Planta Med 2012; 78(1): 39-45
DOI: 10.1055/s-0031-1280266
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Compounds from Arnebia euchroma and Their Related Anti-HCV and Antibacterial Activities

Hong-Mei Li1 , Ying-Lei Tang1 , Zhong-Hua Zhang1 , Chen-Jian Liu1 , Hai-Zhou Li1 , Rong-Tao Li1 , Xue-Shan Xia1
  • 1The College of Life Science and Technology, Kunming University of Science and Technology, Kunming, Yunnan, P. R. China
Further Information

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 (13), 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.

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

    >