title: Acidolysis of p-coumaric acid with omega-3 oils and antioxidant activity of phenolipid products in in vitro and biological model systems.
abstract: Lipase-catalyzed acidolysis of p-coumaric acid with seal blubber oil (SBO) and menhaden oil (MHO) was carried out, followed by identification of major phenolipids in the resultant acidolysis mixture using high-performance liquid chromatography/mass spectrometry. Separation of phenolipid components from the resultant acidolysis mixture was achieved using flash column chromatography. The antioxidant activities of the phenolipids were examined in in vitro assays and biological model systems. The major phenolipids identified from acidolysis mixtures with both SBO and MHO included eight phenolic monoacylglycerols and eight phenolic diacylglycerols. Phenolipids derived from SBO and MHO generally showed good antioxidant potential in the systems tested. The prepared phenolipids exhibited high scavenging capacity toward 1,1-diphenyl-2-picrylhydrazyl (DPPH) and peroxyl radicals and displayed reducing power, strong inhibitory effect on bleaching of β-carotene, human low-density lipoprotein (LDL) cholesterol oxidation, as well as radical-induced DNA cleavage, thus suggesting that phenolipids derived from omega-3 oils may be used as potential stable products for health promotion and disease risk reduction.
authors.affiliation: Departments of Biology and ‡Biochemistry, Memorial University of Newfoundland , St. John's, Newfoundland and Labrador A1B 3 × 9, Canada.
authors.forename: Jiankang
authors.initials: J
authors.lastname: Wang
authors.forename: Fereidoon
authors.initials: F
authors.lastname: Shahidi
mesh_terms: D000975:Antioxidants / Q000494:pharmacology; D001713:Biphenyl Compounds; D008078:Cholesterol, LDL / Q000737:chemistry; D003373:Coumaric Acids / Q000378:metabolism*; D004249:DNA Damage / Q000187:drug effects; D004075:Diglycerides / Q000032:analysis; D015525:Fatty Acids, Omega-3 / Q000378:metabolism*; D005395:Fish Oils / Q000378:metabolism; D016166:Free Radical Scavengers / Q000737:chemistry; D006293:Health Promotion; D019787:Linoleic Acid / Q000737:chemistry; D008049:Lipase / Q000378:metabolism*; D050178:Monoglycerides / Q000032:analysis; D010084:Oxidation-Reduction; D010636:Phenols / Q000032:analysis; D010851:Picrates; D011422:Propionates; D019207:beta Carotene / Q000737:chemistry
chemical_list: D000975:Antioxidants; D001713:Biphenyl Compounds; D008078:Cholesterol, LDL; D003373:Coumaric Acids; D004075:Diglycerides; D015525:Fatty Acids, Omega-3; D005395:Fish Oils; D016166:Free Radical Scavengers; D050178:Monoglycerides; D010636:Phenols; D010851:Picrates; D011422:Propionates; D019207:beta Carotene; C033266:Menhaden oil; D019787:Linoleic Acid; C004931:1,1-diphenyl-2-picrylhydrazyl; D008049:Lipase; C495469:p-coumaric acid
keywords: DNA; DPPH radical scavenging activity; human LDL cholesterol; lipase-catalyzed acidolysis; menhaden oil; oxygen radical absorbance capacity; p-coumaric acid; phenolipid; reducing power; seal blubber oil; β-carotene−linoleate