Cytotoxic effect of some natural compounds isolated from Lauraceae plants and synthetic derivatives
Keywords:
biological products, Lauraceae, straining, diterpenes, in vitro
Abstract
Introduction. The antiproliferative effect of eleven neolignans, two lignans and one diterpene isolated from three Lauraceae plants, four benzofurans and two bicyclooctanes synthetic derivatives was evaluated in vitro on a set of five human cancer cells from solid tumors with a high incidence in Colombia.
Objective. To evaluate the cytotoxic effect of twenty compounds on the tumor cell lines HeLa, A-549, Hep-2, PC-3, and MCF-7.
Materials and methods. Fourteen natural compounds were isolated by chromatographic techniques from three native colombian plants (Pleurothyrium cinereum, Ocotea macrophylla and Nectandra amazonum), whose structures were established by spectroscopic methods; six synthetic derivatives were prepared by oxyarylation and diazomethane methylation. Antiproliferative effect and cell recovery were performed by means of in vitro treatment of tumor cell lines with test compounds, evaluating cell viability by resazurin staining.
Results. Among test compounds, only neolignans ocophyllal A, cinerin D, kaurenoic acid, two benzofuran-derivatives, and synthetic (-)-cinerin A were found to have antiproliferative effect at different levels. Bicyclooctanoids as well as kaurenoic acid exhibited activity against all human cancer cells while benzofuranoids showed selective activity against HeLa. Furthermore, compounds (-)-cinerin A and kaurenoic acid exhibited total lethal effect against all-five cell lines and PC-3, Hep-2, and A549 cell lines, respectively.
Conclusion. Test compounds exhibiting antiproliferative activity showed interesting results, which would promote their use as lead compounds on further studies for anticancer agents development.
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References
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34. Ruiz Y, Rodríguez J, Arvelo F, Usubillaga A, Monsalve M, Galindo-Castro I. Cytotoxic and apoptosis-inducing effect of ent-15-oxo-kaur-16-en-19-oic acid, a derivative of grandiflorolic acid from Espeletia schultzii. Phytochemistry. 2008;69:432-8.
35. Mongelli E, Pomilio AB, Sánchez JB, Guerra FM, Massanet GM. ent-Kaur-16-en-19-oic acid, a KB cells cytotoxic diterpenoid from Elaeoselinum foetidum. Phytother Res. 2002;16:387-8.
36. Coy ED, Cuca LE, Sefkow M. The first diastereoselective synthesis of cinerins A-C, PAF-antagonistic macrophyllin-type bicyclo[3.2.1]octane neolignans, using a novel Pd-catalysed oxyarylation. Org Biomol Chem. 2010;8:2003-5.
37. Boyd M. The NCI in vitro anticancer drug discovery screen. Concept, implementation, and operation, 1985-1995. In: Teicher B, Totowa NJ, editors. Anticancer drug development guide: Preclinical screening, clinical trials and approval. New York; Humana Press: 1997. p. 23-42.
2. Lieberman MM, Patterson GM, Moore RE. In vitro bioassays for anticancer drug screening: Effects of cell concentration and other assay parameters on growth inhibitory activity. Cancer Lett. 2001;173:21-9.
3. Nobili S, Lippi D, Witort E. Natural compounds for cancer treatment and prevention. Pharmacol Res. 2009;59:365-78.
4. Mans DR, Da Rocha A, Schwartsmann G. Anti-cancer drug discovery and development in Brazil: Targeted plant collection as a rational strategy to acquire candidate anti-cancer compounds. Oncologist. 2000;5:185-99.
5. Organización Mundial de la Salud. Descriptive note number 297: Cancer. Geneva: WHO; 2009.
6. Instituto Nacional de Cancerología. Anuario estadístico 2005: Por el control del cáncer. Volumen 3. Bogotá: Legis; 2007.
7. Whiting DA. Lignans, neolignans and related compounds. Nat Prod Rep. 1985;2:191-211.
8. Apers S, Vlietinck A, Pieters L. Lignans and neolignans as lead compounds. Phytochem Rev. 2003;2:201-17.
9. Tsai IL, Hsieh CF, Duh CY, Chen IS. Cytotoxic neolignans from Persea obovatifolia. Phytochemistry. 1996; 43: 1261-3.
10. Tsai IL, Hsieh CF, Duh CY. Additional cytotoxic neolignans from Persea obovatifolia. Phytochemistry. 1998;48:1371-5.
11. van Miert S, van Dyck S, Schmidt TJ, Brun R, Vlietinck A, Lemiére G, et al. Antileishmanial activity, cytotoxicity and QSAR analysis of synthetic dihydrobenzofuran lignans and related benzofurans. Bioorg Med Chem. 2005;13:661-9.
12. Cherigo L, Polanco V, Ortega-Barria E, Heller MV, Capson TL, Rios LC. Antitrypanosomal activity of a novel norlignan purified from Nectandra lineata. Nat Prod Res. 2005;19:373-7.
13. Pessini GL, Filho BPD, Nakamura CV, Cortez DA. Antibacterial activity of extracts and neolignans from Piper regnellii (Miq.) C. DC. var. pallescens (C. DC.) Yunck. Mem Inst Oswaldo Cruz. 2003;98:1115-20.
14. Ma Y, Han GQ, Wang YY. PAF antagonistic benzofuran neolignans from Piper kadsura. Acta Pharm Sin. 1993;28:370-3.
15. Sefkow M. The stereoselective synthesis of neolignans. Synthesis. 2003;17:2595-625.
16. Han G. PAF receptor antagonistic principles from Chinese traditional drugs. Progr Nat Sci. 1995;5:299-306.
17. Iida T, Ito K. Four phenolic neolignans from Magnolia liliflora. Phytochemistry. 1983;22:763-6.
18. Nascimento IR, Lopes LM. 2,3-dihydrobenzofuran neolignans from Aristolochia pubescens. Phytochemistry. 1999;52:345-50.
19. Coy-Barrera ED, Cuca-Suárez LE, Sefkow M. PAF-antagonistic bicyclo[3.2.1]octanoid neolignans from leaves of Ocotea macrophylla Kunth. (Lauraceae). Phytochemistry. 2009;70:1309-14.
20. Coy ED, Cuca LE. Chemical constituents from Pleurothyrium cinereum (van der Werff) (Lauraceae) from Colombia. Biochem Syst Ecol. 2008;36:674-7.
21. Coy ED, Cuca LE, Sefkow M. Macrophyllin-type bicyclo[3.2.1]octanoid neolignans from the leaves of Pleurothyrium cinereum. J Nat Prod. 2009;72:1245-8.
22. Han GQ, Dai P, Xu L, Wang SC, Zheng QT. Bicyclooctanoid neolignans from Piper kadsura. Chin Chem Lett. 1992;3:521-4.
23. Coy ED, Cuca LE. Three New 7.3',8.5'-connected bicyclo[3.2.1]octanoids and other neolignans from leaves of Nectandra amazonum NEES. (Lauraceae). Chem Pharm Bull. 2009;57:639-42.
24. Patra A, Mitra AK, Mitra SR, Kirtaniya CL, Adityachaudhury N. Carbon-13 NMR spectra of kauranoid diterpenes. Org Magn Reson. 1980;14:58-60.
25. Coy ED, Jovanovic L, Sefkow M. One-pot, Pd-catalyzed synthesis of trans-dihydrobenzofurans from o-aminophenols. Org Lett. 2010;12:1976-9.
26. Arndt F. Diazomethane. In: Organic syntheses. Collection Volume 2. New York: Wiley; 1943. p. 165.
27. Freshney I. Culture of animal cells: A manual of basic technique. 4th edition. England: John Wiley and Sons Inc.; 2000.
28. León CJ, Gómez SM, Morantes SJ, Cordero CP, Aristizabal FA. Caracterización del perfil de sensibilidad de un panel de líneas celulares para valoración de citotoxicidad in vitro. Biomédica. 2006;26:161-8.
29. Escobar L, Rivera A, Aristizabal F. Comparison of resazurin and MTT methods on studies of citotoxicity in human tumor cell lines. Vitae. 2010;17:67-74.
30. Escobar L, Aristizabal F. Fluorometric assay for cell proliferation in human tumor cell lines application. Vitae. 2010;17:173-80.
31. Cordero CP, Aristizabal FA. Evaluación preliminar in vitro de citotoxicidad de extractos vegetales sobre líneas derivadas de tumores humanos, empleando dos métodos colorimétricos. Rev Colomb Biotecnol. 2002;4:100-6.
32. Cordero CP, Gómez S, León CJ, Morantes SJ, Aristizabal FA. Cytotoxic activity of compounds isolated from Colombian plants. Fitoterapia. 2004;75:225-7.
33. Costa-Lotufo LV, Cunha GM, Farias PA, Viana GS, Cunha KM, Pessoa C, et al. The cytotoxic and embryotoxic effects of kaurenoic acid, a diterpene isolated from Copaifera langsdorffii oleo-resin. Toxicon. 2002;40:1231-4.
34. Ruiz Y, Rodríguez J, Arvelo F, Usubillaga A, Monsalve M, Galindo-Castro I. Cytotoxic and apoptosis-inducing effect of ent-15-oxo-kaur-16-en-19-oic acid, a derivative of grandiflorolic acid from Espeletia schultzii. Phytochemistry. 2008;69:432-8.
35. Mongelli E, Pomilio AB, Sánchez JB, Guerra FM, Massanet GM. ent-Kaur-16-en-19-oic acid, a KB cells cytotoxic diterpenoid from Elaeoselinum foetidum. Phytother Res. 2002;16:387-8.
36. Coy ED, Cuca LE, Sefkow M. The first diastereoselective synthesis of cinerins A-C, PAF-antagonistic macrophyllin-type bicyclo[3.2.1]octane neolignans, using a novel Pd-catalysed oxyarylation. Org Biomol Chem. 2010;8:2003-5.
37. Boyd M. The NCI in vitro anticancer drug discovery screen. Concept, implementation, and operation, 1985-1995. In: Teicher B, Totowa NJ, editors. Anticancer drug development guide: Preclinical screening, clinical trials and approval. New York; Humana Press: 1997. p. 23-42.
How to Cite
1.
Cuca LE, Coy ED, Alarcón MA, Fernández A, Aristizábal FA. Cytotoxic effect of some natural compounds isolated from Lauraceae plants and synthetic derivatives. biomedica [Internet]. 2011 Mar. 31 [cited 2024 May 17];31(3):335-43. Available from: https://revistabiomedica.org/index.php/biomedica/article/view/347
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