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Laccase Catalyzed Synthesis of Iodinated Phenolic Compounds with Antifungal Activity
Iodine is a well known antimicrobial compound. Laccase, an oxidoreductase which couples the one electron oxidation of diverse phenolic and non-phenolic substrates to the reduction of oxygen to water, is capable of oxidizing unreactive iodide to reactive iodine. We have shown previously that laccase-...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Public Library of Science
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3940670/ https://www.ncbi.nlm.nih.gov/pubmed/24594755 http://dx.doi.org/10.1371/journal.pone.0089924 |
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author | Ihssen, Julian Schubert, Mark Thöny-Meyer, Linda Richter, Michael |
author_facet | Ihssen, Julian Schubert, Mark Thöny-Meyer, Linda Richter, Michael |
author_sort | Ihssen, Julian |
collection | PubMed |
description | Iodine is a well known antimicrobial compound. Laccase, an oxidoreductase which couples the one electron oxidation of diverse phenolic and non-phenolic substrates to the reduction of oxygen to water, is capable of oxidizing unreactive iodide to reactive iodine. We have shown previously that laccase-iodide treatment of spruce wood results in a wash-out resistant antimicrobial surface. In this study, we investigated whether phenolic compounds such as vanillin, which resembles sub-structures of softwood lignin, can be directly iodinated by reacting with laccase and iodide, resulting in compounds with antifungal activity. HPLC-MS analysis showed that vanillin was converted to iodovanillin by laccase catalysis at an excess of potassium iodide. No conversion of vanillin occurred in the absence of enzyme. The addition of redox mediators in catalytic concentrations increased the rate of iodide oxidation ten-fold and the yield of iodovanillin by 50%. Iodinated phenolic products were also detected when o-vanillin, ethyl vanillin, acetovanillone and methyl vanillate were incubated with laccase and iodide. At an increased educt concentration of 0.1 M an almost one to one molar ratio of iodide to vanillin could be used without compromising conversion rate, and the insoluble iodovanillin product could be recovered by simple centrifugation. The novel enzymatic synthesis procedure fulfills key criteria of green chemistry. Biocatalytically produced iodovanillin and iodo-ethyl vanillin had significant growth inhibitory effects on several wood degrading fungal species. For Trametes versicolor, a species causing white rot of wood, almost complete growth inhibition and a partial biocidal effect was observed on agar plates. Enzymatic tests indicated that the iodinated compounds acted as enzyme responsive, antimicrobial materials. |
format | Online Article Text |
id | pubmed-3940670 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | Public Library of Science |
record_format | MEDLINE/PubMed |
spelling | pubmed-39406702014-03-06 Laccase Catalyzed Synthesis of Iodinated Phenolic Compounds with Antifungal Activity Ihssen, Julian Schubert, Mark Thöny-Meyer, Linda Richter, Michael PLoS One Research Article Iodine is a well known antimicrobial compound. Laccase, an oxidoreductase which couples the one electron oxidation of diverse phenolic and non-phenolic substrates to the reduction of oxygen to water, is capable of oxidizing unreactive iodide to reactive iodine. We have shown previously that laccase-iodide treatment of spruce wood results in a wash-out resistant antimicrobial surface. In this study, we investigated whether phenolic compounds such as vanillin, which resembles sub-structures of softwood lignin, can be directly iodinated by reacting with laccase and iodide, resulting in compounds with antifungal activity. HPLC-MS analysis showed that vanillin was converted to iodovanillin by laccase catalysis at an excess of potassium iodide. No conversion of vanillin occurred in the absence of enzyme. The addition of redox mediators in catalytic concentrations increased the rate of iodide oxidation ten-fold and the yield of iodovanillin by 50%. Iodinated phenolic products were also detected when o-vanillin, ethyl vanillin, acetovanillone and methyl vanillate were incubated with laccase and iodide. At an increased educt concentration of 0.1 M an almost one to one molar ratio of iodide to vanillin could be used without compromising conversion rate, and the insoluble iodovanillin product could be recovered by simple centrifugation. The novel enzymatic synthesis procedure fulfills key criteria of green chemistry. Biocatalytically produced iodovanillin and iodo-ethyl vanillin had significant growth inhibitory effects on several wood degrading fungal species. For Trametes versicolor, a species causing white rot of wood, almost complete growth inhibition and a partial biocidal effect was observed on agar plates. Enzymatic tests indicated that the iodinated compounds acted as enzyme responsive, antimicrobial materials. Public Library of Science 2014-03-03 /pmc/articles/PMC3940670/ /pubmed/24594755 http://dx.doi.org/10.1371/journal.pone.0089924 Text en © 2014 Ihssen et al http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are properly credited. |
spellingShingle | Research Article Ihssen, Julian Schubert, Mark Thöny-Meyer, Linda Richter, Michael Laccase Catalyzed Synthesis of Iodinated Phenolic Compounds with Antifungal Activity |
title | Laccase Catalyzed Synthesis of Iodinated Phenolic Compounds with Antifungal Activity |
title_full | Laccase Catalyzed Synthesis of Iodinated Phenolic Compounds with Antifungal Activity |
title_fullStr | Laccase Catalyzed Synthesis of Iodinated Phenolic Compounds with Antifungal Activity |
title_full_unstemmed | Laccase Catalyzed Synthesis of Iodinated Phenolic Compounds with Antifungal Activity |
title_short | Laccase Catalyzed Synthesis of Iodinated Phenolic Compounds with Antifungal Activity |
title_sort | laccase catalyzed synthesis of iodinated phenolic compounds with antifungal activity |
topic | Research Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3940670/ https://www.ncbi.nlm.nih.gov/pubmed/24594755 http://dx.doi.org/10.1371/journal.pone.0089924 |
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