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Etude d'une famille de diterpènes d'origine naturelle ayant une activité anti-inflammatoire

Abstract : Andrographis paniculata is an Asian Echinacea. This plant is widely used in traditionnal remedies and folkloric medicines for thousands years and is reported to possess a wide spectrum of biological activities. A large number of diterpenoid ent-labdanes have been isolated from this plant, where the major compound is andrographolide, a diterpenoid lactone, that exhibits interesting anti-inflammatory activities on the NFB way. In order to understand and improve the anti-inflammatory activity of these compounds, we implemented a program aimed at their study. Qualitative analysis of crude extracts from dietary supplements allowed to obtain three major natural compounds, which were in a second time chemically modified. These products, as well as the crude extracts, where the composition was determined by a quantitative method, were used for the study of anti-inflammatory activity. Our aim was also to modify andrographolide on some positions not accessible by hemisynthesis. So total and enantioselective synthesis of andrographolide was investigated. Two ways were studied: biomimetic pathway, and modification of a bicyclic precursor that already possessed the ent-labdane configuration (Wieland-Miescher ketone). Methodology using Wieland-Miescher ketone was divided in three parts (enantioselective cyclisation, cycle A functionalisation, cycle B functionalisation). By this way, the bicyclic core was successfully functionnalised and analogues of andrographolide were prepared.
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Submitted on : Thursday, April 12, 2012 - 8:17:14 AM
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  • HAL Id : tel-00687029, version 1



Emmanuelle Villedieu Villedieu-Percheron. Etude d'une famille de diterpènes d'origine naturelle ayant une activité anti-inflammatoire. Autre. Université d'Orléans, 2011. Français. ⟨NNT : 2011ORLE2046⟩. ⟨tel-00687029⟩



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