxy-4-oxo-alpha-lapachone (2), and (4S,4aR,10R,10aR)-4, 10-dihydroxy-2,2-dimethyl-2,3,4,4alpha,10, 10alpha-hexahydrobenzo[g]chromen-5-one (3), which is a 1,4-reductive form of 6. The known compounds 3-hydroxydehydroiso-alpha-lapachone (4), 4,9-dihydroxy-alpha-lapachone (5), 4-hydroxy-alpha-lapachone (6), and 9-methoxy-alpha-lapachone (7), and catalpalactone (8) were also isolated. Their structures were elucidated by spectral methods. These compounds all exhibited significant inhibitory activity against 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced Epstein-Barr virus early antigen (EBV-EA) activation in Raji cells.
authors.affiliation: Faculty of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-01, Japan.
authors.forename: A
authors.initials: A
authors.lastname: Fujiwara
authors.forename: T
authors.initials: T
authors.lastname: Mori
authors.forename: A
authors.initials: A
authors.lastname: Iida
authors.forename: S
authors.initials: S
authors.lastname: Ueda
authors.forename: Y
authors.initials: Y
authors.lastname: Hano
authors.forename: T
authors.initials: T
authors.lastname: Nomura
authors.forename: H
authors.initials: H
authors.lastname: Tokuda
authors.forename: H
authors.initials: H
authors.lastname: Nishino
mesh_terms: D000956:Antigens, Viral / Q000187:drug effects; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification*; D002460:Cell Line; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry / Q000302:isolation & purification*; D010946:Plants, Medicinal / Q000737:chemistry*; D013755:Tetradecanoylphorbol Acetate / Q000494:pharmacology; D014197:Trees / Q000737:chemistry
chemical_list: D000956:Antigens, Viral; D000972:Antineoplastic Agents, Phytogenic; C033305:Epstein-Barr virus early antigen; D009285:Naphthoquinones; D013755:Tetradecanoylphorbol Acetate