Improved enzyme-mediated synthesis and supramolecular self-assembly of naturally occurring conjugates of beta-sitosterol
Naturally occurring acylated beta-sitostetyl glucosides have been investigated for their novel properties. The synthetic protocol based on the literature data was improved and optimized. The main improveinent consists in employing systems of ionic liquids combined with organic solvents in lipase-med...
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Online Access: | https://doi.org/10.1016/j.steroids.2016.09.009 http://hdl.handle.net/11104/0271064 |
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ftczacademyscien:oai:asep.lib.cas.cz:CavUnEpca/0473961 2024-02-04T09:54:24+01:00 Improved enzyme-mediated synthesis and supramolecular self-assembly of naturally occurring conjugates of beta-sitosterol Wimmerová, M. (Martina) Siglerová, V. (Věra) Šaman, D. (David) Šlouf, M. (Miroslav) Kaletová, E. (Eva) Wimmer, Z. (Zdeněk) 2017 https://doi.org/10.1016/j.steroids.2016.09.009 http://hdl.handle.net/11104/0271064 eng eng doi:10.1016/j.steroids.2016.09.009 urn:pissn: 0039-128x urn:eissn: 1878-5867 http://hdl.handle.net/11104/0271064 info:eu-repo/semantics/openAccess glycosides esterification resolution sterols esters foods l beta-Sitosterol Acylated steryl glycoside Lipase Ionic liquid Supramolecular self-assembly Pharmacological activity info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion 2017 ftczacademyscien https://doi.org/10.1016/j.steroids.2016.09.009 2024-01-09T17:38:41Z Naturally occurring acylated beta-sitostetyl glucosides have been investigated for their novel properties. The synthetic protocol based on the literature data was improved and optimized. The main improveinent consists in employing systems of ionic liquids combined with organic solvents in lipase-mediated esterification of (3 beta)-stigmast-5-en-3-yl beta-D-glucopyranoside to get (3 beta)-stigmast-5-en-3-yl 6-O-acyl-beta-D-glucopyranosides. Maximum yields of these products were achieved with Candida antarctica lipase B immobilized on Immobead 150, recombinant from yeast, in absolute THE and in the presence of either ionic liquid [1-butyl-3-methyl imidazolium tetrafluoroborate ([BMIM]BF4) or 1-butyl-3-methyl imidazolium hexafluorophosphate ([BMIM]PF6)] employed. Pharmacological activity of (3 beta)-stigmast-5-en3-yl 6-O-acyl-beta-D-glucopyranosides was studied in tests on MCF7 tumor cell lines, the compounds displayed moderate activity which was higher than the activity of B-sitosterol. Supramolecular characteristics were discovered at (3 beta)-stigmast-5-en-3-yl 6-O-dodecanoyl-beta-D-glucopyranoside that formed supramolecular polymer through multiple H-bonds in a methanol/water system (60/40). Its formation was confirmed by the independent UV-vis measurements during certain time period, by variable temperature DOSY-NMR measurement in deuteriochloroform, and visualized by transmission electron microscopy (TEM) and atomic force microscopy (AFM) showing chiral helical structures and complex superassembly systems based on fibrous supramolecular polymer. In contrary, no such properties have been observed for the other two (3 beta)-stigmast-5-en-3-yl 6-O-acyl-beta-D-glucopyranosides under the given experimental conditions. Article in Journal/Newspaper Antarc* Antarctica The Czech Academy of Sciences: Publication Activity (ASEP) Steroids 117 38 43 |
institution |
Open Polar |
collection |
The Czech Academy of Sciences: Publication Activity (ASEP) |
op_collection_id |
ftczacademyscien |
language |
English |
topic |
glycosides esterification resolution sterols esters foods l beta-Sitosterol Acylated steryl glycoside Lipase Ionic liquid Supramolecular self-assembly Pharmacological activity |
spellingShingle |
glycosides esterification resolution sterols esters foods l beta-Sitosterol Acylated steryl glycoside Lipase Ionic liquid Supramolecular self-assembly Pharmacological activity Wimmerová, M. (Martina) Siglerová, V. (Věra) Šaman, D. (David) Šlouf, M. (Miroslav) Kaletová, E. (Eva) Wimmer, Z. (Zdeněk) Improved enzyme-mediated synthesis and supramolecular self-assembly of naturally occurring conjugates of beta-sitosterol |
topic_facet |
glycosides esterification resolution sterols esters foods l beta-Sitosterol Acylated steryl glycoside Lipase Ionic liquid Supramolecular self-assembly Pharmacological activity |
description |
Naturally occurring acylated beta-sitostetyl glucosides have been investigated for their novel properties. The synthetic protocol based on the literature data was improved and optimized. The main improveinent consists in employing systems of ionic liquids combined with organic solvents in lipase-mediated esterification of (3 beta)-stigmast-5-en-3-yl beta-D-glucopyranoside to get (3 beta)-stigmast-5-en-3-yl 6-O-acyl-beta-D-glucopyranosides. Maximum yields of these products were achieved with Candida antarctica lipase B immobilized on Immobead 150, recombinant from yeast, in absolute THE and in the presence of either ionic liquid [1-butyl-3-methyl imidazolium tetrafluoroborate ([BMIM]BF4) or 1-butyl-3-methyl imidazolium hexafluorophosphate ([BMIM]PF6)] employed. Pharmacological activity of (3 beta)-stigmast-5-en3-yl 6-O-acyl-beta-D-glucopyranosides was studied in tests on MCF7 tumor cell lines, the compounds displayed moderate activity which was higher than the activity of B-sitosterol. Supramolecular characteristics were discovered at (3 beta)-stigmast-5-en-3-yl 6-O-dodecanoyl-beta-D-glucopyranoside that formed supramolecular polymer through multiple H-bonds in a methanol/water system (60/40). Its formation was confirmed by the independent UV-vis measurements during certain time period, by variable temperature DOSY-NMR measurement in deuteriochloroform, and visualized by transmission electron microscopy (TEM) and atomic force microscopy (AFM) showing chiral helical structures and complex superassembly systems based on fibrous supramolecular polymer. In contrary, no such properties have been observed for the other two (3 beta)-stigmast-5-en-3-yl 6-O-acyl-beta-D-glucopyranosides under the given experimental conditions. |
format |
Article in Journal/Newspaper |
author |
Wimmerová, M. (Martina) Siglerová, V. (Věra) Šaman, D. (David) Šlouf, M. (Miroslav) Kaletová, E. (Eva) Wimmer, Z. (Zdeněk) |
author_facet |
Wimmerová, M. (Martina) Siglerová, V. (Věra) Šaman, D. (David) Šlouf, M. (Miroslav) Kaletová, E. (Eva) Wimmer, Z. (Zdeněk) |
author_sort |
Wimmerová, M. (Martina) |
title |
Improved enzyme-mediated synthesis and supramolecular self-assembly of naturally occurring conjugates of beta-sitosterol |
title_short |
Improved enzyme-mediated synthesis and supramolecular self-assembly of naturally occurring conjugates of beta-sitosterol |
title_full |
Improved enzyme-mediated synthesis and supramolecular self-assembly of naturally occurring conjugates of beta-sitosterol |
title_fullStr |
Improved enzyme-mediated synthesis and supramolecular self-assembly of naturally occurring conjugates of beta-sitosterol |
title_full_unstemmed |
Improved enzyme-mediated synthesis and supramolecular self-assembly of naturally occurring conjugates of beta-sitosterol |
title_sort |
improved enzyme-mediated synthesis and supramolecular self-assembly of naturally occurring conjugates of beta-sitosterol |
publishDate |
2017 |
url |
https://doi.org/10.1016/j.steroids.2016.09.009 http://hdl.handle.net/11104/0271064 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
doi:10.1016/j.steroids.2016.09.009 urn:pissn: 0039-128x urn:eissn: 1878-5867 http://hdl.handle.net/11104/0271064 |
op_rights |
info:eu-repo/semantics/openAccess |
op_doi |
https://doi.org/10.1016/j.steroids.2016.09.009 |
container_title |
Steroids |
container_volume |
117 |
container_start_page |
38 |
op_container_end_page |
43 |
_version_ |
1789973535237603328 |