Chemical constituents and anticancer effects of the essential oil from leaves of xylopia laevigata

Planta Medica

Volumn 79, Issue 2, 2013, Pages 123-130

  Quintans, Jullyanade S S ^a   Soares, Brunom ^b   Ferraz, Rosanap C ^a   Oliveira, Allanc A ^a   Da Silva, Thananyb ^a   Menezes, Leocileyr A ^a   Sampaio, Maríliaf C ^a   Prata, Anapaula Do N ^a   Moraes, Manoelo ^b   Pessoa, Claudia ^b   Antoniolli, Angelor ^a   Costa, Emmanoelv ^a   Bezerra, Danielp ^a  

^a FEDERAL UNIVERSITY OF SERGIPE   (Brazil)

^b FEDERAL UNIVERSITY OF CEARÁ   (Brazil)

Author keywords

Annonaceae; antitumor; chemical composition; essential oil; Xylopia laevigata

Indexed keywords

ALPHA BISABOLENE; ALPHA CADINENE; ALPHA CALACORENE; ALPHA MUUROLOL; ANTINEOPLASTIC AGENT; BETA BISABOLENE; BETA CALACORENE; BICYCLOGERMACRENE; CADINA 1,4 DIENE; CALAMENE; CARYOPHYLLENE; CARYOPHYLLENE OXIDE; COPAENE; DELTA AMORPHENE; DELTA CADINENE; DELTA CADINOL; DOXORUBICIN; ESSENTIAL OIL; FLUOROURACIL; GAMMA CADINENE; GAMMA MUUROLENE; GERMACRENE B; GERMACRENE D; KAURENE; PIMARADIENE; PLANT EXTRACT; SPATHULENOL; TERPENOID; UNCLASSIFIED DRUG; UNINDEXED DRUG; XYLOPIA LAEVIGATA EXTRACT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; BODY WEIGHT; CANCER INHIBITION; CHEMICAL COMPOSITION; CONTROLLED STUDY; CYTOTOXICITY TEST; FEMALE; GAS CHROMATOGRAPHY; GENOTOXICITY; HEMOLYSIS; HUMAN; HUMAN CELL; IC 50; LEUKOCYTE COUNT; MALE; MASS SPECTROMETRY; MOUSE; NONHUMAN; PLANT LEAF; SARCOMA; TUMOR CELL; TUMOR GROWTH; XYLOPIA; XYLOPIA LAEVIGATA;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BRAZIL; CELL LINE, TUMOR; CELLS, CULTURED; ERYTHROCYTES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; LEUKOCYTES, MONONUCLEAR; MALE; MEDICINE, TRADITIONAL; MICE; OILS, VOLATILE; PLANT LEAVES; PLANT OILS; PLANTS, MEDICINAL; SARCOMA 180; SESQUITERPENES; SESQUITERPENES, GERMACRANE; XYLOPIA;

ANNONACEAE; XYLOPIA;

EID: 84873060163     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0032-1328091     Document Type: Article

References (39)

1. Choumessi A. T., Danel M., Chassaing S., Truchet I., Penlap V. B., Pieme A. C., Asonganyi T., Ducommun B., Valette A. Characterization of the antiproliferative activity of Xylopia aethiopica. Cell Div: 2012; 7 1 8
2. Taylor P., Arsenak M., Abad M. J., Fernández A., Milano B., Gonto R., Ruiz M. C., Fraile S., Taylor S., Estrada O., Michelangeli F. Screening of Venezuelan medicinal plant extracts for cytostatic and cytotoxic activity against tumor cell lines. Phytother Res advance online publication: 2012; 10.1002/ptr.4752
3. Castello-Branco M. V., Anazetti M. C., Silva M. S., Tavares J. F., Diniz M. F., Frungillo L., Haun M., Melo P. S. Diterpenes from Xylopia langsdorffiana inhibit cell growth and induce differentiation in human leukemia cells. Z Naturforsch C: 2009; 64 650 656
4. Cavalcanti B. C., Ferreira J. R., Moura D. J., Rosa R. M., Furtado G. V., Burbano R. R., Silveira E. R., Lima M. A., Camara C. A., Saffi J., Henriques J. A., Rao V. S., Costa-Lotufo L. V., Moraes M. O., Pessoa C. Structure- mutagenicity relationship of kaurenoic acid from Xylopia sericeae (Annonaceae). Mutat Res: 2010; 701 153 163
5. Pontes A. F., Barbosa M. RV, Maas P. JM. Flora Paraibana: Annonaceae Juss. Acta Bot Braz: 2004; 18 281 293
6. Silva D. M., Costa E. V., Nogueira P. CL, Moraes V. RS, Cavalcanti S. CH, Salvador M. J., Ribeiro L. HG, Gadelha F. R., Barison A., Ferreira A. G. Ent -kaurane diterpenoids and other constituents from the stem of Xylopia laevigata (Annonaceae). Quim Nova: 2012; 35 1570 1576
7. Costa E. V., Dutra L. M., De Jesus H. CR, Nogueira P. CL, Moraes V. RS, Salvador M. J., Cavalcanti S. CH, Dos Santos R. LC, Prata A. PN. Chemical composition and antioxidant, antimicrobial, and larvicidal activities of the essential oils of Annona salzmannii and A. pickelii (Annonaceae). Nat Prod Commun: 2011; 6 907 912
8. Van Den Dool H., Kratz P. D. A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J Chromatogr: 1963; 11 463 471
9. Adams R. P. Identification of essential oil components by gas chromatography/mass spectrometry. Illinois Allured Publishing Corporation: 2007
10. Mossman T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods: 1983; 65 55 63
11. Ahmed S. A., Gogal R. M., Walsh J. E. A new rapid and simple non-radioactive assay to monitor and determine the proliferation of lymphocytes an alternative to [3H] thymidine incorporation assay. J Immunol Methods: 1994; 170 211 224 (Pubitemid 24122510)
12. Jimenez P. C., Fortier S. C., Lotufo T. MC, Pessoa C., Moraes M. EA, Moraes M. O., Costa-Lotufo L. V. Biological activity in extracts of ascidians (Tunicata, Ascidiacea) from the northeastern Brazilian coast. J Exp Mar Biol Ecol: 2003; 287 93 101 (Pubitemid 36199093)
13. Singh N. P., Mccoy M. T., Tice R. R., Schneider E. LA. Single technique for quantitation of low levels of DNA damage in individual cells. Exp Cell Res: 1988; 175 184 191
14. Hartmann A., Speit G. The contribution of cytotoxicity to DNA effects in the single cell gel test (comet assay). Toxicol Lett: 1997; 90 183 188 (Pubitemid 27096533)
15. Speit G., Hartmann A. The comet assay (single-cell gel test). A sensitive genotoxicity test for the detection of DNA damage and repair. Methods Mol Biol: 1999; 113 203 212
16. Bezerra D. P., Castro F. O., Alves A. PNN, Pessoa C., Moraes M. O., Silveira E. R., Lima M. AS, Elmiro F. JM, Costa-Lotufo L. V. In vivo growth-inhibition of sarcoma 180 by piplartine and piperine, two alkaloid amides from Piper. Braz J Med Biol Res: 2006; 39 801 807 (Pubitemid 43880939)
17. Bezerra D. P., Castro F. O., Alves A. PNN, Pessoa C., Moraes M. O., Silveira E. R., Lima M. AS, Elmiro F. JM, Alencar N. MN, Mesquita R. O., Lima M. W., Lotufo L. VC. In vitro and in vivo antitumor effect of 5-FU combined with piplartine and piperine. J Appl Toxicol: 2008; 28 156 163 (Pubitemid 351428288)
18. Britto A. CS, Oliveira A. CA, Henriques R. M., Cardoso G. MB, Bomfim D. S., Carvalho A. A., Moraes M. O., Pessoa C., Pinheiro M. LB, Costa E. V., Bezerra D. P. In vitro and in vivo antitumor effects of the essential oil from the leaves of Guatteria friesiana. Planta Med: 2012; 78 409 414
19. Bezerra D. P., Marinho Filho J. D., Alves A. P., Pessoa C., de Moraes M. O., Pessoa O. D., Torres M. C., Silveira E. R., Viana F. A., Costa-Lotufo L. V. Antitumor activity of the essential oil from the leaves of Croton regelianus and its component ascaridole. Chem Biodivers: 2009; 6 1224 1231
20. Lago J. HG, De Ávila P. Jr., Moreno P. RH, Limberger R. P., Apel M. A., Henriques A. T. Analysis, comparison and variation on the chemical composition from the leaf volatile oil of Xylopia aromatica (Annonaceae). Biochem Syst Ecol: 2003; 31 669 672 (Pubitemid 36568063)
21. Maia J. GS, Andrade E. HA, Da Silva A. CM, Oliveira J., Carreira L. MM, Araújo J. S. Leaf volatile oils from four Brazilian Xylopia species. Flavour Fragr J: 2005; 20 474 477 (Pubitemid 41288562)
22. Tavares J. F., Silva M. VB, Queiroga K. F., Martins R. M., Silva T. MS, Camara C. A., Agra M. F., Barbosa-Filho J. M., Da Silva M. S. Composition and molluscicidal properties of essential oils from leaves of Xylopia langsdorffiana A. St. Hil. Et Tul. (Annonaceae). J Essent Oil Res: 2007; 19 282 284
23. Suffness M., Pezzuto J. M. Assays related to cancer drug discovery. In: Hostettmann K. editor Methods in plant biochemistry: assays for bioactivity. London Academic Press: 1990; 71 133
24. Aki H., Yamamoto M. Drug binding to human erythrocytes in the process of ionic drug-induced hemolysis. Flow microcalorimetric approaches. Biochem Pharmacol: 1991; 41 133 138
25. Kuete V., Krusche B., Youns M., Voukeng I., Fankam A. G., Tankeo S., Lacmata S., Efferth T. Cytotoxicity of some Cameroonian spices and selected medicinal plant extracts. J Ethnopharmacol: 2011; 134 803 812
26. Asekun O. T., Adeniyi B. A. Antimicrobial and cytotoxic activities of the fruit essential oil of Xylopia aethiopica from Nigeria. Fitoterapia: 2004; 75 368 370 (Pubitemid 38670569)
27. Suffredini I. B., Paciencia M. L., Varella A. D., Younes R. N. In vitro cytotoxic activity of Brazilian plant extracts against human lung, colon and CNS solid cancers and leukemia. Fitoterapia: 2007; 78 223 226 (Pubitemid 46551474)
28. Colman-Saizarbitoria T., Gu Z. M., Zhao G. X., Zeng L., Kozlowski J. F., McLaughlin J. L. Venezenin: a new bioactive Annonaceous acetogenin from the bark of Xylopia aromatica. J Nat Prod: 1995; 58 532 539
29. Colman-Saizarbitoria T., Zambrano J., Ferrigni N. R., Gu Z. M., Ng J. H., Smith D. L., McLaughlin J. L. Bioactive annonaceous acetogenins from the bark of Xylopia aromatica. J Nat Prod: 1994; 57 486 493 (Pubitemid 24152903)
30. Castello-Branco M. VS, Tavares J. F., Silva M. S., Filho J. MB, Anazetti M. C., Frungillo L., Haun M., Diniz M. FFM, Melo P. S. Xylodiol from Xylopia langsdorfiana induces apoptosis in HL60 cells. Braz J Pharmacogn: 2011; 21 1035 1042
31. Pita J. C., Xavier A. L., de Sousa T. K., Mangueira V. M., Tavares J. F., de Oliveira Júnior R. J., Veras R. C., Pessoa Hde L., da Silva M. S., Morelli S., Ávila Vde M., da Silva T. G., Diniz Mde F., Castello-Branco M. V. In vitro and in vivo antitumor effect of trachylobane-360, a diterpene from Xylopia langsdorffiana. Molecules: 2012; 17 9573 9589
32. Ribeiro S. S., Jesus A. M., Anjos C. S., Silva T. B., Santos A. DC, Jesus J. R., Andrade M. S., Sampaio T. S., Gomes W. F., Alves P. B., Carvalho A. A., Pessoa C., Moraes M. O., Pinheiro M. LB, Prata A. PN, Blank A. F., Silva-Mann R., Moraes V. RS, Costa E. V., Nogueira P. CL, Bezerra D. P. Evaluation of the cytotoxic activity of some Brazilian medicinal plants. Planta Med: 2012; 78 1601 1606
33. Tundis R., Loizzo M. R., Bonesi M., Menichini F., Dodaro D., Passalacqua N. G., Statti G., Menichini F. In vitro cytotoxic effects of Senecio stabianus Lacaita (Asteraceae) on human cancer cell lines. Nat Prod Res: 2009; 23 1707 1718
34. Amiel E., Ofir R., Dudai N., Soloway E., Rabinsky T., Rachmilevitch S. β -Caryophyllene, a compound isolated from the biblical balm of gilead (Commiphora gileadensis), is a selective apoptosis inducer for tumor cell lines. Evid Based Complement Alternat Med: 2012; 2012 872394
35. Loizzo M. R., Tundis R., Statti G. A., Menichini F. Jacaranone: A cytotoxic constituent from Senecio ambiguus subsp. ambiguus (Biv.) DC. against renal adenocarcinoma ACHN and prostate carcinoma LNCaP cells. Arch Pharm Res: 2007; 30 701 707
36. Areche C., Schmeda-Hirschmann G., Theoduloz C., Rodríguez J. A. Gastroprotective effect and cytotoxicity of abietane diterpenes from the Chilean Lamiaceae Sphacele chamaedryoides (Balbis) Briq. J Pharm Pharmacol: 2009; 61 1689 1697
37. Lu X. G., Feng B. A., Zhan L. B., Yu Z. H. D-limonene induces apoptosis of gastric cancer cells. Zhonghua Zhong Liu Za Zhi: 2003; 25 325 327
38. Lu X. G., Zhan L. B., Feng B. A., Qu M. Y., Yu L. H., Xie J. H. Inhibition of growth and metastasis of human gastric cancer implanted in nude mice by d-limonene. World J Gastroenterol: 2004; 10 2140 2144
39. Takiguchi N., Saito N., Nunomura M., Kouda K., Oda K., Furuyama N., Nakajima N. Use of 5-FU plus hyperbaric oxygen for treating malignant tumors: evaluation of antitumor effect and measurement of 5-FU in individual organs. Cancer Chemother Pharmacol: 2001; 47 11 14 (Pubitemid 32664506)