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Antioxidant activities of phlorotannins isolated from Japanese Laminariaceae

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Abstract

The antioxidant activities of brown algal phlorotannins were evaluated using the inhibition of phospholipid peroxidation in the liposome system, and by determining radical scavenging activities against the superoxide anion and 1,1-diphenyl-2-picrylhydrazyl (DPPH). Oligomers of phloroglucinol (1,3,5-trihydroxybenzene), eckol (a trimer), phlorofucofuroeckol A (a pentamer), dieckol and 8,8′-bieckol (hexamers), isolated from the Laminarian brown algae Eisenia bicyclis, Ecklonia cava and Ecklonia kurome, showed potent inhibition of phospholipid peroxidation at 1 μM in the liposome system. The phlorotannins had significant radical scavenging activities against the superoxide anion (50% effective concentration values: 6.5–8.4 μM) and DPPH (50% effective concentration values: 12–26 μM), and were more effective compared to ascorbic acid and α-tocopherol. For the purpose of using phlorotannins as functional food ingredients, the antioxidant activity of a complex of crude phlorotannins and soybean protein was examined. The complex had a pronounced DPPH-radical scavenging activity. These results suggest that phlorotannins are potent anti-inflammatory substances, and that the Laminariaceous brown algae, which are abundant in phlorotannins, may be useful as a new functional foodstuff or supplement with anti-inflammatory activity.

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References

  • Aggarwal BB, Shishodia S (2006) Molecular targets of dietary agents for prevention and therapy of cancer. Biochem Pharmacol 71:1397–1421

    Article  PubMed  CAS  Google Scholar 

  • Esaki H, Onozaki H, Kawakishi S, Osawa T (1997) Antioxidant activity and isolation from soybeans fermented with Aspergillus spp. J Agric Food Chem 45:2020–2024

    Article  CAS  Google Scholar 

  • Esaki H, Watanabe R, Onozaki H, Kawakishi S, Osawa T (1999a) Formation mechanism for potent antioxidative o-dihydroxyisoflavones in soybeans fermented with Aspergillus saitoi. Biosci Biotechnol Biochem 63:851–858

    Article  CAS  Google Scholar 

  • Esaki H, Kawakishi S, Morimitsu Y, Osawa T (1999b) New potent antioxidative o-dihydroxyisoflavones in fermented Japanese soybean products. Biosci Biotechnol Biochem 63:1637–1639

    Article  PubMed  CAS  Google Scholar 

  • Folch J, Less M, Sloan Stanley GH (1957) A simple method for the isolation and purification of total lipids from animal tissues. J Biol Chem 226:497–509

    PubMed  CAS  Google Scholar 

  • Haslam E (1989) Plant polyphenols, Cambridge University Press, Cambridge

    Google Scholar 

  • Havsteen BH (2002) The biochemistry and medical significance of the flavonoids. Pharmacol Ther 96:67–202

    Article  PubMed  CAS  Google Scholar 

  • Herbert RB (1989) The biosynthesis of secondary metabolites, 2nd edn. Chapman and Hall, New York

    Google Scholar 

  • Huang S-M, Shigetomi N, Tanaka N, Terahara N, Fujioka T, Yoshida M, Ishimaru K (2004) Preparation and functional evaluation of plant polyphenol-bean protein complex. Nippon Shokuhin Kagaku Kogaku Kaishi 51:626–632

    Google Scholar 

  • Ishimaru K, Nonaka G (2001) Rapid purification of catechins using soybean protein. Nippon Shokuhin Kagaku Kogaku Kaihi 48:664–670

    CAS  Google Scholar 

  • Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, Beecher CWW, Fong HHS, Farnsworth NR, Kinghorn AD, Mehta RG, Moon RC, Pezzuto JM (1997) Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 275:218–220

    Article  PubMed  CAS  Google Scholar 

  • Kondo K, Kurihara M, Miyata N, Suzuki T, Toyoda M (1999) Mechanistic studies of catechins as antioxidants against radical oxidation. Arch Biochem Biophys 362:79–86

    Article  PubMed  CAS  Google Scholar 

  • Krebs KG, Heusser D, Wimmer H (1969) Spray reagents. In: Stahl E (ed) Thin-layer chromatography. Springer, Heidelberg, pp 854–909

    Google Scholar 

  • MacDonald RC, MacDonald RI, Menco BPhM, Takeshita K, Subbarao NK, Hu L-R (1991) Small-volume extrusion apparatus for preparation of large, unilamellar vesicles. Biochim Biophys Acta 1061:297–303

    Article  PubMed  CAS  Google Scholar 

  • Messina MJ, Persky V, Setchell KDR, Barnes S (1994) Soy intake and cancer risk: a review of the in vitro and in vivo data. Nutr Cancer 21:113–131

    Article  PubMed  CAS  Google Scholar 

  • 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

    Article  PubMed  CAS  Google Scholar 

  • Nagayama K, Shibata T, Fujimoto K, Honjo T, Nakamura T (2003) Algicidal effect of phlorotannins from the brown alga Ecklonia kurome on red tide microalgae. Aquaculture 218:601–611

    Article  CAS  Google Scholar 

  • Nakamura T, Mukaiyama T, Nagayama K (1991) A rapid and simple method to detect antioxidant substances on a thin-layer chromatography plate. J Fac Agric Kyushu Univ 36:93–98

    Google Scholar 

  • Nakamura T, Nagayama K, Uchida K, Tanaka R (1996) Antioxidant activity of phlorotannins isolated from the brown alga Eisenia bicyclis. Fisheries Sci 62:923–926

    CAS  Google Scholar 

  • Ragan MA, Glombitza K-W (1986) Phlorotannins, brown algal polyphenols. Progr Phycol Res 4:129–241

    CAS  Google Scholar 

  • Sasazuki S, Kodama H, Yoshimasu K, Liu Y, Washio M, Tanaka K, Tokunaga S, Kono S, Arai H, Doi Y, Kawano T, Nakagaki O, Takada K, Koyanagi S, Hiyamuta K, Nii T, Shirai K, Ideishi M, Arakawa K, Mohri M, Takeshita A (2000) Relation between green tea consumption and the severity of coronary atherosclerosis among Japanese men and women. Ann Epidemiol 10:401–408

    Article  PubMed  CAS  Google Scholar 

  • Shibata T, Yamaguchi K, Nagayama K, Kawaguchi S, Nakamura T (2002a) Inhibitory activity of brown algal phlorotannins against glycosidases from the viscera of the turban shell Turbo cornutus. Eur J Phycol 37:493–500

    Article  Google Scholar 

  • Shibata T, Fujimoto K, Nagayama K Yamaguchi K, Nakamura T (2002b) Inhibitory activity of brown algal phlorotannins against hyaluronidase. Int J Food Sci Technol 37:703–709

    Article  CAS  Google Scholar 

  • Shibata T, Nagayama K, Tanaka R, Yamaguchi K, Nakamura T (2003) Inhibitory effects of brown algal phlorotannins on secretory phospholipase A2s, lipoxygenases and cyclooxygenases. J Appl Phycol 15:61–66

    Article  CAS  Google Scholar 

  • Shibata T, Kawaguchi S, Hama Y, Inagaki M, Yamaguchi K, Nakamura T (2004) Local and chemical distribution of phlorotannins in brown algae. J Appl Phycol 16:291–296

    Article  CAS  Google Scholar 

  • Shibata T, Nagayama K, Kawaguchi S, Hama Y (2006a) Antioxidant and radical scavenging activities of brown algal phlorotannins. ITE Lett Batter New Tecnol Med 7:69–72

    CAS  Google Scholar 

  • Shibata T, Hama Y, Miyasaki T, Ito M, Nakamura T (2006b) Extracellular secretion of phenolic substances from living brown algae. J Appl Phycol 18:787–794

    Article  CAS  Google Scholar 

  • Sugiura Y, Matsuda K, Yamada Y, Nishikawa M, Shioya K, Katsuzaki H, Imai K, Amano H (2006) Isolation of a new anti-allergic phlorotannin, phlorofucofuroeckol-B, from an edible brown alga, Eisenia arborea. Biosci Biotechnol Biochem 70:2807–2811

    Article  PubMed  CAS  Google Scholar 

  • Tsukui K, Kakinuma M, Amano H, Uchiyama Y, Shioya K, Katsuzaki H, Imai K (2006) Identification of elastase inhibitors from brown alga, Eisenia arborea. ITE Lett Batter New Tecnol Med 7:616–619

    CAS  Google Scholar 

  • Ukeda H, Kawana D, Maeda S, Sawamura M (1999) Spectrophotometric assay for superoxide dismutase based on the reduction of highly water-soluble tetrazolium salts by xanthine–xanthine oxidase. Biosci Biotechnol Biochem 63:485–488

    Article  CAS  Google Scholar 

  • Wu JM, Wang ZR, Hsieh TC, Bruder JL, Zou JG, Huang YZ (2001) Mechanism of cardioprotection by resveratrol, a phenolic antioxidant present in red wine. Int J Mol Med 8:3–17

    PubMed  CAS  Google Scholar 

  • Yamaguchi T, Takamura H, Matoba T, Terao J (1998) HPLC method for evaluation of the free radical-scavenging activity of foods by using 1, 1-diphenyl-2-picrylhydrazyl. Biosci Biotechnol Biochem 62:1201–1204

    Article  PubMed  CAS  Google Scholar 

  • Zhao B-L, Guo Q, Xin W-J (2001) Free radical scavenging by green tea polyphenols In: Packer L (ed) Flavonoids and other polyphenols. Methods in enzymology, vol 335. Academic, New York, pp 217–231

    Google Scholar 

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Acknowledgments

We thank grateful to Dr. Takashi Nakamura of the Graduate school of Kyushu University for his cooperation throughout this study. This work was supported in part by the Comprehensive Research Laboratory of Fukuoka Institute of Technology.

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Authors and Affiliations

  1. Laboratory of Quality in Marine Products, Department of Life Sciences, Graduate School of Bioresources, Mie University, 1577 Kurimamachiya, Tsu, 514-8507, Japan

    Toshiyuki Shibata

  2. Department of Applied Biological Sciences, Faculty of Agriculture, Saga University, 1Honjo, Saga, 840-8502, Japan

    Kanji Ishimaru

  3. Department of Animal and Marine Bioresource Sciences, Faculty of Agriculture, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka, 812-8581, Japan

    Shigeo Kawaguchi

  4. Department of Life, Environment and Materials Sciences, Faculty of Engineering, Fukuoka Institute of Technology, 3-30-1 Wajiro-Higashi, Higashi-ku, Fukuoka, 811-0295, Japan

    Hiromichi Yoshikawa

  5. Department of Applied Biochemistry and Food Sciences, Faculty of Agriculture, Saga University, 1 Honjo, Saga, 840-8502, Japan

    Yoichiro Hama

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  1. Toshiyuki Shibata
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  2. Kanji Ishimaru
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  3. Shigeo Kawaguchi
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  4. Hiromichi Yoshikawa
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  5. Yoichiro Hama
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Correspondence to Toshiyuki Shibata.

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Shibata, T., Ishimaru, K., Kawaguchi, S. et al. Antioxidant activities of phlorotannins isolated from Japanese Laminariaceae. J Appl Phycol 20, 705–711 (2008). https://doi.org/10.1007/s10811-007-9254-8

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  • DOI: https://doi.org/10.1007/s10811-007-9254-8

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