ALGAE

The Korean Society of Phycology (한국조류학회(藻類))
권호 표지
DOI QR코드

DOI QR Code

Thermostability of a marine polyphenolic antioxidant dieckol, derived from the brown seaweed Ecklonia cava

  • Kang, Min-Cheol (Department of Marine Life Sciences, Jeju National University) ;
  • Kim, Eun-A (Department of Marine Life Sciences, Jeju National University) ;
  • Kang, Sung-Myung (Department of Marine Life Sciences, Jeju National University) ;
  • Wijesinghe, W.A.J.P. (Department of Marine Life Sciences, Jeju National University) ;
  • Yang, Xiudong (Department of Marine Life Sciences, Jeju National University) ;
  • Kang, Na-Lae (Department of Marine Life Sciences, Jeju National University) ;
  • Jeon, You-Jin (Department of Marine Life Sciences, Jeju National University)
  • Received : 2012.05.05
  • Accepted : 2012.08.13
  • Published : 2012.09.15
Download PDF
⟨ Previous Next ⟩

Abstract

The thermostability of antioxidant activity of dieckol, a phlorotannin isolated from brown seaweed Ecklonia cava was investigated. The thermostable antioxidant properties of dieckol were evaluated at 30, 60, and $90^{\circ}C$ for 7 days using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and hydroxyl radical scavenging activities, and comparing its performance to that of ascorbic acid. The intracellular reactive oxygen species (ROS) scavenging activity and apoptotic body formation were investigated using DCF-DA assay and nuclear staining with Hoechst 33342, propidium iodide and flow cytometry. Dieckol treated at different temperatures during 7 days showed stable scavenging activities on towards DPPH and hydroxyl radicals. In addition, dieckol showed a stable protective effect against $H_2O_2$-induced apoptotic body formation in Vero cells. On the other hand, the radical scavenging activities and intracellular ROS scavenging activities of ascorbic acid, used as a positive control, were significantly decreased at $60^{\circ}C$ and $90^{\circ}C$ from on the 4th day and 3rd days, respectively. In conclusion, the results indicated that food grade antioxidant extracts containing dieckol derived from E. cava remain a stable during the temperatures encountered during the processing of food and cosmetics.

Keywords

References

  1. Ahn, G. -N., Kim, K. -N., Cha, S. -H., Song, C. -B., Lee, J., Heo, M. -S., Yeo, I. -K., Lee, N. -H., Jee, Y. -H., Kim, J. -S., Heu, M. -S. & Jeon, Y. -J. 2007. Antioxidant activities of phlorotannins purified from Ecklonia cava on free radical scavenging using ESR and $H_{2}O_{2}$-mediated DNA damage. Eur. Food Res. Technol. 226:71-79. https://doi.org/10.1007/s00217-006-0510-y
  2. Alwazeer, D., Delbeau, C., Divies, C. & Cachon, R. 2003. Use of redox potential modification by gas improves microbial quality, color retention, and ascorbic acid stability of pasteurized orange juice. Int. J. Food Microbiol. 89:21-29. https://doi.org/10.1016/S0168-1605(03)00125-9
  3. Amarowicz, R., Naczk, M. & Shahidi, F. 2000. Antioxidant activity of various fractions of non-tannin phenolics of canola hulls. J. Agric. Food Chem. 48:2755-2759. https://doi.org/10.1021/jf9911601
  4. Athukorala, Y. & Jeon, Y. J. 2005. Screening for angiotensin 1-converting enzyme inhibitory activity of Ecklonia cava. J. Food Sci. Nutr. 10:134-139. https://doi.org/10.3746/jfn.2005.10.2.134
  5. Choi, Y., Lee, S. M., Chun, J., Lee, H. B. & Lee, J. 2006. Influence of heat treatment on the antioxidant activities and polyphenolic compounds of Shiitake (Lentinus edodes) mushroom. Food Chem. 99:381-387. https://doi.org/10.1016/j.foodchem.2005.08.004
  6. Cordenunsi, B. R., Oliveira do Nascimento, J. R., Genovese, M. I. & Lajolo, F. M. 2002. Influence of cultivar on quality parameters and chemical composition of strawberry fruits grown in Brazil. J. Agric. Food Chem. 50:2581-2586. https://doi.org/10.1021/jf011421i
  7. Devi, G. K., Mamivannan, K., Thirumaran, G., Rajathi, F. A. A. R. & Anantharaman, P. 2011. In vitro antioxidant activities of selected seaweeds from Southeast coast of India. Asian Pac. J. Trop. Med. 4:205-211. https://doi.org/10.1016/S1995-7645(11)60070-9
  8. Dykens, J. A., Shick, J. M., Benoit, C., Buettner, G. R. & Winston, G. W. 1992. Oxygen radical production in the sea anemone Anthopleura elegantissima and its endosymbiotic algae. J. Exp. Biol. 168:219-241.
  9. Esteve, M. J., Farre, R., Frigola, A. & Clemente, G. 1995. Changes in ascorbic acid content of green asparagus during the harvesting period and storage. J. Agric. Food Chem. 43:2058-2061. https://doi.org/10.1021/jf00056a019
  10. Fritsch, C. W. 1981. Measurements of frying fat deterioration: a brief review. J. Am. Oil Chem. Soc. 58:272-274. https://doi.org/10.1007/BF02582355
  11. Frei, B., England, L. & Ames, B. N. 1989. Ascorbate is an outstanding antioxidant in human blood plasma. Proc. Natl. Acad. Sci. U. S. A. 86:6377-6381. https://doi.org/10.1073/pnas.86.16.6377
  12. Frolich, I. & Riederer, P. 1995. Free radical mechanisms in dementia of Alzheimer type and the potential for antioxidative treatment. Arzneimittelforschung 45:443-446.
  13. Gschwind, M. & Huber, G. 1995. Apoptotic cell death induced by $\beta$-amyloid 1-42 peptide is cell type dependent. J. Neurochem. 65:292-300.
  14. Gupta, S., Lakshmi, A. J. & Prakash, J. 2008. Effect of different blanching treatments on ascorbic acid retention in green leafy vegetables. Nat. Prod. Radiance 7:111-116.
  15. Heo, S. -J & Jeon, Y. -J. 2008. Radical scavenging capacity and cytoprotective effect of enzymatic digests of Ishige okamurae. J. Appl. Phycol. 20:1087-1095. https://doi.org/10.1007/s10811-008-9320-x
  16. Heo, S. -J., Yoon, W. -J., Kim, K. -N., Ahn, G. -N., Kang, S. -M., Kang, D. -H., affan, A., Oh, C., Jung, W. -K. & Jeon, Y. -J. 2010. Evaluation of anti-inflammatory effect of fucoxanthin isolated from brown algae in lipopolysaccharidestimulated RAW 264.7 macrophages. Food Chem. Toxicol. 48:2045-2051. https://doi.org/10.1016/j.fct.2010.05.003
  17. Im, M. H., Park, Y. -S., Leontowicz, H., Leontowicz, M., Namiesnik, J., Ham, K. -S., Kang, S. -G., Najman, K. & Gorinstein, S. 2011. The thermostability, bioactive compounds and antioxidant activity of some vegetables subjected to different durations of boiling: investigation in vitro. LWT-Food Sci. Technol. 44:92-99. https://doi.org/10.1016/j.lwt.2010.05.037
  18. Kang, K. A., Lee, K. H., Chae, S., Zhang, R., Jung, M. S., Lee, Y., Kim, H. S., Joo, H. G., Park, J. W., Ham, Y. M., Lee, N. H. & Hyun, J. W. 2005. Eckol isolated from Ecklonia cava attenuates oxidative stress induced cell damage in lung fibroblast cells. FEBS Lett. 579:6295-6304. https://doi.org/10.1016/j.febslet.2005.10.008
  19. Kotake-Nara, E., Asai, A. & Nagao, A. 2005. Neoxanthin and fucoxanthin induce apoptosis in PC-3 human prostate cancer cells. Cancer Lett. 220:75-84. https://doi.org/10.1016/j.canlet.2004.07.048
  20. Laguerre, M., Lecomte, J. & Villeneuve, P. 2007. Evaluation of the ability of antioxidants to counteract lipid oxidation: existing methods, new trends and challenges. Prog. Lipid Res. 46:244-282. https://doi.org/10.1016/j.plipres.2007.05.002
  21. Lee, S. -H., Han, J. -S., Heo, S. -J., Hwang, J. -Y. & Jeon, Y. -J. 2010. Protective effects of dieckol isolated from Ecklonia cava against high glucose-induced oxidative stress in human umbilical vein endothelial cells. Toxicol. In Vitro 24:375-381. https://doi.org/10.1016/j.tiv.2009.11.002
  22. Lehtinen, P., Kiiliäinen, K., Lehtomäki, I. & Laakso, S. 2003. Effect of heat treatment on lipid stability in processed oats. J. Cereal Sci. 37:215-221. https://doi.org/10.1006/jcrs.2002.0496
  23. Li, Y., Qian, Z. -J., Ryu, B. M., Lee, S. -H., Kim, M. -M. & Kim, S. -K. 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
  24. Lizard, G., Fournel, S., Genestier, L., Dhedin, N., Chaput, C., Flacher, M., Mutin, M., Panaye, G. & Revillard, J. -P. 1995. Kinetics of plasma membrane and mitochondrial alterations in cells undergoing apoptosis. Cytometry 21:275-283. https://doi.org/10.1002/cyto.990210308
  25. Lordan, S., Ross, R. P. & Stanton, C. 2011. Marine bioactives as functional food ingredients: potential to reduce the incidence of chronic diseases. Mar. Drugs 9:1056-1100. https://doi.org/10.3390/md9061056
  26. Matsukawa, R., Dubinsky, Z., Kishimoto, E., Masaki, K., Masuda, Y., Takeuchi, T., Chihara, M., Yamamoto, Y., Niki, E. & Karube, I. 1997. A comparison of screening methods for antioxidant activity in seaweeds. J. Appl. Phycol. 9:29-35. https://doi.org/10.1023/A:1007935218120
  27. Mayer, A. M. S. & Hamann, M. T. 2004. Marine pharmacology in 2000: marine compounds with antibacterial, anticoagulant, antifungal, anti-inflammatory, antimalarial, antiplatelet, antituberculosis, and antiviral activities, affecting the cardiovascular, immune, and nervous systems and other miscellaneous mechanisms of action. Mar. Biotechnol. 6:37-52. https://doi.org/10.1007/s10126-003-0007-7
  28. Nagayama, K., Iwamura, Y., Shibata, T., Hirayama, I. & 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
  29. Nagy, S. & Smoot, J. M. 1977. Temperature and storage effects on percent retention and percent U. S. recommended dietary allowance of vitamin C in canned single-strength orange juice. J. Agric. Food Chem. 25:135-138. https://doi.org/10.1021/jf60209a031
  30. Nanjo, F., Goto, K., Seto, R., Suzuki, M., Sakai, M. & Hara, Y. 1996. Scavenging effects of tea catechins and their derivatives on 1,1-diphenyl-2-picrylhydrazyl radical. Free Radical Biol. Med. 6:895-902.
  31. Nicoletti, I., Migliorati, G., Pagliacci, M. C., Grignani, F. G. & Riccardi, C. 1991. A rapid and simple method for measuring thymocyte apoptosis by propidium iodide staining and flow cytometry. J. Immunol. Methods 2:271-279.
  32. Park, P. -J., Heo, S. -J., Park, E. -J., Kim, S. -K., Byun, H. -G., Jeon, B. -T. & Jeon, Y. -J. 2005. Reactive oxygen scavenging effect of enzymatic extracts from Sargassum thunbergii. J. Agric. Food Chem. 53:6666-6672. https://doi.org/10.1021/jf050582+
  33. Park, S. -J., Ahn, G., Lee, N. H., Park, J. W., Jeon, Y. -J. & Jee, Y. 2011. Phloroglucinol (PG) purified from Ecklonia cava attenuates radiation-induced apoptosis in blood lymphocytes and splenocytes. Food Chem. Toxicol. 49:2236- 2242. https://doi.org/10.1016/j.fct.2011.06.021
  34. Sherwin, E. R. 1990. Antioxidants. In: Branen, R. (Ed.) Food Additives. Marcel Dekker, New York, pp. 139-193.
  35. Spigno, G., Tramelli, L. & De Faveri, D. M. 2007. Effects of extraction time, temperature and solvent on concentration and antioxidant activity of grape marc phenolics. J. Food Eng. 81:200-208. https://doi.org/10.1016/j.jfoodeng.2006.10.021
  36. Sukenik, A., Zmora, O. & Carmeli, Y. 1993. Biochemical quality of marine unicellular algae with special emphasis lipid composition.II. Nannochloropsis sp. Aquaculture 117:313-326. https://doi.org/10.1016/0044-8486(93)90328-V
  37. Ukeda, H., Shimamura, T., Tsubouchi, M., Harada, Y., Nakai, Y. & Sawamura, M. 2002. Spectrophotometric assay of superoxide anion formed in Maillard reaction based on highly water-soluble Terazolium salt. Jpn. Soc. Anal. Sci. 18:1151-1154.
  38. Wijesinghe, W. A. J. P., Ko, S. -C. & Jeon, Y. -J. 2011. Effect of phlorotannins isolated from Ecklonia cava on angiotensin I-converting enzyme (ACE) inhibitory activity. Nutr. Res. Pract. 5:93-100. https://doi.org/10.4162/nrp.2011.5.2.93
  39. Yang, Y. M., Han, K. Y. & Noh, B. S. 2000. Analysis of lipid oxidation of soybean oil using the portable electronic nose. Food Sci. Biotechnol. 9:146-150.
  40. Ye, H., Zhou, C., Sun, Y., Zhang, X., Liu, J., Hu, Q. & Zeng, X. 2009. Antioxidant activities in vitro of ethanol extract from brown seaweed Sargassum pallidum. Eur. Food Res. Technol. 230:101-109. https://doi.org/10.1007/s00217-009-1147-4

Cited by

  1. Structure and antioxidative property of a polysaccharide from an ammonium oxalate extract of Phellinus linteus vol.91, 2016, https://doi.org/10.1016/j.ijbiomac.2016.05.063
  2. In vitro and in vivo antioxidant activities of polysaccharide purified from aloe vera (Aloe barbadensis) gel vol.99, 2014, https://doi.org/10.1016/j.carbpol.2013.07.091
  3. Total phenolic content and biological activities of enzymatic extracts from Sargassum muticum (Yendo) Fensholt 2017, https://doi.org/10.1007/s10811-017-1086-6
  4. Purification of antioxidative peptide from peptic hydrolysates of Mideodeok (Styela clava) flesh tissue vol.22, pp.2, 2013, https://doi.org/10.1007/s10068-013-0112-y
  5. Protective effect of a marine polyphenol, dieckol against carbon tetrachloride-induced acute liver damage in mouse vol.35, pp.3, 2013, https://doi.org/10.1016/j.etap.2013.02.013
  6. Protective effect of polyphenol extracted from Ecklonia cava against ethanol induced oxidative damage in vitro and in zebrafish model vol.6, 2014, https://doi.org/10.1016/j.jff.2013.10.025
  7. Protective effects of polysaccharides from Psidium guajava leaves against oxidative stresses vol.91, 2016, https://doi.org/10.1016/j.ijbiomac.2016.05.111
  8. Protective effect of fucoxanthin isolated from Ishige okamurae against high-glucose induced oxidative stress in human umbilical vein endothelial cells and zebrafish model vol.11, 2014, https://doi.org/10.1016/j.jff.2014.09.007
  9. Profiling of the Molecular Weight and Structural Isomer Abundance of Macroalgae-Derived Phlorotannins vol.13, pp.1, 2015, https://doi.org/10.3390/md13010509
  10. New insights into seaweed polyphenols on glucose homeostasis vol.53, pp.8, 2015, https://doi.org/10.3109/13880209.2014.959615
  11. Bioactive properties and potentials cosmeceutical applications of phlorotannins isolated from brown seaweeds: A review vol.162, 2016, https://doi.org/10.1016/j.jphotobiol.2016.06.027
  12. The chemical and antioxidant stability of isolated low molecular weight phlorotannins vol.221, 2017, https://doi.org/10.1016/j.foodchem.2016.11.050
  13. Fucoxanthin derivatives from Sargassum siliquastrum inhibit matrix metalloproteinases by suppressing NF-κB and MAPKs in human fibrosarcoma cells vol.29, pp.4, 2014, https://doi.org/10.4490/algae.2014.29.4.355
  14. Phytochemical Analysis and Evaluation of the Antioxidant, Anti-Inflammatory, and Antinociceptive Potential of Phlorotannin-Rich Fractions from Three Mediterranean Brown Seaweeds vol.20, pp.1, 2018, https://doi.org/10.1007/s10126-017-9787-z
  15. Sargassum horneri (Turner) C. Agardh ethanol extract inhibits the fine dust inflammation response via activating Nrf2/HO-1 signaling in RAW 264.7 cells vol.18, pp.1, 2018, https://doi.org/10.1186/s12906-018-2314-6
  16. Biological activity of a polyphenolic complex of Arctic brown algae vol.31, pp.5, 2012, https://doi.org/10.1007/s10811-019-01840-7
  17. Protective effects of extracts from six local strains of Pyropia yezoensis against oxidative damage in vitro and in zebrafish model vol.35, pp.2, 2020, https://doi.org/10.4490/algae.2020.35.5.14
  18. Optimization of Ultrasound-Assisted Extraction of Anti-Glycation Agents from Ecklonia cava vol.30, pp.6, 2021, https://doi.org/10.1080/10498850.2021.1924906
  19. Dieckol: a brown algal phlorotannin with biological potential vol.142, pp.None, 2012, https://doi.org/10.1016/j.biopha.2021.111988