Synthesis of Lysoglycerophosphocholines from Crude Soybean Lecithins as Sustainable and Non-toxic Antifouling Agents against the Golden Mussel Limnoperna fortunei

Abstract

This research aimed to produce, on a multigram scale, a new class of non-toxic, halogen- and metal-free antifouling agents from the abundant lecithin byproducts of industrial soybean oil extraction. Three glycerophospholipid analogues were prepared by a facile methanolysis of crude soybean lecithins and a subsequent solvent-free O-alkylation: lysoglycerophosphocholines (LGPCs) and its ether derivatives O-alkyl lysoglycerophosphocholines (ALPCs). As efficient antiproliferative agents, LGPCs and ALPCs are an eco-friendly alternative to current commercial antifoulants which possess significant toxicity to aquatic life. In situ immersion tests of coated stainless-steel nets with previously incorporated automotive paint products, LGPCs and ALPCs (1-O-octadecyl-2-O-acyl-sn-glycero-3-phosphocholine, ALPC18, and 1-O-hexadecyl-2-O-acyl-sn-glycero-3-phosphocholine, ALPC16), in an aquaculture reservoir in SP-Brazil revealed significant growth inhibition against macrofouling species, especially the epibiotic golden mussel (Limnoperna fortunei), when compared with the control. These results promise a more sustainable and ecologically innocuous approach to combating the biofouling phenomenon and the deeply concerning dissemination of the golden mussel which has provoked an economic crisis in the energy and aquaculture sectors.