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Evidence-Based Complementary and Alternative Medicine
Volume 2015, Article ID 341216, 6 pages
http://dx.doi.org/10.1155/2015/341216
Research Article

Uncommon Trimethoxylated Flavonol Obtained from Rubus rosaefolius Leaves and Its Antiproliferative Activity

1Programa de Pós-Graduação em Ciências Farmacêuticas, Núcleo de Investigações Químico-Farmacêuticas (NIQFAR), Universidade do Vale do Itajaí (UNIVALI), 88302-901 Itajaí, SC, Brazil
2Centro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas (CPQBA), Universidade Estadual de Campinas (UNICAMP), 13083-970 Campinas, SP, Brazil
3Faculdade de Ciências Farmacêuticas, Universidade Estadual de Campinas (UNICAMP), 13083-859 Campinas, SP, Brazil

Received 4 October 2015; Revised 16 November 2015; Accepted 29 November 2015

Academic Editor: Daniela Rigano

Copyright © 2015 Marcel Petreanu et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. J. Ferlay, I. Soerjomataram, M. Ervik et al., “GLOBOCAN 2012 1.0,” International Agency for Research on Cancer, 2013, http://globocan.iarc.fr/.
  2. D. J. Newman and G. M. Cragg, “Natural products as sources of new drugs over the 30 years from 1981 to 2010,” Journal of Natural Products, vol. 75, no. 3, pp. 311–335, 2012. View at Publisher · View at Google Scholar · View at Scopus
  3. R. Niero and V. Cechinel-Filho, “Therapeutic potential and chemical composition of plants from the genus Rubus: a mini review of the last 10 years,” Natural Product Communications, vol. 3, pp. 437–444, 2008. View at Google Scholar
  4. B. Tribess, G. M. Pintarelli, L. A. Bini et al., “Ethnobotanical study of plants used for therapeutic purposes in the Atlantic Forest region, Southern Brazil,” Journal of Ethnopharmacology, vol. 164, pp. 136–146, 2015. View at Publisher · View at Google Scholar
  5. J.-H. Nam, H.-J. Jung, J. Choi, K.-T. Lee, and H.-J. Park, “The anti-gastropathic and anti-rheumatic effect of niga-ichigoside F1 and 23-hydroxytormentic acid isolated from the unripe fruits of Rubus coreanus in a rat model,” Biological and Pharmaceutical Bulletin, vol. 29, no. 5, pp. 967–970, 2006. View at Publisher · View at Google Scholar · View at Scopus
  6. N. P. Seeram, L. S. Adams, Y. Zhang et al., “Blackberry, black raspberry, blueberry, cranberry, red raspberry, and strawberry extracts inhibit growth and stimulate apoptosis of human cancer cells in vitro,” Journal of Agricultural and Food Chemistry, vol. 54, no. 25, pp. 9329–9339, 2006. View at Publisher · View at Google Scholar · View at Scopus
  7. S. Y. Wang, L. Bowman, and M. Ding, “Methyl jasmonate enhances antioxidant activity and flavonoid content in blackberries (Rubus sp.) and promotes antiproliferation of human cancer cells,” Food Chemistry, vol. 107, no. 3, pp. 1261–1269, 2008. View at Publisher · View at Google Scholar · View at Scopus
  8. E. Y. Baek, S. M. Lee, J. E. Lee et al., “Effect of Rubus coreanus Miquel on prostate tumour growth,” Journal of Functional Foods, vol. 5, no. 3, pp. 1478–1486, 2013. View at Publisher · View at Google Scholar · View at Scopus
  9. P. E. Berté, J. Da Silva Lopes, N. G. Comandulli et al., “Evaluation of the gastroprotective activity of the extracts, fractions, and pure compounds obtained from aerial parts of Rubus imperialis in different experimental models,” Naunyn-Schmiedeberg's Archives of Pharmacology, vol. 387, no. 4, pp. 313–319, 2014. View at Publisher · View at Google Scholar · View at Scopus
  10. A. B. C. R. Alves, R. S. D. Santos, S. D. S. Calil et al., “Genotoxic assessment of Rubus imperialis (Rosaceae) extractin vivo and its potential chemoprevention against cyclophosphamide-induced DNA damage,” Journal of Ethnopharmacology, vol. 153, no. 3, pp. 694–700, 2014. View at Publisher · View at Google Scholar · View at Scopus
  11. F. Tolentino, P. A. Araújo, E. S. Marques et al., “In vivo evaluation of the genetic toxicity of Rubus niveus Thunb. (Rosaceae) extract and initial screening of its potential chemoprevention against doxorubicin-induced DNA damage,” Journal of Ethnopharmacology, vol. 164, pp. 89–95, 2015. View at Publisher · View at Google Scholar
  12. M. Kanegusuku, D. Sbors, E. S. Bastos et al., “Phytochemical and analgesic activity of extract, fractions and a 19-hydroxyursane-type triterpenoid obtained from Rubus rosaefolius (Rosaceae),” Biological and Pharmaceutical Bulletin, vol. 30, no. 5, pp. 999–1002, 2007. View at Publisher · View at Google Scholar · View at Scopus
  13. E. A. Ostrosky, E. M. C. Marcondes, S. D. O. Nishikawa et al., “Rubus rosaefolius extract as a natural preservative candidate in topical formulations,” AAPS PharmSciTech, vol. 12, no. 2, pp. 732–737, 2011. View at Publisher · View at Google Scholar · View at Scopus
  14. D. Ravishankar, A. K. Rajora, F. Greco, and H. M. I. Osborn, “Flavonoids as prospective compounds for anti-cancer therapy,” International Journal of Biochemistry and Cell Biology, vol. 45, no. 12, pp. 2821–2831, 2013. View at Publisher · View at Google Scholar · View at Scopus
  15. O. Burmistrova, M. T. Marrero, S. Estévez et al., “Synthesis and effects on cell viability of flavonols and 3-methyl ether derivatives on human leukemia cells,” European Journal of Medicinal Chemistry, vol. 84, pp. 30–41, 2014. View at Publisher · View at Google Scholar · View at Scopus
  16. T. A. Dias, C. L. Duarte, C. F. Lima, M. F. Proença, and C. Pereira-Wilson, “Superior anticancer activity of halogenated chalcones and flavonols over the natural flavonol quercetin,” European Journal of Medicinal Chemistry, vol. 65, pp. 500–510, 2013. View at Publisher · View at Google Scholar · View at Scopus
  17. V. F. Paula, L. C. A. Barbosa, W. Errington, O. W. Howarth, and M. P. Cruz, “Chemical constituents from Bombacopsis glabra (Pasq.) A. Robyns: complete 1H and 13C NMR assignments and X ray structure of 5-hydroxy-3,6,7,8,4′-pentamethoxyflavone,” Journal of the Brazilian Chemical Society, vol. 13, no. 2, pp. 276–280, 2002. View at Publisher · View at Google Scholar · View at Scopus
  18. V. S. P. Chaturvedula and I. Prakash, “Isolation and structure elucidation of two triterpene acids from the leaves of Perilla frutescens,” Journal of Pharmacognosy and Phytochemistry, vol. 1, no. 6, pp. 49–53, 2013. View at Google Scholar
  19. T. Horie, Y. Ohtsuru, K. Shibata, K. Yamashita, M. Tsukayama, and Y. Kawamura, “13C NMR spectral assignment of the A-ring of polyoxygenated flavones,” Phytochemistry, vol. 47, no. 5, pp. 865–874, 1998. View at Publisher · View at Google Scholar · View at Scopus
  20. F. Weisheng, L. Qian, Z. Xiaoke, and K. Haixue, “Chemical constituents from Lysionotus pauciflora,” Tianran Chanwu Yanjiu Yu Kaifa, vol. 18, no. 4, pp. 617–620, 2006. View at Google Scholar
  21. W. M. Alarif, A. Abdel-Lateff, A. M. Al-Abd et al., “Selective cytotoxic effects on human breast carcinoma of new methoxylated flavonoids from Euryops arabicus grown in Saudi Arabia,” European Journal of Medicinal Chemistry, vol. 66, pp. 204–210, 2013. View at Publisher · View at Google Scholar · View at Scopus
  22. G. D. G. Rocha, M. Simões, K. A. Lúcio, R. R. Oliveira, M. A. C. Kaplan, and C. R. Gattass, “Natural triterpenoids from Cecropia lyratiloba are cytotoxic to both sensitive and multidrug resistant leukemia cell lines,” Bioorganic and Medicinal Chemistry, vol. 15, no. 23, pp. 7355–7360, 2007. View at Publisher · View at Google Scholar · View at Scopus
  23. R. Csuk, B. Siewert, C. Dressel, and R. Schäfer, “Tormentic acid derivatives: synthesis and apoptotic activity,” European Journal of Medicinal Chemistry, vol. 56, pp. 237–245, 2012. View at Publisher · View at Google Scholar · View at Scopus
  24. G. L. Badke, A. T. Panagopoulos, G. B. Aguiar, and J. C. E. Veiga, “Glioblastoma multiforme em idosos: uma revisão sobre seu tratamento com ênfase na abordagem cirúrgica,” Arquivos Brasileiros de Neurocirurgia, vol. 33, no. 1, pp. 45–51, 2014. View at Google Scholar
  25. R. H. Shoemaker, “The NCI60 human tumour cell line anticancer drug screen,” Nature Reviews Cancer, vol. 6, no. 10, pp. 813–823, 2006. View at Publisher · View at Google Scholar · View at Scopus
  26. A. Monks, D. Scudiero, P. Skehan et al., “Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines,” Journal of the National Cancer Institute, vol. 83, no. 11, pp. 757–766, 1991. View at Publisher · View at Google Scholar · View at Scopus
  27. B.-H. Moon, Y. Lee, J.-H. Ahn, and Y. Lim, “Complete assignment of 1H and 13C NMR data of some flavonol derivatives,” Magnetic Resonance in Chemistry, vol. 43, no. 10, pp. 858–860, 2005. View at Publisher · View at Google Scholar · View at Scopus