Synthesis and Antiradical Activity of Isoquercitrin Esters with Aromatic Acids and Their Homologues
Isoquercitrin, (IQ, quercetin-3-O-beta-D-glucopyranoside) is known for strong chemoprotectant activities. Acylation of flavonoid glucosides with carboxylic acids containing an aromatic ring brings entirely new properties to these compounds. Here, we describe the chemical and enzymatic synthesis of a...
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ftczacademyscien:oai:asep.lib.cas.cz:CavUnEpca/0476153 2024-09-15T17:44:34+00:00 Synthesis and Antiradical Activity of Isoquercitrin Esters with Aromatic Acids and Their Homologues Heřmánková, E. (Eva) Křenková, A. (Alena) Petrásková, L. (Lucie) Chambers, Christopher S. Zápal, J. (Jakub) Kuzma, M. (Marek) Valentová, K. (Kateřina) Křen, V. (Vladimír) 2017 https://doi.org/10.3390/ijms18051074 http://hdl.handle.net/11104/0272685 eng eng doi:10.3390/ijms18051074 urn:pissn: 1422-0067 urn:eissn: 1422-0067 http://hdl.handle.net/11104/0272685 isoquercitrin aromatic acid gallic acid info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion 2017 ftczacademyscien https://doi.org/10.3390/ijms18051074 2024-08-19T05:33:01Z Isoquercitrin, (IQ, quercetin-3-O-beta-D-glucopyranoside) is known for strong chemoprotectant activities. Acylation of flavonoid glucosides with carboxylic acids containing an aromatic ring brings entirely new properties to these compounds. Here, we describe the chemical and enzymatic synthesis of a series of IQ derivatives at the C-6'. IQ benzoate, phenylacetate, phenylpropanoate and cinnamate were prepared from respective vinyl esters using Novozym 435 (Lipase B from Candida antarctica immobilized on acrylic resin). The enzymatic procedure gave no products with 'hydroxyaromatic' acids, their vinyl esters nor with their benzyl-protected forms. A chemical protection/deprotection method using Steglich reaction yielded IQ 4-hydroxybenzoate, vanillate and gallate. In case of p-coumaric, caffeic, and ferulic acid, the deprotection lead to the saturation of the double bonds at the phenylpropanoic moiety and yielded 4-hydroxy-, 3,4-dihydroxy- and 3-methoxy-4-hydroxy-phenylpropanoates. Reducing capacity of the cinnamate, gallate and 4-hydroxyphenylpropanoate towards Folin-Ciocalteau reagent was significantly lower than that of IQ, while other derivatives displayed slightly better or comparable capacity. Compared to isoquercitrin, most derivatives were less active in 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, but they showed significantly better 2,2 0 -azinobis-(3-ethylbenzothiazoline-6-sulfonic acid, ABTS) scavenging activity and were substantially more active in the inhibition of tert-butylhydroperoxide induced lipid peroxidation of rat liver microsomes. The most active compounds were the hydroxyphenylpropanoates. Article in Journal/Newspaper Antarc* Antarctica The Czech Academy of Sciences: Publication Activity (ASEP) International Journal of Molecular Sciences 18 5 1074 |
institution |
Open Polar |
collection |
The Czech Academy of Sciences: Publication Activity (ASEP) |
op_collection_id |
ftczacademyscien |
language |
English |
topic |
isoquercitrin aromatic acid gallic acid |
spellingShingle |
isoquercitrin aromatic acid gallic acid Heřmánková, E. (Eva) Křenková, A. (Alena) Petrásková, L. (Lucie) Chambers, Christopher S. Zápal, J. (Jakub) Kuzma, M. (Marek) Valentová, K. (Kateřina) Křen, V. (Vladimír) Synthesis and Antiradical Activity of Isoquercitrin Esters with Aromatic Acids and Their Homologues |
topic_facet |
isoquercitrin aromatic acid gallic acid |
description |
Isoquercitrin, (IQ, quercetin-3-O-beta-D-glucopyranoside) is known for strong chemoprotectant activities. Acylation of flavonoid glucosides with carboxylic acids containing an aromatic ring brings entirely new properties to these compounds. Here, we describe the chemical and enzymatic synthesis of a series of IQ derivatives at the C-6'. IQ benzoate, phenylacetate, phenylpropanoate and cinnamate were prepared from respective vinyl esters using Novozym 435 (Lipase B from Candida antarctica immobilized on acrylic resin). The enzymatic procedure gave no products with 'hydroxyaromatic' acids, their vinyl esters nor with their benzyl-protected forms. A chemical protection/deprotection method using Steglich reaction yielded IQ 4-hydroxybenzoate, vanillate and gallate. In case of p-coumaric, caffeic, and ferulic acid, the deprotection lead to the saturation of the double bonds at the phenylpropanoic moiety and yielded 4-hydroxy-, 3,4-dihydroxy- and 3-methoxy-4-hydroxy-phenylpropanoates. Reducing capacity of the cinnamate, gallate and 4-hydroxyphenylpropanoate towards Folin-Ciocalteau reagent was significantly lower than that of IQ, while other derivatives displayed slightly better or comparable capacity. Compared to isoquercitrin, most derivatives were less active in 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, but they showed significantly better 2,2 0 -azinobis-(3-ethylbenzothiazoline-6-sulfonic acid, ABTS) scavenging activity and were substantially more active in the inhibition of tert-butylhydroperoxide induced lipid peroxidation of rat liver microsomes. The most active compounds were the hydroxyphenylpropanoates. |
format |
Article in Journal/Newspaper |
author |
Heřmánková, E. (Eva) Křenková, A. (Alena) Petrásková, L. (Lucie) Chambers, Christopher S. Zápal, J. (Jakub) Kuzma, M. (Marek) Valentová, K. (Kateřina) Křen, V. (Vladimír) |
author_facet |
Heřmánková, E. (Eva) Křenková, A. (Alena) Petrásková, L. (Lucie) Chambers, Christopher S. Zápal, J. (Jakub) Kuzma, M. (Marek) Valentová, K. (Kateřina) Křen, V. (Vladimír) |
author_sort |
Heřmánková, E. (Eva) |
title |
Synthesis and Antiradical Activity of Isoquercitrin Esters with Aromatic Acids and Their Homologues |
title_short |
Synthesis and Antiradical Activity of Isoquercitrin Esters with Aromatic Acids and Their Homologues |
title_full |
Synthesis and Antiradical Activity of Isoquercitrin Esters with Aromatic Acids and Their Homologues |
title_fullStr |
Synthesis and Antiradical Activity of Isoquercitrin Esters with Aromatic Acids and Their Homologues |
title_full_unstemmed |
Synthesis and Antiradical Activity of Isoquercitrin Esters with Aromatic Acids and Their Homologues |
title_sort |
synthesis and antiradical activity of isoquercitrin esters with aromatic acids and their homologues |
publishDate |
2017 |
url |
https://doi.org/10.3390/ijms18051074 http://hdl.handle.net/11104/0272685 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
doi:10.3390/ijms18051074 urn:pissn: 1422-0067 urn:eissn: 1422-0067 http://hdl.handle.net/11104/0272685 |
op_doi |
https://doi.org/10.3390/ijms18051074 |
container_title |
International Journal of Molecular Sciences |
container_volume |
18 |
container_issue |
5 |
container_start_page |
1074 |
_version_ |
1810492212146864128 |