Enzymatic Production of Lauroyl and Stearoyl Monoesters of <span style="font-variant: small-caps">d</span>-Xylose, <span style="font-variant: small-caps">l</span>-Arabinose, and <span style="font-variant: small-caps">d</span>-Glucose as Potential Lignocellulosic-Derived Products, and Their Evaluation as Antimicrobial Agents
Forestry and agricultural industries constitute highly relevant economic activities globally. They generate large amounts of residues rich in lignocellulose that have the potential to be valorized and used in different industrial processes. Producing renewable fuels and high-value-added compounds fr...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-06-01
|
| Series: | Catalysts |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2073-4344/12/6/610 |
| _version_ | 1797489038991556608 |
|---|---|
| author | Victoria Giorgi Emiliana Botto Carolina Fontana Luca Della Mea Silvio Vaz Pilar Menéndez Paula Rodríguez |
| author_facet | Victoria Giorgi Emiliana Botto Carolina Fontana Luca Della Mea Silvio Vaz Pilar Menéndez Paula Rodríguez |
| author_sort | Victoria Giorgi |
| collection | DOAJ |
| description | Forestry and agricultural industries constitute highly relevant economic activities globally. They generate large amounts of residues rich in lignocellulose that have the potential to be valorized and used in different industrial processes. Producing renewable fuels and high-value-added compounds from lignocellulosic biomass is a key aspect of sustainable strategies and is central to the biorefinery concept. In this study, the use of biomass-derived monosaccharides for the enzymatic synthesis of sugar fatty acid esters (SFAEs) with antimicrobial activity was investigated to valorize these agro-industrial residues. With the aim to evaluate if lignocellulosic monosaccharides could be substrates for the synthesis of SFAEs, <span style="font-variant: small-caps;">d</span>-xylose, <span style="font-variant: small-caps;">l</span>-arabinose, and <span style="font-variant: small-caps;">d</span>-glucose, lauroyl and stearoyl monoesters were synthetized by transesterification reactions catalyzed by Lipozyme RM IM as biocatalyst. The reactions were performed using commercial <span style="font-variant: small-caps;">d</span>-xylose, <span style="font-variant: small-caps;">l</span>-arabinose, and <span style="font-variant: small-caps;">d</span>-glucose separately as substrates, and a 74:13:13 mixture of these sugars. The proportion of monosaccharides in the latter mixture corresponds to the composition found in hemicellulose from sugarcane bagasse and switchgrass, as previously described in the literature. Products were characterized using nuclear magnetic resonance (NMR) spectroscopy and showed that only the primary hydroxyl group of these monosaccharides is involved in the esterification reaction. Antimicrobial activity assay using several microorganisms showed that 5-<i>O</i>-lauroyl-<span style="font-variant: small-caps;">d</span>-xylofuranose and 5-<i>O</i>-lauroyl-<span style="font-variant: small-caps;">l</span>-arabinofuranose have the ability to inhibit the growth of Gram-positive bacteria separately and in the products mix. Furthermore, 5-<i>O</i>-lauroyl-<span style="font-variant: small-caps;">l</span>-arabinofuranose was the only product that exhibited activity against <i>Candida albicans</i> yeast, and the four tested filamentous fungi. These results suggest that sugar fatty acid esters obtained from sustainable and renewable resources and produced by green methods are promising antimicrobial agents. |
| first_indexed | 2024-03-10T00:10:49Z |
| format | Article |
| id | doaj.art-219cf8c515ac4461a62967e0324d6724 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T00:10:49Z |
| publishDate | 2022-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-219cf8c515ac4461a62967e0324d67242023-11-23T15:59:18ZengMDPI AGCatalysts2073-43442022-06-0112661010.3390/catal12060610Enzymatic Production of Lauroyl and Stearoyl Monoesters of <span style="font-variant: small-caps">d</span>-Xylose, <span style="font-variant: small-caps">l</span>-Arabinose, and <span style="font-variant: small-caps">d</span>-Glucose as Potential Lignocellulosic-Derived Products, and Their Evaluation as Antimicrobial AgentsVictoria Giorgi0Emiliana Botto1Carolina Fontana2Luca Della Mea3Silvio Vaz4Pilar Menéndez5Paula Rodríguez6Laboratorio de Biocatálisis y Biotransformaciones, Departamento de Biociencias y Departamento de Química Orgánica, Universidad de la República, Gral. Flores 2124, Montevideo 11800, UruguayLaboratorio de Biocatálisis y Biotransformaciones, Departamento de Biociencias y Departamento de Química Orgánica, Universidad de la República, Gral. Flores 2124, Montevideo 11800, UruguayLaboratorio de Espectroscopía y Fisicoquímica Orgánica, Departamento de Química del Litoral, CENUR Litoral Norte (S.R.A. Facultad de Química), UdelaR, Ruta 3 km 363, Paysandú 60000, UruguayLaboratorio de Biocatálisis y Biotransformaciones, Departamento de Biociencias y Departamento de Química Orgánica, Universidad de la República, Gral. Flores 2124, Montevideo 11800, UruguayBrazilian Agricultural Research Corporation, National Research Center for Agroenergy (Embrapa Agroenergy) Embrapa Agroenergia, Parque Estação Biológica, Brasília 70770-901, BrazilLaboratorio de Biocatálisis y Biotransformaciones, Departamento de Biociencias y Departamento de Química Orgánica, Universidad de la República, Gral. Flores 2124, Montevideo 11800, UruguayLaboratorio de Biocatálisis y Biotransformaciones, Departamento de Biociencias y Departamento de Química Orgánica, Universidad de la República, Gral. Flores 2124, Montevideo 11800, UruguayForestry and agricultural industries constitute highly relevant economic activities globally. They generate large amounts of residues rich in lignocellulose that have the potential to be valorized and used in different industrial processes. Producing renewable fuels and high-value-added compounds from lignocellulosic biomass is a key aspect of sustainable strategies and is central to the biorefinery concept. In this study, the use of biomass-derived monosaccharides for the enzymatic synthesis of sugar fatty acid esters (SFAEs) with antimicrobial activity was investigated to valorize these agro-industrial residues. With the aim to evaluate if lignocellulosic monosaccharides could be substrates for the synthesis of SFAEs, <span style="font-variant: small-caps;">d</span>-xylose, <span style="font-variant: small-caps;">l</span>-arabinose, and <span style="font-variant: small-caps;">d</span>-glucose, lauroyl and stearoyl monoesters were synthetized by transesterification reactions catalyzed by Lipozyme RM IM as biocatalyst. The reactions were performed using commercial <span style="font-variant: small-caps;">d</span>-xylose, <span style="font-variant: small-caps;">l</span>-arabinose, and <span style="font-variant: small-caps;">d</span>-glucose separately as substrates, and a 74:13:13 mixture of these sugars. The proportion of monosaccharides in the latter mixture corresponds to the composition found in hemicellulose from sugarcane bagasse and switchgrass, as previously described in the literature. Products were characterized using nuclear magnetic resonance (NMR) spectroscopy and showed that only the primary hydroxyl group of these monosaccharides is involved in the esterification reaction. Antimicrobial activity assay using several microorganisms showed that 5-<i>O</i>-lauroyl-<span style="font-variant: small-caps;">d</span>-xylofuranose and 5-<i>O</i>-lauroyl-<span style="font-variant: small-caps;">l</span>-arabinofuranose have the ability to inhibit the growth of Gram-positive bacteria separately and in the products mix. Furthermore, 5-<i>O</i>-lauroyl-<span style="font-variant: small-caps;">l</span>-arabinofuranose was the only product that exhibited activity against <i>Candida albicans</i> yeast, and the four tested filamentous fungi. These results suggest that sugar fatty acid esters obtained from sustainable and renewable resources and produced by green methods are promising antimicrobial agents.https://www.mdpi.com/2073-4344/12/6/610hemicellulosemonosaccharidebiocatalysistransesterificationsugar fatty acid estersantibacterial |
| spellingShingle | Victoria Giorgi Emiliana Botto Carolina Fontana Luca Della Mea Silvio Vaz Pilar Menéndez Paula Rodríguez Enzymatic Production of Lauroyl and Stearoyl Monoesters of <span style="font-variant: small-caps">d</span>-Xylose, <span style="font-variant: small-caps">l</span>-Arabinose, and <span style="font-variant: small-caps">d</span>-Glucose as Potential Lignocellulosic-Derived Products, and Their Evaluation as Antimicrobial Agents Catalysts hemicellulose monosaccharide biocatalysis transesterification sugar fatty acid esters antibacterial |
| title | Enzymatic Production of Lauroyl and Stearoyl Monoesters of <span style="font-variant: small-caps">d</span>-Xylose, <span style="font-variant: small-caps">l</span>-Arabinose, and <span style="font-variant: small-caps">d</span>-Glucose as Potential Lignocellulosic-Derived Products, and Their Evaluation as Antimicrobial Agents |
| title_full | Enzymatic Production of Lauroyl and Stearoyl Monoesters of <span style="font-variant: small-caps">d</span>-Xylose, <span style="font-variant: small-caps">l</span>-Arabinose, and <span style="font-variant: small-caps">d</span>-Glucose as Potential Lignocellulosic-Derived Products, and Their Evaluation as Antimicrobial Agents |
| title_fullStr | Enzymatic Production of Lauroyl and Stearoyl Monoesters of <span style="font-variant: small-caps">d</span>-Xylose, <span style="font-variant: small-caps">l</span>-Arabinose, and <span style="font-variant: small-caps">d</span>-Glucose as Potential Lignocellulosic-Derived Products, and Their Evaluation as Antimicrobial Agents |
| title_full_unstemmed | Enzymatic Production of Lauroyl and Stearoyl Monoesters of <span style="font-variant: small-caps">d</span>-Xylose, <span style="font-variant: small-caps">l</span>-Arabinose, and <span style="font-variant: small-caps">d</span>-Glucose as Potential Lignocellulosic-Derived Products, and Their Evaluation as Antimicrobial Agents |
| title_short | Enzymatic Production of Lauroyl and Stearoyl Monoesters of <span style="font-variant: small-caps">d</span>-Xylose, <span style="font-variant: small-caps">l</span>-Arabinose, and <span style="font-variant: small-caps">d</span>-Glucose as Potential Lignocellulosic-Derived Products, and Their Evaluation as Antimicrobial Agents |
| title_sort | enzymatic production of lauroyl and stearoyl monoesters of span style font variant small caps d span xylose span style font variant small caps l span arabinose and span style font variant small caps d span glucose as potential lignocellulosic derived products and their evaluation as antimicrobial agents |
| topic | hemicellulose monosaccharide biocatalysis transesterification sugar fatty acid esters antibacterial |
| url | https://www.mdpi.com/2073-4344/12/6/610 |
| work_keys_str_mv | AT victoriagiorgi enzymaticproductionoflauroylandstearoylmonoestersofspanstylefontvariantsmallcapsdspanxylosespanstylefontvariantsmallcapslspanarabinoseandspanstylefontvariantsmallcapsdspanglucoseaspotentiallignocellulosicderivedproductsandtheirevaluationasantimicrobialage AT emilianabotto enzymaticproductionoflauroylandstearoylmonoestersofspanstylefontvariantsmallcapsdspanxylosespanstylefontvariantsmallcapslspanarabinoseandspanstylefontvariantsmallcapsdspanglucoseaspotentiallignocellulosicderivedproductsandtheirevaluationasantimicrobialage AT carolinafontana enzymaticproductionoflauroylandstearoylmonoestersofspanstylefontvariantsmallcapsdspanxylosespanstylefontvariantsmallcapslspanarabinoseandspanstylefontvariantsmallcapsdspanglucoseaspotentiallignocellulosicderivedproductsandtheirevaluationasantimicrobialage AT lucadellamea enzymaticproductionoflauroylandstearoylmonoestersofspanstylefontvariantsmallcapsdspanxylosespanstylefontvariantsmallcapslspanarabinoseandspanstylefontvariantsmallcapsdspanglucoseaspotentiallignocellulosicderivedproductsandtheirevaluationasantimicrobialage AT silviovaz enzymaticproductionoflauroylandstearoylmonoestersofspanstylefontvariantsmallcapsdspanxylosespanstylefontvariantsmallcapslspanarabinoseandspanstylefontvariantsmallcapsdspanglucoseaspotentiallignocellulosicderivedproductsandtheirevaluationasantimicrobialage AT pilarmenendez enzymaticproductionoflauroylandstearoylmonoestersofspanstylefontvariantsmallcapsdspanxylosespanstylefontvariantsmallcapslspanarabinoseandspanstylefontvariantsmallcapsdspanglucoseaspotentiallignocellulosicderivedproductsandtheirevaluationasantimicrobialage AT paularodriguez enzymaticproductionoflauroylandstearoylmonoestersofspanstylefontvariantsmallcapsdspanxylosespanstylefontvariantsmallcapslspanarabinoseandspanstylefontvariantsmallcapsdspanglucoseaspotentiallignocellulosicderivedproductsandtheirevaluationasantimicrobialage |