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Distribution of Phlorotannins in the Brown Alga Ecklonia cava and Comparison of Pretreatments for Extraction

  • Received : 2011.03.23
  • Accepted : 2011.08.12
  • Published : 2011.09.30

Abstract

The brown seaweed Ecklonia cava is known to be a rich source of phlorotannins that have diverse biological activities. Among the phlorotannins in E. cava, concentrations of dieckol and phlorofucofuroeckol-A, which were identified as major active components, were determined in different parts of the tissue. We compared the efficacy of different pretreatments for their extraction. A high-performance liquid chromatography (HPLC) method to determine phlorotannin concentrations showed good accuracy (92.64 and 94.02%, respectively), precision (3.92 and 3.94%, respectively), and linearity (r>0.996). Mature thalli contained 1.5-fold more dieckol (1.82 mg/g-dry tissue) than young thalli. In the tissues of E. cava, blade tissue contained more phlorotannins than the stipe or holdfast. Among differently dried thalli, approximately 90% or more dieckol and phlorofucofuroeckol-A were extracted from shadow-dried tissue as compared with lyophilized tissue. In sun-dried and oven-dried thalli, approximately 60% of the phlorotannins were extracted. Thalli washed with fresh water, boiled thalli, and steamed thalli showed reduced extraction of the compounds.

Keywords

References

  1. Arnold TM and Targett NM. 2003. To grow and defend: lack of tradeoffs for brown algal phlorotannins. Oikas 100, 406-408. https://doi.org/10.1034/j.1600-0706.2003.11680.x
  2. Artan M, Li Y, Karadeniz F, Lee SH, Kim MM and Kim SK. 2008. Anti-HIV-1 activity of phlorogluycinol derivative, 6,6'-bieckol from Ecklonia cava. Bioorg Med Chem 16, 7921-7926. https://doi.org/10.1016/j.bmc.2008.07.078
  3. Carrillo S, Castro MI, Perez-Gil F, Rosales E and Manzano RE. 1992. The seaweed (Sargassum sinicola Setchel & Gardner) as an alternative for animal feeding. Cuban J Agric Sci 26, 177-181.
  4. Chen RZ, Petterson U, Beard C, Jackson-Grusby L and Jaenisch R. 1998. DNA hypomethylation leads to elevated mutation rates. Nature 395, 89-93. https://doi.org/10.1038/25779
  5. Davis AR, Targett NM, McConnell OJ and Young CM. 1989. Epibiosis of marine algae and benthic invertebrates: natural products chemistry and other mechanisms inhibiting settlement and overgrowth. Bioorg Mar Chem 3, 85-114. https://doi.org/10.1007/978-3-642-74560-7_4
  6. Donguibogam Committee. 1999. Translated Donguibogam. Bubinmunwha Press, Seoul, KR.
  7. Folch J, Lees M and Sloane Stanley GH. 1957. A simple method for the isolation and purification of total lipid from animal tissues. J Biol Chem 226, 497-509.
  8. Hamdy AEA and Dawes CJ. 1988. Proximate constituents and lipid chemistry in two species of Sargassum from the west coast of Florida. Bot Mar 31, 79-81. https://doi.org/10.1515/botm.1988.31.1.79
  9. Heo SJ, Ko SC, Cha SH, Kang DH, Park HS, Choi YU, Kim D, Jung WK and Jeon YJ. 2009. Effects of phlorotannins isolated from Ecklonia cava on melanogenesis and their protective effect against photo-oxidative stress induced by UV-B radiation. Toxicol in Vitro 23, 1123-1130. https://doi.org/10.1016/j.tiv.2009.05.013
  10. Kim AR, Shin TS, Lee MS, Park JY, Park KE, Yoon NY, Kim JS, Choi JS, Jang BC, Byun DS, Park NK and Kim HR. 2009. Isolation and identification of phlorotannins from Ecklonia stolonifera with anti-oxidant and anti-inflammatory properties. J Agric Food Chem 57, 3483-3489. https://doi.org/10.1021/jf900820x
  11. Koivikko R, Loponen J, Pihlaja K and Jormalainen V. 2007. High-performance liquid chromatographic analysis of phlorotannins from the brown alga Fucus vesiculosus. Phytochem Anal 18, 326-332. https://doi.org/10.1002/pca.986
  12. Li Y, Lee SH, Le QT, Kim MM and Kim SK. 2008. Anti-allergic effects of phlorotannins on histamine release via binding inhibition between IgE and FcεRI. J Agric Food Chem 56, 12073-12080. https://doi.org/10.1021/jf802732n
  13. Li Y, Qian ZJ, Ryu B, Lee SH, Kim MM and Kim SK. 2009. Chemical components and its antioxidant properties in vitro: an edible marine brown alga Ecklonia cava. Bioorg Med Chem 17, 1963-1973. https://doi.org/10.1016/j.bmc.2009.01.031
  14. Mabeau S and Fleurence J. 1993. Seaweed in food products: biochemical and nutritional aspects. Trends Food Sci Technol 4, 103-107. https://doi.org/10.1016/0924-2244(93)90091-N
  15. Maegawa M. 1990. Ecological studies of Eisenia bicyclis (Kjellma) Setchell and Ecklonia cava Kjellma. Bull Fac Biores Mie Univ 4, 73-145.
  16. Mueller-Harvey I. 2001. Analysis of hydrolysable tannins. Anim Feed Sci Technol 91, 3-20. https://doi.org/10.1016/S0377-8401(01)00227-9
  17. Myung CS, Shin HC, Bao HY, Yeo SJ, Lee BH and Kang JS. 2005. Improvement of memory by dieckol and phlorofucofuroeckol in ethanol-treated mice: possible improvement of the inhibition of acetylcholinesterase. Arch Pharm Res 28, 691-698. https://doi.org/10.1007/BF02969360
  18. Nagayama K, Iwamura Y, Shibata T, Hirayama I and Nakamura T. 2002. Bactericidal activity of phlorotannins from the brown alga Ecklonia kurome. J Antimicrob Chemother 50, 889-893. https://doi.org/10.1093/jac/dkf222
  19. Nakayama Y, Takahashi M, Fukuyama Y and Kinzyo Z. 1989. An anti-plasmin inhibitor, eckol, isolated from the brown alga Ecklonia kurome Okamura. Agric Biol Chem 53, 3025-3030. https://doi.org/10.1271/bbb1961.53.3025
  20. Oetgen GW and Haseley P. 2004. Freeze-drying. Wiley-VCH Verling Gmbh & Co., Weinheim, DE.
  21. Pavia H and Toth GB. 2000. Inducible chemical resistance to herbivory in the brown seaweed Ascophyllum nodosum. Ecology 81, 3212-3225. https://doi.org/10.3354/meps157139
  22. Pavia H, Cervin G, Lindgren A and Åberg P. 1997. Effects of UV-B radiation and simulated herbivory on phlorotannins in the brown alga Ascophyllum nodosum. Mar Ecol Prog Ser 157, 139-146. https://doi.org/10.3354/meps157139
  23. Ragan MA and Glombitza KW. 1986. Phlorotannins: brown algal polyphenols. Prog Phycol Res 4, 130-241. https://doi.org/10.2216/i0031-8884-41-2-125.1
  24. Schoenwaelder MEA. 2002. The occurrence and cellular significance of physodes in brown algae. Phycologia 41, 125-139. https://doi.org/10.1046/j.1529-8817.1998.340969.x
  25. Schoenwaelder MEA and Clayton MN. 1998. Secretion of phenolic substances into the zygote wall and cell plate in embryos of Hormosira and Acrocarpia (Fucales, Phaeophyceae). J Phycol 34, 969-980. https://doi.org/10.1023/B:JAPH.0000047781.24993.0a
  26. Shibata T, Kawaguchi S, Hama Y, Inagaki M, Yamaguchi K and Nakamura T. 2004. Local and chemical distribution of phlorotannins in brown algae. J Appl Phycol 16, 291-296. https://doi.org/10.1023/B:JAPH.0000047781.24993.0a
  27. Snyder LR, Kirkland JJ and Glajch JL. 1997. Practical HPLC Method Development. 2nd ed. John Willey & Sons, Inc., New York, US. https://doi.org/10.1126/science.223.4634.405
  28. Steinberg PD. 1984. Algal chemical defense against herbivores: allocation of phenolic compounds in the kelp Alaria marginata. Science 223, 405-407. https://doi.org/10.1126/science.223.4634.405
  29. Stern JL, Hagerman AE, Steinberg PD, Winter FC and Estes JA. 1998. A new assay for quantifying brown algal phlorotannins and comparisons to previous methods. J Chem Ecol 22, 1273-1293. https://doi.org/10.3136/fstr.13.54
  30. Sugiura Y, Matsuda K, Yamada K, Nishikawa M, Shioya K, Katsuzaki H, Imai K and Amano H. 2007. Anti-allergic phlorotannins from the edible brown alga Eisenia arborea. Food Sci Technol Res 13, 54-60. https://doi.org/10.1046/j.1529-8817.1998.340195.x
  31. Targett NM and Arnold TM. 1998. Predicting the effects of brown algal phlorotannins on marine herbivores in tropical and temperate oceans. J Phycol 34, 195-205. https://doi.org/10.1046/j.1529-8817.1998.340195.x
  32. Targett NM and Arnold TM. 2001. Effects of secondary metabolites on digestion in marine herbivores. In: Marine Chemical Ecology. McClinlock JB and Baker BJ, eds. CRC Press, Boca Raton, FL, US, pp. 391-412.
  33. Waterman PG and Mole S. 1994. Analysis of Phenolic Plant Metabolites. Blackwell Scientific Publications, Oxford, GB. https://doi.org/10.1111/j.1444-2906.2007.01511.x
  34. Yoon NY, Chung HY, Kim HR and Choi JS. 2008. Acetyl- and butyrylcholinesterase inhibitory activities of sterols and phlorotannins from Ecklonia stolonifera. Fish Sci 74, 200-207. https://doi.org/10.1111/j.1444-2906.2007.01511.x

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