Enzymatic synthesis of feruloylated lysophospholipid in a selected organic solvent medium

•This was the first report on production of feruloylated lysophospholipid.•Two-steps reaction was applied to the modification of phospholipid with ferulic acid.•The structure of feruloylated lysophospholipids was first confirmed by HPLC–MS.•The binary solvent and molecular sieve could obviously incr...

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Bibliographic Details
Published in:Food chemistry 2013-12, Vol.141 (4), p.3317-3322
Main Authors: Yang, Hongli, Mu, Ying, Chen, Hongtao, Xiu, Zhilong, Yang, Tiankui
Format: Article
Language:English
Subjects:
Biocatalysis
Biological and medical sciences
Biotechnology - methods
Caffeic Acids - chemistry
Chemical and industrial products toxicology. Toxic occupational diseases
Enzymatic modification
Esterification
Ethyl ferulate
Feruloylated lysophospholipids
Lipase
Lipase - chemistry
Lysophospholipids - chemistry
Medical sciences
Phosphatidylcholine
Phosphatidylcholines - chemistry
Solvents
Toxicology
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Summary:•This was the first report on production of feruloylated lysophospholipid.•Two-steps reaction was applied to the modification of phospholipid with ferulic acid.•The structure of feruloylated lysophospholipids was first confirmed by HPLC–MS.•The binary solvent and molecular sieve could obviously increase the yield of product. Feruloylated lysophospholipids (FLPs) were firstly synthesized from phosphatidylcholine (PC) and ethyl ferulate (EF) using lipase-catalysed interesterification in selected solvents at controlled water content. Kinds of lipases and single solvents were screened. Novozym 435 and toluene were found to be the suitable biocatalyst and solvent, respectively. Then tert-butanol, n-butanol, chloroform, isopropanol, acetone and DMSO were respectively added into toluene in order to increase conversion of products. The results showed that toluene/chloroform could significantly increase the conversion and the optimal combination of toluene and chloroform was 90:10 (v/v). The optimal conditions generated for FLPs production were a substrate molar ratio of 5:1 (PC/EF), a PC’s hydrolytic time of 1.5h, an enzyme load of 60mg/ml, a solvent dosage of 5ml and a molecular sieves concentration (4Å) of 100mg/ml. Under these conditions, 40.51% of EF can be converted to FLPs, which were identified by TLC and HPLC–MS.
ISSN:0308-8146
1873-7072
DOI:10.1016/j.foodchem.2013.06.012