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United States Department of Agriculture

Agricultural Research Service

Research Project: CHEMISTRY OF NATURAL PRODUCTS FOR PEST MANAGEMENT AND CROP DEVELOPMENT

Location: Natural Products Utilization Research

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?
This project is aligned with NP 306, Quality and Utilization of Agricultural Products (70%) and NP 302, Plant Molecular and Biological Processes (30%). Damage caused by weeds, insects, and other pests amounts to billions of dollars per year, and can lead to lower quality products, increased costs of production, restriction of U.S. products from foreign markets, or complete crop failure. The use of synthetic pesticides to control pests, however, has met with toxicologic and undesirable environmental effects. Increasing evolution of resistance in pest populations further drives the need to search for new bioactive compounds with as wide a range of new modes of action as possible. The health-based safety standard enforced through the 1996 Food Quality and Protection Act addressed these concerns and required the re-evaluation of maximum safe level for pesticide residues and the reassessment of pesticide active ingredients scheduled for completion in August 2006. This process is resulting in the elimination of key pesticides. Phasing out of key pesticide classes could have a negative impact on crop production.

There is a need to search for alternative pesticides that will meet safety standards. Natural products are tapped, as they present not only a huge potential in the discovery of bioactive compounds in general, but is probably the best source of novel structures with novel modes of action (of paramount importance in the development of active compounds against organisms resistant to currently used pesticides).

In addition to being a source of pest management agents, natural products are also a rich source of nutraceuticals. Natural compounds imparting health benefits can be used to substitute or complement synthetic medicinal agents. Nutraceutical properties of natural products can be utilized to enhance the value of existing crops or to develop alternative crops.

The primary goal of this project is to discover and identify natural products with pest management and/or nutraceutical properties. A secondary goal is to support the development of crops with enhanced capability to synthesize the herbicidal, insecticidal, fungicidal, and/or nutraceutical constituent.

In general, this project will benefit farmers, as new natural sources are discovered for the control of pests affecting crop yield and quality. This project will also benefit the human population in regard to the protection of houses and buildings from devastation from termites, with discovery of new natural termiticides. This project also has potential impact in human health, from discovery of nutraceuticals in berries. Additionally, natural mosquito repellants discovered in this research will provide protection from disease-carrying mosquitoes.


2.List by year the currently approved milestones (indicators of research progress)
Year 1 (FY 2004) Milestone: Identify stilbenes in Vaccinium species. Identify allelochemicals in alleopathic rice varieties.

Anticipated accomplishment: Isolate and identify termiticidal compounds. Isolate and identify bioactive compounds from other sources for pesticide use.

Year 2 (FY 2005) Milestone: Continue identification of allelochemicals in allelopathic rice varieties. Continue work on identification of natural compounds for activity against the Formosan subterranean termite.

Anticipated accomplishment: Develop technology to enhance resistance of blueberries to fungal pathogens through transformation of binary vector containing genes that will synthesize disease-resistance conferring compound(s). Continue work to discover constituents for pesticidal and nutraceutical use. Develop new methods and analytical procedures to identify phytochemicals, neutraceuticals, and other biologically active agents.

Year 3 (FY 2006) Milestone: Perform chemical analysis of disease-resistance conferring compounds in transformed plants.

Anticipated accomplishment: Determine biosynthesis of rice allelochemicals through microarray technologies. Determine enzyme activity, as related to synthesis of known allelochemicals in rice. Isolate and identify antifungal compounds from Lasiodiplodia species. Continue studies on the mosquito repellent constituents isolated from the American beautyberry. Perform additional repellency studies using callicarpenal to determine its potential use as a broad spectrum insect repellent. Continue work to discover constituents for pesticidal and nutraceutical use. Develop new methods and analytical procedures to identify phytochemicals, neutraceuticals, and other biologically active agents.

Year 4 (FY 2007) Milestone: Develop technology for use of identified active pesticide in field applications. Continue work to discover constituents for pesticidal and nutraceutical use.

Anticipated accomplishment: Develop new methods and analytical procedures to identify phytochemicals, neutraceuticals, and other biologically active agents.

Year 5 (FY 2008) Milestone: Continue development of technology for the use of identified highly active pesticides in field applications.

Anticipated accomplishment: Transfer technology for the use of identified highly active pesticides in field applications. Continue work to discover constituents for pesticidal and nutraceutical use. Develop new methods and analytical procedures to identify phytochemicals, neutraceuticals, and other biologically active agents.


4a.List the single most significant research accomplishment during FY 2006.
Callicarpenal was identified as a highly effective arthropod repellent with activity against the yellow fever mosquito vector, Aedes aegypti, the malaria mosquito vector, Anopheles stephensi, the Lyme disease deer tick vector, Ixodes scapularis, and two species of fire ants, Solenopsis invicta and S. richteri. Dose-response studies indicated callicarpenal to be as effective as DEET against the deer tick, Ixodes scapularis. This research aligns with National Program 306, specifically, the component on “New Processes, New Uses, and Value-Added Foods and Biobased Products”.


4b.List other significant research accomplishment(s), if any.
Several novel classes of termiticides have been isolated from plants and based on these natural products more active analogs have been synthesized. This includes thiophenes isolated and identified from several species of Echinops and found to be highly active against the invasive Formosan subterranean termite, Coptotermes formosanus.

A collaborative research has been initiated with the Deployed War Fighter Protection program ARS at Gainesville, FL, to test natural and synthetic compounds against mosquitoes and sand flies. Several compounds have shown significant activities against mosquitoes.

A novel class of an algicide against O. perornata has been identified.


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


4d.Progress report.
None.


5.Describe the major accomplishments to date and their predicted or actual impact.
Discovery of the cholesterol lowering and cancer chemopreventive properties of pterostilbene, and its occurrence in blueberries, helped boost the sales of blueberries. The increase in sales of blueberry in the UK was attributed to this discovery. (http://enjoyment.independent.co.uk/food_and_drink/news/article221799.ece; 5/17/05); and a record of up to 185% increase in sales in Britain was reported (http://foodnavigator.com/news/ng-nocache.asp?id=60073, 5/18/2005). In the U.S., increase in blueberry sales has also been reported, and studies have contributed to the increase (e.g. http://www.youngagain.com/blmaybeefinp.html, May 27, 2006, blueberry sales were reported to have boomed from $21 million USD in 2003 to almost $60 million in 2005; see also Arkansas Democrat Gazette, June 25, 2006). Dietary supplements have recently appeared on the market and are being standardized for their content of pterostilbene (e.g., Life Extension Blueberry Extract Capsule, Swanson Premium Brand Wild Blueberry Juice Super Concentrate, Swanson Green Foods Formulas Wild Blueberry Extract (Pterostilbene), Young Again Source Naturals Gluco-Science tablet). Furthermore, not previously commercially available, pterostilbene is now sold by a number of chemical companies due to increased demand for use in various research studies. At least one chemical company cites the research in its product literature (http://www.emdbiosciences.com/Products/ProductDisplay.asp?catno=523310&).


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?
Cantrell, C.L. et al., “Novel Clerodanes and Methods for Repelling Arthropods,” patent filed on April 14th, 2006.

A Non-Funded Cooperative Research Agreement has been established by NPURU with the Hawaii Dept. of Agriculture to conduct field trials on vulgarone B as a potential molluscicide.


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).
The unit's work on American Beautyberry mosquito repellent constituents, specifically callicarpenal, has attracted national and international attention. A live interview was recorded and aired on the CBS morning show, “Live at 9”. Numerous radio stations picked up the story and recorded interviews appeared on the Canadian Broadcasting Inc. (CBC) national program “As It Happens”; “Capital Ideas – Live!” a monthly program recorded and produced by the Alabama Forest Owners' Association Inc. and broadcast throughout the south; and SuperTalk Radio’s “Paul Gallo Show”, which airs throughout Mississippi.

Science magazine did a feature news article (7 July 2006, Vol 313, pages 36-38) called “Keeping the Bugs at Bay” that discussed this research within the article. Additionally, International Pest Control published a news article (May/June 2006, Vol 48, 3, pages 153-154) entitled “Folk Remedy Yields Mosquito-thwarting Compound”.

Many websites provided information on his work: e.g., DiscoveryChannel.ca (Canadian), InTheNews.co.uk, PCTOnline.com (Pest Control Technology), PoliticalGateway.com, MosquitoBuzz.com, TheDMOnline.com, Newswise.com, OleMiss.edu, MyWestTexas.com. ScienceDaily.com, AxcessNews.com, etc.

Several newspapers picked up the story as well: e.g., Chicago Tribune, Virginian Pilot, The Richmond Times Dispatch, The Daily Mississippian, The Oxford Eagle, etc.

Invited presentations:

Cantrell, C. L., "ARS Research at the National Center for Natural Products" Institut National de la Recherche Agronomique (INRA), Jabat, Morocco, January 2006.

Rimando, A. M., Khan, S. I., Feller, D. R., Yokoyama, W., Mikstacka, R. Studies on mechanism of cholesterol lowering and cancer chemopreventive action of pterostilbene. WORLDNUTRA 2005. 6th International Conference and Exhibition on Nutraceuticals and Functional Foods. October 16-19, 2005, Crowne Plaza Anaheim Resort, Anaheim, CA. (was unable to present talk due to time constraint, paper was presented by co-author Wallace Yokoyama).

Rimando, A. M. Exploring the biological activities of pterostilbene. Seminar at Uppsala University, Department of Genetics and Pathology, November 18, 2005.

Rimando, A. M. Sorgoleone and analogues from Sorghum bicolor: Phytotoxic activity and biosynthetic studies. Seminar at The Royal Veterinary and Agricultural University, Department of Agricultural Sciences, Høbakkegård Campus, 28 November 2005.

Rimando, A. M. Determination of stilbenes in blueberries and studies on their antioxidant, cancer preventive and cholesterol lowering properties. American Society for Horticultural Science Annual Meeting, Pre-Congress Symposium on Medicinal Plants, New Orleans, LA, 26 July 2006.

Research works has also been presented at other conferences including the Spring and Fall 2006 American Chemical Society, the 2006 Phytochemical Society of North America, and the Second Scientific Meeting of the Metabolomics Society, June 2006.


Review Publications
Fokialakis, N., Cantrell, C.L., Duke, S.O., Skaltsounis, A.L., Wedge, D.E. 2006. Antifungal activity of thiophenes from echinops ritro. Journal of Agricultural and Food Chemistry. 54: 1651-1655.

Joshi, R.C., Meepagala, K.M., Sturtz, G., Cagauan, A.G., Mendoza, C.O., Dayan, F.E., Duke, S.O. 2005. Molluscicidal activity of vulgarone b from artemisia douglasiana (besser) against the invasive, alien, mollusc pest, pomacea canaliculata (lamarck). International Journal of Pest Management. 51(3):175-180.

Meepagala, K.M., Osbrink, W.L., Sturtz, G., Lax, A.R. 2006. Plant derived natural products exhibiting activity against formosan subterranean termites (coptotermes formosanus). Pest Management Science. 62:565-570.

Mikstacka, R., Rimando, A.M., Szalaty, K., Stasik, K., Baer-Dubowska, W. 2006. Effect of natural analogues of trans-resveratrol on cytochrome p450 1A2 and 2E1 catalytic activities. Xenobiotica. 36(4):269-285.

Rimando, A.M., Cody, R. 2005. Determination of stilbenes in blueberries. LCGC North America. 23(11):1192-1200.

Rimando, A.M., Duke, S.O. 2006. Natural products for pest management. Rimando, A.M., Duke, S.O., editors. American Chemical Society, Washington, DC. Natural Products for Pest Management. p. 2-21.

Meepagala, K.M., Schrader, K., Wedge, D.E., Duke, S.O. 2005. Algicidal and antifungal compounds from the roots of ruta graveolens and synthesis of their analogs. Phytochemistry. 66(22): 2689-2695.

Fokialakis, N., Osbrink, W.L., Mamonov, L.K., Gemejieva, N.G., Mims, A.B., Skaltsounis, A.L., Lax, A.R., Cantrell, C.L. 2006. Antifeedant and toxicity effect of thiophenes from four echinops species against the formosan subterranean termite, coptotermes formosanus. Pest Management Science. 62:832-838.

Last Modified: 4/19/2014
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