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A curcuminoid and two sesquiterpenoids from Curcuma zedoaria as inhibitors of nitric oxide synthesis in activated macrophages

Authors
Jang, MKLee, HJKim, JSRyu, JH
Issue Date
Dec-2004
Publisher
PHARMACEUTICAL SOC KOREA
Keywords
nitric oxide synthase; inhibitor; Curcuma zedoaria; curcuminoid; sesquiterpene
Citation
ARCHIVES OF PHARMACAL RESEARCH, v.27, no.12, pp 1220 - 1225
Pages
6
Journal Title
ARCHIVES OF PHARMACAL RESEARCH
Volume
27
Number
12
Start Page
1220
End Page
1225
URI
https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/17475
DOI
10.1007/BF02975885
ISSN
0253-6269
1976-3786
Abstract
The overproduction of nitric oxide (NO) by inducible nitric oxide synthase (iNOS) is known to be responsible for vasodilation and hypotension observed in septic shock and inflammation. Inhibitors of iNOS, thus, may be useful candidates for the treatment of inflammatory diseases accompanied by overproduction of NO. In the course of screening oriental anti-inflammatory herbs for the inhibitory activity of NO synthesis, a crude methanolic extract of Curcuma zedoaria exhibited significant activity. The activity-guided fractionation and repetitive chromatographic procedures with the EtOAc soluble fraction allowed us to isolate three active compounds. They were identified as 1,7-bis (4-hydroxyphenyl)-1,4,6-heptatrien-3-one (1), procurcumenol (2) and epiprocurcumenol (3) by spectral data analyses. Their concentrations for the 50% inhibition of NO production (IC50) in lipopolysaccharide (LPS)-activated macrophages were 8, 75, 77 muM, respectively. Compound 1 showed the most potent inhibitory activity for NO production in LPS-activated macrophages, while the epimeric isomers, compound 2 and 3 showed weak and similar potency. Inhibition of NO synthesis by compound 1 was very weak when activated macrophages were treated with 1 after iNOS induction. In the immunoblot analysis, compound 1 suppressed the expression of iNOS in a dose-dependent manner. In summary, 1,7-bis (4-hydroxyphenyl)-1,4,6-heptatrien-3-one from Curcuma zedoaria inhibited NO production in LPS-activated macrophages through suppression of iNOS expression. These results imply that the traditional use of C. zedoaria rhizome as anti-inflammatory drug may be explained at least in part, by inhibition of NO production.
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