Trypanocidal structure-activity relationship for cis- and trans-methylpluviatolide

Phytochemistry

Volumn 69, Issue 9, 2008, Pages 1890-1894

  da Silva, R ^a   Saraiva, J ^b   de Albuquerque, S ^b   Curti, C ^b   Donate, P M ^b   Bianco, T N C ^a   Bastos, J K ^b   Silva, M L A ^a  

^a UNIVERSIDADE DE FRANCA   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Lignans; Methylpluviatolide; Structure activity relationship; Trypanocidal activity

Indexed keywords

ANTITRYPANOSOMAL AGENT; LACTONE; LIGNAN; METHYLPLUVIATOLIDE; NITRIC OXIDE;

ANIMAL; ARTICLE; BIOSYNTHESIS; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; MACROPHAGE; METABOLISM; MOUSE; STRUCTURE ACTIVITY RELATION; TRYPANOSOMA CRUZI;

ANIMALS; CELL LINE; LACTONES; LIGNANS; MACROPHAGES; MICE; MOLECULAR STRUCTURE; NITRIC OXIDE; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOCIDAL AGENTS; TRYPANOSOMA CRUZI;

TRYPANOSOMA CRUZI;

EID: 44549087382     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2008.04.002     Document Type: Article

References (43)

1. Bakker B.M., Michels P.A.M., Opperdoes F.R., and Westerhoff H.V. What controls glycolysis in bloodstream from Trypanosoma brucei?. J. Biol. Chem. 274 21 (1999) 14551-14559
2. Bakker B.M., Westerhoff H.V., Opperdoes F.R., and Michels P.A.M. Metabolic control analysis of glycolysis in trypanosomes as an approach to improve selectivity and effectiveness of drugs. Mol. Biochem. Parasitol. 106 1 (2000) 1-10
3. Barata L.E.S., Santos L.S., Ferri P.H., Phillipson J.D., Paine A., and Croft S.L. Antileishmanial activity of neolignans from Virola species and synthetic analogues. Phytochemistry 55 (2000) 589-595
4. Bastos J.K., Burandt C.L., Nanayakkara N.P.D., Bryant L., and McChesney J.D. Quantification of aryltetralin lignans in plant parts and among different populations of Podophyllum peltatum by reversed-phase high-performance liquid chromatography. J. Nat. Prod. 59 (1996) 406-408
5. Bastos J.K., Albuquerque S., and Silva M.L.A.E. Evaluation of the Trypanocidal activity of lignans isolated from the leaves of Zanthoxylum naranjillo. Planta Med. 65 (1999) 541-544
6. Bianchi E., Caldwell M.E., and Cole J.R. Antitumor agents from Bursera microphylla (Burseraceae) I. Isolation and characterization of deoxypodophyllotoxin. J. Pharm. Sci. 57 (1968) 678-679
7. Broomhead A.J., and Dewick P.M. Tumour-inhihitory aryltetralin lignans in Podophyllum versipelle, Diphylleia cymosa and Diphylleia grayi. Phytochemistry 29 (1990) 3831-3837
8. Caniato R., and Puricelli L. Review: natural antimalarial agents. Crit. Rev. Plant. Sci. 22 (2003) 79-105
9. Carthcart R., Schwiers E., and Ames B. Detection of picomole levels of hydroperoxides using a dichlorofluorescein fluorescent assay. Anal. Biochem. 134 (1983) 111-116
10. Charlton J.L., and Chee G.L. Asymmetric synthesis of lignans using oxazolidinones as chiral auxiliaries. Aust. J. Chem. 75 (1997) 1076-1083
11. Chen Y.-g., Sun H.-d., Z-h Xu., and G-w Qin. Studies on chemical constituents of Stellera chamejasma L. China Zhongguo Zhongyao Zazhi 26 (2001) 477-479
12. Cho J.Y., Yim A.E., Yoo E.S., Baik K.U., and Park M.H. Immunomodulatory effect of arctigenin, a lignan compound, on tumour necrosis factor-alpha and nitric oxide production, and lymphocyte proliferation. J. Pharm. Pharmacol. 51 (1999) 1267-1273
13. Da Silva Filho A.A., Bueno P.C.P., Gregório L.E., Silva M.L.A., Albuquerque S., and Bastos J.K. In vitro trypanocidal activity evaluation of crude extract and isolated compounds from Baccharis dracunculifolia D.C. (Asteraceae). J. Pharm. Pharmacol. 56 (2004) 1195-1199
14. Fang J., and Beattie D.S. Alternative oxidase present in procyclic Trypanosoma brucei may act to lower the mitochondrial production of superoxide. Arch. Biochem. Biophys. 414 (2003) 294-302
15. Giorgio S., Barão S.C., Augusto O., and Kwee J.K. Leishmania amazonensis infection is reduced macrophages treated with guanine ribonucleosides. Acta Trop. 70 (1998) 119-122
16. Green L.C., Wagner D.A., Glogowski J., Shipper P.L., Wishnok J.S., and Tannenbaum S.R. Analysis of nitrate, nitrite, and [15N] nitrate in biological fluids. Annal. Biochem. 26 1 (1982) 131-138
17. Hull R.N., Cherry W.R., and Tritch O.J. Growth characteristics of monkey kidney cell strains LLC-MK1, LLC-MK2, and LLC-MK2 (NCTC-3196) and their utility in virus research. J. Exp. Med. 115 (1962) 903-918
18. Landais Y., Robin J.P., and Lebrun A. Ruthenium dioxide in fluoro acid medium: I. A new agent in the biaryl oxidative coupling. Application to the synthesis of non phenolic bisbenzocyclooctadiene lignan lactones. Tetrahedron 47 (1991) 3787-3804
19. Lin R.C., Skaltsounis A.L., Seguin E., Tillequin F., and Koch M. Phenolic constituents of Selaginella doederleinii. Planta Med. 60 (1994) 168-170
20. Muelas-Serrano S., Nogal-Ruiz J.J., and Gómez-Barrio A. Setting a colorimetric method to determine the viability of Trypanosoma cruzi epimastigotes. Parasitol. Res. 86 (2000) 999-1002
21. Norval M. Mechanism of persistence of rubella virus in LLC-MK2 cells. J. Gen. Virol. 43 (1979) 289-298
22. Opperdoes F.R. Compartmentation of carbohydrate metabolism in trypanosomes. Annu. Rev. Microbiol. 41 (1987) 127-151
23. Opperdoes F.R., and Michels P.A.M. Enzymes of carbohydrate metabolism as potential drug targets. Int. J. Parasitol. 31 (2001) 482-490
24. Piaggio E., Anceau J., Revelli S., Bottasso O., Wietzerbin J., and Serra E. Trypanocidal drug benznidazole impairs lipopolysaccharide induction of macrophage nitric oxide synthase gene transcription through inhibition of NF-KappaB activation. J. Immunol. 167 (2001) 3422-3426
25. Raether W., and Hanel H. Nitroheterocyclic drugs with broad sectrum activity. Parasitol. Res. 90 (2003) 19-39
26. Rocha L.G., Almeida J.R.G.S., Macedo R.O., and Barbosa-Filho J.M. A review of natural products with antileishmanial activity. Phytomedicine 12 (2005) 514-535
27. Royo V.A., Souza F.F.S., Pereira A.C., Silva R., Vinhólis A.H.C., Donate P.M., Silva M.L.A., Albuquerque S., and Bastos J.K. Biological activity evaluation of dibenzylbutyrolactone lignans derivatives against Leishmania braziliensis. Braz. J. Pharmacog. 13 (2003) 18-21
28. Saraiva J., Albuquerque S., Uyemura S.A., Silva R., Donate P.M., Bastos J.K., Silva M.L.A.E., Siqueira C.M., and Tudella V.G. The effects of cubebin derivatives on mitochondrial respiration. Rev. Bras. Ciênc. Farm. 41 1 (2005) 125
29. 50 values and cell survival. Eur. J. Clin. Chem. Clin. Biochem. 33 (1995) 813-823
30. Silva, M.L.A., Albuquerque, S., Souza, G.H.,B., Silva, R., Bastos, J.K., 2003. Patente WO 03080600.
31. Souza G.H.B., Da Silva Filho A.A., Souza V.A., Pereira A.C., Royo V.A., Silva M.L.A., Silva R., Donate P.M., Carvalho J.C.T., and Bastos J.K. Analgesic and anti-inflammatory activities evaluation of (-)-O-acetyl, (-)-O-methyl, (-)-O-dimethylethylamine cubebin and their preparation from (-) cubebin. Farmaco 59 (2004) 55-61
32. Souza V.A., Silva R., Pereira A.C., Royo V.A., Saraiva J., Montanheiro M., Souza G.H.B., Da Silva Filho A.A., Grando M.D., Donate P.M., Bastos J.K., Albuquerque S., and Silva M.L.A. Trypanocidal activity of (-)-cubebin derivatives against free amastigote forms of Trypanosoma cruzi. Bioorg. Med. Chem. 15 (2005) 303-307
33. Stoppani A.O. The chemotherapy of Chagas disease. Medicina (B Aires) 59 2 (1999) 147-165
34. Turrens J.F., and MCcord J.M. The iron-containing superoxide dismutases of trypanosomatidae. Free Rad. Biol. Med. 40 (2006) 193-195
35. Uchiyama N., Kabututu Z., Kubata B.K., Kiuchi F., Ito M., Nakajima-Shimada J., Aoki T., Ohkubo K., Fukuzumi S., Martin S.K., Honda G., and Urade Y. Antichagasic activity of komaroviquinone is due to generation of reactive oxygen species catalyzed by Trypanosoma cruzi old yellow enzyme. Antimicrob. Agents Chemother. 49 12 (2005) 5123-5126
36. Umezawa T., Davin L.B., and Lewis N.G. Formation of lignans (-)-secoisolariciresinol and (-)-matairesinol with Forsythia intermedia cell-free extracts. J. Biol. Chem. 266 (1991) 10210-10217
37. Umezawa, T., Isohata, T., Kuroda, H., Higuchi, T., Shimada, M., 1992. Chiral HPLC and LC-MS analysis of several lignans. In: Kuwahara M., Shimada M. (Eds.), Biotechnology in Pulp and Paper Industry. Uni. Publ., Tokyo. pp. 507-512.
38. Umezawa T., and Shimada M. Formation of the lignan (+)-secoisolariciresinol by cell-free extracts of Arctium lappa. Biosci. Biotech. Biochem. 60 (1996) 736-737
39. Umezawa T., Okunishi T., and Shimada M. Stereochemical diversity in lignan biosynthesis. Wood Res. 84 (1997) 62-75
40. Umezawa T., Okunishi T., and Shimada M. Mechanisms of lignan biosynthesis. Ann. Rep. Interdiscipl. Res. Inst. Environ. Sci. 16 (1997) 65-71
41. Vieira P.C., Mafezoli J., Pupo M.T., Fernandes J.B., Silva M.F.G., Albuquerque S., Oliva G., and Pavão F. Strategies for the isolation and identification of trypanocidal compounds from the Rutales. Pure Appl. Chem. 73 3 (2001) 617-622
42. Xu Z.-h., G-w Qin., X-y Li., and R-s Xu. New biflavanones and bioactive compounds from Stellera chamaejasme L. Acta Pharmac. Sin 36 (2001) 668-671
43. Zhang H.J., Tamez P.A., Hoang V.D., Tan G.T., Hung N.V., Xuang L.T., Huong L.M., Cuong N.M., Thao D.T., Soerjano D.D., Fong H.H.S., and Pezzuto J.M. Antimalarial compounds from Rhaphidophora decursiva. J. Nat. Prod. 66 (2001) 772-777