Skip to main content

Antimicrobial browning-inhibitory effect of flavor compounds in seaweeds

  • Conference paper

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

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (Canada)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   169.00
Price excludes VAT (Canada)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   219.99
Price excludes VAT (Canada)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   219.99
Price excludes VAT (Canada)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • 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.

    CrossRef  PubMed  CAS  Google Scholar 

  • 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 

  • Conner DE (1993) Naturally occurring compounds. In Davidson, PM, Branen AL (eds), Antimicrobials in Food, Marcel Dekker, New York, pp. 441–468.

    Google Scholar 

  • Davis PL, Smoot JJ (1972) Germination of Penicillium digetatum spores as affected by solution of volatile compounds of citrus fruits. Phytochemistry 62: 488–489.

    CAS  Google Scholar 

  • 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 

  • Friedman H (1996) Food browning and its prevention: An Overview. J. Ag. Food Chem. 44: 630–653.

    Google Scholar 

  • 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 

  • 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.

    CAS  Google Scholar 

  • Kajiwara T, Kodama K, Hatanaka A, Matsui K (1993) Volatile compounds from Japanese marine brown algae. Am. Chem. Soc. Symp. Ser. 525: 103–120.

    CAS  Google Scholar 

  • Kajiwara T, Matsui K, Akakabe Y (1996) Biogeneration of volatile compounds via oxylipins in edible seaweeds. Am. Chem. Soc. Symp. Ser. 637: 146–166.

    CAS  Google Scholar 

  • 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.

    CrossRef  CAS  Google Scholar 

  • Kubo A, Christopher SL, Kubo I (1995) Antimicrobial activity of the olive oil flavor compounds. J. Ag. Food Chem. 43: 1629–1633.

    CrossRef  CAS  Google Scholar 

  • Kubo I, Kinst-Hori I (1999) Tyrosinase inhibitory activity of the olive oil flavor compounds. J. Ag. Food Chem. 47: 4574–4578.

    CrossRef  CAS  Google Scholar 

  • 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.

    CrossRef  CAS  Google Scholar 

  • Maruzzella JC, Sicurella NA (1960) Antibacterial activity of essential oil vapors. J. Am. Pharmaceut. Ass. 49: 692–694.

    CrossRef  CAS  Google Scholar 

  • Mayer AM (1987) Polyphenol oxidase in plants-recent progress. Phytochemistry 26: 11–20.

    CrossRef  Google Scholar 

  • Morris JA, Khettry A, Seitz EW (1979) Antimicrobial activity of aroma chemicals and essential oils. JAOCS 56: 595–603.

    CrossRef  PubMed  CAS  Google Scholar 

  • 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.

    CrossRef  CAS  Google Scholar 

  • Negishi O, Ozawa T (2000) Inhibition of enzymatic browning and protection of sulfhyryl enzymes by thiol compounds. Phytochemistry 54: 481–487.

    CrossRef  PubMed  CAS  Google Scholar 

  • 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 

  • 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.

    CrossRef  CAS  Google Scholar 

  • 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.

    CrossRef  PubMed  CAS  Google Scholar 

  • 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.

    CrossRef  CAS  Google Scholar 

  • Whitaker JR (1995) Polyphenol oxidase. In Wong DWS. (ed.), Food Enzymes, Structure and Mechanism, Chapman & Hall, New York: pp. 271–307.

    Google Scholar 

  • Zaika LL (1988) Spices and herbs: their antimicrobial activity and its determination. J. Food Safety 9: 97–118.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2006 Springer

About this paper

Cite this paper

Kajiwara, T., Matsui, K., Akakabe, Y., Murakawa, T., Arai, C. (2006). Antimicrobial browning-inhibitory effect of flavor compounds in seaweeds. In: Anderson, R., Brodie, J., Onsøyen, E., Critchley, A.T. (eds) Eighteenth International Seaweed Symposium. Developments in Applied Phycology, vol 1. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-5670-3_24

Download citation

Publish with us

Policies and ethics