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United States Department of Agriculture

Agricultural Research Service

Research Project: BIOCATALYTIC FUNCTIONALIZATION OF PLANT LIPIDS
2006 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? Why 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, and in other cases the oil will be dissolved in compressed carbon dioxide (supercritical carbon dioxide) or other environmentally benign fluids such as ionic liquids.

These efforts directly support the 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 by year the currently approved milestones (indicators of research progress)
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.


4a.List the single most significant research accomplishment during FY 2006.
Improvements in the Production of Soyscreen: Alternative reaction pathways were determined which accelerate the enzyme catalyzed production of ferulic acid modified vegetable oils. Ferulic acid modified oils are used in human skincare formulations. The current commercial process for making these materials is slow. Our findings will improve the production process, allowing the technology to be more broadly applied. (Short title: “Accelerated process for skincare product production.”) 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.


4b.List other significant research accomplishment(s), if any.
This project is aligned with the National Program 306, Quality and Utilization of Agricultural Products. Role of Ionic Liquids on Membranes: Specific ratios of phospholipids were identified that allow formation of artificial membranes on various surfaces. It was found that ionic liquids would swell, but not disrupt, the membranes. These findings suggest that artificial membranes can be used in conjunction with ionic liquids for non-aqueous biocatalytic processing of lipids.


4c.List 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 with BRDC under a Cooperative Research and Development Agreement (CRADA).


5.Describe the major accomplishments to date and their predicted or actual impact.
This project is aligned with the National Program 306, Quality and Utilization of Agricultural Products. 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, environmentally benign, 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?
An additional patent broadening the coverage of this technology has been submitted to the U.S. Patent and Trademark Office. The technology has been licensed to a biotechnology company. Limited volume sales of product have begun. Research to develop new products and improved processes continues under a CRADA agreement with the Biotechnology Research and Development Corporation.


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).
1. Natural Sunscreen. Organic Style, 2003, July/August, page 79. 2. Soja: mil e uma utilidades. Jornal da Embrapa Soja (Brazil), 2004, vol 9, No. 21 (April), page 6-7. 3. Where the best ideas take wing. Time 2004, 164, No. 15 (October 11), page 68-72.


Review Publications
Laszlo, J.A., Compton, D.L., Li, X.-L. 2006. Feruloyl esterase hydrolysis and recovery of ferulic acid from jojoba meal. Industrial Crops and Products. 23:46-53.

Evans, K.O. 2005. Room-temperature ionic liquid cations act as short-chain surfactants and disintegrate a phospholipid bilayer. Colloids and Surfaces A: Physicochemical and Engineering Aspects. 274:11-17.

Dunlap, C.A., Evans, K.O., Schisler, D.A. Osmotic shock tolerance and membrane properties of cryptococcus nodaensis OH 182.9: A biocontrol agent of fusarium head blight [abstract]. National Fusarium Head Blight Forum Proceedings. p. 193.

Warner, K.A., Laszlo, J.A. 2005. Addition of ferulic acid, ethyl ferulate, and feruloylated monoacyl- and diacylglycerols to salad oils and frying oils. Journal of the American Oil Chemists' Society. 82(9):647-652.

Dicarlo, C.M., Compton, D.L., Evans, K.O., Laszlo, J.A. 2006. Bioelectrocatalysis in ionic liquids. Examining specific cation and anion effects on electrode-immobilized cytochrome c. Bioelectrochemistry. 68:134-143.

Laszlo, J.A., Compton, D.L., Willis, R.A. 2005. Sunscreen active derived from soybean oil and ferulic acid: Synthesis and applications. Proceedings of the 6th International Symposium on the Role of Soy in Preventing and Treating Chronic Disease, Chicago, IL. p. 51

Laszlo, J.A., Compton, D.L., Li, X. 2006. Feruloyl esterase hydrolysis and recovery of ferulic acid from jojoba meal [abstract]. Proceedings of the Great Lakes Regional American Chemical Society Symposium. p. 125

Evans, K.O. 2005. Vesicle-surface interactions on self-assembled monolayer lead to flattened vesicles: a qcm-d study [abstract]. Proceedings of the 2005 Q-Sense Users Invitational Symposium. p. 6.

Evans, K.O. 2006. Supported phospholipid membrane interactions with 1-butyl-3-methyl imidazolium chloride, a room-temperature ionic liquid, on surfaces--a quartz crystal microbalance with dissipation study [abstract]. Proceedings of the Annual Biophysical Meeting. 2006 CD-ROM. p. B129.

Behle, R.W., Compton, D.L., Laszlo, J.A., Shapiro Ilan, D.I. 2006. Potential use of SoyScreen in formulations of Beauveria bassiana for UV protection. Entomological Society of America Annual Meeting North Central Branch. Paper No. D-215.

Compton, D.L., Laszlo, J.A., Isbell, T., Behle, R.W., Kurth, T.L. 2005. Synthesis and applications of biocatalytically derived UV absorbing vegetable oils [abstract]. Royal Society of Chemistry Meetings. p. 026.

Last Modified: 4/16/2014
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