Subscribe to RSS
DOI: 10.1055/s-0031-1280266
© Georg Thieme Verlag KG Stuttgart · New York
Compounds from Arnebia euchroma and Their Related Anti-HCV and Antibacterial Activities
Publication History
received June 1, 2011
revised Sept. 1, 2011
accepted Sept. 5, 2011
Publication Date:
07 October 2011 (online)
Abstract
Three new hydroquinone terpenoids with benzogeijerene skeletons, euchroquinols A–C (1–3), and a new monoterpenylbenzenoid, 9,17-epoxyarnebinol (4), along with five known compounds were isolated from the stem bark of Arnebia euchroma. Shikonin (6) exhibited potent anti-HCV activity with a selective index of 43.56, and compounds 1, 6, and des-O-methyllasiodiplodin (7) showed anti-Staphylococcus aureus activity with MICs of 0.5, 0.125, and 0.125 mg/mL, respectively.
Key words
Arnebia euchroma - Boraginaceae - hydroquinone terpenoids - monoterpenylbenzenoid - anti-HCV activity - antibacterial activity
References
- 1 Alter M J, Margolis H S, Krawczynski K, Judson F N, Mares S, Alexander W J, Hu P Y, Miller J K, Gerber M A. The natural history of community-acquired hepatitis C in the United States. The Sentinel Counties Chronic non-A, non-B Hepatitis Study Team. N Engl J Med. 1992; 327 1899-1905
- 2 Niederau C, Lange S, Heintges T, Erhardt A, Buschkamp M, Hurter D, Nawrocki M, Kruska L, Hensel F, Petry W, Haussinger D. Prognosis of chronic hepatitis C: results of a large, prospective cohort study. Hepatology. 1998; 28 1687-1695
- 3 Saito I, Miyamura T, Ohbayashi A, Harada H, Katayama T, Kikuchi S, Watanabe Y, Koi S, Onji M, Ohta Y, Choo Q L, Houghton M, Kuo G. Hepatitis C virus infection is associated with the development of hepatocellular carcinoma. Proc Natl Acad Sci USA. 1990; 87 6547-6549
- 4 Sarrazin C, Mihm U, Herrmann E, Welsch C, Albrecht M, Sarrazin U, Traver S, Lengauer T, Zeuzem S. Clinical significance of in vitro replication-enhancing mutations of the hepatitis C virus (HCV) replicon in patients with chronic HCV infection. J Infect Dis. 2005; 192 1710-1719
- 5 Walker M P, Appleby T C, Zhong W, Lau J Y, Hong Z. Hepatitis C virus therapies: current treatments, targets and future perspectives. Antivir Chem Chemother. 2003; 14 1-21
- 6 De Francesco R, Tomei L, Altamura S, Summa V, Migliaccio G. Approaching a new era for hepatitis C virus therapy: inhibitors of the NS3-4A serine protease and the NS5B RNA-dependent RNA polymerase. Antiviral Res. 2003; 58 1-16
- 7 Bacon B R, McHutchison J G. Hepatitis C update: strategies for treatment, compliance, and long-term health. Am J Manag Care. 2005; 11 S284-S285
- 8 Wohlfarth C, Efferth T. Natural products as promising drug candidates for the treatment of hepatitis B and C. Acta Pharmacol Sin. 2009; 30 25-30
- 9 Hu J F, Patel R, Li B, Garo E, Hough G W, Goering M G, Yoo H D, O'Neil-Johnson M, Eldridge G R. Anti-HCV bioactivity of pseudoguaianolides from Parthenium hispitum. J Nat Prod. 2007; 70 604-607
- 10 Lindenbach B D. Complete replication of hepatitis C virus in cell culture. Science. 2005; 309 623-626
- 11 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 1983; 65 55-63
- 12 Wiegand I, Hilpert K, Hancock R E W. Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances. Nat Protoc. 2008; 3 163-175
- 13 Moir M, Thomson R H. Naturally occurring quinones. Part XXIII. Cordiachromes from Patagonula americana L. J Chem Soc [Perkin I]. 1973; 1556-1561
- 14 Moir M, Thomson R H. Naturally occurring quinones. Part XXII. Terpenoid quinones in Cordia spp. J Chem Soc [Perkin I]. 1973; 1352-1357
- 15 Manners G D, Jurd L. The hydroquinone terpenoids of Cordia alliodora. J Chem Soc [Perkin I]. 1977; 405-410
- 16 Yao X S, Ebizuka Y, Noguchi H, Kiuchi F, Shibuya M, Iitaka Y, Seto H, Sankawa U. Biologically active constituents of Arnebia euchroma: structure of arnebinol, an ansa-type monoterpenylbenzenoid with inhibitory activity on prostaglandin biosynthesis. Chem Pharm Bull. 1991; 39 2956-2961
- 17 Shen C C, Syu W J, Li S Y, Lin C H, Lee G H, Sun C M. Antimicrobial activities of naphthazarins from Arnebia euchroma. J Nat Prod. 2002; 65 1857-1862
- 18 Cho M H, Paik Y S, Hahn T R. Physical stability of shikonin derivatives from the roots of Lithospermum erythrorhizon cultivated in Korea. J Agric Food Chem. 1999; 47 4117-4120
Prof. Rong-Tao Li
College of Life Science and Technology
Kunming University of Science and Technology
Kunming 650224, Yunnan
P. R. China
Phone: +86 871 5 10 38 45
Fax: +86 871 3 80 19 56
Email: rongtaolikm@yahoo.cn
Prof. Xue-Shan Xia
College of Life Science and Technology
Kunming University of Science and Technology
Kunming 650224, Yunnan
P. R. China
Phone: +86 871 5 10 38 45
Fax: +86 871 3 80 19 56
Email: oliverxia2000@yahoo.com.cn