Immunosuppressive activity of buxidin and E-buxenone from buxus hyrcana

Chemical Biology and Drug Design

Volumn 75, Issue 3, 2010, Pages 310-317

  Mesaik, M Ahmed ^a   Halim, Sobia A ^a   Ul Haq, Zaheer ^a   Choudhary, M Iqbal ^a   Shahnaz, Salma ^a   Ayatollahi, S A M ^b   Murad, Shahnaz ^c   Ahmad, Aqeel ^a  

^a UNIVERSITY OF KARACHI   (Pakistan)

^b SHAHID BEHESHTI UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c INSTITUTE FOR MEDICAL RESEARCH   (Malaysia)

Author keywords

Buxidin; E Buxenone; FlexX; Immunosuppressive agents; Molecular docking

Indexed keywords

BUXIDIN; E BUXENONE; GAMMA INTERFERON; IMMUNOSUPPRESSIVE AGENT; INTERLEUKIN 2; INTERLEUKIN 4; PHYTOHEMAGGLUTININ; UNCLASSIFIED DRUG; E-BUXENONE; STEROID;

ARTICLE; BUXUS; BUXUS HYRCANA; CELL MIGRATION; CHEMOTAXIS; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOKINE PRODUCTION; DRUG ACTIVITY; DRUG PROTEIN BINDING; DRUG STRUCTURE; HUMAN; HUMAN CELL; IMMUNOMODULATION; IN VITRO STUDY; LYMPHOCYTE PROLIFERATION; MOLECULAR DOCKING; NEUTROPHIL; PHAGOCYTOSIS; PRIORITY JOURNAL; RESPIRATORY BURST; T LYMPHOCYTE; ANTAGONISTS AND INHIBITORS; BINDING SITE; CHEMISTRY; COMPUTER SIMULATION; CYTOLOGY; ENZYME ACTIVE SITE; IMMUNOLOGY; ISOLATION AND PURIFICATION; METABOLISM;

BUXUS;

BINDING SITES; BUXUS; CATALYTIC DOMAIN; COMPUTER SIMULATION; IMMUNOSUPPRESSIVE AGENTS; INTERLEUKIN-2; INTERLEUKIN-4; NEUTROPHILS; STEROIDS;

EID: 76049120254     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2009.00906.x     Document Type: Article

References (49)

1. Masri M.A. (2003) The mosaic of immunosuppressive drugs. Mol Immunol 39 : 1073 1077.
2. Farnsworth N.R., Akerele O., Bingel A.S., Soejarto D.D., Guo Z. (1985) Medicinal plants in therapy. Bull World Health Organ 63 : 965 981.
3. Nelson R.L. (1982) The comparative clinical pharmacology and pharmacokinetics of vindesine, vincristine, and vinblastine in human patients with cancer. Med Pediatr Oncol 10 : 115 127.
4. Loru F., Duval D., Aumelas A., Akeb F., Guédon D., Guedj R. (2000) Four steroidal alkaloids from the leaves of Buxus sempervirens. Phytochemistry 54 : 951 957.
5. Rahman A.U., Parveen S., Khalid A., Farooq A., Choudhary M.I. (2001) Acetyl and butyrylcholinesterase-inhibiting triterpenoid alkaloids from Buxus papillosa. Phytochemistry 58 : 963 968.
6. Rahman A.U., Noor-e-ain F., Choudhary M.I., Parveen Z., Turkoz S., Sener B. (1997) New steroidal alkaloids from Buxus longifolia. J Nat Prod 60 : 976 981.
7. Rahman A.U., Ata A., Naz S., Choudhary M.I., Sener B., Turkoz S. (1999) New steroidal alkaloids from the roots of Buxus sempervirens. J Nat Prod 62 : 665 669.
8. Rahman A.U., Choudhary M.I. (1999) Recent studies on bioactive natural products. Pure Appl Chem 71 : 1079 1081.
9. Cordell G.A. (1981) Introduction to Alkaloids: A Biogenetic Approach. New York : Wiley.
10. Wang Y.X., Liu J.W., Tan Y.H., Sheng B.H. (1989) Positive inotropic effect of cycloprotobuxine-A on isolated guinea pig myocardium. Acta Pharmacol Sin 10 : 516 519.
11. Wang Y.X., Tan Y.H., Sheng B.H. (1992) Protective effect of cycloprotobuxine-A against cardiac arrhythmias induced by ouabain. Acta Pharmacol Sin 13 : 226 230.
12. Dildar A. (1990) Isolation and structural studies of the chemical constituents of Buxus species. Doct. Dissertation. Pakistan : University of Karachi.
13. Puckett R.T., Sim G.A., Abushanab E., Kupchan S.M. (1966) Structure of buxenine-G. Tetrahedron Lett 7 : 3815 3818.
14. Brown K.S., Kupchan S.M. (1962) The structure of cyclobuxine. J. Am. Chem. Soc 84 : 4590 4591.
15. Vincent D., Mathou T. (1945) Inhibiting action of boxwood (Buxus sempervirens and Buxus balearica) on the cholinesterase of serum. C R Hebd Seances Acad Sci 220 : 474 476.
16. Mahler H.R., Dutton G. (1964) Nucleic acid interactions vs effects of cyclobuxine. J Mol Biol 10 : 157 175.
17. Mahler H.R., Goutarel R., Khuong-Huu Q., Ho M.T. (1966) Nucleic acid interactions. VI. Effects of steroidal diamines. Biochemistry 5 : 2177 2191.
18. Lee J.H., Kwon J.T., Cho B.H., Moon C.K. (1993) Cyclobuxine protects the isolated rat heart from the myocardial injuries produced by ischemia and reperfusion. Planta Med 59 : 296 301.
19. Durant J., Gozalez G., Chantre P., Vandermander J., Halfon P., Rousse B., Guedon D., Rahelinirina V., Chamaret S., Montagnier L., Dellamonica P. (1998) Efficacy and safety of Buxus sempervirens L. preparation (SPV30) in HIV-infected asymptomatic patients: a multicentre, randomised, double-blind, placebo-controlled trial. Phytomedicine 5 : 1 10.
20. Döpke W., Müller B., Spiteller G., Friedmann S.M. (1967) On the alkaloids buxazidine B and buxeridine. Naturwissenschaften 54 : 200.
21. Choudhary M.I., Shahnaz S., Parveen S., Khalid A., Mesaik M.A., Ayatollahi M.A., Rahman A.U., Parvez M. (2006) New cholinesterase-inhibiting triterpenoid alkaloids from Buxus hyrcana. Chem Biodivers 3 : 1039 1052.
22. Koko W.S., Mesaik M.A., Yousaf S., Galal M., Choudhary M.I. (2008) In vitro immunomodulating properties of selected Sudanese medicinal plants. J Ethnopharmacol 118 : 26 34.
23. Mesaik M.A., Azim M.K., Mohiuddin S. (2008) Honey modulates oxidative burst of professional phagocytes. Phytother Res 22 : 1404 1408.
24. Wansi J.D., Mesaik M.A., Chiozem D.D., Devkota K.P., Gaboriaud-Kolar N., Lallemand M.C., Wandji J., Choudhary M.I., Sewald N. (2008) Oxidative burst inhibitory and cytotoxic indoloquinazoline and furoquinoline alkaloids from Oricia suaveolens. J Nat Prod 71 : 1942 1945.
25. Demirkiran O., Mesaik M.A., Beynek H., Abbaskhan A., Choudhary M.I. (2009) Cellular reactive oxygen species inhibitory constituents of Hypericum thasium Griseb. Phytochemistry 70 : 244 249.
26. Saeed S.A., Connor J.D., Imran, Quadri J., Tasneem S., Ahmed S., Mesaik M.A., Choudhary M.I. (2007) Inhibitors of phosphatidylinositide 3-kinase: effects on reactive oxygen species and platelet aggregation. Pharmacol Rep 59 : 238 243.
27. Mesaik M.A., Murad S., Ismail Z., Abdullah N.R., ul-Haq Z., Murad S., Ismail Z., Abdullah N.R., Gill H.K., Rahman A.U., Yousaf M., Siddiqui R.A., Ahmad A., Choudhary M.I. (2006) Biological and molecular docking studies on coagulin-H: human IL-2 novel natural inhibitor. Mol Immunol 43 : 1855 1863.
28. Mesaik M.A., Khan K.M., Rahat S., Zia-Ullah Z.U., Choudhary M.I., Murad S., Abdullah N.R., Rahman A.U., Ahmad A., Siddiqui R.A. (2005) Immunomodulatory properties of synthetic imidazolone derivatives. Lett Drug Des Discov 2 : 490 496.
29. Mesaik M.A., Rahat S., Khan K.M., Ullah Z., Choudhary M.I., Murad S., Ismail Z., Rahman A.U., Ahmad A. (2004) Synthesis and immunomodulatory properties of selected oxazolone derivatives. Bioorg Med Chem 12 : 2049 2057.
30. Helfand S.L., Werkmeister J., Roder J.C. (1982) Chemiluminescence response of human natural killer cells. I. The relationship between target cell binding, chemiluminescence, and cytolysis. J Exp Med 156 : 492 505. (Pubitemid 12041410)
31. Boyden S. (1962) The chemotactic effect of mixtures of antibody and antigen on polymorphonuclear leucocytes. J Exp Med 115 : 453 466.
32. Boyum A. (1968) Isolation of mononuclear cells and granulocytes from human blood. Scand J Clin Lab Invest 21 : 77 89.
33. Nielsen M.B., Gerwien J., Nielsen M., Geisler C., Röpke C., Svejgaard A., Ødum N. (1998) MHC class II ligation induces CD58 (LFA-3)-mediated adhesion in human T cells. Exp Clin Immunogenet 15 : 61 68.
34. Clark M., Cramer R.D. III., Van Opdenbosch N. (1989) Validation of the general purpose Tripos 5.2 force field. J Comput Chem 10 : 982 1012.
35. Kramer B., Rarey M., Lengauer T. (1999) Evaluation of the F LEX X incremental construction algorithm for protein-ligand docking. Prot Struc Func and Gen 37 : 228 241.
36. Rarey M., Kramer B., Lengauer T., Klebe G. (1996) A fast flexible docking method using an incremental construction algorithm. J Mol Biol 261 : 470 489.
37. Pettersen E.F., Goddard T.D., Huang C.C., Couch G.S., Greenblatt D.M., Meng E.C., Ferrin T.E. (2004) UCSF Chimera-a visualization system for exploratory research and analysis. J Comput Chem 25 : 1605 1612.
38. Cragg G.M., Newman D.J. (2001) Natural product drug discovery in the next millennium. Pharm Biol 39 : 8 17.
39. Tyler V.E. (1996) What pharmacists should know about herbal remedies. J Am Pharm Assoc 36 : 29 37.
40. Higgins J.A., Ibrahim M.S., Knauert F.K., Ludwig G.V., Kijek T.M., Ezzell J.W., Courtney B.C., Henchal E.A. (1999) Sensitive and rapid identification of biological threat agents. Ann N Y Acad Sci 894 : 130 148.
41. Hosker H.S., Kelly C., Corris P.A. (1989) Assessment of phagocytic function using chemiluminescence. Blood Rev 3 : 88 93.
42. Talati A.J., Crouse D.T., English B.K., Newman C., Harrison L., Meals E. (2001) Immunomodulation by exogenous surfactant: effect on TNF-a secretion and luminol-enhanced chemiluminescence activity by murine macrophages stimulated with group B streptococci. Microbes Infect 3 : 267 273.
43. Zollner T.M., Podda M., Ochsendorf F.R., Wolter M., Kaufmann R., Boehncke W.H. (2001) Monitoring of phagocytic activity in histiocytic cytophagic panniculitis. J Am Acad Dermatol 44 : 120 123.
44. Ata A., Naz S., Choudhary M.I., Rahman A.U., Sener B., Turkoz S. (2002) New triterpenoidal alkaloids from Buxus sempervirens. Z Naturforsch C 57 : 21 28.
45. Adams D.H., Wang L.F.U., Neuberger J.M., Elias E. (1990) Inhibition of leukocyte chemotaxis by immunosuppressive agents: specific inhibition of lymphocyte chemotaxis by cyclosporin. Transplantation 50 : 845 850.
46. Gallin J.I., Rosenthal A.S. (1974) The regulatory role of divalent cations in human granulocyte chemotaxis: evidence for an Association between Calcium Exchanges and Microtubule Assembly. J Cell Biol 62 : 594 609.
47. Naccache P.H., McColl S.R., Caon A.C., Borgeat P. (1989) Arachidonic acid-induced mobilization of calcium in human neutrophils: evidence for a multicomponent mechanism of action. Br J Pharmacol 97 : 461 468.
48. Tsai T.F., Hsieh C.H., Lin Y.S., Tsai W.J., Kuo Y.C. (2001) Enhancement of cell proliferation and cytokines production in human peripheral blood mononuclear cells by extracts from blood enriching dang-gui decoction. Chin Med J 12 : 191 202.
49. Arkin M.R., Randal M., DeLano W.L., Hyde J., Luong T.N., Oslob J.D., Raphael D.R., Taylor L., Wang J., McDowell R.S., Wells J.A., Braisted A.C. (2003) Binding of small molecules to an adaptive protein-protein interface. Proc Natl Acad Sci U S A 100 : 1603 1608.