Naphthoquinones from Catalpa ovata and their inhibitory effects on the production of nitric oxide.
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-1H-naphthalen-1-one (10), 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. 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.
Park
Byeong Min
BM
College of Pharmacy, Chungbuk National University, Cheongju, 361-763, Korea.
Hong
Seong Su
SS
Lee
Chul
C
Lee
Moon Soon
MS
Kang
Shin Jung
SJ
Shin
Yu Su
YS
Jung
Jae-Kyung
JK
Hong
Jin Tae
JT
Kim
Youngsoo
Y
Lee
Mi Kyeong
MK
Hwang
Bang Yeon
BY
D029402:Bignoniaceae / Q000737:chemistry; D001681:Biological Assay; D002460:Cell Line; D005591:Chemical Fractionation; D002851:Chromatography, High Pressure Liquid; D015536:Down-Regulation; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D009569:Nitric Oxide / Q000378:metabolism*; D018547:Plant Stems; D021241:Spectrometry, Mass, Electrospray Ionization; D013329:Structure-Activity Relationship
D008070:Lipopolysaccharides; D009285:Naphthoquinones; D009569:Nitric Oxide