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BioMed Research International
Volume 2015, Article ID 392674, 21 pages
http://dx.doi.org/10.1155/2015/392674
Review Article

Antitumor Phenylpropanoids Found in Essential Oils

1Núcleo de Farmácia, Universidade Federal de Sergipe, 58051-970 Lagarto, SE, Brazil
2Departamento de Farmácia, Universidade Federal de Sergipe, 49100-000 São Cristóvão, SE, Brazil
3Departamento de Ciências Farmacêuticas, Universidade Federal da Paraíba, CP 5009, 58051-970 João Pessoa, PB, Brazil

Received 5 July 2014; Accepted 12 October 2014

Academic Editor: Gagan Deep

Copyright © 2015 Adriana Andrade Carvalho 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. D. Hanahan and R. A. Weinberg, “The hallmarks of cancer,” Cell, vol. 100, no. 1, pp. 57–70, 2000. View at Publisher · View at Google Scholar · View at Scopus
  2. D. P. de Sousa, “Analgesic-like activity of essential oils constituents,” Molecules, vol. 16, no. 3, pp. 2233–2252, 2011. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  3. R. N. de Almeida, M. de Fátima Agra, F. N. S. Maior, and D. P. de Sousa, “Essential oils and their constituents: anticonvulsant activity,” Molecules, vol. 16, no. 3, pp. 2726–2742, 2011. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  4. R. D. C. Da Silveira E Sá, L. N. Andrade, R. D. R. B. De Oliveira, and D. P. De Sousa, “A review on anti-inflammatory activity of phenylpropanoids found in essential oils,” Molecules, vol. 19, no. 2, pp. 1459–1480, 2014. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  5. Y.-C. Su and C.-L. Ho, “Composition, in-vitro anticancer, and antimicrobial activities of the leaf essential oil of Machilus mushaensis from Taiwan,” Natural Product Communications, vol. 8, no. 2, pp. 273–275, 2013. View at Google Scholar · View at Scopus
  6. A. Manjamalai and V. M. B. Grace, “The chemotherapeutic effect of essential oil of Plectranthus amboinicus (Lour) on lung metastasis developed by B16F-10 cell line in C57BL/6 mice,” Cancer Investigation, vol. 31, no. 1, pp. 74–82, 2013. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  7. H. M. Ashour, “Antibacterial, antifungal, and anticancer activities of volatile oils and extracts from stems, leaves, and flowers of Eucalyptus sideroxylon and Eucalyptus torquata,” Cancer Biology and Therapy, vol. 7, no. 3, pp. 399–403, 2008. View at Publisher · View at Google Scholar · View at Scopus
  8. A. L. Medina-Holguín, F. Omar Holguín, S. Micheletto, S. Goehle, J. A. Simon, and M. A. O'Connell, “Chemotypic variation of essential oils in the medicinal plant, Anemopsis californica,” Phytochemistry, vol. 69, no. 4, pp. 919–927, 2008. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  9. P. Kathirvel and S. Ravi, “Chemical composition of the essential oil from basil (Ocimum basilicum Linn.) and its in vitro cytotoxicity against HeLa and HEp-2 human cancer cell lines and NIH 3T3 mouse embryonic fibroblasts,” Natural Product Research, vol. 26, no. 12, pp. 1112–1118, 2012. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  10. D. Pal, S. Banerjee, S. Mukherjee, A. Roy, C. K. Panda, and S. Das, “Eugenol restricts DMBA croton oil induced skin carcinogenesis in mice: downregulation of c-Myc and H-ras, and activation of p53 dependent apoptotic pathway,” Journal of Dermatological Science, vol. 59, pp. 31–39, 2010. View at Publisher · View at Google Scholar · View at PubMed
  11. B. S. Park, Y. S. Song, S.-B. Yee et al., “Phospho-ser 15-p53 translocates into mitochondria and interacts with Bcl-2 and Bcl-xL in eugenol-induced apoptosis,” Apoptosis, vol. 10, no. 1, pp. 193–200, 2005. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  12. S. K. Jaganathan and E. Supriyanto, “Antiproliferative and molecular mechanism of eugenol-induced apoptosis in cancer cells,” Molecules, vol. 17, no. 6, pp. 6290–6304, 2012. View at Publisher · View at Google Scholar · View at Scopus
  13. A. Jaafari, M. Tilaoui, H. A. Mouse et al., “Comparative study of the antitumor effect of natural monoterpenes: relationship to cell cycle analysis,” Brazilian Journal of Pharmacognosy, vol. 22, no. 3, pp. 534–540, 2012. View at Publisher · View at Google Scholar · View at Scopus
  14. H. Satooka and I. Kubo, “Effects of eugenol on murine B16-F10 melanoma cells,” in Proceedings of the 238th ACS National Meeting, pp. 16–20, Washington, DC, USA, 2009.
  15. R. Ghosh, N. Nadiminty, J. E. Fitzpatrick, W. L. Alworth, T. J. Slaga, and A. P. Kumar, “Eugenol causes melanoma growth suppression through inhibition of E2F1 transcriptional activity,” Journal of Biological Chemistry, vol. 280, no. 7, pp. 5812–5819, 2005. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  16. M. Pisano, G. Pagnan, M. Loi et al., “Antiproliferative and pro-apoptotic activity of eugenol-related biphenyls on malignant melanoma cells,” Molecular Cancer, vol. 6, article 8, 2007. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  17. S. Fujisawa, T. Atsumi, K. Satoh et al., “Radical generation, radical-scavenging activity, and cytotoxicity of eugenol-related compounds,” In Vitro and Molecular Toxicology, vol. 13, no. 4, pp. 269–279, 2000. View at Google Scholar · View at Scopus
  18. D. Slameňová, E. Horváthová, L. Wsólová, M. Šramková, and J. Navarová, “Investigation of anti-oxidative, cytotoxic, DNA-damaging and DNA-protective effects of plant volatiles eugenol and borneol in human-derived HepG2, Caco-2 and VH10 cell lines,” Mutation Research—Genetic Toxicology and Environmental Mutagenesis, vol. 677, no. 1-2, pp. 46–52, 2009. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  19. S. Hemaiswarya and M. Doble, “Combination of phenylpropanoids with 5-fluorouracil as anti-cancer agents against human cervical cancer (HeLa) cell line,” Phytomedicine, vol. 20, no. 2, pp. 151–158, 2013. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  20. A. Hussain, K. Brahmbhatt, A. Priyani, M. Ahmed, T. A. Rizvi, and C. Sharma, “Eugenol enhances the chemotherapeutic potential of gemcitabine and induces anticarcinogenic and anti-inflammatory activity in human cervical cancer cells,” Cancer Biotherapy and Radiopharmaceuticals, vol. 26, no. 5, pp. 519–527, 2011. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  21. S. Stoichev, G. Zolotovich, C. Nachev, and K. Silyanovska, “Cytotoxic effect of phenols, phenol ethers, furan derivatives, and oxides isolated from essential oils,” Comptes Rendus de l'Academie Bulgare des Sciences, vol. 20, pp. 1341–1344, 1967. View at Google Scholar
  22. P. Zhang, E. Zhang, M. Xiao, C. Chen, and W. Xu, “Enhanced chemical and biological activities of a newly biosynthesized eugenol glycoconjugate, eugenol α-d-glucopyranoside,” Applied Microbiology and Biotechnology, vol. 97, no. 3, pp. 1043–1050, 2013. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  23. G. Zolotovich, K. Silyanovska, S. Stoichev, and C. Nachev, “Cytotoxic effect of essential oils and their individual components. II. Oxygen-containing compounds excluding alcohols,” Parfuemerie und Kosmetik, vol. 50, pp. 257–260, 1969. View at Google Scholar
  24. R. Ghosh, M. Ganapathy, W. L. Alworth, D. C. Chan, and A. P. Kumar, “Combination of 2-methoxyestradiol (2-ME2) and eugenol for apoptosis induction synergistically in androgen independent prostate cancer cells,” The Journal of Steroid Biochemistry and Molecular Biology, vol. 113, no. 1-2, pp. 25–35, 2009. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  25. S. Fujisawa, T. Atsumi, M. Ishihara, and Y. Kadoma, “Cytotoxicity, ROS-generation activity and radical-scavenging activity of curcumin and related compounds,” Anticancer Research, vol. 24, no. 2, pp. 563–569, 2004. View at Google Scholar · View at Scopus
  26. G. Awuti, G. Tuerxun, A. Tuerxun, and J. Tuerxun, “Cytotoxicity of two different pulp capping materials on human dental pulp cells in vitro,” Journal of Oral Science Research, vol. 28, no. 5, pp. 485–487, 2012. View at Google Scholar
  27. S. K. Mahapatra, S. Bhattacharjee, S. P. Chakraborty, S. Majumdar, and S. Roy, “Alteration of immune functions and Th1/Th2 cytokine balance in nicotine-induced murine macrophages: immunomodulatory role of eugenol and N-acetylcysteine,” International Immunopharmacology, vol. 11, no. 4, pp. 485–495, 2011. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  28. A. H. Carrasco, C. L. Espinoza, V. Cardile et al., “Eugenol and its synthetic analogues inhibit cell growth of human cancer cells (Part I),” Journal of the Brazilian Chemical Society, vol. 19, no. 3, pp. 543–548, 2008. View at Publisher · View at Google Scholar · View at Scopus
  29. S. Fujisawa, T. Atsumi, Y. Kadoma, and H. Sakagami, “Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity,” Toxicology, vol. 177, no. 1, pp. 39–54, 2002. View at Publisher · View at Google Scholar · View at Scopus
  30. K. Satoh, Y. Ida, H. Sakagami, T. Tanaka, and S. Fujisawa, “Effect of antioxidants on radical intensity and cytotoxic activity of eugenol,” Anticancer Research, vol. 18, no. 3 A, pp. 1549–1552, 1998. View at Google Scholar · View at Scopus
  31. Y. Kashiwagi, “A cytotoxic study of eugenol and its ortho dimer (bis-eugenol),” Meikai Daigaku Shigaku Zasshi, vol. 29, pp. 176–188, 2001. View at Google Scholar
  32. R. Gerosa, M. Borin, G. Menegazzi, M. Puttini, and G. Cavalleri, “In vitro evaluation of the cytotoxicity of pure eugenol,” Journal of Endodontics, vol. 22, no. 10, pp. 532–534, 1996. View at Publisher · View at Google Scholar · View at Scopus
  33. J. H. Jeng, L. J. Hahn, F. J. Lu, Y. J. Wang, and M. Y. Kuo, “Eugenol triggers different pathobiological effects on human oral mucosal fibroblasts,” Journal of Dental Research, vol. 73, no. 5, pp. 1050–1055, 1994. View at Google Scholar · View at Scopus
  34. H. Babich, A. Stern, and E. Borenfreund, “Eugenol cytotoxicity evaluated with continuous cell lines,” Toxicology in Vitro, vol. 7, no. 2, pp. 105–109, 1993. View at Publisher · View at Google Scholar · View at Scopus
  35. M. Anpo, K. Shirayama, and T. Tsutsui, “Cytotoxic effect of eugenol on the expression of molecular markers related to the osteogenic differentiation of human dental pulp cells,” Odontology, vol. 99, no. 2, pp. 188–192, 2011. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  36. T. Atsumi, I. Iwakura, S. Fujisawa, and T. Ueha, “Reactive oxygen species generation and photo-cytotoxicity of eugenol in solutions of various pH,” Biomaterials, vol. 22, no. 12, pp. 1459–1466, 2001. View at Publisher · View at Google Scholar · View at Scopus
  37. T. Atsumi, S. Fujisawa, K. Satoh et al., “Cytotoxicity and radical intensity of eugenol, isoeugenol or related dimers,” Anticancer Research, vol. 20, no. 4, pp. 2519–2524, 2000. View at Google Scholar · View at Scopus
  38. A. Hussain, A. Priyani, L. Sadrieh, K. Brahmbhatt, M. Ahmed, and C. Sharma, “Concurrent sulforaphane and eugenol induces differential effects on human cervical cancer cells,” Integrative Cancer Therapies, vol. 11, no. 2, pp. 154–165, 2012. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  39. T. Atsumi, S. Fujisawa, and K. Tonosaki, “A comparative study of the antioxidant/prooxidant activities of eugenol and isoeugenol with various concentrations and oxidation conditions,” Toxicology in Vitro, vol. 19, no. 8, pp. 1025–1033, 2005. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  40. Y. Suzuki, K. Sugiyama, and H. Furuta, “Eugenol-mediated superoxide generation and cytotoxicity in guinea pig neutrophils,” Japanese Journal of Pharmacology, vol. 39, no. 3, pp. 381–386, 1985. View at Publisher · View at Google Scholar · View at Scopus
  41. A. Maralhas, A. Monteiro, C. Martins et al., “Genotoxicity and endoreduplication inducing activity of the food flavouring eugenol,” Mutagenesis, vol. 21, no. 3, pp. 199–204, 2006. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  42. G. Kaur, M. Athar, and M. Sarwar Alam, “Eugenol precludes cutaneous chemical carcinogenesis in mouse by preventing oxidative stress and inflammation and by inducing apoptosis,” Molecular Carcinogenesis, vol. 49, no. 3, pp. 290–301, 2010. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  43. T. Ogiwara, K. Satoh, Y. Kadoma et al., “Radical scavenging activity and cytotoxicity of ferulic acid,” Anticancer Research, vol. 22, no. 5, pp. 2711–2717, 2002. View at Google Scholar · View at Scopus
  44. S. K. Jaganathan, D. Mondhe, Z. A. Wani, H. C. Pal, and M. Mandal, “Effect of honey and eugenol on ehrlich ascites and solid carcinoma,” Journal of Biomedicine and Biotechnology, vol. 2010, Article ID 989163, 5 pages, 2010. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  45. E. Tangke Arung, E. Matsubara, I. Wijaya Kusuma, E. Sukaton, K. Shimizu, and R. Kondo, “Inhibitory components from the buds of clove (Syzygium aromaticum) on melanin formation in B16 melanoma cells,” Fitoterapia, vol. 82, no. 2, pp. 198–202, 2011. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  46. C. M. Marya, G. Satija, J. Avinash, R. Nagpal, R. Kapoor, and A. Ahmad, “In vitro inhibitory effect of clove essential oil and its two active principles on tooth decalcification by apple juice,” International Journal of Dentistry, vol. 2012, Article ID 759618, 6 pages, 2012. View at Publisher · View at Google Scholar · View at Scopus
  47. J. L. Burkey, J.-M. Sauer, C. A. McQueen, and I. G. Sipes, “Cytotoxicity and genotoxicity of methyleugenol and related congeners—a mechanism of activation for methyleugenol,” Mutation Research: Fundamental and Molecular Mechanisms of Mutagenesis, vol. 453, no. 1, pp. 25–33, 2000. View at Publisher · View at Google Scholar · View at Scopus
  48. K.-T. Lee, J. Choi, J.-H. Park, W.-T. Jung, H.-J. Jung, and H.-J. Park, “Composition of the essential oil of Chrysanthemum sibiricum, and cytotoxic properties,” Natural Product Sciences, vol. 8, no. 4, pp. 133–136, 2002. View at Google Scholar · View at Scopus
  49. I. A. Maria Groh, A. T. Cartus, S. Vallicotti et al., “Genotoxic potential of methyleugenol and selected methyleugenol metabolites in cultured Chinese hamster V79 cells,” Food and Function, vol. 3, no. 4, pp. 428–436, 2012. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  50. National Toxicology Program, “Toxicology and carcinogenesis studies of isoeugenol (CAS No. 97-54-1) in F344/N rats and B6C3F1 mice (gavage studies),” National Toxicology Program Technical Report Series, vol. 551, pp. 1–178, 2010. View at Google Scholar
  51. F.-S. Yu, A.-C. Huang, J.-S. Yang et al., “Safrole induces cell death in human tongue squamous cancer SCC-4 cells through mitochondria-dependent caspase activation cascade apoptotic signaling pathways,” Environmental Toxicology, vol. 27, no. 7, pp. 433–444, 2012. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  52. W.-F. Ni, C.-H. Tsai, S.-F. Yang, and Y.-C. Chang, “Elevated expression of NF-κB in oral submucous fibrosis—evidence for NF-κB induction by safrole in human buccal mucosal fibroblasts,” Oral Oncology, vol. 43, no. 6, pp. 557–562, 2007. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  53. H. C. Chang, H. H. Cheng, C. J. Huang et al., “Safrole-induced Ca2+ mobilization and cytotoxicity in human PC3 prostate cancer cells,” Journal of Receptors and Signal Transduction, vol. 26, no. 3, pp. 199–212, 2006. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  54. Y. Nakagawa, T. Suzuki, K. Nakajima, H. Ishii, and A. Ogata, “Biotransformation and cytotoxic effects of hydroxychavicol, an intermediate of safrole metabolism, in isolated rat hepatocytes,” Chemico-Biological Interactions, vol. 180, no. 1, pp. 89–97, 2009. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  55. A. J. Howes, V. S. W. Chan, and J. Caldwell, “Structure-specificity of the genotoxicity of some naturally occurring alkenylbenzenes determined by the unscheduled DNA synthesis assay in rat hepatocytes,” Food and Chemical Toxicology, vol. 28, no. 8, pp. 537–542, 1990. View at Publisher · View at Google Scholar · View at Scopus
  56. S.-Y. Chiang, P.-Y. Lee, M.-T. Lai et al., “Safrole-2′,3′-oxide induces cytotoxic and genotoxic effects in HepG2 cells and in mice,” Mutation Research—Genetic Toxicology and Environmental Mutagenesis, vol. 726, no. 2, pp. 234–241, 2011. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  57. A. Du, B. Zhao, D. Yin, S. Zhang, and J. Miao, “Safrole oxide induces apoptosis by activating caspase-3, -8, and -9 in A549 human lung cancer cells,” Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 1, pp. 81–83, 2006. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  58. M.-J. Fan, S.-Y. Lin, C.-C. Yu et al., “Safrole-modulated immune response is mediated through enhancing the CD11b surface marker and stimulating the phagocytosis by macrophages in BALB/c mice,” Human & Experimental Toxicology, vol. 31, no. 9, pp. 898–904, 2012. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  59. S. E. A. Farag and M. A. A. Abo-Zeid, “Mutagenicity and degradation of natural carcinogenic compound-safrole in spices under different processing methods,” Journal of Pharmaceutical Sciences, vol. 17, pp. 149–158, 1996. View at Google Scholar
  60. B. K. Lee, J. H. Kim, J. W. Jung et al., “Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells,” Toxicology Letters, vol. 157, no. 1, pp. 49–56, 2005. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  61. H. Ahmad, V. Valdivia, A. Cadena et al., “Myristicin: inducer of phase-II drug metabolizing enzymes and prospective chemoprotective agent against cancer,” Acta Horticulturae, vol. 841, pp. 47–54, 2009. View at Google Scholar · View at Scopus
  62. Y. Nakagawa and T. Suzuki, “Cytotoxic and xenoestrogenic effects via biotransformation of trans-anethole on isolated rat hepatocytes and cultured MCF-7 human breast cancer cells,” Biochemical Pharmacology, vol. 66, no. 1, pp. 63–73, 2003. View at Publisher · View at Google Scholar · View at Scopus
  63. E. J. Choo, Y.-H. Rhee, S.-J. Jeong et al., “Anethole exerts antimetatstaic activity via inhibition of matrix metalloproteinase 2/9 and AKT/mitogen-activated kinase/nuclear factor kappa B signaling pathways,” Biological and Pharmaceutical Bulletin, vol. 34, no. 1, pp. 41–46, 2011. View at Publisher · View at Google Scholar · View at Scopus
  64. A. D. Marshall and J. Caldwell, “Influence of modulators of epoxide metabolism on the cytotoxicity of trans-anethole in freshly isolated rat hepatocytes,” Food and Chemical Toxicology, vol. 30, no. 6, pp. 467–473, 1992. View at Publisher · View at Google Scholar · View at Scopus
  65. M. M. Al-Harbi, S. Qureshi, M. Raza, M. M. Ahmed, A. B. Giangreco, and A. H. Shah, “Influence of anethole treatment on the tumour induced by Ehrlich ascites carcinoma cells in paw of Swiss albino mice,” European Journal of Cancer Prevention, vol. 4, no. 4, pp. 307–318, 1995. View at Publisher · View at Google Scholar · View at Scopus
  66. G. B. N. Chainy, S. K. Manna, M. M. Chaturvedi, and B. B. Aggarwal, “Anethole blocks both early and late cellular responses transduced by tumor necrosis factor: effect on NF-κB, AP-1, JNK, MAPKK and apoptosis,” Oncogene, vol. 19, no. 25, pp. 2943–2950, 2000. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  67. S. G. Kim, A. Liem, B. C. Stewart, and J. A. Miller, “New studies on trans-anethole oxide and trans-asarone oxide,” Carcinogenesis, vol. 20, no. 7, pp. 1303–1307, 1999. View at Publisher · View at Google Scholar · View at Scopus
  68. J.-F. Liao, S.-Y. Huang, Y.-M. Jan, L.-L. Yu, and C.-F. Chen, “Central inhibitory effects of water extract of Acori graminei rhizoma in mice,” Journal of Ethnopharmacology, vol. 61, no. 3, pp. 185–193, 1998. View at Publisher · View at Google Scholar · View at Scopus
  69. M. D. Greca, P. Monaco, L. Previtera, G. Aliotta, G. Pinto, and A. Pollio, “Allelochemical activity of phenylpropanes from Acorus gramineus,” Phytochemistry, vol. 28, no. 9, pp. 2319–2321, 1989. View at Publisher · View at Google Scholar · View at Scopus
  70. C. H. Park, K. H. Kim, I. K. Lee et al., “Phenolic constituents of Acorus gramineus,” Archives of Pharmacal Research, vol. 34, no. 8, pp. 1289–1296, 2011. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  71. H. Ka, H.-J. Park, H.-J. Jung et al., “Cinnamaldehyde induces apoptosis by ROS-mediated mitochondrial permeability transition in human promyelocytic leukemia HL-60 cells,” Cancer Letters, vol. 196, no. 2, pp. 143–152, 2003. View at Publisher · View at Google Scholar · View at Scopus
  72. S.-T. Chang, P.-F. Chen, and S.-C. Chang, “Antibacterial activity of leaf essential oils and their constituents from Cinnamomum osmophloeum,” Journal of Ethnopharmacology, vol. 77, no. 1, pp. 123–127, 2001. View at Publisher · View at Google Scholar · View at Scopus
  73. D. T. Shaughnessy, R. W. Setzer, and D. M. DeMarini, “The antimutagenic effect of vanillin and cinnamaldehyde on spontaneous mutation in Salmonella TA104 is due to a reduction in mutations at GC but not AT sites,” Mutation Research—Fundamental and Molecular Mechanisms of Mutagenesis, vol. 480-481, pp. 55–69, 2001. View at Publisher · View at Google Scholar · View at Scopus
  74. W. S. Koh, S. Y. Yoon, B. M. Kwon, T. C. Jeong, K. S. Nam, and M. Y. Han, “Cinnamaldehyde inhibits lymphocyte proliferation and modulates T-cell differentiation,” International Journal of Immunopharmacology, vol. 20, no. 11, pp. 643–660, 1998. View at Publisher · View at Google Scholar · View at Scopus
  75. L. M. Perry, Medicinal Plants of East and Southeast Asia: Attributed Properties and Uses, The MIT Press, Cambridge, Mass, USA, 1980.
  76. H.-S. Lee, S.-Y. Kim, C.-H. Lee, and Y.-J. Ahn, “Cytotoxic and mutagenic effects of Cinnamomum cassia bark-derived materials,” Journal of Microbiology and Biotechnology, vol. 14, no. 6, pp. 1176–1181, 2004. View at Google Scholar · View at Scopus
  77. B. Oehler, A. Scholze, M. Schaefer, and K. Hill, “TRPA1 is functionally expressed in melanoma cells but is not critical for impaired proliferation caused by allyl isothiocyanate or cinnamaldehyde,” Naunyn-Schmiedeberg's Archives of Pharmacology, vol. 385, no. 6, pp. 555–563, 2012. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  78. E.-H. Chew, A. A. Nagle, Y. Zhang et al., “Cinnamaldehydes inhibit thioredoxin reductase and induce Nrf2: potential candidates for cancer therapy and chemoprevention,” Free Radical Biology and Medicine, vol. 48, no. 1, pp. 98–111, 2010. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  79. C. Ekmekcioglu, J. Feyertag, and W. Marktl, “Cinnamic acid inhibits proliferation and modulates brush border membrane enzyme activities in Caco-2 cells,” Cancer Letters, vol. 128, no. 2, pp. 137–144, 1998. View at Publisher · View at Google Scholar · View at Scopus
  80. L.-T. Ng and S.-J. Wu, “Antiproliferative activity of Cinnamomum cassia constituents and effects of pifithrin-alpha on their apoptotic signaling pathways in Hep G2 cells,” Evidence-Based Complementary and Alternative Medicine, vol. 2011, Article ID 492148, 6 pages, 2011. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  81. S.-J. Wu, L.-T. Ng, and C.-C. Lin, “Cinnamaldehyde-induced apoptosis in human PLC/PRF/5 cells through activation of the proapoptotic Bcl-2 family proteins and MAPK pathway,” Life Sciences, vol. 77, no. 8, pp. 938–951, 2005. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  82. J. M. Dornish, E. O. Pettersen, and R. Oftebro, “Synergistic cell inactivation of human NHIK 3025 cells by cinnamaldehyde in combination with cis-diamminedichloroplatinum(II),” Cancer Research, vol. 48, no. 4, pp. 938–942, 1988. View at Google Scholar · View at Scopus
  83. J.-H. Zhang, L.-Q. Liu, Y.-L. He, W.-J. Kong, and S.-A. Huang, “Cytotoxic effect of trans-cinnamaldehyde on human leukemia K562 cells,” Acta Pharmacologica Sinica, vol. 31, no. 7, pp. 861–866, 2010. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  84. K. H. Moon and M. Y. Pack, “Cytotoxicity of cinnamic aldehyde on leukemia L1210 cells,” Drug and Chemical Toxicology, vol. 6, no. 6, pp. 521–535, 1983. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  85. H. Niknahad, A. Shuhendler, G. Galati et al., “Modulating carbonyl cytotoxicity in intact rat hepatocytes by inhibiting carbonyl metabolizing enzymes. II. Aromatic aldehydes,” Chemico-Biological Interactions, vol. 143-144, pp. 119–128, 2003. View at Publisher · View at Google Scholar · View at Scopus
  86. G. G. Hatch, T. M. Anderson, R. A. Lubet et al., “Chemical enhancement of SA7 virus transformation of hamster embryo cells: evaluation by interlaboratory testing of diverse chemicals,” Environmental Mutagenesis, vol. 8, no. 4, pp. 515–531, 1986. View at Publisher · View at Google Scholar · View at Scopus
  87. A. Stammati, P. Bonsi, F. Zucco, R. Moezelaar, H.-L. Alakomi, and A. Von Wright, “Toxicity of selected plant volatiles in microbial and mammalian short-term assays,” Food and Chemical Toxicology, vol. 37, no. 8, pp. 813–823, 1999. View at Publisher · View at Google Scholar · View at Scopus
  88. L.-Y. Chuang, J.-Y. Guh, L. K. Chao et al., “Anti-proliferative effects of cinnamaldehyde on human hepatoma cell lines,” Food Chemistry, vol. 133, no. 4, pp. 1603–1610, 2012. View at Publisher · View at Google Scholar · View at Scopus
  89. J.-Q. Huang, X.-X. Luo, S.-W. Wang, and Y.-H. Xie, “Effect of cinnamaldehyde on activity of tumor and immunological function of S180 sarcoma in mice,” Chinese Journal of Clinical Rehabilitation, vol. 10, no. 11, pp. 107–110, 2006. View at Google Scholar · View at Scopus
  90. E.-Y. Moon, M.-R. Lee, A.-G. Wang et al., “Delayed occurrence of H-ras12V-induced hepatocellular carcinoma with long-term treatment with cinnamaldehydes,” European Journal of Pharmacology, vol. 530, no. 3, pp. 270–275, 2006. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  91. J. A. Hoskins, “The occurrence, metabolism and toxicity of cinnamic acid and related compounds,” Journal of Applied Toxicology, vol. 4, no. 6, pp. 283–292, 1984. View at Publisher · View at Google Scholar · View at Scopus
  92. Y. Zhang, X. Y. Yang, Z. S. Kunag, and C. Xiao, “Inhibitory effect of cinnamic acid germanium on growth of uterocervical carcinoma (U14) cells in mice,” Linchuang Yu Shiyan Binglixue Zazhi, vol. 26, pp. 467–470, 2010. View at Google Scholar
  93. L. P. Zhang and Z. Z. Ji, “Synthesis, antiinflammatory and anticancer activity of cinnamic acids, their derivatives and analogues,” Acta Pharmaceutica Sinica, vol. 27, no. 11, pp. 817–823, 1992. View at Google Scholar · View at Scopus
  94. L. Liu, W. R. Hudgins, S. Shack, M. Q. Yin, and D. Samid, “Cinnamic acid: a natural product with potential use in cancer intervention,” International Journal of Cancer, vol. 62, no. 3, pp. 345–350, 1995. View at Publisher · View at Google Scholar · View at Scopus
  95. Q. Zhang, Y. Wang, W. Chai et al., “Induced-differentiation effects of cinnamic acid on human osteogenic sarcoma cells cultured primarily in vitro,” Zhonghua Zhongliu Fangzhi Zazhi, vol. 16, no. 9, pp. 668–672, 2009. View at Google Scholar · View at Scopus
  96. V. C. G. Soares, C. Bonacorsi, A. L. B. Andrela et al., “Cytotoxicity of active ingredients extracted from plants of the Brazilian `Cerrado’,” Natural Product Communications, vol. 6, no. 7, pp. 983–984, 2011. View at Google Scholar · View at Scopus
  97. E. Bemani, F. Ghanati, L. Y. Boroujeni, and F. Khatami, “Antioxidant activity, total phenolics and taxol contents response of hazel (Corylus avellana L.) cells to benzoic acid and cinnamic acid,” Notulae Botanicae Horti Agrobotanici Cluj-Napoca, vol. 40, no. 1, pp. 69–73, 2012. View at Google Scholar · View at Scopus
  98. H. D. Gravina, N. F. Tafuri, A. Silva Júnior et al., “In vitro assessment of the antiviral potential of trans-cinnamic acid, quercetin and morin against equid herpesvirus 1,” Research in Veterinary Science, vol. 91, no. 3, pp. e158–e162, 2011. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  99. K. Ito, T. Nakazato, M. J. Xian et al., “1′-acetoxychavicol acetate is a novel nuclear factor κB inhibitor with significant activity against multiple myeloma in vitro and in vivo,” Cancer Research, vol. 65, no. 10, pp. 4417–4424, 2005. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  100. A. Kondo, H. Ohigashi, A. Murakami, J. Suratwadee, and K. Koshimizu, “1′-Acetoxychavicol acetate as a potent inhibitor of tumor promoter-induced Epstein-Barr virus activation from Languas galanga, a traditional Thai condiment,” Bioscience, Biotechnology, and Biochemistry, vol. 57, no. 8, pp. 1344–1345, 1993. View at Publisher · View at Google Scholar