Naphthoquinones isolated from Diospyros anisandra exhibit potent activity against pan-resistant first-line drugs Mycobacterium tuberculosis strains

Pulmonary Pharmacology and Therapeutics

Volumn 27, Issue 1, 2014, Pages 114-120

  Uc Cachón, Andrés Humberto ^a,b   Borges Argáez, Rocío ^a   Said Fernández, Salvador ^b,d   Vargas Villarreal, Javier ^b   González Salazar, Francisco ^b,c   Méndez González, Martha ^a   Cáceres Farfán, Mirbella ^a   Molina Salinas, Gloria María ^b  

^a CENTRO DE INVESTIGACIÓN CIENTÍFICA DE YUCATÁN   (Mexico)

^b INSTITUTO MEXICANO DEL SEGURO SOCIAL   (Mexico)

^c UNIVERSIDAD DE MONTERREY   (Mexico)

^d Medicina UANL   (Mexico)

Author keywords

3,3' Biplumbagin; Diospyros anisandra; Maritinone; Multidrug resistant; Mycobacterium tuberculosis; Naphthoquinone

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; 3,3' BIPLUMBAGIN; CHITRANONE; CIS ISOSHINANOLONE; DIMER; DROSERONE; ELIPTINONE; EPOXIDE; HEXANE; MARITINONE; OFLOXACIN; PLUMBAGIN; RIFAMPICIN; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; ZEYLANONE;

ADULT; ANIMAL CELL; ARTICLE; BACTERIAL STRAIN; BACTERIUM ISOLATE; BARK; BIOLOGICAL ACTIVITY; CYTOTOXICITY; DIOSPYROS; DIOSPYROS ANISANDRA; FRACTIONATION; HUMAN; HUMAN CELL; IC 50; LIQUID LIQUID EXTRACTION; MALE; MAMMAL CELL; MASS FRAGMENTOGRAPHY; MIDDLE AGED; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PERIPHERAL BLOOD MONONUCLEAR CELL; PRIMARY CULTURE; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; VERO CELL;

3,3′-BIPLUMBAGIN; DIOSPYROS ANISANDRA; MARITINONE; MULTIDRUG-RESISTANT; MYCOBACTERIUM TUBERCULOSIS; NAPHTHOQUINONE;

ANIMALS; ANTITUBERCULAR AGENTS; CELLS, CULTURED; CERCOPITHECUS AETHIOPS; DIOSPYROS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; LEUKOCYTES, MONONUCLEAR; MALE; MICROBIAL SENSITIVITY TESTS; MIDDLE AGED; MYCOBACTERIUM TUBERCULOSIS; NAPHTHOQUINONES; PLANT BARK; PLANT EXTRACTS; PLANT STEMS; RIFAMPIN; TUBERCULOSIS, MULTIDRUG-RESISTANT; VERO CELLS;

EID: 84892445999     PISSN: 10945539     EISSN: 15229629     Source Type: Journal    
DOI: 10.1016/j.pupt.2013.08.001     Document Type: Article

References (47)

1. WHO World Health Organization global tuberculosis control 2012 2012, Publication of the World Health Organization, Geneva, Switzerland, Available from:. http://www.who.int/tb/publications/global_report/en/.
2. Basso L.A., Pereira da Silva L.H., Fett-Neto A.G., Filgueira de Azevedo W., de Souza-Moreira I., Palma M.S., et al. The use of biodiversity as source of new chemical entities against defined molecular targets for treatment of malaria, tuberculosis, and T-cell mediated diseases - a review. Mem Inst Oswaldo Cruz 2005, 100:475-506.
3. Del Olmo E., López J., San Feliciano A., García A. Desarrollo de nuevos agentes antituberculosos. Enferm Emerg 2005, 7:22-33.
4. Banerjee R., Allen A., Westenhouse J., Oh P., Elms W., Desmond E., et al. Extensively drug-resistant tuberculosis in California, 1993-2006. Clin Infect Dis 2008, 47:450-457.
5. Harve A.L. Natural products in drug discovery. Drug Discov Today 2008, 13:894-901.
6. Newman D., Cragg G. Natural products as sources of new drugs over the last 25 years. J Nat Prod 2007, 70:461-477.
7. Ventura-Pinto A., Lisboa de Castro S. The trypanocidal activity of naphthoquinones: a review. Molecules 2009, 14:4570-4590.
8. Babula P., Adam V., Havel L., Kizek R. Noteworthy secondary metabolites naphthoquinones - their occurrence, pharmacological properties and analysis. Curr Pharm Anal 2009, 5:47-68.
9. Nematollahi A., Aminimoghadamfarouj N., Wiart C. Reviews on 1,4-naphthoquinones from Diospyros L. J Asian Nat Prod Res 2012, 14:80-88.
10. Verma R.P. Anti-cancer activities of 1,4-naphthoquinones: a QSAR study. Anticancer Agents Med Chem 2006, 6:489-499.
11. Mallavadhani U.A., Panda A., Rao Y. Pharmacology and chemotaxonomy of Diospyros. Phytochemistry 1998, 49:901-951.
12. Durán R.J., Trejo C., Ibarra-Manríquez G. Endemic phytotaxa of the peninsula of Yucatan. Harvard Pap Bot 1998, 3:263-314.
13. Borges-Argáez R., Canche-Chay C.I., Peña-Rodríguez L.M., Said-Fernández S., Molina-Salinas G.M. Antimicrobial activity of Diospyros anisandra. Fitoterapia 2007, 78:370-372.
14. Uc-Cachón A.H., Molina-Salinas G.M., Fernández S., Méndez-González M., Cáceres-Farfán M., Borges-Argáez R. New dimeric naphthoquinone from Diospyros anisandra. Nat Prod Res 2013, 27:1174-1178.
15. Molina-Salinas G.M., Ramos-Guerra M.C., Vargas-Villarreal J., Mata-Cárdenas B.D., Becerril-Montes P., Said-Fernández S. Bactericidal activity of organic extracts from Flourensia cernua DC against strains of Mycobacterium tuberculosis. Arch Med Res 2006, 37:45-49.
16. Vilpo J.A., Veromaa T., Eerola E. Effect of cytosine arabinoside on the human immunosystem: toxicity against quiescent human peripheral blood mononuclear cells in vitro. Int J Immunopharmacol 1987, 9:379-383.
17. O'Rourke E.J., Halstead S.B., Allison A.C., Platts-Mills T.A. Specific lethality of silica for human peripheral blood mononuclear phagocytes, in vitro. J Immunol Methods 1978, 19:137-151.
18. Fischer P.H., Weddle M.A., Mossie R.D. Modulation of the metabolism and cytotoxicity of iododeoxyuridine by 5'-amino-5'-deoxythymidine. Mol Pharmacol 1983, 23:709-716.
19. Vicente E., Pérez-Silanes S., Lima L.M., Ancizu-Burguete S.A., Solano B., Villar R., et al. Selective activity against Mycobacterium tuberculosis of new quinoxaline 1,4-di-N-oxides. Bioorg Med Chem 2009, 17:385-389.
20. Navarrete-Vázquez G., Molina-Salinas G.M., Duarte-Fajardo Z.V., Vargas-Villarreal J., Estrada-Soto S., González-Salazar F., et al. Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines. Bioorg Med Chem 2007, 15:5502-5508.
21. Boyum A. Isolation of lymphocytes, granulocytes and macrophages. Scand J Immunol 1976, 5:9-15.
22. Delles A.M., Rittenhouse-Olson K., Morgan J., Oseroff A.R. A simple method for the purification of human peripheral blood antigen presenting cells (dendritic cells, monocytes/macrophages, and B lymphocytes). Immunol Invest 2002, 31:233-245.
23. Louis K.S., Siegel A.C. Cell viability analysis using Trypan blue: manual and automated methods. Methods Mol Biol 2011, 740:7-12.
24. Mossa J., El-Feraly F., Muhammad I. Antimycobacterial constituents from Juniperus procera, Ferula communis and Plumbago zeylanica and their in vitro synergistic activity with isonicotinic acid hydrazide. Phytother Res 2004, 18:934-937.
25. Kuete V., Tangmouoc J., Meyer M., Lall N. Diospyrone, crassiflorone and plumbagin: three antimycobacterial and antigonorrhoeal naphthoquinones from two Diospyros spp. Int J Antimicrob Agents 2009, 34:322-325.
26. Copp B., Pearce N. Natural product growth inhibitors of Mycobacterium tuberculosis. Nat Prod Rep 2007, 24:278-297.
27. Kayser O., Kiderlen A.F., Laatsch H., Croft S.L. In vitro leishmanicidal activity of monomeric and dimeric naphthoquinones. Acta Trop 2000, 77:307-314.
28. Gu J.Q., Graf T.N., Lee D., Chai H.B., Mi Q., Kardono L.M., et al. Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia. J Nat Prod 2004, 67:1156-1161.
29. Quintal-Novelo C., Moo-Puc R.E., Chale-Dzul J., Cáceres-Farfán M., Méndez-Gonzalez M., Borges-Argáez R. Cytotoxic constituents from the stem bark of Diospyros cuneata Standl. Nat Prod Res 2012, [In press]. 10.1080/14786419.2012.738201.
30. Higa M., Noha N., Yokaryo H., Ogihara K., Yogi S. Three new naphthoquinone derivatives from Diospyros maritima BLUME. Chem Pharm Bull (Tokyo) 2002, 50:590-593.
31. Protopopova M., Hanrahan C., Nikonenko B., Samala R., Chen P., Gearhart J., et al. Identification of a new antitubercular drug candidate, SQ109, from a combinatorial library of 1,2-ethylenediamines. J Antimicrob Chemother 2005, 56:968-974.
32. Hartkoorn R.C., Chandler B., Owen A., Ward S.A., Bertel-Squire S., Back D.J., et al. Differential drug susceptibility of intracellular and extracellular tuberculosis and the impact of P-glycoprotein. Tuberculosis 2007, 87:248-255.
33. de Paiva S.R., Lima L.A., Figueiredo M.R., Kaplan M.A.C. Plumbagin quantification in roots of Plumbago scandens L. obtained by different extraction techniques. An Acad Bras Cienc 2004, 76:499-504.
34. Migliori G.B., de Iaco G., Besozzi G., Centis R., Cirillo D.M. First tuberculosis cases in Italy resistant to all tested drugs. Euro Surveill 2007, 12. E070517.1.
35. Velayati A.A., Masjedi M.R., Farnia P., Tabarsi P., Ghanavi J., Ziazarifi A.H., et al. Emergence of new forms of totally drug-resistant tuberculosis bacilli: super extensively drug-resistant tuberculosis or totally drug-resistant strains in Iran. Chest 2009, 136:420-425.
36. Udwadia Z.F., Amale R.A., Ajbani K.K., Rodrigues C. Totally drug-resistant tuberculosis in India. Clin Infect Dis 2011, 54:579-581.
37. Spratt B.G. Resistance to antibiotics mediated by target alterations. Science 1994, 264:388-393.
38. Danilchanka O., Mailaender C., Miederweis M. Identification of a novel multidrug efflux pump of Mycobacterium tuberculosis. Antimicrob Agents Chemother 2008, 52:2503-2511.
39. Pasca M.R., Guglierame P., Arcesi F., Bellinzoni M., De Rossi E., Riccardi G. Rv2686c-Rv2687c-Rv2688c, an ABC fluoroquinolone efflux pump in Mycobacterium tuberculosis. Antimicrob Agents Chemother 2004, 48:3175-3178.
40. Silva P.E.A., Bigi F., Santangelo M.P., Romano M.I., Martín C., Cataldi A., et al. Characterization of P55, a multidrug efflux pump in Mycobacterium bovis and Mycobacterium tuberculosis. Antimicrob Agents Chemother 2001, 45:800-804.
41. Mathew R., Kruthiventi A.K., Prasad J.V., Kumar S.P., Srinu G., Ghatterji D. Inhibition of mycobacterial growth by plumbagin derivatives. Chem Biol Drug Des 2010, 76:34-42.
42. Van der Kooy F., Meyer J.J.M., Lall N. Antimycobacterial activity and possible mode of action of newly isolated neodiospyrin and other naphthoquinones from Euclea natalensis. S Afr J Bot 2006, 72:349-352.
43. Haiqing Y., Zengshan L., Aizhen G., Junchao L., Na G., Fanli Z., et al. Global transcriptional profiles of Mycobacterium tuberculosis treated with plumbagin. World J Microbiol Biotechnol 2011, 27:2261-2269.
44. Li X., Liu N., Zhang H., Knudson S.E., Slayden R.A., Tongea P.J. Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. Bioorg Med Chem Lett 2010, 20:6306-6309.
45. Bender R., Ham A., Osheroff N. Quinone-induced enhancement of DNA cleavage by human topoisomerase IIα: adduction of cysteine residues 392 and 405. Biochemistry 2007, 46:2856-2864.
46. Karkare S., Chung T.T., Collin F., Mitchenall L.A., McKay A.R., Greive S.J., et al. The naphthoquinone diospyrin is an inhibitor of DNA gyrase with a novel mechanism of action. J Biol Chem 2013, 288:5149-5156.
47. Inbaraj J.J., Chignell C.F. Cytotoxic action of juglone and plumbagin: a mechanistic study using HaCaT keratinocytes. Chem Res Toxicol 2004, 17:55-62.