4,9-Dihydroxy-alpha-lapachone
4,9-Dihydroxy-alpha-lapachone has antitumor-promoting effects, it exhibits significant inhibitory activity against 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced Epstein-Barr virus early antigen (EBV-EA) activation in Raji cells. 4,9-Dihydroxy-alpha-lapachone exhibits potent inhibitory effects on lipopolysaccharide-induced NO synthesis in RAW 264.7 cells , with IC(50) value of 2.73 microM.
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Arch Pharm Res. 2010 Mar;33(3):381-5.
Naphthoquinones from Catalpa ovata and their inhibitory effects on the production of nitric oxide.[Pubmed:
20361302]
METHODS AND RESULTS:
Together with nine known compounds, catalponol (1), catalponone (2), catalpalactone (3), alpha-lapachone (4), 9-hydroxy-alpha-lapachone (5), 4,9-Dihydroxy-alpha-lapachone (6), 9-methoxy-alpha-lapachone (7), 4-oxo-alpha-lapachone (8), and 9-methoxy-4-oxo-alpha-lapachone (9). The structures were elucidated on the basis of spectroscopic analyses. The inhibitory effects of these isolates on lipopolysaccharide-induced NO synthesis in RAW 264.7 cells were evaluated.
CONCLUSIONS:
Among them, catapalactone (3), 9-hydroxy-alpha-lapachone (5) and 4,9-Dihydroxy-alpha-lapachone (6) exhibited potent inhibitory effects, with IC(50) values of 9.80, 4.64 and 2.73 microM, respectively.
J Nat Prod. 1998 May;61(5):629-32.
Antitumor-promoting naphthoquinones from Catalpa ovata.[Pubmed:
9599262]
METHODS AND RESULTS:
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.
CONCLUSIONS:
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.
