Synthesis and physico-chemical characterization of fatty esters

Poster (2012, November 16)

Specific antioxidant molecules (e.g. phenolics) help to prevent oxidation reaction of the cell membrane. A fatty chain grafted on these compounds should enhance their capacity to interact with the ... [more ▼]

Specific antioxidant molecules (e.g. phenolics) help to prevent oxidation reaction of the cell membrane. A fatty chain grafted on these compounds should enhance their capacity to interact with the membrane lipids. In our study, three fatty esters comprising an aromatic part were synthesized. They differentiate the aromatic substituent and the number of carbons between the aromatic ring and the ester function. A structure-function relationships study was performed to identify the structural pattern affecting the interfacial properties and the membrane interaction properties. The behavior of their monolayer film at an air-water interface was studied. The interactions with membrane were assessed on living cells and were predicted by a computational approach. In the future, we will investigate the effect of the presence of a sugar unit on these molecules. [less ▲]

Towards the synthesis of mannose derivatives of natural phenolic compounds

Poster (2010, October 14)

The aim of this project is to graft a sugar moiety onto polyfunctional natural phenolic compounds. This should enhance their water solubility. The choice of an adequate sugar such as mannose could provide ... [more ▼]

The aim of this project is to graft a sugar moiety onto polyfunctional natural phenolic compounds. This should enhance their water solubility. The choice of an adequate sugar such as mannose could provide cellular recognition. The synthesis route was first tested on cinnamyl alcohol which is structurally close to the base pattern of natural phenolic compounds. Two compounds are tested to catalyse the glycosilation between cinnamyl alcohol and D-mannose. The first one is an enzyme, the -glucosidase from almond, and the second one is a mineral acid catalyst immobilized on silica. Results show that -glucosidase is able to synthetize cinnamyl mannoside from mannose and cinnamyl alcohol. Furthermore, enzyme-catalyzed route lead to only one product and is so more specific than the chemical route where several products are observed. The obtaining of one product with a unique structure is interesting for the fundamental study of structure-function relationships (Interaction of the product with model membranes by Isothermal Titration Calorymetry and with the Langmuir Trough technique). In a future work, the reaction will be tested with more complex molecules (for example coniferyl alcohol). [less ▲]