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Year 2022, Volume: 7 Issue: 3, 385 - 390, 31.12.2022
https://doi.org/10.31797/vetbio.1173455

Abstract

References

  • Allenspach, M., & Steuer, C. (2021). $α$-Pinene: A never-ending story. Phytochemistry, 190, 112857.
  • Allenspach, M., Valder, C., Flamm, D., Grisoni, F., & Steuer, C. (2020). Verification of chromatographic profile of primary essential oil of Pinus sylvestris L. combined with chemometric analysis. Molecules, 25(13), 2973.
  • Alonso, A., Belda, I., Santos, A., Navascués, E., & Marquina, D. (2015). Advances in the control of the spoilage caused by Zygosaccharomyces species on sweet wines and concentrated grape musts. Food Control, 51, 129–134.
  • Alviano, D. S., & Alviano, C. S. (2009). Plant extracts: search for new alternatives to treat microbial diseases. Current Pharmaceutical Biotechnology, 10(1), 106–121.
  • Andrade, J. M., & Estévez-Pérez, M. G. (2014). Statistical comparison of the slopes of two regression lines: A tutorial. Analytica Chimica Acta, 838, 1–12.
  • Bevilacqua, A., Corbo, M. R., & Sinigaglia, M. (2010). In vitro evaluation of the antimicrobial activity of eugenol, limonene, and citrus extract against bacteria and yeasts, representative of the spoiling microflora of fruit juices. Journal of Food Protection, 73(5), 888–894.
  • Burt, S. A., Ahad, D., Kinjet, M., & Santos, R. R. (2013). Cinnamaldehyde, carvacrol and selected organic acids affect expression of immune related genes in IPEC-J2 cells exposed to Salmonella enterica serotype Typhimurium or Escherichia coli K88. Planta Medica, 79(13), PJ7.
  • Cahyari, K., Syamsiah, S., Hidayat, M., & Sarto, S. (2018). Inhibitory kinetics study of limonene and eugenol towards mixed culture of dark fermentative biohydrogen production. AIP Conference Proceedings, 2026(1), 20038.
  • Cai, R., Hu, M., Zhang, Y., Niu, C., Yue, T., Yuan, Y., & Wang, Z. (2019). Antifungal activity and mechanism of citral, limonene and eugenol against Zygosaccharomyces rouxii. Lwt, 106, 50–56.
  • da Franca Rodrigues, K. A., Amorim, L. V., Dias, C. N., Moraes, D. F. C., Carneiro, S. M. P., & de Amorim Carvalho, F. A. (2015). Syzygium cumini (L.) Skeels essential oil and its major constituent $α$-pinene exhibit anti-Leishmania activity through immunomodulation in vitro. Journal of Ethnopharmacology, 160, 32–40.
  • Ergüden, B., & Ünver, Y. (2022). Phenolic chalcones lead to ion leakage from Gram-positive bacteria prior to cell death. Archives of Microbiology, 204(1), 1–6.
  • Harvey, A. L., Edrada-Ebel, R., & Quinn, R. J. (2015). The re-emergence of natural products for drug discovery in the genomics era. Nature Reviews Drug Discovery, 14(2), 111–129.
  • Hyldgaard, M., Mygind, T., & Meyer, R. L. (2012). Essential oils in food preservation: mode of action, synergies, and interactions with food matrix components. Frontiers in Microbiology, 3, 12.
  • Konuk, H. B., & Ergüden, B. (2017). Antifungal activity of various essential oils against Saccharomyces cerevisiae depends on disruption of cell membrane integrity. Biocell, 41(1), 13.
  • Koudou, J., Abena, A. A., Ngaissona, P., & Bessière, J. M. (2005). Chemical composition and pharmacological activity of essential oil of Canarium schweinfurthii. Fitoterapia, 76(7–8), 700–703.
  • Loizzo, M. R., Saab, A., Tundis, R., Statti, G. A., Lampronti, I., Menichini, F., Gambari, R., Cinatl, J., & Doerr, H. W. (2008). Phytochemical analysis and in vitro evaluation of the biological activity against herpes simplex virus type 1 (HSV-1) of Cedrus libani A. Rich. Phytomedicine, 15(1–2), 79–83.
  • Minnebruggen, G. Van, François, I., Cammue, B. P. A., Thevissen, K., Vroome, V., Borgers, M., & Shroot, B. (2010). A general overview on past, present and future antimycotics. The Open Mycology Journal, 4(1).
  • Nóbrega, J. R., Silva, D. de F., Andrade Júnior, F. P. de, Sousa, P. M. S., Figueiredo, P. T. R. de, Cordeiro, L. V., & Lima, E. de O. (2021). Antifungal action of $α$-pinene against Candida spp. isolated from patients with otomycosis and effects of its association with boric acid. Natural Product Research, 35(24), 6190–6193.
  • Pereira, F. de O., Mendes, J. M., Lima, I. O., Mota, K. S. de L., Oliveira, W. A. de, & Lima, E. de O. (2015). Antifungal activity of geraniol and citronellol, two monoterpenes alcohols, against Trichophyton rubrum involves inhibition of ergosterol biosynthesis. Pharmaceutical Biology, 53(2), 228–234.
  • Shen, Y.-C., Chou, C.-J., Wang, Y.-H., Chen, C.-F., Chou, Y.-C., & Lu, M.-K. (2004). Anti-inflammatory activity of the extracts from mycelia of Antrodia camphorata cultured with water-soluble fractions from five different Cinnamomum species. FEMS Microbiology Letters, 231(1), 137–143.
  • Sikorski, R. S., & Hieter, P. (1989). A system of shuttle vectors and yeast host strains designed for efficient manipulation of DNA in Saccharomyces cerevisiae. Genetics, 122(1), 19–27.
  • Silva, A. C. R. da, Lopes, P. M., Azevedo, M. M. B. de, Costa, D. C. M., Alviano, C. S., & Alviano, D. S. (2012). Biological activities of a-pinene and $β$-pinene enantiomers. Molecules, 17(6), 6305–6316.
  • Stratford, M. (2006). Food and beverage spoilage yeasts. In Yeasts in food and beverages (pp. 335–379). Springer.
  • Wei, L.-J., Zhong, Y.-T., Nie, M.-Y., Liu, S.-C., & Hua, Q. (2020). Biosynthesis of $α$-pinene by genetically engineered Yarrowia lipolytica from low-cost renewable feedstocks. Journal of Agricultural and Food Chemistry, 69(1), 275–285.
  • Yang, C., Hu, D.-H., & Feng, Y. (2015). Antibacterial activity and mode of action of the Artemisia capillaris essential oil and its constituents against respiratory tract infection-causing pathogens. Molecular Medicine Reports, 11(4), 2852–2860.
  • Zarai, Z., Kadri, A., Ben Chobba, I., Ben Mansour, R., Bekir, A., Mejdoub, H., & Gharsallah, N. (2011). The in-vitro evaluation of antibacterial, antifungal and cytotoxic properties of Marrubium vulgare L. essential oil grown in Tunisia. Lipids in Health and Disease, 10(1), 1–8.

Investigation of antifungal activity mechanisms of alpha-pinene, eugenol, and limonene

Year 2022, Volume: 7 Issue: 3, 385 - 390, 31.12.2022
https://doi.org/10.31797/vetbio.1173455

Abstract

Plant essential oils are preferred in cosmetics, medicine, food, and beverage industries for various purposes. α-Pinene is found mainly in eucalyptus oils, eugenol is the active ingredient in clove oil, and limonene is the major component in the oil of citrus fruit peels. In this study, we aimed to determine the antifungal activity of α-pinene, eugenol, and limonene against Saccharomyces cerevisiae yeast cells. Besides, we focused on revealing the target side of the compounds on the yeast cells.
Firstly, the antifungal activity of compounds was tested via minimum inhibitory concentration (MIC) measurement. After that, we performed a sorbitol effect assay to understand whether it acts on the cell wall or not. With sorbitol, the MIC values were not changed. It means that they are not effective on the yeast cell wall. Then, we measured the extracellular conductivity increase upon treatment with the compounds to understand the effect on the cell membrane. Eugenol and limonene were not changed the extracellular conductivity, and there was no ion leakage from the cell membrane. On the other hand, α-pinene damaged the yeast cell membrane causing a sudden increase in conductivity due to ion leakage. An ergosterol effect assay with α-pinene was performed to detect cell membrane disruption via ergosterol or not. With ergosterol, the MIC value was not changed. α-Pinene must have another target than the ergosterol in the yeast cell membrane. Finally, revealing the mode of action of compounds against yeast cells will provide new insights into their usage in various fields.

References

  • Allenspach, M., & Steuer, C. (2021). $α$-Pinene: A never-ending story. Phytochemistry, 190, 112857.
  • Allenspach, M., Valder, C., Flamm, D., Grisoni, F., & Steuer, C. (2020). Verification of chromatographic profile of primary essential oil of Pinus sylvestris L. combined with chemometric analysis. Molecules, 25(13), 2973.
  • Alonso, A., Belda, I., Santos, A., Navascués, E., & Marquina, D. (2015). Advances in the control of the spoilage caused by Zygosaccharomyces species on sweet wines and concentrated grape musts. Food Control, 51, 129–134.
  • Alviano, D. S., & Alviano, C. S. (2009). Plant extracts: search for new alternatives to treat microbial diseases. Current Pharmaceutical Biotechnology, 10(1), 106–121.
  • Andrade, J. M., & Estévez-Pérez, M. G. (2014). Statistical comparison of the slopes of two regression lines: A tutorial. Analytica Chimica Acta, 838, 1–12.
  • Bevilacqua, A., Corbo, M. R., & Sinigaglia, M. (2010). In vitro evaluation of the antimicrobial activity of eugenol, limonene, and citrus extract against bacteria and yeasts, representative of the spoiling microflora of fruit juices. Journal of Food Protection, 73(5), 888–894.
  • Burt, S. A., Ahad, D., Kinjet, M., & Santos, R. R. (2013). Cinnamaldehyde, carvacrol and selected organic acids affect expression of immune related genes in IPEC-J2 cells exposed to Salmonella enterica serotype Typhimurium or Escherichia coli K88. Planta Medica, 79(13), PJ7.
  • Cahyari, K., Syamsiah, S., Hidayat, M., & Sarto, S. (2018). Inhibitory kinetics study of limonene and eugenol towards mixed culture of dark fermentative biohydrogen production. AIP Conference Proceedings, 2026(1), 20038.
  • Cai, R., Hu, M., Zhang, Y., Niu, C., Yue, T., Yuan, Y., & Wang, Z. (2019). Antifungal activity and mechanism of citral, limonene and eugenol against Zygosaccharomyces rouxii. Lwt, 106, 50–56.
  • da Franca Rodrigues, K. A., Amorim, L. V., Dias, C. N., Moraes, D. F. C., Carneiro, S. M. P., & de Amorim Carvalho, F. A. (2015). Syzygium cumini (L.) Skeels essential oil and its major constituent $α$-pinene exhibit anti-Leishmania activity through immunomodulation in vitro. Journal of Ethnopharmacology, 160, 32–40.
  • Ergüden, B., & Ünver, Y. (2022). Phenolic chalcones lead to ion leakage from Gram-positive bacteria prior to cell death. Archives of Microbiology, 204(1), 1–6.
  • Harvey, A. L., Edrada-Ebel, R., & Quinn, R. J. (2015). The re-emergence of natural products for drug discovery in the genomics era. Nature Reviews Drug Discovery, 14(2), 111–129.
  • Hyldgaard, M., Mygind, T., & Meyer, R. L. (2012). Essential oils in food preservation: mode of action, synergies, and interactions with food matrix components. Frontiers in Microbiology, 3, 12.
  • Konuk, H. B., & Ergüden, B. (2017). Antifungal activity of various essential oils against Saccharomyces cerevisiae depends on disruption of cell membrane integrity. Biocell, 41(1), 13.
  • Koudou, J., Abena, A. A., Ngaissona, P., & Bessière, J. M. (2005). Chemical composition and pharmacological activity of essential oil of Canarium schweinfurthii. Fitoterapia, 76(7–8), 700–703.
  • Loizzo, M. R., Saab, A., Tundis, R., Statti, G. A., Lampronti, I., Menichini, F., Gambari, R., Cinatl, J., & Doerr, H. W. (2008). Phytochemical analysis and in vitro evaluation of the biological activity against herpes simplex virus type 1 (HSV-1) of Cedrus libani A. Rich. Phytomedicine, 15(1–2), 79–83.
  • Minnebruggen, G. Van, François, I., Cammue, B. P. A., Thevissen, K., Vroome, V., Borgers, M., & Shroot, B. (2010). A general overview on past, present and future antimycotics. The Open Mycology Journal, 4(1).
  • Nóbrega, J. R., Silva, D. de F., Andrade Júnior, F. P. de, Sousa, P. M. S., Figueiredo, P. T. R. de, Cordeiro, L. V., & Lima, E. de O. (2021). Antifungal action of $α$-pinene against Candida spp. isolated from patients with otomycosis and effects of its association with boric acid. Natural Product Research, 35(24), 6190–6193.
  • Pereira, F. de O., Mendes, J. M., Lima, I. O., Mota, K. S. de L., Oliveira, W. A. de, & Lima, E. de O. (2015). Antifungal activity of geraniol and citronellol, two monoterpenes alcohols, against Trichophyton rubrum involves inhibition of ergosterol biosynthesis. Pharmaceutical Biology, 53(2), 228–234.
  • Shen, Y.-C., Chou, C.-J., Wang, Y.-H., Chen, C.-F., Chou, Y.-C., & Lu, M.-K. (2004). Anti-inflammatory activity of the extracts from mycelia of Antrodia camphorata cultured with water-soluble fractions from five different Cinnamomum species. FEMS Microbiology Letters, 231(1), 137–143.
  • Sikorski, R. S., & Hieter, P. (1989). A system of shuttle vectors and yeast host strains designed for efficient manipulation of DNA in Saccharomyces cerevisiae. Genetics, 122(1), 19–27.
  • Silva, A. C. R. da, Lopes, P. M., Azevedo, M. M. B. de, Costa, D. C. M., Alviano, C. S., & Alviano, D. S. (2012). Biological activities of a-pinene and $β$-pinene enantiomers. Molecules, 17(6), 6305–6316.
  • Stratford, M. (2006). Food and beverage spoilage yeasts. In Yeasts in food and beverages (pp. 335–379). Springer.
  • Wei, L.-J., Zhong, Y.-T., Nie, M.-Y., Liu, S.-C., & Hua, Q. (2020). Biosynthesis of $α$-pinene by genetically engineered Yarrowia lipolytica from low-cost renewable feedstocks. Journal of Agricultural and Food Chemistry, 69(1), 275–285.
  • Yang, C., Hu, D.-H., & Feng, Y. (2015). Antibacterial activity and mode of action of the Artemisia capillaris essential oil and its constituents against respiratory tract infection-causing pathogens. Molecular Medicine Reports, 11(4), 2852–2860.
  • Zarai, Z., Kadri, A., Ben Chobba, I., Ben Mansour, R., Bekir, A., Mejdoub, H., & Gharsallah, N. (2011). The in-vitro evaluation of antibacterial, antifungal and cytotoxic properties of Marrubium vulgare L. essential oil grown in Tunisia. Lipids in Health and Disease, 10(1), 1–8.
There are 26 citations in total.

Details

Primary Language English
Subjects Structural Biology
Journal Section Research Articles
Authors

Hatice Büşra Konuk 0000-0002-7115-7211

Bengü Ergüden 0000-0002-8621-3474

Publication Date December 31, 2022
Submission Date September 10, 2022
Acceptance Date December 29, 2022
Published in Issue Year 2022 Volume: 7 Issue: 3

Cite

APA Konuk, H. B., & Ergüden, B. (2022). Investigation of antifungal activity mechanisms of alpha-pinene, eugenol, and limonene. Journal of Advances in VetBio Science and Techniques, 7(3), 385-390. https://doi.org/10.31797/vetbio.1173455

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