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Antimicrobial browning-inhibitory effect of flavor compounds in seaweeds

  • Tadahiko Kajiwara
  • Kenji Matsui
  • Yoshihiko Akakabe
  • Takushi Murakawa
  • Chikako Arai
Part of the Developments in Applied Phycology book series (DAPH, volume 1)

Abstract

Since ancient times, the antimicrobial properties of seaweeds have been recognized. However, antimicrobial activities of volatile compounds in seaweeds have not been explored so far. Here, essential oils from seaweeds including green, brown and red algae such as Laminaria japonica, Kjellmaniella crassifolia, Gracilaria verrucosa and Ulva pertusa were prepared by using SDE (simultaneous distillation and extraction) apparatus. Volatile compounds in the essential oils were identified as aldehydes, ketones, carboxylic acids, alcohols and hydrocarbons by comparison of GC-retention times and MS data with those of authentic specimens. Flavor compounds such as (3Z)-hexenal, (2E)-hexenal and (2E)-nonenal in some essential oils showed strong antimicrobial activities against Escherichia coli TG-1, and Erwinia carotovora. Inhibition of browning can be achieved during either of two stages, namely, oxidation reaction by tyrosinase or subsequent non-enzymatic polymerization. Tyrosinase activity was measured by monitoring absorbance at 475 nm originating from dopachrome formed from L-DOPA. Many kinds of aliphatic carboxylic acids, aldehydes and alcohols were used as inhibitors for PPO activity. The results indicated that the α,β-unsaturated carbonyl compounds strongly inhibit tyrosinase activity. When seaweeds are damaged or macerated, the α,β-unsaturated aldehydes such as (2E)-hexenal and (2E)-nonenal are biosynthesized via the corresponding (3Z)-unsaturated aldehydes from linolenic acid and arachidonic acid. The flavor compounds that are formed could be valuable as safe antimicrobial browning-inhibitory agents of edible seaweed origin.

Key words

seaweeds essential oils volatile compounds tyrosinase inhibitory activity antimicrobial activity L-DOPA 

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References

  1. Boonprab K, Matsui K, Akakabe Y, Yotsukura N, Kajiwara T (2003a) Hydroperoxy-arachidonic acid mediated n-hexanal and (Z)-3-and (E)-2-nonenal formation in Laminaria angustada. Phytochemistry 63: 669–678.PubMedCrossRefGoogle Scholar
  2. Boonprab K, Matsui K, Yoshida M, Akakabe Y, Chirapart A, Kajiwara T (2003b) C6-Aldehyde formation by fatty acid hydroperoxide lyase in the brown alga Laminaria angustata. Z. Naturf. 58c: 207–214.Google Scholar
  3. Conner DE (1993) Naturally occurring compounds. In Davidson, PM, Branen AL (eds), Antimicrobials in Food, Marcel Dekker, New York, pp. 441–468.Google Scholar
  4. Davis PL, Smoot JJ (1972) Germination of Penicillium digetatum spores as affected by solution of volatile compounds of citrus fruits. Phytochemistry 62: 488–489.Google Scholar
  5. Flament I, Ohloff G (1984) Volatile constituents of algae. Odoriferous constituents of seaweeds and structure of nor-terpenoids identified in Asakusa-nori flavor. In Adda J (ed.), Progress in Flavor Research, Elsevier Science Publishers, Amsterdam B. V., pp. 281–300.Google Scholar
  6. Friedman H (1996) Food browning and its prevention: An Overview. J. Ag. Food Chem. 44: 630–653.Google Scholar
  7. Glombitza KW(1979) Antibiotics from algae. In Hoppe HA, Levring T., Tanaka T (eds), Marine Algae in Pharmaceutical Science, Walter de Gruyter, Berlin, pp. 303–342.Google Scholar
  8. Hatanaka A, Kajiwara T, Matsui K (1995) The biogeneration of green odor by green leaves and its physiological functions-past, present and future. Z. Naturf. 50: 467–472.Google Scholar
  9. Kajiwara T, Kodama K, Hatanaka A, Matsui K (1993) Volatile compounds from Japanese marine brown algae. Am. Chem. Soc. Symp. Ser. 525: 103–120.Google Scholar
  10. Kajiwara T, Matsui K, Akakabe Y (1996) Biogeneration of volatile compounds via oxylipins in edible seaweeds. Am. Chem. Soc. Symp. Ser. 637: 146–166.Google Scholar
  11. Kermasha S, Goetghebeur M, Monfette A, Metche M, Rovel B (1993). Inhibitory effects of cysteine and aromatic acids on tyrosinase activity. Phytochemistry 34: 349–353.CrossRefGoogle Scholar
  12. Kubo A, Christopher SL, Kubo I (1995) Antimicrobial activity of the olive oil flavor compounds. J. Ag. Food Chem. 43: 1629–1633.CrossRefGoogle Scholar
  13. Kubo I, Kinst-Hori I (1999) Tyrosinase inhibitory activity of the olive oil flavor compounds. J. Ag. Food Chem. 47: 4574–4578.CrossRefGoogle Scholar
  14. Kubo I, Kinst-Hori I, Kubo Y, Yamagiwa Y, Kamikawa T, Haraguchi T (2000) Molecular design of antibrowning agents. J. Ag. Food Chem. 48: 1393–1399.CrossRefGoogle Scholar
  15. Maruzzella JC, Sicurella NA (1960) Antibacterial activity of essential oil vapors. J. Am. Pharmaceut. Ass. 49: 692–694.CrossRefGoogle Scholar
  16. Mayer AM (1987) Polyphenol oxidase in plants-recent progress. Phytochemistry 26: 11–20.CrossRefGoogle Scholar
  17. Morris JA, Khettry A, Seitz EW (1979) Antimicrobial activity of aroma chemicals and essential oils. JAOCS 56: 595–603.PubMedCrossRefGoogle Scholar
  18. Nakamura S, Hatanaka A (2002) Green-leaf derived C6-aroma compounds with potent antibacterial action that act on both gramnegative and gram-positive bacteria. J. Ag. Food Chem. 50:7639–7644.CrossRefGoogle Scholar
  19. Negishi O, Ozawa T (2000) Inhibition of enzymatic browning and protection of sulfhyryl enzymes by thiol compounds. Phytochemistry 54: 481–487.PubMedCrossRefGoogle Scholar
  20. Ogawa M, Perdigao NB, Santiago ME, Kozima TT (1984) On physiological aspects of black spot appearance in shrimp. Bull. Japn. Soc. Sci. Fish. 50: 1763–1769.Google Scholar
  21. Schultz TH, Flath RA, Mon TK, Eggling SB, Teranishi R (1977) Isolation of volatile compounds from a model system. J. Ag. Food Chem. 25: 446–449.CrossRefGoogle Scholar
  22. Suhr KI, Nielsen PV (2003) Antifungal activity of essential oils evaluated by two different application techniques against rye bread spoilage fungi. J. Appl. Microbiol. 94: 665–674.PubMedCrossRefGoogle Scholar
  23. Vaughn SF, Spencer GF, Shacha BS (1993) Volatile compounds from raspberry and strawberry fruit inhibit postharvest decay fungi. Journal of Food Science 58: 793–806.CrossRefGoogle Scholar
  24. Whitaker JR (1995) Polyphenol oxidase. In Wong DWS. (ed.), Food Enzymes, Structure and Mechanism, Chapman & Hall, New York: pp. 271–307.Google Scholar
  25. Zaika LL (1988) Spices and herbs: their antimicrobial activity and its determination. J. Food Safety 9: 97–118.Google Scholar

Copyright information

© Springer 2006

Authors and Affiliations

  • Tadahiko Kajiwara
    • 1
  • Kenji Matsui
    • 1
  • Yoshihiko Akakabe
    • 1
  • Takushi Murakawa
    • 1
  • Chikako Arai
    • 1
  1. 1.Department of Biological Chemistry, Faculty of AgricultureYamaguchi UniversityYamaguchiJapan

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