Skip to main content
SpringerLink
Log in

Antimicrobial and Antioxidant Activities of Clove Essential Oil and Eugenyl Acetate Produced by Enzymatic Esterification

  • Published:
Applied Biochemistry and Biotechnology Aims and scope Submit manuscript

Abstract

This work reports the maximization of eugenyl acetate production by esterification of essential oil of clove in a solvent-free system using Novozym 435 as catalyst. The antimicrobial and antioxidant activities of clove essential oil and eugenyl acetate produced were determined. The conditions that maximized eugenyl acetate production were 60 °C, essential oil of clove to acetic anhydride ratio of 1:5, 150 rpm, and 10 wt% of enzyme, with a conversion of 99.87 %. A kinetic study was performed to assess the influence of substrates’ molar ratio, enzyme concentration, and temperature on product yield. Results show that an excess of anhydride, enzyme concentration of 5.5 wt%, 50 °C, and essential oil of clove to acetic anhydride ratio of 1:5 afforded nearly a complete conversion after 2 h of reaction. Comparing the antibacterial activity of the essential oil of clove before and after esterification, we observed a decrease in the antimicrobial activity of eugenyl acetate, particularly with regard to minimum inhibitory concentration (MIC). Both eugenyl acetate and clove essential oil were most effective to the gram-negative than gram-positive bacteria group. The results showed a high antioxidant potential for essential oil before and particularly after the esterification reaction thus becoming an option for the formulation of new antioxidant products.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Paoli, S., Giani, T. S., Presta, G. A., Pereira, M. P., Fonseca, A. S., Brandão Neto, J., et al. (2007). Brazilian Archives of Biology and Technology, 50, 175–182.

    Article  Google Scholar 

  2. Guenette, S. A., Rodd, A., Marier, J. F., Beaudry, F., & Vachon, P. (2007). European Journal of Pharmacology, 562, 60–67.

    Article  CAS  Google Scholar 

  3. Guenette, S. A., Helie, P., Beaudry, F., & Vachon, P. (2007). Veterinary Anaesthesia and Analgesia, 34, 164–170.

    Article  CAS  Google Scholar 

  4. Affonso, R. S., Rennó, M. N., Slana, G. B. C. A., & França, T. C. C. (2012). Revista Virtual de Química, 4, 146–161.

    Article  CAS  Google Scholar 

  5. Chaieb, K., Hajlaoui, H., Zmantar, T., Kahla-Nabki, A. B., Rouabhia, M., Mahdouani, K., et al. (2007). Phytotherapy Research, 21, 501–506.

    Article  CAS  Google Scholar 

  6. Chiaradia, V., Paroul, N., Cansian, R. L., Júnior, C. V., Detofol, M. R., Lerin, L. A., et al. (2012). Applied Biochemistry and Biotechnology, 168, 742–751.

    Article  CAS  Google Scholar 

  7. Silvestri, J. D. F., Paroul, N., Czyewski, E., Lerin, L., Rotava, I., Cansian, R. L., et al. (2010). Revista Ceres, 57, 589–594.

    Article  CAS  Google Scholar 

  8. Scherer, R., Wagner, R., Duarte, M. C. T., & Godoy, H. T. (2009). Brazilian Journal of Medicinal Plants, 11, 442–449.

    CAS  Google Scholar 

  9. Paroul, N., Grzegozeski, L. P., Chiaradia, V., Treichel, H., Cansian, R. L., Oliveira, J. V., et al. (2011). Bioprocess and Biosystems Engineering, 34, 331–337.

    Article  CAS  Google Scholar 

  10. Paroul, N., Grzegozeski, L. P., Chiaradia, V., Treichel, H., Cansian, R. L., Oliveira, J. V., et al. (2010). Journal of Chemical Technology and Biotechnology, 85, 1636–1641.

    Article  CAS  Google Scholar 

  11. Liaw, E. T., & Liu, K. J. (2010). Bioresource Technology, 101, 3320–3324.

    Article  CAS  Google Scholar 

  12. Aguedo, M., Belo, I., Ly, M. H., Teixeira, J. A., Belin, J. M., & Waché, Y. (2004). Food Technology and Biotechnology, 42, 327–336.

    CAS  Google Scholar 

  13. Bartling, K., Thompson, J. U. S., Pfromm, P. H., Czermak, P., & Rezac, M. E. (2001). Biotechnology and Bioengineering, 75, 676–681.

    Article  CAS  Google Scholar 

  14. Valério, A., Fiametti, K. G., Rovani, S., Franceschi, E., Corazza, M. L., Treichel, H., et al. (2009). Journal of Supercritical Fluids, 49, 216–220.

    Article  Google Scholar 

  15. Yang, T., Rebsdorf, M., Engelrud, U., & Xu, X. (2005). Journal of Agricultural and Food Chemistry, 53, 1475–1481.

    Article  CAS  Google Scholar 

  16. Watanabe, T., Shimizu, M., Sugiura, M., Sato, M., Kohori, J., Yamada, N., et al. (2003). Journal of the American Oil Chemists Society, 80, 1201–1207.

    Article  CAS  Google Scholar 

  17. Karra-Châabouni, M., Ghamghi, H., Bezzine, S., Rekik, A., & Gargouri, Y. (2006). Process Biochemistry, 41, 1692–1698.

    Article  Google Scholar 

  18. Horchani, H., Salem, N. B., Zarai, Z., Sayari, A., Gargouri, Y., & Chaâbouni, M. (2010). Bioresource Technology, 101, 2809–2817.

    Article  CAS  Google Scholar 

  19. Chaibakhsh, N., Basri, M., Anuar, S. H. M., Rahman, M. B. A., & Rezayee, M. (2012). Biocatalysis and Agricultural Biotechnology, 1, 226–231.

    Article  CAS  Google Scholar 

  20. Yadav, G. D., & Yadav, A. R. (2012). Chemical Engineering Journal, 192, 146–155.

    Article  CAS  Google Scholar 

  21. Paroul, N., Grzegozeski, L. P., Chiaradia, V., Treichel, H., Cansian, R. L., Oliveira, J. V., et al. (2011). Applied Biochemistry and Biotechnology, 166, 13–21.

    Article  Google Scholar 

  22. Katzung, B. G. (2003). Farmacologia Básica e Clínica (8th ed.). Koogan: Rio de Janeiro – Guanabara.

    Google Scholar 

  23. Holley, R. A., & Patel, D. (2005). Food Microbiology, 22, 273–292.

    Article  CAS  Google Scholar 

  24. Klancnik, A., Piskernik, S., Jersek, B., & Mozina, S. S. (2010). Journal of Microbiological Methods, 81, 121–126.

    Article  CAS  Google Scholar 

  25. Dorman, H. J. D., & Deans, S. G. (2000). Journal of Applied Microbiology, 88, 308–316.

    Article  CAS  Google Scholar 

  26. Lachowicz, K. J., Jones, G. P., Briggs, D. R., Bienvenu, F. E., Wan, J., Wilcock, A., et al. (1998). Letters in Applied Microbiology, 26, 209–214.

    Article  CAS  Google Scholar 

  27. Pei, R. S., Zhou, F., Ji, B. P., & Xu, J. (2009). Journal of Food Science, 74, 379–383.

    Article  Google Scholar 

  28. Ultee, A., Bennik, M. H. J., & Moezelaar, R. (2002). Applied and Environmental Microbiology, 68, 1561–1568.

    Article  CAS  Google Scholar 

  29. Burt, S. A. (2004). International Journal of Food Microbiology, 94, 223–253.

    Article  CAS  Google Scholar 

  30. Skandamis, P., Tsigarida, E., & Nychas, G. J. E. (2002). Food Microbiology, 19, 97–103.

    Article  CAS  Google Scholar 

  31. Mensor, L. L., Menezes, F. S., Leitão, G. G., Reis, A. S., Santos, T. C., Coube, C. S., et al. (2001). Phytotherapy Research, 15, 127–130.

    Article  CAS  Google Scholar 

  32. Ramalho, V. C., & Jorge, N. (2006). Quimica Nova, 29, 755–760.

    Article  CAS  Google Scholar 

  33. Balasundram, N., Sundram, K., & Samman, S. (2006). Food Chemistry, 99, 191–203.

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors thank the CNPq, CAPES, FAPERGS, and SCIT-RS for financial support.

Author information

Authors and Affiliations

  1. Department of Food Engineering, URI—Campus de Erechim, Av. Sete de Setembro, 1621, Erechim, RS, 99700-000, Brazil

    Adriana B. Vanin, Tainara Orlando, Suelen P. Piazza, Bruna M. S. Puton, Rogério L. Cansian & Natalia Paroul

  2. Department of Chemical and Food Engineering, Universidade Federal de Santa Catarina, UFSC, Campus Universitário, Bairro Trindade, Caixa Postal 476, Florianópolis, SC, 88040-900, Brazil

    Debora Oliveira

Authors
  1. Adriana B. Vanin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tainara Orlando
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Suelen P. Piazza
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Bruna M. S. Puton
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Rogério L. Cansian
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Debora Oliveira
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Natalia Paroul
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Debora Oliveira.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Vanin, A.B., Orlando, T., Piazza, S.P. et al. Antimicrobial and Antioxidant Activities of Clove Essential Oil and Eugenyl Acetate Produced by Enzymatic Esterification. Appl Biochem Biotechnol 174, 1286–1298 (2014). https://doi.org/10.1007/s12010-014-1113-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12010-014-1113-x

Keywords

Search

Navigation