L-Rhamnose and Phenolic Esters-Based Monocatenar and Bolaform Amphiphiles: Eco-Compatible Synthesis and Determination of Their Antioxidant, Eliciting and Cytotoxic Properties
Emad Kordkatooli,
Katia Bacha,
Sandra Villaume,
Stephan Dorey,
Jean-Claude Monboisse,
Sylvie Brassart-Pasco,
Jean-Pierre Mbakidi,
Sandrine Bouquillon
Affiliations
Emad Kordkatooli
Molecular Chemistry Reims Institute UMR CNRS 7312, Reims Champagne-Ardenne University, Boîte n° 44, B.P. 1039, 51687 Reims, France
Katia Bacha
Molecular Chemistry Reims Institute UMR CNRS 7312, Reims Champagne-Ardenne University, Boîte n° 44, B.P. 1039, 51687 Reims, France
Sandra Villaume
RIBP—USC INRAE 1488, Université de Reims Champagne-Ardenne Reims, 51100 Reims, France
Stephan Dorey
RIBP—USC INRAE 1488, Université de Reims Champagne-Ardenne Reims, 51100 Reims, France
Jean-Claude Monboisse
Laboratoire de Biochimie Médicale et de Biologie Moléculaire, UMR CNRS/URCA 7369—Reims Champagne Ardenne University, UFR Médecine, 51 Rue Cognacq Jay, 51095 Reims, France
Sylvie Brassart-Pasco
Laboratoire de Biochimie Médicale et de Biologie Moléculaire, UMR CNRS/URCA 7369—Reims Champagne Ardenne University, UFR Médecine, 51 Rue Cognacq Jay, 51095 Reims, France
Jean-Pierre Mbakidi
Molecular Chemistry Reims Institute UMR CNRS 7312, Reims Champagne-Ardenne University, Boîte n° 44, B.P. 1039, 51687 Reims, France
Sandrine Bouquillon
Molecular Chemistry Reims Institute UMR CNRS 7312, Reims Champagne-Ardenne University, Boîte n° 44, B.P. 1039, 51687 Reims, France
Symmetrical and dissymmetrical bolaforms were prepared with good to high yields from unsaturated L-rhamnosides and phenolic esters (ferulic, phloretic, coumaric, sinapic and caffeic) using two eco-compatible synthetic strategies involving glycosylation, enzymatic synthesis and cross-metathesis under microwave activation. The plant-eliciting activity of these new compounds was investigated in Arabidopsis model plants. We found that the monocatenar rhamnosides and bolaforms activate the plant immune system with a response depending on the carbon chain length and the nature of the hydrophilic heads. Their respective antioxidant activities were also evaluated, as well as their cytotoxic properties on dermal cells for cosmetic uses. We showed that phenolic ester-based compounds present good antioxidant activities and that their cytotoxicity is low. These properties are also dependent on the carbon chains used.
