Abstract
Eisenia bicyclis (Kjellman) Setchell is a common brown alga that inhabits the middle Pacific coast around Korea and Japan. In this study, the ethanol extract and its serial solvent fractions were prepared from fresh E. bicyclis, and their hepatoprotective effects were investigated against hepatotoxicity in tert-butyl hyperoxide(t-BHP)-injured HepG2 cells. When these samples were used at a dose of 10–40 μg/mL, they significantly protected the t-BHP-induced cell death in HepG2 cells. Among fractions, ethyl acetate fraction (EF) and n-butanol extract (BF) exhibited potent hepatoprotective activities (62.60% for EF and 64.86% for BF) in t-BHP-injured HepG2 cells at a concentration of 10 μg/mL. To find the potential factors for this activity, the samples were characterized on total phenolics, chlorophylls, carotenoids, and radical scavenging activity. Among them, EF showed the highest content of total phenolics and the strongest antioxidant activity both in on- and offline assays. Five phlorotannin compounds, oligomers of phloroglucinol, were isolated chromatographically from this fraction and structurally identified by 1H-NMR and liquid chromatography–electrospray ionization–mass spectrometry analyses as eckol(1), 6,6′-bieckol(2), 8,8′-bieckol(3), dieckol(4), and phlorofucofuroeckol A(5). Compound 5 among five purified compounds showed the strongest protective activity (45.54%) at a concentration of 10 μM. At the high dose (40 μM), the protective activities of three compounds (compound 2, 4, and 5) were higher than that of quercetin treated with 10 μM concentration. Therefore, we can speculate that they can be developed as potential candidates for natural hepatoprotective agents.
Similar content being viewed by others
References
Tome, S., & Lucey, M. R. (2004). Alimentary Pharmacology & Therapeutics, 19, 707–714.
Negi, A. S., Kumar, J. K., Luqman, S., Shanker, K., Gupta, M. M., & Khanuja, S. P. S. (2008). Medicinal Research Reviews, 28, 746–772.
Dhiman, R. K., & Chawla, Y. K. (2005). Digestive Diseases and Sciences, 50, 1807–1812.
Duan, L., Carrier, D. J., & Clausen, E. C. (2004). Applied Biochemistry and Biotechnology, 114, 559–568.
Saller, R., Meier, R., & Brignili, R. (2001). Drugs, 61, 2035–2063.
Shiki, Y., Shinai, K., Satto, Y., Yoshida, S., Mosi, Y., & Wakashin, M. (1992). Journal of Gastroenterology and Hepatology, 7, 12–16.
van Rossum, T. G., Bulto, A. G., de Man, R. A., Browner, J. T., & Schalm, S. W. (1998). Alimentary Pharmacology & Therapeutics, 12, 199–205.
Kamdem, R. E., Sang, S., & Ho, C. T. (2002). Journal of Agricultural Food Chemisty, 50, 4662–4665.
Kapil, A., Koul, I. B., Banerjee, S. K., & Gupta, B. D. (1993). Biochemical Pharmacology, 46, 182–185.
Das, K. C., & Das, C. K. (2002). Biochemical and Biophysical Research Communications, 295, 62–66.
Manikandan, P., Sumitra, M., Aishwarya, S., Manohar, B. M., Lokanadam, B., & Puvanakrishnan, R. (2004). Intenational Journal of Biochemisty & Cell Biology, 36, 1967–1980.
Cahyana, A. H., Shuto, Y., & Kinoshita, Y. (1992). Bioscience Biotechnology & Biochemistry, 56, 1533–1535.
Kim, Y. M., Han, C. K., Bang, S. J., & Park, J. H. (2006). Journal of Korean Society of Food Science and Nutrition, 35, 841–846.
Kousaka, K., Ogi, N., Akazawa, Y., Fujieda, M., Yamamoto, Y., Takada, Y., et al. (2003). Journal of Natural Products, 66, 1318–1323.
Okada, Y., Ishimaru, A., Suzuki, R., & Okuyama, T. (2004). Journal of Natural Products, 67, 103–105.
Shibata, T., Ishimaru, K., Kawaguchi, S., Yoshikawa, H., & Hama, Y. (2007). Journal of Applied Phycology, 20, 705–711.
Lichtenthaler, H. K., & Buschmann, C. (2001). Current Protocols of Food Analytical Chemiesty, F4.3.1–F4.3.8.
Ozgen, M., Reese, R. N., Tulio, A. Z., Scheerens, J. C., & Miller, A. R. (2006). Journal of Agricultural Food Chemisty, 54, 1151–1157.
Fusco, D., Colloca, G., Lo Monaco, M. R., & Cesari, M. (2008). Journal of Clinical Interventions in Aging, 2, 377–387.
Koleva, I. I., Niederländer, H. A., & van Beek, T. A. (2001). Analytical Chemistry, 73, 3373–3381.
Niederländer, H. A., van Beek, T. A., Bartasiute, A., & Koleva, I. I. (2008). Journal of Chromatography A, 1210, 121–134.
Singh, I. P., & Bharate, S. B. (2006). Natural Product Reports, 23, 558–591.
Kang, K., Pack, Y., Hwang, H. J., Kim, S. H., Lee, J. G., & Shin, H. C. (2003). Archives of Pharmacal Research, 26, 286–293.
Li, Y., Qian, Z. J., Ryu, B. M., Lee, S. H., Kim, M. M., & Kim, S. K. (2009). Bioorganic & Medical Chemistry, 17, 1963–1973.
Sugiura, Y., Matsuda, K., Yamada, Y., Nishikawa, M., Shioya, K., Katsuzaki, H., et al. (2006). Bioscience Biotechnology & Biochemistry, 70, 2807–2811.
Lee, H. U., Bae, E. A., & Kim, D. H. (2005). Journal of Pharmacological Science, 97, 541–544.
Kim, Y. C., An, R. B., Yoon, N. Y., Nam, T. J., & Choi, J. S. (2005). Archives of Pharmacal Research, 28, 1376–1380.
Acknowledgments
This work was supported by grant no. RTI05-01-02 from the Regional Technology Innovation Program of the Ministry of Knowledge Economy (MKE).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kim, S.M., Kang, K., Jeon, JS. et al. Isolation of Phlorotannins from Eisenia bicyclis and Their Hepatoprotective Effect against Oxidative Stress Induced by tert-Butyl Hyperoxide. Appl Biochem Biotechnol 165, 1296–1307 (2011). https://doi.org/10.1007/s12010-011-9347-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12010-011-9347-3