Synthesis and antiviral effects of isosteviol-derived analogues against the hepatitis B virus

Phytochemistry

Volumn 99, Issue , 2014, Pages 107-114

  Huang, Tsurng Juhn ^a   Chou, Bo Hon ^a,b,d   Lin, Cheng Wen ^a   Weng, Jen Hsien ^a   Chou, Chang Hung ^a   Yang, Li Ming ^b,c   Lin, Shwu Jiuan ^b  

^a CHINA MEDICAL UNIVERSITY   (Taiwan)

^b TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^c NATIONAL RESEARCH INSTITUTE OF CHINESE MEDICINE   (Taiwan)

^d Long Shine Biopharma Co   (Taiwan)

Author keywords

Hepatitis B virus; Human hepatoma cells; Isosteviol derivative; NF B; TLR2

Indexed keywords

ANTIVIRUS AGENT; ISOSTEVIOL; KAURANE DERIVATIVE;

CELL CULTURE; CELL SURVIVAL; CHEMISTRY; CONFORMATION; DOSE RESPONSE; DRUG EFFECTS; HEPATITIS B VIRUS; HUMAN; MICROBIAL SENSITIVITY TEST; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTIVIRAL AGENTS; CELL SURVIVAL; CELLS, CULTURED; DITERPENES, KAURANE; DOSE-RESPONSE RELATIONSHIP, DRUG; HEPATITIS B VIRUS; HUMANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84894239751     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2013.12.014     Document Type: Article

References (31)

1. A.G. Avent, J.R. Hanson, and B.H. de Oliveira Hydrolysis of the diterpenoid glycoside, stevioside Phytochemistry 29 1990 2712 2715
2. L.A. Baltina, O.B. Flekhter, L.R. Nigmatullina, E.I. Boreko, N.I. Pavlova, S.N. Nikolaeva, O.V. Savinova, and G.A. Tolstikov Lupane triterpenes and derivatives with antiviral activity Bioorg. Med. Chem. Lett. 13 2003 3549 3552 (Pubitemid 37141427)
3. H.E. Blum, E. Galun, T.J. Liang, F. von Weizsäcker, and J.R. Wands Naturally occurring missense mutation in the polymerase gene terminating hepatitis B virus replication J. Virol. 65 1991 1836 1842
4. S.F. Chang, L.M. Yang, C.H. Lo, J.H. Liaw, L.H. Wang, and S.J. Lin Microbial transformation of isosteviol and bioactivities against the glucocorticoid/androgen response elements J. Nat. Prod. 71 2008 87 92 and references cited therein
5. S.F. Chang, B.H. Chou, L.M. Yang, F.L. Hsu, W.K. Lin, Y. Ho, and S.J. Lin Microbial transformation of isosteviol oxime and the inhibitory effects on NF-B and AP-1 activation in LPS-stimulated macrophages Bioorg. Med. Chem. 17 2009 6348 6353
6. S.Y. Cheng, C.M. Wang, Y.M. Hsu, T.J. Huang, S.C. Chou, E.H. Lin, and C.H. Chou Oleanane-type triterpenoids from the leaves and twigs of Fatsia polycarpa J. Nat. Prod. 74 2011 1744 1750
7. F.V. Chisari, P. Filippi, J. Buras, A. McLachlan, H. Popper, C.A. Pinkert, R.D. Palmiter, and R.L. Brinster Structural and pathological effects of synthesis of hepatitis B virus large envelope polypeptide in transgenic mice Proc. Natl. Acad. Sci. USA 84 1987 6909 6913 (Pubitemid 18025500)
8. F.V. Chisari Viruses, immunity, and cancer: Lessons from hepatitis B Am. J. Pathol. 156 2000 1118 1132 (Pubitemid 30659988)
9. M. Doria, N. Klein, R. Lucito, and R.J. Schneider The hepatitis B virus HBx protein is a dual specificity cytoplasmic activator of Ras and nuclear activator of transcription factors EMBO J. 14 1995 4747 4757
10. O.B. Flekhter, E.I. Boreko, L.R. Nigmatullina, E.V. Tret'yakova, N.I. Pavlova, L.A. Baltina, S.N. Nikolaeva, O.V. Savinova, F.Z. Galin, and G.A. Tolstikov Synthesis and antiviral activity of ureides and carbamates of betulinic acid and its derivatives Russ. J. Bioorg. Chem. 29 2003 594 600 (Pubitemid 39011220)
11. J.M.C. Geuns Stevioside Phytochemistry 64 2003 913 921 (Pubitemid 37295343)
12. R.G. Gish Current treatment and future directions in the management of chronic hepatitis B viral infection Clin. Liver Dis. 9 2005 541 565 (Pubitemid 41406387)
13. N. Gitlin Hepatitis B: diagnosis, prevention, and treatment Clin. Chem. 43 1997 1500 1506 (Pubitemid 27329808)
14. E. Hildt, G. Saher, V. Bruss, and P.H. Hofschneider The hepatitis B virus large surface protein (LHBs) is a transcriptional activator Virology 225 1996 235 239 (Pubitemid 26390072)
15. J.A. Kwon, and H.M. Rho Hepatitis B viral core protein activates the hepatitis B viral enhancer II/pregenomic promoter through the nuclear factor B binding site Biochem. Cell Biol. 80 2002 445 455 (Pubitemid 35366002)
16. Y.C. Lin, E.C. Hsu, and L.P. Ting Repression of hepatitis B viral gene expression by transcription factor nuclear factor-kappaB Cell Microbiol. 11 2009 645 660
17. C.C. Lu, M. Chen, J.H. Ou, and T.S.B. Yen Key role of a CCAAT element in regulating hepatitis B virus surface protein expression Virology 206 1995 1155 1158
18. M. Meyer, W.H. Caselmann, V. Schluter, R. Schreck, P.H. Hofschneider, and P.A. Baeuerle Hepatitis B virus transactivator MHBst: activation of NF-κB, selective inhibition by antioxidants and integral membrane localization EMBO J. 11 1992 2991 3001
19. O.I. Militsina, I.Y. Strobykina, G.I. Kovylyaeva, G.A. Bakaleinik, V.E. Kataev, A.T. Gubaidullin, R.Z. Musin, and A.G. Tolstikov Synthesis of Schiff bases on the basis of the isosteviol terpenoid Russ. J. Gen. Chem. 77 2007 285 296
20. N.H. Park, I.H. Song, and Y.H. Chung Chronic hepatitis B in hepatocarcinogenesis Postgrad. Med. J. 82 2006 507 515 (Pubitemid 44258625)
21. C. Pramoolsinsup Management of viral hepatitis B J. Gastroen. Hepatol. 17 2002 S125 S145
22. S. Preiss, A. Thompson, X. Chen, S. Rodgers, V. Markovska, P. Desmond, K. Visvanathan, K. Li, S. Locarnini, and P. Revill Characterization of the innate immune signalling pathways in hepatocyte cell lines J. Viral Hepat. 15 2008 888 900
23. J.C. Pugh, K. Yaginuma, K. Koike, and J. Summers Duck hepatitis B virus (DHBV) particles produced by transient expression of DHBV DNA in a human hepatoma cell line are infectious in vitro J. Virol. 62 1988 3513 3516
24. J. Sambrook, E.F. Fritsch, and T. Maniatis Molecular Cloning: A Laboratory Manual second ed. 1989 Cold Spring Harbor Laboratory Press New York
25. M. Takasaki, T. Konoshima, M. Kozuka, H. Tokuda, J. Takayasu, H. Nishino, M. Miyakoshi, K. Mizutani, and K.H. Lee Cancer preventive agents. Part 8: Chemopreventive effects of stevioside and related compounds Bioorg. Med. Chem. 17 2009 600 605
26. K. Takeda, and S. Akira Toll-like receptors in innate immunity Int. Immunol. 17 2005 1 14
27. H. Tang, L. Delgermaa, F. Huang, N. Oishi, L. Liu, F. He, L. Zhao, and S. Murakami The transcriptional transactivation function of HBx protein is important for its augmentation role in hepatitis B virus replication J. Virol. 79 2005 5548 5556 (Pubitemid 40548223)
28. A.J. Thompson, D. Colledge, S. Rodgers, R. Wilson, P. Revill, P. Desmond, A. Mansell, K. Visvanathan, and S. Locarnini Stimulation of the interleukin-1 receptor and Toll-like receptor 2 inhibits hepatitis B virus replication in hepatoma cell lines in vitro Antivir. Ther. 14 2009 797 808
29. Y. Wakui, J. Inoue, Y. Ueno, K. Fukushima, Y. Kondo, E. Kakazu, N. Obara, O. Kimura, and T. Shimosegawa Inhibitory effect on hepatitis B virus in vitro by a peroxisome proliferator-activated receptor-γ ligand, rosiglitazone Biochhem. Biophy. Res. Commun. 396 2010 508 514
30. H. Will, R. Cattaneo, G. Darai, F. Deinhardt, H. Schellekens, and H. Schaller Infectious hepatitis B virus from cloned DNA of known nucleotide sequence Proc. Natl. Acad. Sci. USA 82 1985 891 895 (Pubitemid 15142783)
31. S.L. Zhu, Y. Wu, C.J. Liu, C.Y. Wei, J.C. Tao, and H.M. Liu Synthesis and in vitro cytotoxic activity evaluation of novel heterocycle bridged carbothioamide type isosteviol derivatives as antitumor agents Bioorg. Med. Chem. Lett. 23 2013 1343 1346