Enzymatic Synthesis of Novel Feruloylated Lipids and Their Evaluation as Antioxidants

• Published in: Journal of the American Oil Chemists' Society 2010-03, Vol.87 (3), p.305-311
• Main Authors: Zheng, Yan, Branford-White, Christopher, Wu, Xiao-Mei, Wu, Cheng-Yao, Xie, Jian-Gang, Quan, Jing, Zhu, Li-Min
• Format: Article
• Language: English
• Subjects: Agriculture; antioxidant activity; Antioxidants; Bioavailability; Bioconversions. Hemisynthesis; Biological and medical sciences; Biomaterials; Biotechnology; Carcinogenesis; chemical structure; Chemical synthesis; Chemistry; Chemistry and Materials Science; Enzymatic synthesis; Fat industries; Ferulic acid; Food industries; Food Science; free radical scavengers; Free radicals; Free radical–scavenging activity; Fundamental and applied biological sciences. Psychology; glycerol; Health hazards; hydroxyanisole; hydroxyl radical; Hydroxyl radicals; hydroxytoluene; Industrial Chemistry/Chemical Engineering; lipid peroxidation; Lipids; Lipophilic antioxidant; Methods. Procedures. Technologies; Natural products; Nutrition; Original Paper; Peroxidation; spectral analysis; structure-activity relationships; Structure–activity relationship; superoxide anion; transesterification; triacylglycerol lipase; tributyrin
• ISSN: 0003-021X; 1558-9331
• DOI: 10.1007/s11746-009-1496-y

Concerns about the use of chemical synthetic antioxidants that promote carcinogenesis has led to the development of natural antioxidants. Ferulic acid (4-hydroxy-3-methoxy cinnamic acid, FA) is a monophenolic phenylpropanoid present in the plant kingdom. It has shown a high antioxidant capacity and biological activities, including antiviral, anticarcinogenic and antimicrobial ones. However, due to poor solubility in hydrophobic media, FA can only be used in aqueous environments and this is a key factor that to a certain extent limits its application and bioavailability. In the present study, novel feruloylated lipids 1(3)-feruloyl-monobutyryl-glycerol (FMB) and 1(3)-feruloyl-dibutyryl-glycerol (FDB) were prepared by lipase-catalysed transesterification between FA and tributyrin. The structure of FMB and FDB was confirmed by NMR and ESI-MS, respectively. The radical scavenging and antioxidant properties of FA, FMB and FDB were evaluated using several different antioxidant assays, including hydroxyl radical scavenging, superoxide anion radical scavenging, 1,1-diphenyl-2-picrylhydrazyl (DPPH·) radical scavenging, inhibition of peroxidation of linoleic acid and reducing power. The antioxidant activities decreased in the following order: BHT ≥ FMB > FDB > FA. The results suggested that FMB and FDB exhibited a strong effect against oxidation in lipophilic systems making them promising antioxidants.