Subscribe to RSS
DOI: 10.1055/s-2001-16482
© Georg Thieme Verlag Stuttgart · New York
A Curcuminoid and Sesquiterpenes as Inhibitors of Macrophage TNF-α Release from Curcuma zedoaria
Publication History
October 18, 2000
November 19, 2000
Publication Date:
17 August 2001 (online)
Abstract
Tumor necrosis factor-α (TNF-α) is one of the major mediators produced in activated macrophages which contribute to the circulatory failure associated with septic shock. In the course of screening marketed oriental anti-inflammatory herbal drugs for TNF-α antagonistic activity, a crude methanolic extract of the rhizomes of Curcuma zedoaria exhibited significant activity. The activity-guided fractionation and repetitive chromatographic procedures with the EtOAc-soluble fraction resulted in the isolation of 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 analysis. They inhibited the production of TNF-α by lipopolysaccharide (LPS)-activated macrophages from the results of bioassay (IC50 values of 1 and 2 are 12.3 and 310.5 μM, respectively) and Western blot assay. These results imply that the traditional use of C. zedoaria rhizome as anti-inflammatory drug may be explained at least in part, by the inhibition of TNF-α production.
References
- 1 Beutler B. TNF, immunity and inflammatory disease: lessons of the past decade. Journal of Investigative Medicine. 1995; 43 227-35
- 2 Cross A, Asher L, Seguin M, Yuan L, Kelly N, Hammack C, Sadoff J. The importance of a lipopolysaccharide-initiated, cytokine-mediated host defense mechanism in mice against extraintestinally invasive Escherichia coli . Journal of Clinical Investigation. 1995; 96 676-86
- 3 Sidhu R S, Bollon A P. Tumor necrosis factor activities and cancer therapy - a perspective. Pharmacology and Therapeutics. 1993; 57 79-128
- 4 Vassalli P. The pathophysiology of tumor necrosis factor. Annual Review of Immunology. 1992; 10 411-52
- 5 Kondo Y, Takeno F, Hojo H. Suppression of lipopolysaccharide-induced fulminant hepatitis and tumor necrosis factor production by bisbenzylisoquinoline alkaloids in bacillus Calmette-Guerin-treated mice. Biochemical Pharmacology. 1993; 46 1861-3
- 6 Lee H J, Kim N Y, Jang M K, Son H C, Kim K M, Sohn D H, Lee S H, Ryu J-H. A sesquiterpene, dehydrocostus lactone, inhibits the expression of inducible nitric oxide synthase and TNF-alpha in LPS-activated macrophages. Planta Medica. 1999; 65 104-8
- 7 Son H J, Lee H J, Yun-Choi H S, Ryu J-H. Inhibitors of nitric oxide synthesis and TNF-α expression from Magnolia obovata in activated macrophages. Planta Medica. 2000; 66 469-71
- 8 Chan M M. Inhibition of tumor necrosis factor by curcumin, a phytochemical. Biochemical Pharmacology. 1995; 49 1551-6
- 9 Syu W-J, Shen C-C, Don M-J, Ou J-C, Lee G-H, Sun C-M. Cytotoxicity of curcuminoids and some novel compounds from Curcuma zedoaria . Journal of Natural Products. 1988; 61 1531-4
- 10 Yoshioka T, Fujii E, Endo M, Wada K, Tokunaga Y, Shiba N, Hohsho H, Shibuya H, Muraki T. Anti-inflammatory potency of dehydrocurdione, a zedoary-derived sesquiterpene. Inflammation Research. 1998; 47 476-81
- 11 Nakayama R, Tamura Y, Yamanaka H, Kikuzaki H, Nakatani N. Two curcuminoid pigments from Curcuma domestica . Phytochemistry. 1993; 33 501-2
- 12 Yoshihara M, Yang C, Zheng C, Shibuya H, Hamamoto Y, Tanaka N, Kitagawa I. Chemical conversion of (4S,5S)-(+)-germacrone 4,5-epoxide, a plausible biogenetic intermediate found in the essential oil of Zedoariae rhizoma from Yakushima, Japan. Chemical and Pharmaceutical Bulletin. 1986; 34 434-7
- 13 Kuroyanagi M, Ueno A, Koyama K, Natori S. Structures of sesquiterpene of Curcuma aromatica Salisb. II. Studies on minor sesquiterpenes. Chemical and Pharmaceutical Bulletin. 1990; 38 55-8
- 14 Ohshiro M, Kuroyanagi M, Ueno A. Structures of sesquiterpene from Curcuma longa . Phytochemistry. 1990; 29 2201-5
- 15 Matsuda H, Ninomiya K, Morikawa T, Yoshikawa M. Inhibitory effect and action mechanism of sesquiterpenes from Zedoariae rhizoma on D-galactosamine/lipopolysaccharide-induced liver injury. Bioorganic and Medicinal Chemistry Letters. 1998; 8 339-44
- 16 Chapekar M S, Zaremba T G, Kuester R K, Hitchins V M. Synergistic induction of tumor necrosis factor alpha by bacterial lipopolysaccharide and lipoteichoic acid in combination with polytetrafluoroethylene particles in a murine macrophage cell line RAW 264.7 Journal of Biomedical Materials Research. 1996; 31 251-6
- 17 Laemmli U K. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature. 1970; 227 680-5
Prof. Jae-Ha Ryu
College of Pharmacy
Sookmyung Women's University
Chungpa-Dong 2-Ka
Yongsan-Ku
Seoul 140-742
Korea
Email: ryuha@sdic.sookmyung.ac.kr
Fax: +82-2-714-0745
Phone: Tel: +82-2-710-9568