Enzyme mediated-transesterification of verbascoside and evaluation of antifungal activity of synthesised compounds
Enzymatic acylation of verbascoside, a polyhydroxylated natural product, has been reported in this study using five different commercial lipases and taking p -nitrophenyl alkanoates as acyl donors. Out of these enzymes, the immobilised Candida antarctica lipase B was found as the enzyme of choice. M...
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ftdatacite:10.6084/m9.figshare.1254793 2023-05-15T13:39:01+02:00 Enzyme mediated-transesterification of verbascoside and evaluation of antifungal activity of synthesised compounds Jabeena Khazir Intizar Ali Inshad Ali Khan Halmuthur Mahabalarao Sampath Kumar 2015 https://dx.doi.org/10.6084/m9.figshare.1254793 https://tandf.figshare.com/articles/journal_contribution/Enzyme_mediated_transesterification_of_verbascoside_and_evaluation_of_antifungal_activity_of_synthesised_compounds/1254793 unknown Taylor & Francis https://dx.doi.org/10.1080/14786419.2014.984181 Creative Commons Attribution 4.0 International https://creativecommons.org/licenses/by/4.0/legalcode cc-by-4.0 CC-BY Ecology FOS Biological sciences Chemistry Biotechnology Cell Biology Microbiology Biochemistry Text article-journal Journal contribution ScholarlyArticle 2015 ftdatacite https://doi.org/10.6084/m9.figshare.1254793 https://doi.org/10.1080/14786419.2014.984181 2021-11-05T12:55:41Z Enzymatic acylation of verbascoside, a polyhydroxylated natural product, has been reported in this study using five different commercial lipases and taking p -nitrophenyl alkanoates as acyl donors. Out of these enzymes, the immobilised Candida antarctica lipase B was found as the enzyme of choice. Mono- and di-acylated products were formed, with mono as major product indicating high regioselective nature of such transformations. A series of acyl esters of verbascoside have been synthesised by this enzymatic transesterification methodology. The lipophilicity of the synthesised analogues was also checked. The analogues were further subjected to synergistic antifungal activity with amphotericin B (AmB) against Candida albicans. Fourfold reduction in minimum inhibitory concentration of AmB was observed with few synthesised analogues such as verbascoside 4″-octanoate ( 3b ), verbascoside 4″-palmitate ( 3d ) and verbascoside 4″,4′-dipalmitate ( 4d ) at a concentration of 0.5 μg/mL. Text Antarc* Antarctica DataCite Metadata Store (German National Library of Science and Technology) |
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Ecology FOS Biological sciences Chemistry Biotechnology Cell Biology Microbiology Biochemistry |
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Ecology FOS Biological sciences Chemistry Biotechnology Cell Biology Microbiology Biochemistry Jabeena Khazir Intizar Ali Inshad Ali Khan Halmuthur Mahabalarao Sampath Kumar Enzyme mediated-transesterification of verbascoside and evaluation of antifungal activity of synthesised compounds |
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Ecology FOS Biological sciences Chemistry Biotechnology Cell Biology Microbiology Biochemistry |
description |
Enzymatic acylation of verbascoside, a polyhydroxylated natural product, has been reported in this study using five different commercial lipases and taking p -nitrophenyl alkanoates as acyl donors. Out of these enzymes, the immobilised Candida antarctica lipase B was found as the enzyme of choice. Mono- and di-acylated products were formed, with mono as major product indicating high regioselective nature of such transformations. A series of acyl esters of verbascoside have been synthesised by this enzymatic transesterification methodology. The lipophilicity of the synthesised analogues was also checked. The analogues were further subjected to synergistic antifungal activity with amphotericin B (AmB) against Candida albicans. Fourfold reduction in minimum inhibitory concentration of AmB was observed with few synthesised analogues such as verbascoside 4″-octanoate ( 3b ), verbascoside 4″-palmitate ( 3d ) and verbascoside 4″,4′-dipalmitate ( 4d ) at a concentration of 0.5 μg/mL. |
format |
Text |
author |
Jabeena Khazir Intizar Ali Inshad Ali Khan Halmuthur Mahabalarao Sampath Kumar |
author_facet |
Jabeena Khazir Intizar Ali Inshad Ali Khan Halmuthur Mahabalarao Sampath Kumar |
author_sort |
Jabeena Khazir |
title |
Enzyme mediated-transesterification of verbascoside and evaluation of antifungal activity of synthesised compounds |
title_short |
Enzyme mediated-transesterification of verbascoside and evaluation of antifungal activity of synthesised compounds |
title_full |
Enzyme mediated-transesterification of verbascoside and evaluation of antifungal activity of synthesised compounds |
title_fullStr |
Enzyme mediated-transesterification of verbascoside and evaluation of antifungal activity of synthesised compounds |
title_full_unstemmed |
Enzyme mediated-transesterification of verbascoside and evaluation of antifungal activity of synthesised compounds |
title_sort |
enzyme mediated-transesterification of verbascoside and evaluation of antifungal activity of synthesised compounds |
publisher |
Taylor & Francis |
publishDate |
2015 |
url |
https://dx.doi.org/10.6084/m9.figshare.1254793 https://tandf.figshare.com/articles/journal_contribution/Enzyme_mediated_transesterification_of_verbascoside_and_evaluation_of_antifungal_activity_of_synthesised_compounds/1254793 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
https://dx.doi.org/10.1080/14786419.2014.984181 |
op_rights |
Creative Commons Attribution 4.0 International https://creativecommons.org/licenses/by/4.0/legalcode cc-by-4.0 |
op_rightsnorm |
CC-BY |
op_doi |
https://doi.org/10.6084/m9.figshare.1254793 https://doi.org/10.1080/14786419.2014.984181 |
_version_ |
1766114040517492736 |