Advertisement

Fisheries Science

, Volume 74, Issue 5, pp 1166–1172 | Cite as

Antioxidative activities of a mycosporine-like amino acid, porphyra-334

  • Cen Tao
  • Tatsuya Sugawara
  • Sayaka Maeda
  • Xichang Wang
  • Takashi HirataEmail author
Article

Abstract

Antioxidative activities of porphyra-334, a mycosporine-like amino acid extracted from laver were evaluated. Oxidation of linoleic acid induced by an alkyl-radical 2,2′-azobis (2-amidinopropane) dihydrochloride (AAPH) was successfully suppressed by porphyra-334 (0–200 μM). The simultaneous application of 0.02 μM α-tocopherol and 50 μM porphyra-334 effectively suppressed the AAPH induced oxidation level to approximately 40% of a single application of porphyra-334 after 10 min reaction. Porphyra-334 (0–200 μM) efficiently suppressed the lipid peroxidation induced by singlet oxygen although the antioxidative effect observed was relatively moderate at the initial stage of oxidation. These results suggested that porphyra-334 may function as an antioxidant which influences the storage stability of laver.

Key words

antioxidant lipid oxidation mycosporine-like amino acid porphyra-334 singlet oxygen tocopherol 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Dunlap WC, Shick JM. Ultraviolet radiation-absorbing mycosporine-like amino acids in coral reef organisms: a biochemical and environmental perspective. J. Phycol. 1998; 34: 418–430.CrossRefGoogle Scholar
  2. 2.
    Shick JM, Dunlap WC. Mycosporine-like amino acids and related Gadusols: biosynthesis, accumulation, and UV-protective functions in aquatic organisms. Annu. Rev. Physiol. 2002; 64: 223–262.PubMedCrossRefGoogle Scholar
  3. 3.
    Ito S, Hirata Y. Isolation and structure of a mycosporine from the zoanthidian Palythoa tuberculosa. Tetrahedron Lett. 1977; 18: 2429–2430.CrossRefGoogle Scholar
  4. 4.
    Hirata Y, Uemura D, Ueda K, Takano S. Several compounds from Palythoa tuberculosa (Coelenterata). Pure Appl. Chem. 1979; 51: 1875–1883.CrossRefGoogle Scholar
  5. 5.
    Nakamura H, Kobayashi J, Hirata Y. Isolation and structure of a 330-nm UV-absorbing substance, Asterina-330 from the starfish Asterina pecti ifera. Chem. Lett. 1981; 10: 1413–1414.CrossRefGoogle Scholar
  6. 6.
    Takano S, Nakanishi A, Uemura D, Hirata Y. Isolation and structure of a 334 nm UV-absorbing substance, Porphyra-334 from the red alga Porphyra tenera Kjellman. Chem. Lett. 1979; 26: 419–420.CrossRefGoogle Scholar
  7. 7.
    Tsujino I, Yabe K, Sekikawa I. Isolation and structure of a new amino acid, shinorine, from the red alga Chondrus yendoi Yamada Mikami. Bot. Mar. 1980; 23: 65–68.Google Scholar
  8. 8.
    Bandaranayake WM, Bourne DJ, Sim RG. Chemical composition during maturing and spawning of the sponge dysidea herbacea (Porifera: Demospongiae). Comp. Biochem. Physiol. 1997; 118B: 851–859.Google Scholar
  9. 9.
    Oren A. Mycosporine-like amino acids as osmotic solutes in a community of halophilic cyanobacteria. Biomicrobiol. J. 1997; 14: 231–240.CrossRefGoogle Scholar
  10. 10.
    Suh HJ, Lee HW, Jung J. Mycosporine-glycine protects biological systems against photodynamic damage by quenching singlet oxygen with a high efficiency. Photochem. Photobiol. 2003; 78: 109–113.PubMedCrossRefGoogle Scholar
  11. 11.
    Dunlap WC, Yamamoto Y. Small-molecule antioxidant in marine organisms: antioxidant activity of mycosporineglycine. Comp. Biochem. Physiol. 1995; 112: 105–114.CrossRefGoogle Scholar
  12. 12.
    Ministry of Education, Culture, Sports, Science and Technology. Standard tables of food composition in Japan. Ministry of education, culture, sports, science and technology, Fifth Revised and Enlarged Edition. National Printing Bureau, Tokyo. 2005.Google Scholar
  13. 13.
    Fujimoto K, Kaneda T. Test for antioxigenic compounds from marine algae and fractionation from Eisena bicyclis and Undaria pinnatifida. Nippon Suisan Gakkaishi 1980; 46: 1125–1130.Google Scholar
  14. 14.
    Nakayama R, Tamura Y, Kikuzaki H, Nakatani N. Antioxidant effect of constituents of Susabinor (Porphyra yezoensis). J. Am. Oil Chem. Soc. 1999; 76: 649–653.CrossRefGoogle Scholar
  15. 15.
    Hirata T, Iida H, Tanaka M, Ooike M, Tsunomura T, Sakaguchi M. Bio-regulatory functions of biliproteins and phycobilins from algae. Proceedings of International Commemorative Symposium. 70th Anniversary of the Japanese Society of Fisheries Science. Japanese Society of Fisheries Science, Yokohama. 2002; 1449–1452.Google Scholar
  16. 16.
    Figueroa FL, Escassi L, Perez-Rodriguez E, Korbee N, Giles AD, Johnsen G. Effects of short-term irradiation on photo-inhibition and accumulation of mycosporine-like amino acids in sun and shade species of the red algal genus Porphyra. J. Photochem. Photobiol. B Biol. 2003; 69: 21–30.CrossRefGoogle Scholar
  17. 17.
    Wolff SP. Ferrous ion oxidization in presence of xylenol orange for measurement of hydroperoxides. Methods Enzymol. 1994; 233: 182–189.CrossRefGoogle Scholar
  18. 18.
    Buettner G. The pecking order of free radicals and antioxidants: lipid peroxidation, tocopherol, and ascorbate. Arch. Biochem. Biophys. 1993; 300: 535–5543.PubMedCrossRefGoogle Scholar
  19. 19.
    Niki E, Saito T, Kawakami A, Kamiya Y. Inhibition of oxidation of methyl linoleate in solution by Vitamin E and Vitamin C. J. Biol. Chem. 1984; 295: 4177–4182.Google Scholar
  20. 20.
    Tutour BL. Antioxidative activities of algal extracts, synergetic effect with vitamin E. Phytochem. 1990; 29: 3759–3765.CrossRefGoogle Scholar
  21. 21.
    Sugawara T, Komura Y, Hagino H, Hirata T. Phycoerythrin contributes to the photo-oxidation of eicosapentaenoic acid in Porphyra yezoensis during light-exposure. J. Food Sci. 2006; 71: S486-S491.CrossRefGoogle Scholar
  22. 22.
    Hirata T, Tanaka M, Ooike M, Tsunomura T, Niizeki N, Sakaguchi M. Radical scavenging activity of phycocyanobilin prepared from the cyanobacterium. Spirulina platensis. Fish. Sci. 1999; 65: 971–972.Google Scholar

Copyright information

© The Japanese Society of Fisheries Science 2008

Authors and Affiliations

  • Cen Tao
    • 1
    • 2
  • Tatsuya Sugawara
    • 1
  • Sayaka Maeda
    • 1
  • Xichang Wang
    • 2
  • Takashi Hirata
    • 1
    Email author
  1. 1.Division of Applied Biosciences, Graduate School of AgricultureKyoto UniversityKyotoJapan
  2. 2.College of Food Science and TechnologyShanghai Ocean UniversityShanghaiChina

Personalised recommendations