Humulene derivatives from Zingiber zerumbet with the inhibitory effects on lipopolysaccharide-induced nitric oxide production.
A new humulene sesquiterpene, 5-hydroxyzerumbone (5-hydroxy-2E,6E,9E-humulatrien-8-one) (1) and a known compound, zerumboneoxide (2) were isolated from the rhizomes of Zingiber zerumbet (Zingiberaceae), and found to inhibit lipopolysaccharide-induced nitric oxide production in murine macrophage RAW 264.7 cells with IC50 values of 14.1 and 23.5 microM, respectively, by bioassay-guided fractionation (positive control: N(omega)-monomethyl-L-arginine, IC50=21.3 microM). The structure of 1 was determined by spectroscopic methods including 1D and 2D-NMR.
Jang
Dae Sik
DS
Division of Molecular Life Sciences, Ewha Womans University, Seoul, Korea.
Min
Hye-Young
HY
Kim
Moon-Sun
MS
Han
Ah-Reum
AR
Windono
Tri
T
Jeohn
Gwang-Ho
GH
Kang
Sam Sik
SS
Lee
Sang Kook
SK
Seo
Eun-Kyoung
EK
D000818:Animals; D002460:Cell Line; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors* / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D009569:Nitric Oxide / Q000096:biosynthesis*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013057:Spectrum Analysis; D030521:Zingiberaceae / Q000737:chemistry*
C505178:5-hydroxy-2E,6E,9E-humulatrien-8-one; D008070:Lipopolysaccharides; D012717:Sesquiterpenes; C505179:zerumboneoxide; D009569:Nitric Oxide