Balakrishna Marrapu, Kaki Shiva Shanker, Karuna Mallampalli S L, Sarada Sripada, Kumar C Ganesh, Prasad R B N
Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad 500007, India; Academy of Scientific and Innovative Research, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India; Academy of Scientific and Innovative Research, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
Food Chem. 2017 Apr 15;221:664-672. doi: 10.1016/j.foodchem.2016.11.121. Epub 2016 Nov 25.
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 EC 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 EC 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.
新型酚酰化磷脂酰胆碱由1,2-二棕榈酰磷脂酰胆碱/鸡蛋1,2-二酰基磷脂酰胆碱与阿魏酸、芥子酸、香草酸和丁香酸等酚酸合成。通过光谱分析确定了酚酰化磷脂酰胆碱的结构。通过区域选择性酶促水解由磷脂酰胆碱合成2-酰基-1-溶血磷脂酰胆碱，并使其与羟基保护的酚酸反应，以48 - 56%的产率生成相应的酚酰化磷脂酰胆碱。保护的酚酰化磷脂酰胆碱脱保护后得到产率为87 - 94%的酚酰化磷脂酰胆碱。对所制备的化合物进行了初步的体外抗菌和抗氧化活性评估。在活性衍生物中，化合物1-(4-羟基-3,5-二甲氧基)肉桂酰-2-酰基-sn-甘油-3-磷酸胆碱表现出优异的抗氧化活性，EC值为16.43μg/mL。化合物1-(4-羟基-3-甲氧基)肉桂酰-2-酰基-sn-甘油-3-磷酸胆碱和1-(4-羟基-3,5-二甲氧基)肉桂酰-2-棕榈酰-sn-甘油-3-磷酸胆碱表现出良好的抗氧化活性，EC值分别为36.05和33.35μg/mL。化合物1-(4-羟基-3-甲氧基)肉桂酰-2-棕榈酰-sn-甘油-3-磷酸胆碱对植物源克雷伯氏菌表现出良好的抗菌活性，MIC为15.6μg/mL，化合物1-(4-羟基-3-甲氧基)苯甲酰-2-酰基-sn-甘油-3-磷酸胆碱对白色念珠菌表现出良好的抗真菌活性，MIC为15.6μg/mL。
