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United States Department of Agriculture

Agricultural Research Service

2009 Annual Report

1a.Objectives (from AD-416)
Support analytical methods development and analysis of developing new crop germplasm and agronomic trials. Crops that will be studied are lesquerella, cuphea and sicklepod (senna). Develop chemical and physical processes for the isolation of new crop raw materials. Oil, protein, starch, glucosinolates and other phytochemicals will be isolated and produced in pilot quantities. Products to be developed include natural pest control chemicals and hydrocolloids. Develop industrial materials through organic synthesis of novel derivatives based on new crop raw materials. Products to be developed include biodegradable lubricants, viscosity and lubricant additives.

1b.Approach (from AD-416)
New crops will be developed for several growing regions within the U.S. by developing industrial products from these agricultural feed stocks. New crop development is critical to the future sustainability of U.S. agriculture by reduction of the dependance on government subsidies for a select few commodity crops. Development of cuphea, lesquerella, meadowfoam (limnanthes), milkweed (ascelipias) and sicklepod (senna) will occur through a three prong effort. First, germplasm development will be supported through analytical methods which provide procedures to rapidly analyze protein, oil and starch. GC and HPLC methods for partial seed analysis determination of oil and fatty acids will aid germplasm development. In addition non-destructive methods for oil, protein and starch will be developed using pulsed NMR and NIR technologies. Second, new chemical and physical processes for the isolation of new crop raw materials (oil, protein, starch and phytochemicals) will be established and new crop raw materials produced in pilot scale quantities. Expelling will be conducted with optimization of pre-press conditions (seed tempering with temperature and moisture, flake thickness and dehulling). Isolation of speciality chemicals from defatted meal utilizing enzymatic processes will enhance meal quality and aid in offsetting oil production costs. Lastly, development of industrial materials through organic synthesis of novel derivatives based on new crop raw materials. Products to be developed include biodegradable lubricants, viscosity and lubricant additives, natural pest control chemicals and hydrocolloids. Novel new crop chemical structures will drive the direction of isolation, synthesis, evaluation and scale-up of synthetic efforts. Cooperative efforts with academia for germplasm and agronomic development and industry for product evaluation is crucial to the successful completion of this work.

3.Progress Report
The pilot facility at the National Center for Agricultural Utilization Research (NCAUR), in Peoria, IL, addresses a crucial need in U.S. new crop development by creating a unique location where all aspects of small scale oil refining of new crop oil seeds and specialty oils can be accomplished, including seed cleaning, conditioning, sorting, preparation, pressing, and refining. Equipment ranges from a 1-liter oil extractor to an 800-gal batch oil refiner. Work includes: exploring processes for expelling and extruding oil from milkweed, pumpkin, camelina, lesquerella, pennycress, and cuphea, and refining crude oils from cuphea and lesquerella to yield drum quantities of refined oil. The refined oil is used to attract potential Cooperative Research and Development Agreement (CRADA)/end-users for cuphea, lesquerella and other oils, and to support future milestones. Cooperative cuphea development with the North Central Soil Conservation Research Lab in Morris, MN, continued in Fiscal Year (FY) 09 as all new growing conditions and procedures were transferred to Technology Crops, Inc (TCI), although many agronomic issues require additional research. Personnel at the NCAUR directly managed one field of cuphea (~10 acres) in the Peoria, Illinois, area. Field management responsibilities included planting, harvest and post-harvest work while utilizing existing corn and soybean farm production equipment. Seeds were processed using pilot plant crushing equipment and oil was produced for future utilization research.

Germplasm analysis and method development continued in FY 09 to support new crop breeding and research programs.

Peaks and Prairies (P&P), Limited Liability Company (LLC), has continued to license the estolide technology (3-years). P&P is in the second year of its CRADA with the USDA. The CRADA included a formulation and testing component conducted by the Cereal Products and Food Science Research Unit in Peoria, IL. Seeds were processed using pilot plant crushing equipment and oil was produced for future utilization research.

Pennycress development has continued in FY 09. A 26 acre direct planting study was conducted over the winter on a Biofuels Manufacturing of Illinois (BMI) demonstration plot. About 8,000 lbs of pennycress seed, harvested from a cooperator’s demonstration plot, are being cleaned and density-graded using NCAUR pilot plant equipment in preparation for the first commercial grow-out this fall. Both the oil (bio-diesel applications) and the meal (soil fumigant – used to control weeds) are of particular interest. Pennycress is planted in the fall and harvested in late May or early June, thus giving Midwest farmers a two crop/year management practice.

Lesquerella products have been and continue to be developed to aid in the commercialization of this new crop. Clean seeds were screw pressed using NCAUR pilot plant equipment, producing 12 drums (4,400 lbs) of filtered crude oil for TCI.

Research results from these activities are used to develop new product potential to support the development of new crops to benefit the U.S. agriculture industry.

1. DEVELOPMENT OF CUPHEA AS A POTENTIAL NEW CROP. Cuphea is being developed as a new crop that can be grown for income by farmers. In FY 08, ARS scientists re-evaluated direct harvest methods using a more conventional combine, since the ability to use conventional farm equipment would be a significant advantage to farmers who want to grow cuphea for additional income. Ten acres in the Midwest were planted, maintained and harvested. In the summer of 2009, ARS scientists evaluated Illinois cuphea production following a wheat harvest and the impact of late summer insects on production. All data collected continues to be transferred to industrial partners. Progress has been and continues to be made on the production issues as a result of strong collaborations between the National Center of Agricultural Utilization Research (NCAUR), Peoria, Illinois, and the North Central Soil Conservation Research Lab in Morris, Minnesota.

2. COMMERCIALIZATION OF ESTOLIDES AS A BIO-BASED LUBRICANT. There is great demand in the U.S. and world-wide for increased development of bio-based products. Peaks and Prairies (P&P), Limited Liability Company (LLC), continued to license the estolide technology, in spite of the economic downturn and return of lower priced crude oil at the beginning of 2009, which has significantly reduced P&P’s ability to commercialize these estolides. This dynamic demonstrates the extreme value of this technology to industrial users, and the USDA has continued to supply P&P with estolides produced in our pilot plant facilities for sampling to potential industry users. The estolides have physical properties that can make them a leader in fulfilling the demand for increased development of bio-based lubricants in the U.S.

3. SYNTHESIS AND DERIVATIVES OF NEW CROP OILS. New crop oils can have unique chemical structures, compared to commodity crops and, thus, can have very useful physical properties in numerous applications. In FY 09, ARS scientists developed a number of compounds and synthetic procedures for new crop oil modifications. Some of the most notable were a series of esters prepared from pennycress and evaluated for low temperature properties as a potential bio-diesel. Characterization of a new phenoxy ether compound from castor and lesquerella has led to a new collaboration with another research project. A new method for the lactonization of meadowfoam oil and fatty acids was explored for a past CRADA partner. Physical properties of a new sulphur estolides derivative from the Cereal Products and Food Science Research Unit at NCAUR was evaluated. Finally, estolides from coriander fatty acids were synthesized and physical properties evaluated. This new method of lactonization has given the CRADA partner a new cost-effective procedure to make delta-lactones from meadowfoam seed oil.

4. DEVELOPMENT OF PENNYCRESS AS A WINTER ANNUAL. Pennycress is being developed as a winter annual to give farmers a second crop/income to harvest from their commodity crop land. In FY 08, ARS scientists planted 30 acres of pennycress on a collaborator’s field in Illinois. About 8,000 pounds of pennycress seed from about 15 acres were harvested, cleaned and density separated for future commercial planting and research plots. Additionally, five acres of a wild field of pennycress were harvested to yield about 5,000 pounds of seed. The seed from the wild field will be utilized for future oil expelling and refining studies. The oil from past harvests was converted into corresponding esters, which makes them capable of being used as a bio-diesel and potentially branded as a “Wonderfuel”. The demonstrated ability to plant and harvest pennycress will allow for a major acreage increase of this potential new crop in the Fall of 2009.

5. NEW CROP OILSEED PROCESSING. To develop new products from new crop oilseeds, new processing methods must also be developed as most conventional techniques do not work on the wide range of new crop seeds. In FY 08, ARS Scientists continued to develop lesquerella oil processing methods, and oil extraction (the extrusion-expelling process), as well as production studies and mechanical dehulling of seeds. The primary goal was to separate the hulls for the production of seed surface gums. After removing the highly-colored hulls, the extracted oil is lighter in color than the oil obtained from whole seeds. The defatted and dehulled seed meal, which has higher protein (reduced fiber), will be used in a poultry feeding study. Lesquerella seeds, provided by the USDA Maricopa, AZ, lab, were cleaned and crushed. Additionally, cuphea seeds harvested from a 10 acre production plot in August 2008 were dried, cleaned and stored for future use. About 700 pounds of density-graded cuphea seeds were provided to Technology Crops, Inc. (TCI), (Salem, NC), for contract growing this year. Development of these processes led to more than 20,000 pounds of lesquerella seed that was screw pressed to produce 12 drums (4,400 pounds) of filtered crude oil. This oil and 16 additional drums of oil, accumulated from previous seed crushing, were also provided to TCI for their use as our CRADA partner in charge of the commercialization aspect of the project.

6. DEVELOPMENT OF GERMPLASM METHODS AND ANALYSIS FOR NEW CROP SEEDS. Breeders lack the instrumentation, knowledge and experience to analyze new crop seeds for oil and fatty acid information. In FY 08, ARS scientists analyzed 100 Camelina accessions for oil content, fatty acid distribution and percent oil for breeders in Nebraska. Also, more than 1,000 brassica accessions were analyzed for oil content and fatty acid content in a cooperative study with the Plant Introduction Station in Ames, Iowa. In addition, more than 140 Jojoba accessions were analyzed for oil and fatty acid content and percent oil for the National Plant Germplasm System. The information communicated back to the breeders allows the breeders to make sound scientific justifications when selecting plants. These new selections, though slow to develop, will produce seeds that have the best oil currently possible.

7. SICKLEPOD ANALYSIS. Sicklepod has potentially valuable medicinal components; however, due to climatic differences, it is not expected that sicklepod plant species located in the Southeastern U.S. will have the same components (qualitatively or quantitatively) as those in tropical Southeast Asia. In FY 08, ARS scientists designed and executed laboratory scale fractionation of the medicinal components from sicklepod seed meal. Through a complicated series of extractions and separations, components were partitioned in the order of their solubilities. The solutes were recovered and were analyzed by HPLC-MS. Development of these HPLC methods allows for analysis and future comparison of sicklepod grown in the Southeastern U.S. to that grown in tropical Southeast Asia.

8. SAMPLE REQUESTS AND CROP DEVELOPMENT. Around the world, the availability of new crop seed, oil and products are limited by supply. In FY 08, ARS scientists supplied industrial partners and any interested parties with the following new crop oils: cuphea, lesquerella, pennycress, coriander, echium, buglossoides, and various versions of estolides for industrial evaluation. We have on-going crop development groups for cuphea (annual meeting) and lesquerella (bi-annual meetings), from growers to end-users, where all available information is communicated and shared. These many and diverse efforts to support industry and research with new crop oils, products, and information has promoted numerous CRADAs and collaborative new crop projects, ultimately generating increased supplies.

5.Significant Activities that Support Special Target Populations
New crops research offers economic opportunities to small and limited resource farmers through the development of cuphea, pennycress, coriander, milkweed, and lesquerella crops.

6.Technology Transfer

Number of Active CRADAs3
Number of the New/Active MTAs (providing only)1
Number of Invention Disclosures Submitted2
Number of Other Technology Transfer1

Review Publications
Behle, R.W., Hibbard, B.E., Cermak, S.C., Isbell, T.A. 2008. Examining cuphea as a potential host for western corn rootworm (Coleoptera: Chrysomelidae): larval development. Journal of Economic Entomology. 101(3):797-800.

Evangelista, R.L. 2009. Oil extraction from lesquerella seeds by dry extrusion and expelling. Industrial Crops and Products. 29(1):189-196.

Knothe, G.H., Cermak, S.C., Evangelista, R.L. 2009. Cuphea Oil as Source of Biodiesel with Improved Fuel Properties Caused by High Content of Methyl Decanoate. Energy and Fuels. 23:1743-1747.

Harry O Kuru, R.E., Mohamed, A. 2009. Processing scale-up of sicklepod (Senna obtusifolia L.) seed. Journal of Agricultural and Food Chemistry. 57(7):2726-2731.

Hojillaevangelist, M.P., Evangelista, R.L. 2009. Effects of Cooking and Screw-pressing on Functional Properties of Protein in Milkweed (Asclepias spp.) Seed Meals and Press Cakes. Industrial Crops and Products. 29(1)615-621.

Cermak, S.C., Isbell, T. 2009. Synthesis and physical properties of mono-estolides with varying chain lengths. Industrial Crops and Products. 29(1):205-213.

Jham, G.N., Moser, B.R., Shah, S.N., Holser, R.A., Dhingra, O.D., Vaughn, S.F., Berhow, M.A., Moser, J.K., Isbell, T., Holloway, R.K., Walter, E.L., Natalino, R., Anderson, J.A., Stelly, D.M. 2009. Wild Brazilian Mustard (Brassica Juncea L.) Seed Oil Methyl Esters as Biodiesel Fuel. Journal of the American Oil Chemists' Society. 86(1):917-926.

Last Modified: 4/20/2014
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