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United States Department of Agriculture

Agricultural Research Service

Research Project: BIOCATALYTIC FUNCTIONALIZATION OF PLANT LIPIDS
2007 Annual Report


1a.Objectives (from AD-416)
To demonstrate the technical feasibility of using isolated enzymes in nonaqueous media to functionally modify vegetable oils on a scale suitable for commercial deployment. Optimize a pilot-scale system for non-aqueous enzymatic transformation of soybean oil to high value products with novel functional groups and properties, such as feruloylated monoacyl- and diacylglycerides, for food and non-food applications. Create a flexible, durable and environmentally benign platform technology for the bioelectrocatalytic transformation of plant triglycerides and phospholipids to higher-value products.


1b.Approach (from AD-416)
Processes for producing modified plant lipids with novel and valuable functional properties are essential for developing new markets for commodity vegetable oils. Furthermore, these processes and products should have minimal adverse impact on the environment and pose no threat to plant operators and the surrounding community. It is the premise of this proposal that using isolated enzymes in selected nonaqueous media can meet these design goals. Two distinctly different approaches are considered. One approach, for enzymes not having complex cofactor requirements, employs soybean oil as a solvent as well as a reactant, while the other approach, for enzymes having more substantial structural and cofactor needs, places the enzyme in a highly structured environ and specifically tailored media. In the first approach, synthesis of a patented product is examined to optimize reaction variables for pre-commercial production. The second approach addresses several fundamental issues regarding ex vivo use of membrane-associated enzymes for the bioelectrocatalytic transformation of phospholipids and triglycerides. Taken together, new knowledge will be gained and useful processes will be developed that can deliver value-added vegetable oil derivatives for consumers and industry.


3.Progress Report
Processes for improved production of a new skincare product were developed at the National Center for Agricultural Utilization Research, Peoria, IL. This work was conducted with the Biotechnology Research Development Consortium under a Cooperative Research and Development Agreement and Specific Cooperative Agreement with The Grall Company, Inc.

Research was conducted in-house to demonstrate the feasibility of modifying Lesquerella oil with ferulic acid. The modifications were conducted at high temperatures without the use of a catalyst and at lower temperatures with the use of a catalyst.

Overall, work continues to address understanding the foundational steps in developing methods to use immobilized enzymes on electrode surfaces in liquid salts (ionic liquids) and water/liquid salt systems to transform lipids. Work has begun to evaluate how the surface chemistry affects surface-supported lipid thin films. Work is also continuing in understanding liquid salt effects on surface-supported lipid bilayers as a function of composition. Current results show that one particular water-soluble liquid salt disturbs a surface-supported lipid bilayer only if negatively charged lipids are present, regardless of the chemical make-up of the negatively charged lipid. These disturbances take the form of a “blister” in the thin films. Work is also continuing to evaluate the effects liquid salts have on the physical “state” of organized lipids. Recent results show that the “liquid” state of lipids shifts slightly toward a “gel” state as the presence of a water-soluble liquid salt increased.


4.Accomplishments
Determining monoacylglycerol (MAG) concentrations using proton nuclear magnetic resonance spectroscopy. MAG are used in food, pharmaceuticals and cosmetics as emulsifying agents and are convenient feedstock for the development of new, value-added vegetable oils. Previously developed methods detail the use of gas and liquid chromatography to determine the MAG concentrations in samples; however, these techniques are time-intensive and can be inaccurate due to solvent and high temperature effects on MAG concentrations during the measurements. We have developed a method for determining MAG concentrations in less than two minutes that is not subject to solvent and high temperature effects. This offers a fast, convenient method for other researchers for determining MAG concentrations during their pursuits of developing lipid-based food, pharmaceutical and cosmetic ingredients. These efforts directly support National Program 306, Quality and Utilization of Agricultural Products, Action Plan Component 2-New Processes, New Uses, and Value-Added Foods and Biobased Products, Problem Areas 2a-New Product Technology and 2c-New and Improved Processes and Feedstocks.

Correlation of electrode surface properties with enzyme function. Immobilized enzymes are used to modify vegetable oils. The surface upon which the enzyme is immobilized impacts the activity of the enzyme. We determined how the chemical structure of an electrode surface influenced one enzyme's activity. With this knowledge, we will be able to design improved enzyme support materials for biocatalytic processing of vegetable oils. These efforts directly support National Program 306, Quality and Utilization of Agricultural Products, Action Plan Component 2-New Processes, New Uses, and Value-Added Foods and Biobased Products, Problem Areas 2a-New Product Technology and 2c-New and Improved Processes and Feedstocks.


5.Significant Activities that Support Special Target Populations
None.


6.Technology Transfer

Number of active CRADAs and MTAs1
Number of patent applications filed3
Number of non-peer reviewed presentations and proceedings10

Review Publications
Laszlo, J.A., Compton, D.L. 2006. Enzymatic glycerolysis and transesterification of vegetable oil for enhanced production of feruloylated glycerols. Journal of the American Oil Chemists' Society. 83(9):765-770.

Compton, D.L., Laszlo, J.A., Berhow, M.A. 2006. Identification and quantification of feruloylated mono-, di-, and triacylglycerols from vegetable oils. Journal of the American Oil Chemists' Society 83(9):753-758.

Compton, D.L., Kenar, J.A., Laszlo, J.A., Felker, F.C. 2007. Starch-encapsulated, soy-based ultraviolet-absorbing composites with feruloylated monoacyl- and diacylglycerol lipids. Industrial Crops and Products. 25(1):17-23.

Compton, D.L. 2005. Vegetable oil-based sunscreens. Lipid Technology 17:276-279.

Dunlap, C.A., Evans, K.O., Theelen, B., Boekhout, T., Schisler, D.A. 2007. Osmotic shock tolerance and membrane fluidity of cold-adapted Cryptococcus flavescens OH 182.9, previously reported as Cr. nodaensis, a biocontrol agent of Fusarium head blight. Federation of European Microbiological Societies Yeast Research. 7:449-458.

Compton, D.L. 2006. Lipid-based cosmeceuticals. Inform. 17:793-795.

Compton, D.L., Vermillion, K., Laszlo, J.A. 2007. Acyl migration kinetics of 2-monoacylglycerols from soybean oil via 1h Nuclear Magnetic Resonance (NMR). Journal of the American Oil Chemists' Society 84(4):343-348.

Last Modified: 4/19/2014
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