Synthesis and in vitro antioxidant and antimicrobial studies of novel structured phosphatidylcholines with phenolic acids

• Published in: Food chemistry 2017-04, Vol.221, p.664-672
• Main Authors: Balakrishna, Marrapu, Kaki, Shiva Shanker, Karuna, Mallampalli S.L., Sarada, Sripada, Kumar, C. Ganesh, Prasad, R.B.N.
• Format: Article
• Language: English
• Subjects: Anti-Infective Agents - therapeutic use; Antimicrobial; Antioxidant; Antioxidants - therapeutic use; Hydroxybenzoates - chemical synthesis; Hydroxybenzoates - chemistry; Phenolic acids; Phosphatidylcholines; Phosphatidylcholines - chemical synthesis; Phosphatidylcholines - chemistry; Structured phenolipids
• ISSN: 0308-8146; 1873-7072
• DOI: 10.1016/j.foodchem.2016.11.121

•First synthesis of novel phenolic acid based phosphatidylcholines (PC).•PCs and ferulic, sinapic, vanillic, syringic acids were selected for the study.•Chemo-enzymatic synthesis of novel structured phenolic phospholipids is described.•The products can find potential applications as novel antioxidants. Novel phenoylated phosphatidylcholines were synthesized from 1,2-dipalmitoyl phosphatidylcholine/egg 1,2-diacyl phosphatidylcholine and phenolic acids such as ferulic, sinapic, vanillic and syringic acids. The structures of phenoylated phosphatidylcholines were confirmed by spectral analysis. 2-acyl-1-lyso phosphatidylcholine was synthesized from phosphatidylcholine via regioselective enzymatic hydrolysis and was reacted with hydroxyl protected phenolic acids to produce corresponding phenoylated phosphatidylcholines in 48–56% yields. Deprotection of protected phenoylated phosphatidylcholines resulted in phenoylated phosphatidylcholines in 87–94% yields. The prepared compounds were evaluated for their preliminary in vitro antimicrobial and antioxidant activities. Among the active derivatives, compound 1-(4-hydroxy-3,5-dimethoxy) cinnamoyl-2-acyl-sn-glycero-3-phosphocholine exhibited excellent antioxidant activity with EC50 value of 16.43μg/mL. Compounds 1-(4-hydroxy-3-methoxy) cinnamoyl-2-acyl-sn-glycero-3-phosphocholine and 1-(4-hydroxy-3,5-dimethoxy) cinnamoyl-2-palmitoyl-sn-glycero-3-phosphocholine exhibited good antioxidant activity with EC50 values of 36.05 and 33.35μg/mL respectively. Compound 1-(4-hydroxy-3-methoxy) cinnamoyl-2-palmitoyl-sn-glycero-3-phosphocholine exhibited good antibacterial activity against Klebsiella planticola with MIC of 15.6μg/mL and compound 1-(4-hydroxy-3-methoxy) benzoyl-2-acyl-sn-glycero-3-phosphocholine exhibited good antifungal activity against Candida albicans with MIC of 15.6μg/mL.