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Abstract
Ethyl ferulate was transesterified with Enova Oil (a soy-based vegetable oil containing 80–85% diacylglycerol) using Novozym 435 at 60 °C. The resultant feruloylated vegetable oil reaction product produced a precipitate (96.4 g, 4.02 wt%) after 7 d of standing at room temperature. Preliminary characterization of the precipitate identified the natural phenylpropenoids 1,3-diferuloyl-sn-glycerol (F2G) and 1-feruloyl-sn-glycerol (FG) as the major components. A flash chromatography method was developed and optimized (e.g., mass of sample load, flow rate, binary solvent gradient slope, and separation run length) using a binary gradient of hexane and acetone mobile phase and silica gel stationary phase to separate and isolate F2G and FG. The optimized parameters afforded F2G (1.188 ± 0.052 g, 39.6 ± 1.7%) and FG (0.313 ± 0.038 g, 10.4 ± 1.3%) from 3.0 g of the transesterification precipitate, n = 10 trials. Overall, all flash chromatography separations combined, F2G (39.1 g, 40.6%) and FG (9.4 g, 9.8%) were isolated in a combined yield of 48.5 g (51.4%), relative to the 96.4 g of transesterification precipitate collected. The optimized flash chromatography method was a necessary improvement over previously reported preparative HPLC and column chromatography methods used to purify milligram to low gram quantities of F2G and FG to be able to process ~100 g of material in a timely, efficient manner.
Highlights
The phenylpropenoid, ferulic acid, is a 4-hydroxy-3-methoxy-substituted cinnamic acid and is a nearly ubiquitous component throughout the higher plant kingdom, and as such is a common dietary component [1]
We have developed a pilot-scale (1 metric ton/year) continuously fed, packed bed, enzymatic bioreactor employing a commercial lipase to transesterify ethyl ferulate and vegetable oil triacylglycerols (TAG) to form a mixture of feruloylated di- and triacylglycerols where there is at least one feruloyl moiety and one fatty acid moiety on the glycerol backbone [22,23]
Ethyl ferulate and vegetable oil form a miscible solution at 60 ◦C that can be converted by lipase-catalyzed transesterification to a mixture of feruloylated vegetable oil TAG and DAG [22,23]
Summary
The phenylpropenoid, ferulic acid, is a 4-hydroxy-3-methoxy-substituted cinnamic acid and is a nearly ubiquitous component throughout the higher plant kingdom, and as such is a common dietary component [1]. The enzymatic catalyzed esterification of ferulic acid with glycerol has been demonstrated [20,21] While these studies demonstrate that FG and F2G can be obtained through extraction of plant components or the direct esterification of ferulic acid (or ethyl ferulate) and glycerol, the methods are limited due to low yields, the need for solvents (e.g., DMSO, toluene, THF), chemical catalysts (e.g., triphenylphosphine, sulfonic acids) or 10- to 100-fold excess of glycerol. We report methods for harvesting FG and F2G and purifying them in >10 g quantities by flash chromatography, an improvement over the milligram to low gram quantities obtained by preparative HPLC and column chromatography methods reported to date [5,14,26]
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