Chem. Pharm. Bull., 53(7),829-831, July 2005

Notes

Humulene Derivatives from Zingiber zerumbet with the Inhibitory Effects on Lipopolysaccharide-Induced Nitric Oxide Production

Dae Sik JANG,^a,e Hye-Young MIN,^b Moon-Sun KIM,^b Ah-Reum HAN,^b Tri WINDONO,^c Gwang-Ho JEOHN,^d Sam Sik KANG,^f Sang Kook LEE,^b and Eun-Kyoung SEO^*,b

^a Division of Molecular Life Sciences, Ewha Womans University; and ^b College of Pharmacy, Ewha Womans University; 11-1 Daehyun-dong, Seodaemun-gu, Seoul 120-750, Korea: ^c Faculty of Pharmacy, University of Surabaya; Raya Kalirungkut, Surabaya 60293, Indonesia: ^d Faculty of Science, Brawijaya University; Malang 65145, Indonesia: ^e Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine; 461-24 Jeonmin-dong, Yuseong-gu, Daejeon 305-811, Korea: and ^f Natural Product Research Institute, Seoul National University; Seoul 110-460, Korea. * To whom correspondence should be addressed. e-mail: yuny@ewha.ac.kr

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 μM, respectively, by bioassay-guided fractionation (positive control: Nω-monomethyl-L-arginine, IC₅₀=21.3 μM). The structure of 1 was determined by spectroscopic methods including 1D and 2D-NMR.

Key words 5-hydroxyzerumbone; zerumboneoxide; Zingiber zerumbet; nitric oxide production