Extraction, identification, characterization of biological activities of Nitraria retusa flavonoids and enzymatic synthesis of acylated derivatives of these molecules
The present work firstly consisted in studying the extraction and the identification of major flavonoids contained in Nitraria retusa leaves and evaluating their biological activities. Four flavonoids were identified in extracts and fractions: isorhamnetin, isorhamnetin-3-O-glucoside and the two iso...
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2009
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ftccsdartic:oai:HAL:tel-01748769v1 2023-05-15T13:49:11+02:00 Extraction, identification, characterization of biological activities of Nitraria retusa flavonoids and enzymatic synthesis of acylated derivatives of these molecules Extraction, identification, caractérisation des activités biologiques de flavonoïdes de Nitraria retusa et synthèse de dérivés acylés de ces molécules par voie enzymatique Hadj Salem, Jamila Laboratoire des Sciences du Génie Chimique (LSGC) Institut National Polytechnique de Lorraine (INPL)-Centre National de la Recherche Scientifique (CNRS) Institut National Polytechnique de Lorraine Michel Fick Catherine Humeau 2009-10-09 https://hal.univ-lorraine.fr/tel-01748769 https://hal.univ-lorraine.fr/tel-01748769/document https://hal.univ-lorraine.fr/tel-01748769/file/2009_HADJ_SALEM_J.pdf fr fre HAL CCSD NNT: 2009INPL057N tel-01748769 https://hal.univ-lorraine.fr/tel-01748769 https://hal.univ-lorraine.fr/tel-01748769/document https://hal.univ-lorraine.fr/tel-01748769/file/2009_HADJ_SALEM_J.pdf info:eu-repo/semantics/OpenAccess https://hal.univ-lorraine.fr/tel-01748769 Autre. Institut National Polytechnique de Lorraine, 2009. Français. ⟨NNT : 2009INPL057N⟩ Nitraria. retusa Antioxidant activity Antiproliferative activity Enzymatic acylation Flavonoids Nitraria retusa Activité antiproliférative Activité antioxydante Acylation enzymatique Flavonoïdes Flavonö ides Nitraria Acylation [SPI.OTHER]Engineering Sciences [physics]/Other [SDV.AEN]Life Sciences [q-bio]/Food and Nutrition info:eu-repo/semantics/doctoralThesis Theses 2009 ftccsdartic 2021-02-28T01:06:31Z The present work firstly consisted in studying the extraction and the identification of major flavonoids contained in Nitraria retusa leaves and evaluating their biological activities. Four flavonoids were identified in extracts and fractions: isorhamnetin, isorhamnetin-3-O-glucoside and the two isomers isorhamnetin-3-O-rutinoside and isorhamnetin-3-O-robinobioside. The evaluation of the biological activities of extracts and fractions of N. retusa allowed to establish a linear relationship between their antioxidant and antiproliferative activities and their total flavonoids content, the most enriched exhibiting the highest activities. The nature of the flavonoids present in the extracts and fractions was shown to be important too. Thus, the strong xanthine oxidase inhibition activity and the high DPPH radical scavenging capacity observed for the chloroform fraction can be attributed to its high content in the aglycone flavonoid isorhamnetin, a structural analogue of quercetin which is well known for its antioxidant activities. In a second part, the enzymatic acylation of isoquercitrin as a model compound and isorhamnetin-3-O-glucoside was studied in order to improve their properties. The enzymatic acylation of isoquercitrin by fatty acid ethyl esters of different chain lengths, catalyzed by the lipase B of Candida antarctica, showed that the performance of the reaction is inversely proportional to the acyl donor chain length. Similar results were obtained when acylating the isorhamnetin-3-O-glucoside. The activities of isoquercitrin and isorhamnetin-3-O-glucoside esters were determined and compared to that of initial flavonoids. Esters exhibited higher antiproliferative towards Caco2 cells and xanthine oxidase inhibition activities than original compounds. Finally, this work led to a better understanding of the structure-activity relationship of flavonoids and their acylated derivatives Ce travail a consisté, dans un premier temps, à extraire et à identifier les flavonoïdes majeurs contenus dans les feuilles ... Doctoral or Postdoctoral Thesis Antarc* Antarctica Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) |
institution |
Open Polar |
collection |
Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) |
op_collection_id |
ftccsdartic |
language |
French |
topic |
Nitraria. retusa Antioxidant activity Antiproliferative activity Enzymatic acylation Flavonoids Nitraria retusa Activité antiproliférative Activité antioxydante Acylation enzymatique Flavonoïdes Flavonö ides Nitraria Acylation [SPI.OTHER]Engineering Sciences [physics]/Other [SDV.AEN]Life Sciences [q-bio]/Food and Nutrition |
spellingShingle |
Nitraria. retusa Antioxidant activity Antiproliferative activity Enzymatic acylation Flavonoids Nitraria retusa Activité antiproliférative Activité antioxydante Acylation enzymatique Flavonoïdes Flavonö ides Nitraria Acylation [SPI.OTHER]Engineering Sciences [physics]/Other [SDV.AEN]Life Sciences [q-bio]/Food and Nutrition Hadj Salem, Jamila Extraction, identification, characterization of biological activities of Nitraria retusa flavonoids and enzymatic synthesis of acylated derivatives of these molecules |
topic_facet |
Nitraria. retusa Antioxidant activity Antiproliferative activity Enzymatic acylation Flavonoids Nitraria retusa Activité antiproliférative Activité antioxydante Acylation enzymatique Flavonoïdes Flavonö ides Nitraria Acylation [SPI.OTHER]Engineering Sciences [physics]/Other [SDV.AEN]Life Sciences [q-bio]/Food and Nutrition |
description |
The present work firstly consisted in studying the extraction and the identification of major flavonoids contained in Nitraria retusa leaves and evaluating their biological activities. Four flavonoids were identified in extracts and fractions: isorhamnetin, isorhamnetin-3-O-glucoside and the two isomers isorhamnetin-3-O-rutinoside and isorhamnetin-3-O-robinobioside. The evaluation of the biological activities of extracts and fractions of N. retusa allowed to establish a linear relationship between their antioxidant and antiproliferative activities and their total flavonoids content, the most enriched exhibiting the highest activities. The nature of the flavonoids present in the extracts and fractions was shown to be important too. Thus, the strong xanthine oxidase inhibition activity and the high DPPH radical scavenging capacity observed for the chloroform fraction can be attributed to its high content in the aglycone flavonoid isorhamnetin, a structural analogue of quercetin which is well known for its antioxidant activities. In a second part, the enzymatic acylation of isoquercitrin as a model compound and isorhamnetin-3-O-glucoside was studied in order to improve their properties. The enzymatic acylation of isoquercitrin by fatty acid ethyl esters of different chain lengths, catalyzed by the lipase B of Candida antarctica, showed that the performance of the reaction is inversely proportional to the acyl donor chain length. Similar results were obtained when acylating the isorhamnetin-3-O-glucoside. The activities of isoquercitrin and isorhamnetin-3-O-glucoside esters were determined and compared to that of initial flavonoids. Esters exhibited higher antiproliferative towards Caco2 cells and xanthine oxidase inhibition activities than original compounds. Finally, this work led to a better understanding of the structure-activity relationship of flavonoids and their acylated derivatives Ce travail a consisté, dans un premier temps, à extraire et à identifier les flavonoïdes majeurs contenus dans les feuilles ... |
author2 |
Laboratoire des Sciences du Génie Chimique (LSGC) Institut National Polytechnique de Lorraine (INPL)-Centre National de la Recherche Scientifique (CNRS) Institut National Polytechnique de Lorraine Michel Fick Catherine Humeau |
format |
Doctoral or Postdoctoral Thesis |
author |
Hadj Salem, Jamila |
author_facet |
Hadj Salem, Jamila |
author_sort |
Hadj Salem, Jamila |
title |
Extraction, identification, characterization of biological activities of Nitraria retusa flavonoids and enzymatic synthesis of acylated derivatives of these molecules |
title_short |
Extraction, identification, characterization of biological activities of Nitraria retusa flavonoids and enzymatic synthesis of acylated derivatives of these molecules |
title_full |
Extraction, identification, characterization of biological activities of Nitraria retusa flavonoids and enzymatic synthesis of acylated derivatives of these molecules |
title_fullStr |
Extraction, identification, characterization of biological activities of Nitraria retusa flavonoids and enzymatic synthesis of acylated derivatives of these molecules |
title_full_unstemmed |
Extraction, identification, characterization of biological activities of Nitraria retusa flavonoids and enzymatic synthesis of acylated derivatives of these molecules |
title_sort |
extraction, identification, characterization of biological activities of nitraria retusa flavonoids and enzymatic synthesis of acylated derivatives of these molecules |
publisher |
HAL CCSD |
publishDate |
2009 |
url |
https://hal.univ-lorraine.fr/tel-01748769 https://hal.univ-lorraine.fr/tel-01748769/document https://hal.univ-lorraine.fr/tel-01748769/file/2009_HADJ_SALEM_J.pdf |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
https://hal.univ-lorraine.fr/tel-01748769 Autre. Institut National Polytechnique de Lorraine, 2009. Français. ⟨NNT : 2009INPL057N⟩ |
op_relation |
NNT: 2009INPL057N tel-01748769 https://hal.univ-lorraine.fr/tel-01748769 https://hal.univ-lorraine.fr/tel-01748769/document https://hal.univ-lorraine.fr/tel-01748769/file/2009_HADJ_SALEM_J.pdf |
op_rights |
info:eu-repo/semantics/OpenAccess |
_version_ |
1766250978631221248 |