The Cytotoxic Activity of 3,4,5-Trihydroxybenzoic Acid Methylester and Related Compounds against Skin and Oral Cancer Cell Lines

3,4,5-Trihydroxybenzoic Acid Methylester와 관련 화합물의 피부암 및 구강암 세포주에 대한 세포독성

  • Lee, Jae-Sug (Department of Beauty Science, Kwangju Wonmen's University) ;
  • Han, Du-Seok (Department of Oral Anatomy, School of Dentistry, Wonkwang University) ;
  • Kang, Jeong-Il (Department of Physical Therapy, Daebul University Youngam) ;
  • Baek, Jong-Min (R&D Center, BRNScience Co. LTD., Seoul National University) ;
  • Baek, Seung-Hwa (Department of Herbal Resources, Professional School of Oriental Medicine, Wonkwang University)
  • 이재숙 (광주여자대학교 미용과학과) ;
  • 한두석 (원광대학교 치과대학 구강해부학교실) ;
  • 강정일 (대불대학교 물리치료학과) ;
  • 백종민 (서울대학교 비알엔사이언스 연구개발부) ;
  • 백승화 (원광대학교 한의학전문대학원 한약자원개발학과)
  • Received : 2009.09.29
  • Accepted : 2010.01.14
  • Published : 2010.04.30

Abstract

The cytotoxic activity of 33,4,5-trihydroxybenzoic acid methylester and related compounds on the growth of normal cell lines, human skin melanoma cells and human oral epithelioid cell line were evaluated by the 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) and 2,3-bis-[2-methoxy-4-nitro-5-sulfo-phenyl]-2-H-tetrazolium-5-caboxanilide (XTT) methods. 3,4,5-Trihydroxybenzoic acid methylester decreased the cell viability of human skin melanoma cells and human oral epithelioid cells shown by the MTT method and the cell adhesion activity of human skin melanoma cells and human oral epithelioid cells shown by the XTT method. In light microscopy, 100 ${\mu}M$ 3,4,5-trihydroxybenzoic acid methylester showed the highest cytotoxic activity. These results suggest that 3,4,5-trihydroxybenzoic acid methylester has a potential anticancer activity.

Keywords

References

  1. Duthie, G. G. : Parsley, polyphenols and nutritional antioxidants. Br. J. Nutr. 81, 425 (1999).
  2. Duthie, G. and Crozier, A. : Plant-derived phenolic antioxidants. Current Opinion in Clinical Nutrition and Metabolic Care 3, 447 (2000). https://doi.org/10.1097/00075197-200011000-00006
  3. Isuzugawa, K., Ogihara, Y. and Inoue, M. : Different generation of inhibitors against gallic acid-induced apoptosis produces different sensitivity to gallic acid. Biol. Pharm. Bull. 24, 249 (2001). https://doi.org/10.1248/bpb.24.249
  4. Inoue, M., Suzuki, R., Koide, T., Sakaguchi, N., Ogihara, Y. and Yabu, Y. : Antitoxidant, gallic acid, induces apoptosis in HL- 60RG cells. Biochem. Biophys. Res. Commum. 204, 898 (1994). https://doi.org/10.1006/bbrc.1994.2544
  5. Sakagami, H., Jiang, Y., Kusama, K., Atsumi, T., Ueha, T., Toguchi, M., Iwakura, I., Satoh, K., Ito, H., Hatano, T. and Yoshida, T. : Cytotoxic activity of hydrolyzable tannins against human oral tumor cell lines-a possible mechanism. Phytomed. 7, 39 (2000). https://doi.org/10.1016/S0944-7113(00)80020-3
  6. Furuya, S., Takayama, F., Mimaki, Y., Sashida, Y., Satoh, K. and Sakagami, H. : Cytotoxic activity of saponins from Camassia leichtlinii against human oral tumor cell lines. Anticancer Res. 21, 959 (2001).
  7. Peng, X., Misawa, N. and Harayama, S. : Isolation and characterization of themophilic bacilli degrading cinnamic, 4-coumaric, and ferulic acids. Appl. Environ. Microbiol. 69, 1417 (2003). https://doi.org/10.1128/AEM.69.3.1417-1427.2003
  8. Riaz, N., Anis, I., Khan, P. M., Shah, R. and Malik, A. : Alysinola new triterpene from Alysicarpus monolifer. Nat. Prod. Lett. 16, 415 (2002). https://doi.org/10.1080/10575630290034258
  9. Femia, A. P., Caderni, G., Buzzigoli, C., Cocca, E., Salvadori, M. and Dolara, P. : Effect of simple phenolic compounds on azoxymethane-induced aberrant crypt foci in rat colon. Nutr. Cancer 41, 107 (2001). https://doi.org/10.1080/01635581.2001.9680620
  10. Yanez, J., Vicente, V., Alcaraz, M., Castillo, J., Benavente-Garcia, O., Canteras, M. and Teruel, J. A. L. : Cytotoxicity and antiproliferative activities of several phenolic compounds against three melanocytes cell lines: relationship between structure and activity. Nutr. Cancer 49, 191 (2004). https://doi.org/10.1207/s15327914nc4902_11
  11. Ma, J., Luo, X. D., Protiva, P., Yang, H., Ma, C., Basile, M. J., Weinstein, I. B. and Kennelly, E. J. : Bioactive novel polyphenols from the fruit of Manilkara zapota (Sapodilla). J. Nat. Prod. 66, 983 (2003). https://doi.org/10.1021/np020576x
  12. Salucci, M., Stivala, L. A., Maiani, G., Bugianesi, R. and Vannini, V. : Flavonoids uptake and their effect on cell cycle of human colon adenocarcinoma cells (Caco2). Br. J. Cancer 86, 1645 (20020. https://doi.org/10.1038/sj.bjc.6600295
  13. Son, Y. O., Lee, K. Y., Kook, S. H., Lee, J. C., Kim, J. G., Jeon, Y. M. and Jang, Y. S. : Selective effects of quercetin on the cell growth and antioxidant defense system in normal versus transformed mouse hepatic cell lines. Eur. J. Pharmacol. 502, 195 (2004). https://doi.org/10.1016/j.ejphar.2004.09.012
  14. Chen, Y. C., Shen, S. C., Chow, J. M., Ko, C. H. and Tseng, S. W. : Flavone inhibition of tumor growth via apoptosis in vitro and in vivo. Int. J. Oncol. 25, 661 (2004).
  15. Hakimuddin, F., Paliyath, G. and Meckling, K. : Selective cytotoxicity of a red grape wine flavonoid fraction against MCF-7 cells. Breast Cancer Res. Treat. 85, 65 (2004). https://doi.org/10.1023/B:BREA.0000021048.52430.c0
  16. Wilhelm, K.P ., Bottjer, B. and Siegers, C. P. : Quantitative assessment of primary skin irritants in vitro in a cytotoxicity model: comparison with in vivo human irritation tests. Br. J. Dermatol. 145, 709 (2001). https://doi.org/10.1046/j.1365-2133.2001.04497.x
  17. Nunez-Selles, A. J., Velez-Castro, H. T., Aguero-Aguero, J., Gonzalez- Gonzalez, J., Naddeo, F., De Simone, F. and Rastrelli, L. : Isolation and quantitative analysis of phenolic antioxidants, free sugars, and polyols from mango (Mangifera indica L.) stem bark aqueous decoction used in Cuba as a nutritional supplement. J. Agric. Food Chem. 50, 762 (2002). https://doi.org/10.1021/jf011064b
  18. Murakami, K., Matsuura, T., Sano, M., Hashimoto, A., Yonekura, K., Sakukawa, R., Yamada, Y. and Saiki, I. : 4-[3,5- Bis(trimethylsilyl)-benzamido]benzoic acid (TAC-101) inhibits the intrahepatic spread of hepatocellular carcinoma and prolongs the life-span of tumor-bearing animals. Clin. Exp. Metastasis 16, 633 (1998). https://doi.org/10.1023/A:1006567229929
  19. Ray, D., Sarma, K. D. and Antony, A. : Differential effects of trin-butylstannyl benzoates on induction of apoptosis in K562 and MCF-7 cells. IUBMB Life 49, 519 (2000). https://doi.org/10.1080/15216540050167061
  20. De Graff, W. G., Myers, L. S. Jr., Mitchell, J. B. and Hahn, S. M. : Protection against Adriamycin cytotoxicity and inhibition of DNA topoisomerase II activity by 3,4-dihydroxybenzoic acid. Int. J. Oncol. 23, 159 (2003).
  21. Costa-Lotufo, L. V., Jimenez, P. C., Wilke, D. V., Leal, L. K., Cunha, G. M., Silveira, E. R., Canuto, K. M., Viana, G. S., Moraes, M. E., de Moraes, M. O. and Pessoa, C. : Antiproliferative effects of several compounds isolated from Amburana cearen is A. C. Smith. Z. Naturforsch. [C] 58, 675 (2003).
  22. Marom, M., Haklai, R., Ben-Baruch, G., Marciano, D., Egozi, Y. nd Kloog, Y. : Selective inhibition of Ras-dependent cell growth by farnesylthiosalisylic acid. J. Biol. Chem. 270, 22263 (1995). https://doi.org/10.1074/jbc.270.38.22263
  23. Mosmann, T. : Rapid colorimetric assays for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 65, 55 (1983). https://doi.org/10.1016/0022-1759(83)90303-4
  24. Hatano, T., Edamatsu, R., Hiramatus, M., Mori, A., Fujita, Y., Yasuhara, T., Yoshida, T. and Okuda, T. : Effects of the interaction of tannins with co-existing substances. IV. Effects of tannins and related polyphenols on superxide anion radical and on 1-diphenyl-2-picrylhydrazyl radical. Chem. Pharm. Bull. 37, 2016 (1989). https://doi.org/10.1248/cpb.37.2016
  25. Umamaheswari, M., Asokkumar, F., Rathidevi, R., Sivashanmugam, A. T., Subhadradevi, V. and Ravi, T. K. : Antiulcer and in vitro antioxidant activities of Jasminum grandiflorum L. J. Ehnopharmacol. 110, 464 (2007). https://doi.org/10.1016/j.jep.2006.10.017
  26. 채영암, 구자옥, 서학수, 이영만 : 기초생물통계학 제 9장 직선회귀. 서울, 학문사. pp. 179-198 (1991).
  27. Valgimigli, M., Merli, E., Malagutti, P., Soukhomovskaia, O., Cicchitelli, G., Antelli, A., Canistro, D., Francolini, G., Macri, G., Mastrorilli, F., Paolini, M. and Gerrari, R. : Hydroxyl radical generation, levels of tumor necrosis factor-alpha, and progression to heart failure after acute myocardial in farction. J. Am. Coll. Cardiol. 43, 2000 (2004). https://doi.org/10.1016/j.jacc.2004.01.036
  28. Kalenilova, E. I., Gorodetskaya, E. A., Murashev, A. N., Ruuge, E. K. and Medvedev, O. S. : Role of reactive oxygen species in the sensitivity of rat hypertrophied myocardium to ischemia. Biochem. (Mosc) 69, 311 (2004). https://doi.org/10.1023/B:BIRY.0000022063.32185.7c
  29. Hashimoto, T., Yonetani, M. and Nakamura, H. : Selective brain hypothermia protects against hypoxic-ischemic injury in newborn rats by reducing hydroxyl radical production. Kobe J. Med. Sci. 49, 83 (2003).
  30. Han, D. S., Chun, J. W., Jeon, S. W. and Baek, S. H. : The inhibitory effect of ferulic acid and related phenolic compounds against cancer cell lines. J. Pharm. Soc. Kor. 49, 365 (2005).
  31. Borenfreund, E., Babichi, H. and Matin-Alcuacil, N. : Comparisons of two in vitro cytotoxicity assay. The neutral red (NR) and tetrazolium MTT tests. Toxicol. In Vitro 2, 1(1988). https://doi.org/10.1016/0887-2333(88)90030-6
  32. Locatelli, C., Leal, P. C., Yunes, R. A., Nunes, R. J. and Creczynski-Pasa, T. B. : Gallic acid ester derivatives induce apoptosis and cell adhesion inhibition in melanoma cells: The relationship between free radical generation, glutathione depletion and cell death. Chem. Biol. Interact. 181, 175 (2009). https://doi.org/10.1016/j.cbi.2009.06.019