Genotoxicity of 15-deoxygoyazensolide in bacteria and yeast

Mutation Research - Genetic Toxicology and Environmental Mutagenesis

Volumn 631, Issue 1, 2007, Pages 16-25

  Vasconcellos, Marne C ^a   Rosa, Renato M ^b   Machado, Miriana S ^b   Villela, Izabel V ^b   Crotti, Antônio Eduardo Miller ^c   Lopes, João Luis Callegari ^c   Pessoa, Cláudia ^a   de Moraes, Manoel Odorico ^a   Lopes, Norberto Peporine ^c   Costa Lotufo, Letícia V ^a   Saffi, Jenifer ^d   Henriques, João Antônio Pegas ^b,e  

^a FEDERAL UNIVERSITY OF CEARÁ   (Brazil)

^b FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

^d UNIVERSIDADE LUTERANA DO BRASIL   (Brazil)

^e UNIVERSITY OF CAXIAS DO SUL   (Brazil)

Author keywords

15 Deoxygoyazensolide; Glutathione; Saccharomyces cerevisiae; Salmonella microsome assay; Sesquiterpene lactones

Indexed keywords

15 DEOXYGOYAZENSOLIDE; CHECKPOINT KINASE RAD3; DNA TOPOISOMERASE; GLUTATHIONE; RAD52 PROTEIN; SESQUITERPENE LACTONE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIUM; CHROMATIN ASSEMBLY AND DISASSEMBLY; COMPLEX FORMATION; CYTOTOXICITY; DNA DAMAGE; DNA METABOLISM; DNA STRAND BREAKAGE; DOSE RESPONSE; EXCISION REPAIR; FUNGAL STRAIN; GENOTOXICITY; HYPERSENSITIVITY REACTION; INTERCALATION COMPLEX; MUTAGENIC ACTIVITY; NONHUMAN; PRIORITY JOURNAL; SACCHAROMYCES CEREVISIAE; SALMONELLA TYPHIMURIUM; YEAST;

BASE SEQUENCE; DNA DAMAGE; DNA REPAIR; DNA, BACTERIAL; GLUTATHIONE; HETEROCYCLIC COMPOUNDS, 3-RING; MUTAGENICITY TESTS; MUTAGENS; MUTATION; SACCHAROMYCES CEREVISIAE; SALMONELLA TYPHIMURIUM;

SACCHAROMYCES CEREVISIAE; SALMONELLA TYPHIMURIUM;

EID: 34249752076     PISSN: 13835718     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.mrgentox.2007.04.002     Document Type: Article

References (66)

1. Picman A.K. Biological activities of sesquiterpene lactones. Biochem. Syst. Ecol. 14 (1986) 255-281
2. Zang S., Won Y.K., Ong C.N., and Shen H.M. Anti-cancer potential of sesquiterpene lactones: bioactivity and molecular mechanisms. Curr. Med. Chem. Anticancer Agents 5 (2005) 239-249
3. Taniguchi M., Kataoka T., Suzuki H., Uramoto M., Ando M., Arao K., Magae J., Nishimura T., Otake N., and Nagai K. Costunolide and dehydrocostus lactone as inhibitors of killing function of cytotoxic T lymphocytes. Biosci. Biotechnol. Biochem. 59 (1995) 2064-2067
4. Lee H.J., Kim N.Y., Son H.J., Kim K.M., Sohn D.H., Lee S.H., and Ryu J.H. A sesquiterpene, dehydrocostus lactone, inhibits the expression of inducible nitric oxide synthase and TNF-alpha in LPS-activated macrophages. Planta Med. 65 (1999) 104-108
5. Chen H.C., Chou C.K., Lee S.D., Wang J.C., and Yeh S.F. Active compounds from Saussurea lappa Clarks that suppress hepatitis B virus surface antigen gene expression in human hepatoma cells. Antiviral Res. 27 (1995) 99-109
6. Hall I.H., Lee K.H., Starnes C.O., Sumida Y., Wu R.Y., Waddell T.G., Cochran T.W., and Gerhart K.G. Anti-inflammatory activity of sesquiterpene lactones and related compounds. J. Pharm. Sci. 68 1979 (1979) 537-541
7. Hall I.H., Lee K.H., Mar E.C., Starnes C.O., and Wadell T.G. Antitumor agents: 21. A proposed mechanism for inhibition of cancer growth by tenulin and helenalin and related cyclopentenones. J. Med. Chem. 20 (1977) 333-337
8. Hwang D., Fischer N.H., Jang B.C., Tak H., Kim J.K., and Lee W. Inhibition of the expression of inducible cyclooxygenase and proinflammatory cytokines by sesquiterpene lactones in macrophages correlates with the inhibition of MAP kinases. Biochem. Biophys. Res. Commun. 226 (1996) 810-818
9. Bork P.M., Schmitz M.L., Kuhnt M., Escher C., and Heinrich M. Sesquiterpene lactone containing Mexican Indian medicinal plants and pure sesquiterpene lactones as potent inhibitors of transcription factor NF-kappaB. FEBS Lett. 402 (1997) 85-90
10. Hehner S.P., Heinrich M., Bork P.M., Vogt M., Ratter F., Lehmann V., Schulze-Osthoff K., Droge W., and Schmitz M.L. Sesquiterpene lactones specifically inhibit activation of NF-kappa B by preventing the degradation of I kappa B-alpha and I kappa B-beta. J. Biol. Chem. 272 (1998) 135-143
11. Cho J.Y., Baik K.U., Jung J.H., and Park M.H. In vitro anti-inflammatory effects of cynaropicrin, a sesquiterpene lactone, from Saussurea lappa. Eur. J. Pharmacol. 398 (2000) 399-407
12. Cho J.Y., Kimb A.R., Jungb J.H., Chunc T., Rheed M.H., and Yooe E.S. Cytotoxic pro-apoptotic activities of cynaropicrin, a sesquiterpene lactone, on the viability of leukocyte cancer cell lines. Eur. J. Pharmacol. 492 (2004) 85-94
13. Schimidt T.J. Helenanolide-type sesquiterpene lactones. III. Rates and stereochemistry in the reaction of helenalin and releated helenanolides with sulfhydryl containing biomolecules. Bioorg. Med. Chem. 5 (1997) 645-653
14. Tukov F.F., Anand S., Gadepalli R.S., Gunatilaka A.A., Matthews J.C., and Rimoldi J. Inactivation of the cytotoxic activity of repin, a sesquiterpene lactone from Centaurea repen. Chem. Res. Toxicol. 17 (2004) 1170-1176
15. Rüngeler P., Castro V., Mora G., Goren N., Vichenewski W., Pahl H.L., Melfort L., and Schimidt T.J. Inhibition of transcription factor NF-kappaB by sesquiterpene lactones: a proposed molecular mechanism of action. Bioorg. Med. Chem. 7 (1999) 2343-2352
16. Siedle B., García-Piñeres A.J., Murillo R., Schulte-Monting J., Castro V., Rüngeler P., Klaas C.A., Da Costa F.B., Kisiel W., and Merfort I. Quantitative structure-activity relationship of sesquiterpene lactones as inhibitors of the transcription factor NF-κB. J. Med. Chem. 47 (2004) 6042-6054
17. Dirsch V.M., Stuppner H., and Vollmar A.M. Cytotoxic sesquiterpene lactones mediate their death-inducing effect in leukemia T cells by triggering apoptosis. Planta Med. 67 (2001) 557-559
18. Dirsch V.M., Stuppner H., and Vollmar A.M. The sesquiterpene lactone helenalin triggers apoptosis in leukemia Jurkat T cells independently of the CD95 receptor and even in cells overexpressing Bcl-xL or Bcl-2. Cancer Res. 61 (2001) 5817-5823
19. Park H.J., Kwon S.H., Han Y.N., Choi J.W., Miyamoto K., Lee S.H., and Lee K.T. Apoptosis-inducing costunolide and a novel acyclic monoterpene from the stem bark of Magnolia sieboldii. Arch. Pharm. Res. 24 (2001) 342-348
20. Wen J., You K.R., Lee S.Y., Song C.H., and Kim D.G. Oxidative stress-mediated apoptosis: the anticancer effect of the sesquiterpene lactone parthenolide. J. Biol. Chem. 277 (2002) 38954-38964
21. Ramos A., Rivero R., Visozo A., Piloto J., and García A. Parthenin, a sesquiterpene lactone of Parthenium hysterophorus L. is a high toxicity clastogen. Mutat. Res. 514 (2002) 19-27
22. Jones D.H., Kim H.L., and Donnelly K.C. DNA damaging effects of three sesquiterpene lactones in repair-deficient mutants of Bacillus subtilis. Res. Commun. Chem. Pathol. Pharmacol. 34 (1981) 161-164
23. Roos W.P., and Kaina B. DNA damage-induced cell death by apoptosis. Trends Mol. Med. 12 (2006) 440-450
24. Sakamoto H.T., Flausino D., Castellano E.E., Stark B.W.C., Gates J.P., and Lopes N.P. Sesquiterpene lactones from Lychnophora ericoides. J. Nat. Prod. 66 (2003) 693-695
25. Crotti A.E.M., Cunha W.R., Lopes N.P., and Lopes J.L.C. Sesquiterpene lactones from Minasia alpestris. J. Br. Chem. Soc. 16 (2005) 677-680
26. Santos P.A., Amarante M.F.C., Pereira A.M.S., Bertoni B., Castro Franca S., Pessoa C., Moraes M.O., Costa-Lotufo L.V., Pereira M.R.P., and Lopes N.P. Production of an furanoheliangolide by Lychnophora ericoides cell culture. Chem. Pharm. Bull. 12 (2004) 1433-1435
27. Crotti A.E.M., Lopes J.L.C., and Lopes N.P. Triple quadrupole tandem mass spectrometry of sesquiterpene lactones: a study of goyazensolide and its congeners. J. Mass Spectrom. 40 (2005) 1030-1034
28. Mortelmans K., and Zeiger E. The Ames Salmonella/microsome mutagenicity assay. Mutat. Res. 455 (2000) 29-60
29. Prakash L., and Prakash S. Nucleotide excision repair in yeast. Mutat. Res. 451 (2000) 13-24
30. Game J.C. The Saccharomyces cerevisiae DNA repair genes at the end of the century. Mutat. Res. 451 (2000) 277-293
31. Kupiec M. Damage-induced recombination in the yeast Saccharomyces cerevisiae. Mutat. Res. 451 (2000) 91-105
32. Henriques J.A.P., Da Silva K.V.C.L., and Moustacchi E. Interaction between genes controlling sensitivity to psoralen (pso) and to radiation (rad) after 3carbethoxypsoralen plus 365 nm UV light treatment in yeast. Mol. Gen. Genet. 201 (1985) 415-420
33. Burke D., Dawson D., and Stearns T. Methods in Yeast Genetics, Cold Spring Harbour Laboratory Course Manual (2000), CSH Laboratory Press, Cold Spring Harbour
34. Maron D.M., and Ames B.N. Revised methods for the Salmonella mutagenicity test. Mutat. Res. 113 (1983) 173-215
35. Brendel M., Grey M., Maris A., Hietkamp J., Fesus Z., Pich C., Dafré L., Schmidt M., Eckardt-Schupp F., and Henriques J. Low glutathione pools in the original pso3 mutant of Saccharomyces cerevisiae are responsible for its pleiotropic sensitivity phenotype. Curr. Genet. 33 (1998) 4-9
36. Snow S. Absence of suppressible alleles at the his 1 locus of yeast. Mol. Gen. Genet. 164 (1978) 341-342
37. Hawthorne D.C. Identification of nonsense codons in yeast. J. Mol. Biol. 43 (1969) 71-75
38. Hawthorne D.C., and Mortimer R.K. Suppressors in yeast. Genetics 48 (1963) 617-620
39. Von Borstel R.C., Cain K.T., and Steinberg C.M. Inheritance of spontaneous mutability in yeast. Genetics 69 (1971) 17-27
40. Schuller R.C., and von Borstel R.C. Spontaneous mutability in yeast. I. Stability of lysine reversion rates to variation of adenine concentration. Mutat. Res. 24 (1974) 17-23
41. Akerboom T.P., and Sies H. Assay of glutathione, glutathione disulfide and glutathione mixed disulfides in biological samples. Meth. Enzymol. 77 (1981) 373-382
42. Bradford M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein dye binding. Anal. Biochem. 72 (1976) 248-254
43. Myers L., Adams N., Kier L., Rao T.K., Shaw B., and Williams L. Microcomputer software for data management and statistical analysis of the Ames/Salmonella test. In: Krewski D., and Franklin C.A. (Eds). Statistics in Toxicology (1991), Gordon and Breach, New York 265-279
44. Cavalcante A.A.M., Rubensam G., Picada J.N., da Silva E.G., Moreira J.C.F., and Henriques J.A.P. Mutagenicity, antioxidant potential, and antimutagenic activity against hydrogen peroxide of cashew (Anacardium occidentale) apple juice and cajuina. Environ. Mol. Mutagen. 41 (2003) 360-369
45. Picada J.N., Maris A.F., Ckless K., Salvador M., Khromov-Borisov N.N., and Henriques J.A.P. Differential mutagenic, antimutagenic and cytotoxic responses induced by apomorphine and its oxidation product, 8-oxo-apomorphine-semiquinone, in bacterial and yeast. Mutat. Res. 539 (2003) 29-41
46. Camussi A., Moller F., Ottavianio M., and Gorla S. Distribuizone campionarie e stima dei parametri in una popolazione. Metodi statistici per la sperimentazione biologica vol. 3 (1986), Zanichelli, Bologna pp. 68-70
47. Robles M., Aregullin M., West J., and Rodriguez E. Recent studies on the zoopharmacognosy, pharmacology, and neurotoxicology of sesquiterpene lactone. Planta Med. 61 (1995) 199-203
48. Machida K., Tanaka T., and Taniguchi M. Depletion of glutathione as a cause of the promotive effects of polygodial, a sesquiterpene on the production of reactive oxygen species in Saccharomyces cerevisiae. J. Biosci. Bioeng. 88 (1999) 526-530
49. Brigadão M.R.P.L., Lopes N.P., and Colepícolo P. Inhibitory mechanism of leukocyte respiratory burst by the sesquiterpene lactone Lychnopholide through protein glutathionylation decrease. Free Radic. Biol. Med. 36 (2004) S57-S58
50. Cunningham M., Peak J., and Peak M. Single-strand DNA breaks in rodent and human cells produced by superoxide anion or its reduction products. Mutat. Res. 184 (1987) 217-222
51. Meneghini R. Iron homeostasis, oxidative stress and DNA damage. Free Radic. Biol. Med. 23 (1997) 783-792
52. Barbouti A., Paschalis-Thomas D., Nousis L., Tenopoulou M., and Galares D. DNA damage and apoptosis in hydrogen peroxide-exposed Jurkat cells: bolus addition versus continuous generation of hydrogen peroxide. Free Radic. Biol. Med. 33 (2002) 691-702
53. Kirpnick Z., Homiski M., Rubitski E., Repnevskaya M., Howlett N., Aubrecht J., and Schiestl R.H. Yeast DEL assay detects clastogens. Mutat. Res. 582 (2005) 116-134
54. Brennan R.J., and Schiestl R.H. Free radicals generated in yeast by the Salmonella test-negative carcinogens benzene, urethane, thiourea and auramine O. Mutat. Res. 403 (1998) 65-73
55. Nunoshiba T., Watanabe E., Takahashi T., Daigaku Y., Ishikawa S., Mochiziki M., Ui A., Enomoto T., and Yakamoto K. Ames test-negative carcinogen, ortho-phenyl phenol, binds tubulin and causes aneuploidy in budding yeast. Mutat. Res. 617 (2007) 90-97
56. Jones D.H., Kim H.L., and Donnelly H.C. DNA damaging effects of three sesquiterpene lactones in repair deficient mutants of Bacillus subtilis. Res. Commun. Chem. Pathol. Pharmacol. 34 (1981) 161-164
57. Burim R.V., Canalle R., Lopes J.L.C., and Takahashi C.S. Genotoxic Action of the sesquiterpene lactone Glaucolide B on mammalian in vitro and in vivo. Genet. Mol. Biol. 22 (1999) 401-406
58. Mantovani M.S., Takahashi C.S., and Vichnewski W. Evaluation of the genotoxic activity of the sesquiterpene lactone goyazensolide in mammalian systems in vitro and in vivo. Rev. Br. Genét. 16 (1993) 967-975
59. Vaidya V.G., Kulkarni I., and Nagasampagi B.A. In vitro and in vivo cytogenetic effects of sesquiterpene lactone parthenin derived from Parthenium hysterophorus Linn. Indian J. Exp. Biol. 16 (1978) 1117-1118
60. V.E.P. Vicentini-Dias, Estudo da ação citotóxica das lactonas sesquiterpênicas eremantolido C e 15-desoxigoyazensolido, sobre medula óssea de ratos e linfócitos humanos, Ph.D. thesis, Faculdade de Medicina de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, São Paulo, 1992.
61. Abdulovic A., Kim N., and Jinks-Robertaon S. Mutagenesis and the three R's in yeast. DNA Repair (Amst) 8 5 (2006) 409-421
62. Pommier Y., Redon C., Rao V.A., Seiler J.A., Sordet O., Takemura H., Antony S., Meng L.H., Liao Z.Y., Kohlhagen G., Zhang H.L., and Kohn K.W. Repair of and checkpoint to topoisomerase I-mediated DNA damage. Mutat. Res. 532 (2003) 173-203
63. Pourquier P., and Pommier Y. Topoiserase I-mediated DNA damage. Adv. Cancer Res. 80 (2001) 189-216
64. Sordet O., Khan Q.A., and Pommier Y. Apoptotic topoisomerase I-DNA complex induced by oxygen radicals and mitochondrial dysfunction. Cell Cycle 3 (2004) 1095-1097
65. Daroui P., Desai S.D., Lin T.K., Liu A.A., and Liu L.F. Hydrogen peroxide induces topoisomerase I-mediated DNA damage and cell death. J. Biol. Chem. 15 (2004) 14587-14594
66. Sabourin M., Nitiss J.L., Nitiss K.C., Tatebayashi K., Ikeda H., and Osheroff N. Yeast recombination pathways triggered by topoisomerase II-mediated DNA breaks. Nucl. Acids Res. 31 (2003) 4373-4384