Naphthoquinones from Catalpa ovata and their inhibitory effects on the production of nitric oxide

• Published in: Archives of pharmacal research Vol. 33; no. 3; pp. 381 - 385
• Main Authors: Park, Byeong Min, Hong, Seong Su, Lee, Chul, Lee, Moon Soon, Kang, Shin Jung, Shin, Yu Su, Jung, Jae-Kyung, Hong, Jin Tae, Kim, Youngsoo, Lee, Mi Kyeong, Hwang, Bang Yeon
• Format: Journal Article
• Language: English
• Published: Heidelberg Pharmaceutical Society of Korea 01.03.2010; 대한약학회
• Subjects: Bignoniaceae - chemistry; Biological Assay; Cell Line; Chemical Fractionation; Chromatography, High Pressure Liquid; Down-Regulation; Lipopolysaccharides - pharmacology; Macrophages - drug effects; Macrophages - metabolism; Magnetic Resonance Spectroscopy; Medicine; Molecular Structure; Naphthoquinones - chemistry; Naphthoquinones - isolation & purification; Naphthoquinones - pharmacology; Nitric Oxide - metabolism; Pharmacology/Toxicology; Pharmacy; Plant Stems; Spectrometry, Mass, Electrospray Ionization; Structure-Activity Relationship; 약학; Naphthoquinone; Bignoniaceae; Nitric oxide inhibitor
• ISSN: 0253-6269; 1976-3786; 1976-3786
• DOI: 10.1007/s12272-010-0306-2

Bioassay-guided fractionation of a CH2Cl2-soluble fraction of the stems of Catalpa ovata led to isolation of a new naphthoquinone, 4-hydroxy-2-(2-methoxy-3-hydroxy-3-methyl-but-1-enyl)-4-hydro-1 H -naphthalen-1-one ( 10 ), together with nine known compounds, catalponol ( 1 ), catalponone ( 2 ), catalpalactone ( 3 ), α-lapachone ( 4 ), 9-hydroxy-α-lapachone ( 5 ), 4,9-dihydroxy-α-lapachone ( 6 ), 9-methoxy-α-lapachone ( 7 ), 4-oxo-α-lapachone ( 8 ), and 9-methoxy-4-oxo-α-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. Among them, catapalactone ( 3 ), 9-hydroxy-α-lapachone ( 5 ) and 4,9-dihydroxy-α-lapachone ( 6 ) exhibited potent inhibitory effects, with IC 50 values of 9.80, 4.64 and 2.73 μM, respectively.