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United States Department of Agriculture

Agricultural Research Service

Research Project: BIOCATALYTIC FUNCTIONALIZATION OF PLANT LIPIDS
2005 Annual Report


1.What major problem or issue is being resolved and how are you resolving it (summarize project aims and objectives)? How serious is the problem? What does it matter?
New uses for commodity oilseed crops are needed to raise the value of the crop to the American farmer and agribusiness. We are examining technologies to modify vegetable oil to produce new and high-value products. These products will have enhanced food and nutritional value, or serve as custom-made feedstock materials for industry. Our approach is to use enzymes to catalyze the transformation of vegetable oils. Unlike traditional fermentative methods, we will use isolated enzymes instead of whole microorganisms, which will eliminate the production of undesired products. Furthermore, the enzymes will be deployed in non-aqueous (i.e., without water) media, which will provide a cleaner synthetic route. In some cases this may involve using the enzyme directly in the vegetable oil or other environmentally benign fluids such as ionic liquids.

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.


2.List the milestones (indicators of progress) from your Project Plan.
FY 2004 (Year 1): Demonstrate the electrocatalytic activity of an enzyme in thin films on electrodes in ionic liquids. Initiate studies on phase behavior of lipids in ionic liquids.

FY 2005 (Year 2): The influence of ionic liquids on cytochrome c immobilized on electrode surfaces will be determined. Conclude initial study of phospholipid phase behavior in the presence of the cationic and anionic components of ionic liquids. Pilot-scale synthesis of a soy-based sunscreen will be accomplished.

FY 2006 (Year 3): Optimal conditions for transforming soybean oil with ferulic acid on a pilot scale will be determined. Modified surfaces of gold electrodes will be identified that facilitate the use of enzymes in non-aqueous bioelectrocatalytic processes. Ionic liquids will be identified that can be used as solvents for processing lipids and phospholipids.

FY 2007 (Year 4): Alternative enzymes will be evaluated for processing lipids in novel, unconventional fluids to perform valuable biotransformations. Interactions of ionic liquids with surface-modified electrodes will be elucidated to determine whether ionic liquids can be used in bioelectrocatalytic applications. The effect of electrode surface modification on the ability of enzymes and lipids to interact with an electrode will be elucidated.

FY 2008 (Year 5): Conclude studies of the effect of ionic liquids on protein-modified electrodes. Conclude examination of the stability of lipid-modified electrode surfaces in ionic liquids.


4a.What was the single most significant accomplishment this past year?
The influence of ionic liquid structure on the physical properties of phospholipids was elucidated.


4b.List other significant accomplishments, if any.
The critical effects of ionic liquid components on protein-electrode interactions was determined.


4c.List any significant activities that support special target populations.
None.


4d.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 under a CRADA with Biotechnology Research and Development Consortium (BRDC) in support of this project.


5.Describe the major accomplishments over the life of the project, including their predicted or actual impact.
We have created a new “all-natural” sunscreen active ingredient derived from vegetable oil and other natural plant components (cinnamates). This patented product can be used to provide UVA and UVB protection from the sun. It can replace the synthetic chemicals currently used in sunscreen formulations as well as many other related cosmetic applications. This product represents a new and novel market for commodity vegetable oils and specialty plant-derived components. The work also highlights the great potential of unconventional solvents and enzymes to perform environmentally friendly chemistry. We have introduced an entirely new medium called ionic liquids for bioelectrocatalytic applications. Thus, in accordance with the milestones of our project, we are establishing new technological platforms for introducing novel and valuable functionalities into vegetable oils.


6.What science and/or technologies have been transferred and to whom? When is the science and/or technology likely to become available to the end-user (industry, farmer, other scientists)? What are the constraints, if known, to the adoption and durability of the technology products?
A patent has been granted disclosing the nature of a vegetable oil-based sunscreen active ingredient and its synthesis method. We entered into a Confidentiality Agreement with a U.S.-based company considering the licensing of this technology. Technical discussions were entered into with a chemical manufacturer concerning the development requirements for production. This product should enter the skin care market in the next several years. FDA approval will need to be obtained for this product to be listed as an active sunscreen agent.


7.List your most important publications in the popular press and presentations to organizations and articles written about your work. (NOTE: List your peer reviewed publications below).
Natural Sunscreen. Organic Style, 2003, July/August, page 79.

Soja: mil e uma utilidades. Jornal da Embrapa Soja (Brazil), 2004, Vol. 9, No. 21 (April), page 6-7.

Where the Best Ideas take Wing. Time Magazine, October 2004, Vol. 16, No. 15, page 68-72.


Review Publications
Compton, D.L., Laszlo, J.A., Isbell, T.A. 2004. Cinnamoyl esters of lesquerella and castor oil: Novel sunscreen active ingredients. Journal of the American Oil Chemists' Society. 81:945-951.

DiCarlo, C.M., Compton, D.L. 2005. Unexpected retention of electrostatically adsorbed cytochrome c in high ionic strength solutions. Chemical Communications. 2:218-220.

Last Modified: 4/18/2014
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