Synthesis of lipophilic tyrosyl esters derivatives and assessment of their antimicrobial and antileishmania activities
Abstract Background Preparation of tyrosyl lipophilic derivatives was carried out as a response to the food, cosmetic and pharmaceutical industries' increasing demand for new lipophilic antioxidants. Results A large series of tyrosyl esters ( TyC 2 to TyC 18:1 ) with increasing lipophilicity wa...
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crspringernat:10.1186/1476-511x-11-13 2023-05-15T14:05:42+02:00 Synthesis of lipophilic tyrosyl esters derivatives and assessment of their antimicrobial and antileishmania activities Aissa, Imen Sghair, Rabiaa Manel Bouaziz, Mohamed Laouini, Dhafer Sayadi, Sami Gargouri, Youssef 2012 http://dx.doi.org/10.1186/1476-511x-11-13 https://link.springer.com/content/pdf/10.1186/1476-511X-11-13.pdf en eng Springer Science and Business Media LLC Lipids in Health and Disease volume 11, issue 1 ISSN 1476-511X Biochemistry (medical) Clinical Biochemistry Endocrinology Endocrinology, Diabetes and Metabolism journal-article 2012 crspringernat https://doi.org/10.1186/1476-511x-11-13 2022-01-04T14:51:40Z Abstract Background Preparation of tyrosyl lipophilic derivatives was carried out as a response to the food, cosmetic and pharmaceutical industries' increasing demand for new lipophilic antioxidants. Results A large series of tyrosyl esters ( TyC 2 to TyC 18:1 ) with increasing lipophilicity was synthesized in a good yield using lipase from Candida antarctica (Novozyme 435). Spectroscopic analyses of purified esters showed that the tyrosol was esterified on the primary hydroxyl group. Synthetized compounds were evaluated for either their antimicrobial activity, by both diffusion well and minimal inhibition concentration (MIC) methods, or their antileishmanial activity against Leishmania major and Leishmania infantum parasite species. Among all the tested compounds, our results showed that only TyC 8 , TyC 10 and TyC 12 exhibited antibacterial and antileishmanial activities. When MIC and IC 50 values were plotted against the acyl chain length of each tyrosyl derivative, TyC 10 showed a parabolic shape with a minimum value. This nonlinear dependency with the increase of the chain length indicates that biological activities are probably associated to the surfactant effectiveness of lipophilic derivatives. Conclusion These results open up potential applications to use medium tyrosyl derivatives surfactants, antioxidants, antimicrobial and antileishmanial compounds in cosmetic, food and pharmaceutical industries. Article in Journal/Newspaper Antarc* Antarctica Springer Nature (via Crossref) Lipids in Health and Disease 11 1 |
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Springer Nature (via Crossref) |
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English |
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Biochemistry (medical) Clinical Biochemistry Endocrinology Endocrinology, Diabetes and Metabolism |
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Biochemistry (medical) Clinical Biochemistry Endocrinology Endocrinology, Diabetes and Metabolism Aissa, Imen Sghair, Rabiaa Manel Bouaziz, Mohamed Laouini, Dhafer Sayadi, Sami Gargouri, Youssef Synthesis of lipophilic tyrosyl esters derivatives and assessment of their antimicrobial and antileishmania activities |
topic_facet |
Biochemistry (medical) Clinical Biochemistry Endocrinology Endocrinology, Diabetes and Metabolism |
description |
Abstract Background Preparation of tyrosyl lipophilic derivatives was carried out as a response to the food, cosmetic and pharmaceutical industries' increasing demand for new lipophilic antioxidants. Results A large series of tyrosyl esters ( TyC 2 to TyC 18:1 ) with increasing lipophilicity was synthesized in a good yield using lipase from Candida antarctica (Novozyme 435). Spectroscopic analyses of purified esters showed that the tyrosol was esterified on the primary hydroxyl group. Synthetized compounds were evaluated for either their antimicrobial activity, by both diffusion well and minimal inhibition concentration (MIC) methods, or their antileishmanial activity against Leishmania major and Leishmania infantum parasite species. Among all the tested compounds, our results showed that only TyC 8 , TyC 10 and TyC 12 exhibited antibacterial and antileishmanial activities. When MIC and IC 50 values were plotted against the acyl chain length of each tyrosyl derivative, TyC 10 showed a parabolic shape with a minimum value. This nonlinear dependency with the increase of the chain length indicates that biological activities are probably associated to the surfactant effectiveness of lipophilic derivatives. Conclusion These results open up potential applications to use medium tyrosyl derivatives surfactants, antioxidants, antimicrobial and antileishmanial compounds in cosmetic, food and pharmaceutical industries. |
format |
Article in Journal/Newspaper |
author |
Aissa, Imen Sghair, Rabiaa Manel Bouaziz, Mohamed Laouini, Dhafer Sayadi, Sami Gargouri, Youssef |
author_facet |
Aissa, Imen Sghair, Rabiaa Manel Bouaziz, Mohamed Laouini, Dhafer Sayadi, Sami Gargouri, Youssef |
author_sort |
Aissa, Imen |
title |
Synthesis of lipophilic tyrosyl esters derivatives and assessment of their antimicrobial and antileishmania activities |
title_short |
Synthesis of lipophilic tyrosyl esters derivatives and assessment of their antimicrobial and antileishmania activities |
title_full |
Synthesis of lipophilic tyrosyl esters derivatives and assessment of their antimicrobial and antileishmania activities |
title_fullStr |
Synthesis of lipophilic tyrosyl esters derivatives and assessment of their antimicrobial and antileishmania activities |
title_full_unstemmed |
Synthesis of lipophilic tyrosyl esters derivatives and assessment of their antimicrobial and antileishmania activities |
title_sort |
synthesis of lipophilic tyrosyl esters derivatives and assessment of their antimicrobial and antileishmania activities |
publisher |
Springer Science and Business Media LLC |
publishDate |
2012 |
url |
http://dx.doi.org/10.1186/1476-511x-11-13 https://link.springer.com/content/pdf/10.1186/1476-511X-11-13.pdf |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Lipids in Health and Disease volume 11, issue 1 ISSN 1476-511X |
op_doi |
https://doi.org/10.1186/1476-511x-11-13 |
container_title |
Lipids in Health and Disease |
container_volume |
11 |
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1 |
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1766277577248342016 |