An international research team has discovered a new molecule with potential to revolutionize the biosurfactant market.
Led by Professor Charles Gauthier from the Institut national de la recherche scientifique (INRS), the team characterized a new biosurfactant in a study published in Chemical Science, the Royal Society of Chemistry’s flagship journal. Surfactants are synthesized from petroleum and are the main active ingredient in most soaps, detergents, and shampoos. Biosurfactants, produced by bacteria, are safer and can replace synthetic surfactants.
Rhamnolipid molecules are some of the safest surfactants known and are particularly attractive, thanks to their biodegradability, minimal toxicity, and amenability to be produced from industrial waste. But there’s a problem. They are made using Pseudomonas aeruginosa, a pathogenic bacterium harmful to humans.
“If we want to fully gain the benefits of rhamnolipids, we need to grow these pathogenic bacteria on a huge scale. And because that’s a health risk, the industry is looking for alternatives.”Charles Gauthier, specialist in chemistry of carbohydrates and natural products
The molecules produced by these bacteria are usually mixed with other compounds or virulence factors, making them trickier to use.
To address the problem, the research team identified molecules that resemble rhamnolipids in Pantoea ananatis, a non-pathogenic bacterium. The team was then able to chemically synthesize these molecules, called ananatosides, in the laboratory, raising the possibility that they could be produced on a larger scale than using bacteria. The industry is already showing interest in these promising new biosurfactants.
The new molecule comes in two different forms, A and B. Ananatoside A structure is described as closed, while B is open. The molecule A is closed in on itself to form a loop. The process that closes the loop is called lactonization, and it has also been achieved with rhamnolipids to create new molecules.
The team has shown that the lactonized form has a large impact on the biological action of the molecules. It minimizes the surface-active properties of rhamnolipids and renders them toxic. Now the researchers want to characterize further new biosurfactants and make the molecules more stable.
INRS professor Éric Déziel helped with the research as an expert on biosurfactants. His team produced and isolated ananatosides produced naturally from the bacteria Pantoea.
Mayri Alejandra Dìaz De Rienzo, a lecturer at the Liverpool John Moores University in England, also took part as an INRS guest professor. Her expertise in the fermentation and downstream processing of biosurfactants helped the team identify the surface-active properties of these new biosurfactants.
Maude Cloutier, a PhD student and recipient of a Vanier Canada Graduate Scholarship, and Marie-Joëlle Prévost, a recipient of a summer scholarship from the Natural Sciences and Engineering Research Council of Canada (NSERC), aided the team with their chemical synthesis work in the laboratory.
The article “Total synthesis, isolation, surfactant properties, and biological evaluation of ananatosides and related macrodilactone-containing rhamnolipids“, by Maude Cloutier, Marie-Joëlle Prévost, Serge Lavoie, Thomas Feroldi, Marianne Piochon, Marie-Christine Groleau, Jean Legault, Sandra Villaume, Jérôme Crouzet, Stéphan Dorey, Mayri Alejandra Dìaz De Rienzo, Eric Déziel and Charles Gauthier, was published May 4 in the journal Chemical Science. The study received financial support from the Natural Sciences and Engineering Research Council of Canada (NSERC), the Fonds de recherche du Québec – Santé (FRQS), the Fonds de recherche du Québec – Nature et technologies (FRQNT), the Centre national de la recherche scientifique (CNRS) and the ministère français de l’Enseignement supérieur, de la Recherche et de l’Innovation.
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