Lipase-catalyzed biosynthesis of cinnamoylated lipids in a selected organic solvent medium.
Biosynthesis of cinnamoylated lipids through the lipase-catalyzed transesterification reaction of cinnamic acid with triolein was investigated in organic solvent media. Electrospray ionization-mass spectroscopy (ESI-MS) structural analysis of the reaction mixture revealed the formation of two major end products, monoleyl-1(3)-cinnamate and dioleyl-2-cinnamate. Decreasing the molar ratio of cinnamic acid to triolein from 1:1 to 1:4.5 resulted in an increase in the maximum bioconversion yield of cinnamoylated lipids from 19 to 42%, which remained constant at a lower ratio of 1:6. However, an excess of triolein appeared to have a more beneficial effect on the formation of dioleyl-2-cinnamate than monoleyl-1(3)-cinnamate, leading to different end product compositions at ratios of substrates. With cinnamic acid to triolein ratios of 1:4.5 and 1:6.0, an increase in the bioconversion yield of cinnamoylated lipids to 55% was achieved by adding 2.2 mgmL(-1) silica gel to the reaction mixture. Radical scavenging activity of cinnamoylated lipids, with 50% of radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging, was found to be higher than that of its corresponding phenolic acid.
Karboune
Salwa
S
Department of Food Science and Agricultural Chemistry, McGill University, 21,111 Lakeshore, Ste-Anne de Bellevue, Que., Canada H9X 3V9.
Safari
Mohammad
M
Lue
Bena-Marie
BM
Yeboah
Faustinus K
FK
Kermasha
Selim
S
D000975:Antioxidants / Q000737:chemistry; D001709:Biotechnology / Q000379:methods*; D001713:Biphenyl Compounds; D002625:Chemistry, Organic / Q000379:methods; D002851:Chromatography, High Pressure Liquid; D002934:Cinnamates / Q000737:chemistry; D016166:Free Radical Scavengers / Q000494:pharmacology; D005990:Glycerol / Q000737:chemistry; D006868:Hydrolysis; D062385:Hydroxybenzoates / Q000737:chemistry; D007202:Indicators and Reagents / Q000494:pharmacology; D008049:Lipase / Q000737:chemistry* / Q000235:genetics*; D008055:Lipids / Q000096:biosynthesis* / Q000737:chemistry; D013058:Mass Spectrometry; D008956:Models, Chemical; D019800:Phenol / Q000737:chemistry; D010851:Picrates / Q000737:chemistry; D012997:Solvents; D021241:Spectrometry, Mass, Electrospray Ionization; D013997:Time Factors; D014304:Triolein / Q000737:chemistry; D014466:Ultraviolet Rays
D000975:Antioxidants; D001713:Biphenyl Compounds; D002934:Cinnamates; D016166:Free Radical Scavengers; D062385:Hydroxybenzoates; D007202:Indicators and Reagents; D008055:Lipids; D010851:Picrates; D012997:Solvents; D014304:Triolein; C029010:cinnamic acid; D019800:Phenol; C004931:1,1-diphenyl-2-picrylhydrazyl; D008049:Lipase; C017616:phenolic acid; D005990:Glycerol