Antitumor-promoting naphthoquinones from Catalpa ovata

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.