From the traditional Chinese medicine plant Schisandra chinensis new scaffolds effective on HIV-1 reverse transcriptase resistant to non-nucleoside inhibitors

Journal of Microbiology

Volumn 53, Issue 4, 2015, Pages 288-293

  Xu, Lijia ^a   Grandi, Nicole ^b   Del Vecchio, Claudia ^c   Mandas, Daniela ^b   Corona, Angela ^b   Piano, Dario ^b   Esposito, Francesca ^b   Parolin, Cristina ^c   Tramontano, Enzo ^b  

^a INSTITUTE OF MEDICINAL PLANT DEVELOPMENT   (China)

^b UNIVERSITY OF CAGLIARI   (Italy)

^c UNIVERSITY OF PADOVA   (Italy)

Author keywords

HIV resistance; HIV 1; plant diversity; plant extracts; reverse transcriptase; Schisandra chinensis

Indexed keywords

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; CYCLOOCTANE DERIVATIVE; HERBACEOUS AGENT; LIGNAN; POLYCYCLIC HYDROCARBON; REVERSE TRANSCRIPTASE, HUMAN IMMUNODEFICIENCY VIRUS 1; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR; SCHIZANDRIN A; SCHIZANDRIN B;

ANTAGONISTS AND INHIBITORS; CHEMISTRY; DRUG EFFECTS; FRUIT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN IMMUNODEFICIENCY VIRUS 1; ISOLATION AND PURIFICATION; METABOLISM; MULTIDRUG RESISTANCE; MUTATION; PHYSIOLOGY; SCHISANDRA; VIRUS REPLICATION;

ANTI-HIV AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOOCTANES; DRUG RESISTANCE, MULTIPLE, VIRAL; DRUGS, CHINESE HERBAL; FRUIT; HIV REVERSE TRANSCRIPTASE; HIV-1; LIGNANS; MUTATION; POLYCYCLIC COMPOUNDS; REVERSE TRANSCRIPTASE INHIBITORS; SCHISANDRA; VIRUS REPLICATION;

EID: 84939979429     PISSN: 12258873     EISSN: 19763794     Source Type: Journal    
DOI: 10.1007/s12275-015-4652-0     Document Type: Article

References (40)

1. Chang, R., Li, Y., Yang, X., Yue, Y., Dou, L., Wang, Y., Zhang, W., and Li, X. 2013. Protective role of deoxyschizandrin and schisantherin A against myocardial ischemia-reperfusion injury in rats. PLoS One8, e61590.
2. Chen, M., Kilgore, N., Lee, K.H., and Chen, D.F. 2006. Rubrisandrins A and B, lignans and related anti-HIV compounds from Schisandra rubriflora. J. Nat. Prod. 69, 1697–1701.
3. Chen, P., Pang, S., Yang, N., Meng, H., Liu, J., Zhou, N., Zhang, M., Xu, Z., Gao, W., Chen, B., et al. 2013. Beneficial effects of schisandrin B on the cardiac function in mice model of myocardial infarction. PLoS One8, e79418.
4. Corona, A., Di Leva, F.S., Thierry, S., Pescatori, L., Cuzzucoli Crucitti, G., Subra, F., Delelis, O., Esposito, F., Rigogliuso, G., Costi, R., et al. 2014 Identification of highly conserved residues involved in the inhibition of the HIV-1 ribonuclease H function by diketoacid derivatives. Antimicrob. Agents Chemother. 58, 6101–1610.
5. Corona, A., Masaoka, T., Tocco, G., Tramontano, E., and Le Grice, S.F. 2013. Active site and allosteric inhibitors of the ribonuclease H activity of HIV reverse transcriptase. Future Med. Chem. 5, 2127–2139.
6. Cos, P., Maes, L., Vlietinck, A., and Pieters, L. 2008. Plant-derived leading compounds for chemotherapy of human immunodeficiency virus (HIV) infection — an update (1998–2007). Planta Med. 74, 1323–1337.
7. Distinto, S., Esposito, F., Kirchmair, J., Cardia, M.C., Gaspari, M., Maccioni, E., Alcaro, S., Markt, P., Wolber, G., Zinzula, L., et al. 2012. Identification of HIV-1 reverse transcriptase dual inhibitors by a combined shape-, 2D-fingerprint- and pharmacophorebased virtual screening approach. Eur. J. Med. Chem. 50, 216–229.
8. Domaoal, R.A. and Demeter, L.M. 2004. Structural and biochemical effects of human immunodeficiency virus mutants resistant to non-nucleoside reverse transcriptase inhibitors. Int. J. Biochem. Cell. Biol. 36, 1735–1751.
9. Esposito, F., Corona, A., and Tramontano, E. 2012. HIV-1 reverse transcriptase still remains a new drug target: structure, function, classical inhibitors, and new inhibitors with innovative mechanisms of actions. Mol. Biol. Int. doi: 10.1155/2012/586401.
10. Esposito, F., Sanna, C., Del Vecchio, C., Cannas, V., Venditti, A., Corona, A., Bianco, A., Serrilli, A.M., Guarcini, L., Parolin, C., et al. 2013. Hypericum hircinum L. components as new singlemolecule inhibitors of both HIV-1 reverse transcriptase-associated DNA polymerase and ribonuclease H activities. Path. Dis. 68, 116–124.
11. Hancke, J.L., Burgos, R.A., and Ahumada, F. 1999. Schisandra chinensis (Turcz.) Baill. Fitoterapia70, 451–471.
12. Helseth, E., Kowalski, M., Gabuzda, D., Olshevsky, U., Haseltine, W., and Sodroski, J. 1990. Rapid complementation assays measuring replicative potential of human immunodeficiency virus type 1 envelope glycoprotein mutants. J. Virol. 64, 2416–2420.
13. Hu, J., Mao, C., Gong, X., Lu, T., Chen, H., Huang, Z., and Cai, B. 2013. Simultaneous determination of eleven characteristic lignans in Schisandra chinensis by high-performance liquid chromatography. Pharmacogn. Mag. 9, 155–161.
14. Lam, P.Y. and Ko, K.M. 2012. Schisandrin B as a hormetic agent for preventing age-related neurodegenerative diseases. Oxid. Med. Cell Longev. Article ID 250825.
15. Li, T. and Peng, T. 2013. Traditional Chinese herbal medicine as a source of molecules with antiviral activity. Antiv. Res.97, 1–9.
16. Li, J. and Vederas, J.C. 2009. Drug discovery and natural products: end of an era or an endless frontier? Science325, 161–165.
17. Liu, G.T., Chang, H.M., Yeung, H.W., Tso, W.W., and Koo, A. 1985. Hepato-pharmacology of Fructus Schizandrae. Advances in Chinese medicinal materials research, pp. 257–268. Singapore, World Scientific.
18. Liu, K.T. and Lesca, P. 1982. Pharmacological properties of dibenzo [a,c]cyclooctene derivatives isolated from Fructus Schizandrae chinensis III. Inhibitory effects on carbon tetrachloride-induced lipid peroxidation, metabolism and covalent binding of carbon tetrachloride to lipids. Chem-Biol. Interact. 41, 39–47.
19. Maga, G., Amacker, M., Ruel, N., Hubscher, U., and Spadari, S. 1997. Resistance to nevirapine of HIV-1 reverse transcriptase mutants: loss of stabilizing inter-actions and thermodynamic or steric barriers are induced by different single amino acid substitutions. J. Mol. Biol. 274, 738–747.
20. Mehellou, Y. and De Clercq, E. 2010. Twenty-six years of anti-HIV drug discovery: where do we stand and where do we go? J. Med. Chem. 53, 521–538.
21. Mellors, J.W., Dutschman, G.E., Im, G.J., Tramontano, E., Winkler, S.R., and Cheng, Y.C. 1992. In vitro selection and molecular characterization of human immunodeficiency virus-1 resistant to non-nucleoside inhibitors of reverse transcriptase. Mol. Pharmacol. 41, 446–451.
22. Mellors, J., Im, G.J., Tramontano, E., Winkler, S.R., Medina, D.J., Dutschman, G.E., Bazmi, H.Z., Piras, G., Gonzales, C.J., and Cheng, Y.C. 1993. A single conservative amino acid substitution in the reverse transcriptase of human immunodeficiency virus-1 confers resistance to (+)-(5S)-4,5,6,7-tetrahydro-5-methyl-6-(3-methyl-2butenyl)imidazo[4,5,1,jk][1,4] benzodiazepin-2(1H)- thione (TIBO R82150). Mol. Pharmacol. 43, 11–16.
23. Mossmann, T. 1983. Rapid colorimetric assay for cell growth and survival. Application to proliferation and cytotoxicity. J. Immunol. Methods65, 55–63.
24. National Pharmacopoeia Committee. 2010. Pharmacopoeia of People Republic of China. Chemical Industry Press, Beijing, China.
25. Nishida, H., Tatewaki, N., Nakajima, Y., Magara, T., Ko, K.M., Hamamori, Y., and Konishi, T. 2009. Inhibition of ATR protein kinase activity by schisandrin B in DNA damage response. Nucleic Acids Res.37, 5678–5689.
26. Opletal, L., Sovová, H., and Bártlová, M. 2004. Dibenzo[a,c]cyclooctadiene lignans of the genus Schisandra: importance, isolation and determination. J. Chromatog. 812, 357–371.
27. Pan, M.H., Chiou, Y.S., Tsai, M.L., and Ho, C.T. 2011. Anti-inflammatory activity of traditional Chinese medicinal herbs. J Tradit. Complement. Med. 1, 8–24.
28. Pan, S.Y., Zhou, S.F., Gao, S.H., Yu, Z.L., Zhang, S.F., Tang, M.K., Sun, J.N., Ma, D.L., Han, Y.F., Fong, W.F., et al. 2013. New perspectives on how to discover drugs from herbal medicines: CAM’s outstanding contribution to modern therapeutics. Evid. Based Complement Alternat. Med. Article ID 627375.
29. Panossian, A. and Wikman, G. 2008. Pharmacology of Schisandra chinensis Bail.: an overview of Russian research and uses in medicine. J. Ethnopharmacol. 118, 183–212.
30. Pao, T.T., Liu, K.T., Hsu, K.F., and Sung, C.Y. 1975. Studies on Fructus Schizandrae I: effects on increased SGPT levels in animals caused by hepatotoxic chemical agents. J. Chinese Med. 54, 275–277.
31. Parolin, C., Gatto, B., Del Vecchio, C., Pecere, T., Tramontano, E., Cecchetti, V., Fravolini, A., Masiero, S., Palumbo, M., and Palù, G. 2003. New anti-human immunodeficiency virus type 1 6-aminoquinolones: mechanism of action. Antimicrob. Agents Chemother. 47, 889–896.
32. Pu, H.J., Cao, Y.F., He, R.R., Zhao, Z.L., Song, J.H., Jiang, B., Huang, T., Tang, S.H., Lu, J.M., and Kurihara, H. 2012. Correlation between Antistress and hepatoprotective effects of Schisandra Lignans was related with its antioxidative actions in liver cells. Evid. Based Complement. Alternat. Med. 2012, 161062.
33. Ren, J. and Stammers, D.K. 2008. Structural basis for drug resistance mechanisms for non-nucleoside inhibitors of HIV reverse transcriptase. Virus Res. 134, 157–170.
34. Suchaud, V., Bailly, F., Lion, C., Tramontano, E., Esposito, F., Corona, A., Christ, F., Debyser, Z., and Cotelle, P. 2010. Development of a series of 3-hydroxyquinolin-2(1H)-ones as selective inhibitors of HIV-1 reverse transcriptase associated RNase H activity. Bioorg. Med. Chem. Lett. 22, 3988–3992.
35. Sun, H.D., Qiu, S.X., Lin, L.Z., Wang, Z.Y., Lin, Z.W., Pengsuparp, T., Pezzuto, J.M., Fong, H.H., Cordell, G.A., and Farnsworth, N.R. 1996. Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase. J. Nat. Prod. 59, 525–527.
36. Tramontano, E. and Di Santo, R. 2010. HIV-1 RT-associated RNase H function inhibitors: Recent advances in drug development. Curr. Med. Chem. 17, 2837–2853.
37. Tramontano, E., Esposito, F., Badas, R., Di Santo, R., Costi, R., and La Colla, P. 2005. 6-[1-(4-Fluorophenyl)methyl-1H-pyrrol-2-yl]- 2,4-dioxo-5-hexenoic acid ethyl ester a novel diketo acid derivative which selectively inhibits the HIV-1 viral replication in cell culture and the ribonuclease H activity in vitro. Antiv. Res.65, 117–124.
38. Xiao, W., Wang, R., Zhao, W., Tian, R., Shang, S., Yang, L., and Yang, J. 2010. Anti-HIV-1 activity of lignans from the fruits of Schisandra rubriflora. Arch. Pharm. Res.33, 697–701.
39. Xu, M., Wang, G., Xie, H., Wang, R., Wang, W., Li, X., Li, H., Zhu, D., and Yue, L. 2005. Determination of schizandrin in rat plasma by high-performance liquid chromatography-mass spectrometry and its application in rat pharmacokinetic studies. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 828, 55–61.
40. Yu, D., Morris-Natschke, S.L., and Lee, K.H. 2007. New developments in natural products-based anti-AIDS research. Med. Res. Rev.1, 108–132.