Page Banner

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

2008 Annual Report


1a.Objectives (from AD-416)
Objective.
1)Identify bioactive natural compounds for herbicidal, insecticidal, fungicidal, antimicrobial and nutraceutical use from Vaccinium species, allelopathic rice varieties, and other sources. Objective.
2)Determine and manipulate the biosynthetic pathways of bioactive compound(s) in blueberry and rice.


1b.Approach (from AD-416)
General procedures for isolation of secondary metabolites will be employed such as solvent extractions, distillations, column chromatography and thin layer chromatography. Identification of biologically active compounds will be done using spectroscopic methods (UV, IR, MS, NMR). Extracts, fractions, and pure compounds will be tested for phytotoxic, antifungal, algaecidal and/or termiticidal activities. Phytotoxicity, antifungal and algaecidal assays being carried out routinely at NPURU will be utilized. Activity against the Formosan subterranean termite will be performed at the USDA-ARS, Formosan Subterranean Research Unit, New Orleans, LA. Biosynthetic studies will be performed by feeding with 13C-labelled precursors and incorporation will be determined by 13C-NMR spectroscopy. Molecular biology experiments will be performed using standard protocols.


3.Progress Report
Pterostilbene was previously identified as a component from blueberries that lowers serum lipid levels by acting as Peroxisome Proliferator Activated Receptor alpha (PPARa) agonist. To understand the mode of interaction with this nuclear receptor, modeling of pterostilbene into the PPARa active site was performed. Analogs of pterostilbene were synthesized and docking of the analogs into PPARa performed. This study provided fundamental knowledge on the observed activation of PPARa by pterostilbene. Resulting from the discovery of pterostilbene as a PPARa agonist and its occurrence in blueberries, a study was undertaken to investigate whether pterostilbene would improve memory decrements associated with ageing. Aged rat fed with pterostilbene-supplemented diet demonstrated significantly greater cognitive and motor function compared to rats fed non-supplemented diet. Pterostilbene was likewise detected in the hippocampus, and levels were in agreement with improved learning and performance of the pterostilbene-supplemented rat group. These studies address the following objectives of NP 306 Problem Area 2a:.
1)Identify and characterize functional compounds and components in agricultural commodities and their byproducts, and.
2)Improve understanding of the relationship between composition, molecular structure, and physical state and end-use functionality of these compounds and components. Four separate field experiments and publications were completed on basil (Ocimum basilicum L.) to determine its potential for being grown as an alternative crop in the Southern United States. The results indicate that basil can and should be grown in this region of the country. Yield and quality assessments of the primary product from basil growing, the essential oil, was compared directly to commercially available basil oil and the results indicate the product to be comparable. In one study the yield and oil composition of thirty-eight basil accessions grown in Mississippi were determined. Other studies compared the varieties of basil grown at multiple locations across the state, established optimum fertilization rates for the crop, and determined the biological activities associated with the essential oil. This accomplishment addresses NP 306 Problem Area 2a. New Product Technology (Objective: Identify and characterize functional compounds and components in agricultural commodities and their byproducts). An experiment was conducted to investigate how barnyardgrass influences the synthesis of the rice allelochemicals momilactones A and B. Seventy-five-day old rice plants were collected and are in the process of being extracted for chemical analysis of the allelochemicals. Root gene expression is also being analyzed. This study will provide knowledge on the genetic and biochemical control of value-added traits in rice that will allow for the development of improved varieties and also create the potential for high-value crop. This study addresses the following objective of NP 306 Problem Area 2a: Improve understanding of the relationship between composition, molecular structure, and physical state and end-use functionality of these compounds and components.


4.Accomplishments
1. Analysis of yield, chemical composition and biological activity of volatile oils of Basil.

Thirty-eight basil accessions were obtained from the ARS National Plant Germplasm Collection and cultivated throughout Mississippi to demonstrate that with supplemental crop irrigation and nutrients, large-scale basil producers could successfully compete in the world basil oil marketplace. The dry basil yield from all 38 accessions was relatively high, most of them exceeding 3,500 pounds per acre, and were generally consistent with yields reported from other studies. In addition, the accessions contained a range of different essential oil compositions and essential oil volumes. The Mississippi basil crops did not appear to be susceptible to insect pests that typically infest basil varieties grown in southeast Europe, which is a significant center of production. The team harvested the basil crops three times during the growing season, when the plants were in full bloom, and observed that harvesting practices affected essential oil content and herbage production. Sweet basil harvests yielded higher levels of essential oils and herbage after a second and third cut, but holy basils (O. sanctum L.) exhibited increased oil and herbage yields with the third cut. All the essential oils were tested for antimicrobial, antimalarial, antileishmanial and cytotoxic activities. No antimicrobial or antimalarial activity was observed. However, all the essential oils were found to inhibit the growth of Leishmania donovani promastigotes. Minor basil oil constituents (+)-d-cadinene, 3-carene, a-humulene, citral, and (-)-trans-caryophyllene were responsible for the antileishmanial activity, while other constituents were ineffective.

This accomplishment addresses NP 306 Problem Area 2a. New Product Technology (Objective: Identify and characterize functional compounds and components in agricultural commodities and their byproducts).

2. Discovery of pterostilbene as a natural product that can improve cognitive and motor functions in ageing.

As the population of aged individuals is increasing, problems associated with neurodegenerative disorders are also increasing. Indeed, Alzheimer's disease is listed by the Centers for Disease Control as one of the leading causes of death in the United States. In collaboration with scientists at the USDA ARS Human Nutrition Research Center on Aging, a feeding study was conducted to investigate whether pterostilbene can improve performance and memory decrements associated with ageing. Aged rats fed with diet supplemented with pterostilbene showed improved performance, assessed using Morris water maze (MWM) test, as compared to control group fed with diet without pterostilbene. Pterostilbene was found in the hippocampus of the rats. A statistically significant correlation was found between the level of pterostilbene in the hippocampus and performance in the MWM test; i.e., there was a decrease in the latency and distance to find the platform in the MWM test with increased pterostilbene level in the hippocampus, the region of the brain most associated with learning and memory. Pterostilbene is known to occur in blueberries as well as in grapes. While blueberry extracts have previously been demonstrated to reverse performance decrements in aged rats, no single blueberry constituent has been shown to give these effects as effectively as the whole extract. This research provided the first results that pterostilbene can accumulate in brain tissues and at low doses can reverse cognitive and motor function deficits in aged rats. This discovery provides further basis for the development of Vaccinium species and/or grapes as sources of this nutraceutical.

This accomplishment addresses NP 306, Problem Area 1d. (Objective: Enhance nutritional value of agricultural products).


6.Technology Transfer

Number of Invention Disclosures Submitted2
Number of Non-Peer Reviewed Presentations and Proceedings3
Number of Newspaper Articles and Other Presentations for Non-Science Audiences1

Review Publications
Zheljazkov, V.D., Callahan, A.N., Cantrell, C.L. 2007. Yield and Oil Composition of Thirty-Eight Basil (Ocimum basilicum L.) Accessions Grown in Mississippi. Journal of Agricultural and Food Chemistry. 56(1):241-245.

Zheljazkov, V.D., Cantrell, C.L., Tekwani, B., Khan, S.I. 2008. Content, Composition and Bioactivity of the Essential Oils of Three Basil Genotypes as a Function of Harvesting. Journal of Agricultural and Food Chemistry. 56:380-385.

Favi, F., Cantrell, C.L., Mebrahtu, T., Kraemer, M.E. 2008. Leaf Peltate Glandular Trichomes of Vernonia galamensis ssp. galamensis var. ethiopica Gilbert: Development, Ultrastructure and Chemical Composition. International Journal of Plant Science. 169(5):605-614.

Evidente, A., Cimmino, A., Andolfi, A., Vurro, M., Zonno, M.C., Cantrell, C.L., Motta, A. 2007. Phyllostictines A-D, Oxazatricycloalkenones Produced by Phyllosticta cirsii, A Potential Mycoherbicide for Cirsium arvense Biocontrol. Tetrahedron. 64:1612-1619.

Zheljazkov, V.D., Cantrell, C.L., Evans, W.B., Ebelhar, M., Coker, C. 2008. Yield and Composition of Ocimum basilicum L. and Ocimum sanctum L. Grown at Four Locations. HortScience. 43(3):737-741.

Kobaisy, M., Cantrell, C.L., Mims, A.B., Lax, A.R., Tellez, M., Osbrink, W.L. 2008. Activity of 1,4-Benzoquinones Against Formosan Subterranean Termites, Coptotermes formosanus. Journal of Agricultural and Food Chemistry. 56:4021-4026.

Vassilyev, J., Gemedjiyeva, N., Sitpaeva, G., Cantrell, C.L., Mamonov, L. 2008. Preparation of Plant Samples for Phytochemical Research and the Study of Their Biological Activities. Book Chapter. In: Introduction to Phytochemical Investigations and Discovering Biological Activities of Phytogenous Substances. Eds. B.M. Butin and B.A. Sarsenbaev. Institute of Plant Biology and Biotechnology, Almaty, Kazakhstan. pp. 42-47.

Muzychkina, L., Korulkin, D., Zavadskiy, V., Cantrell, C.L. 2008. Extraction, Separation, Identification and Quantity Analysis of Plant Substances. Book Chapter. Vassilyev, J., Gemedjiyeva, N., Sitpaeva, G., Cantrell, C.L., Mamonov, L. 2008. Preparation of Plant Samples for Phytochemical Research and the Study of Their Biological Activities. Book Chapter. In: Introduction to Phytochemical Investigations and Discovering Biological Activities of Phytogenous Substances. Eds. B.M. Butin and B.A. Sarsenbaev. Institute of Plant Biology and Biotechnology, Almaty, Kazakhstan. pp. 87-126.

Cantrell, C.L., Mamonov, L., Vassilyev, J., Mukanova, G., Achmetova, D. 2008. Revealing of Biological Activity in Crude Extracts, Seperated Fractions, Groups of Chemical Substance and Individual Compounds. Book Chapter. In: Introduction to Phytochemical Investigations and Discovering Biological Activities of Phytogenous Substances. Eds. B.M. Butin and B.A. Sarsenbaev. Institute of Plant Biology and Biotechnology, Almaty, Kazakhstan. pp. 127-157.

Zavadskiy, V., Gemedjiyeva, N., Mamonov, L., Cantrell, C.L. 2008. Key Rules of the Safety Precautions. Book Chapter. In: Introduction to Phytochemical Investigations and Discovering Biological Activities of Phytogenous Substances. Eds. B.M. Butin and B.A. Sarsenbaev. Institute of Plant Biology and Biotechnology, Almaty, Kazakhstan. pp. 170-189.

Cichocki, M., Paluszczak, J., Szaefer, H., Piechowiak, A., Rimando, A.M., Baer-Dubowska, W. 2008. Pterostilbene Is Equally Potent as Resveratrol in Inhibiting 12-O-tetradecanoylphorbol-13-acetate Activated NFkappaB, AP-1, COX-2 and iNOS in Mouse Epidermis. Molecular Nutrition and Food Research. 52(S1):S62-S70.

Mizuno, C.S., Ma, G., Khan, S., Patny, A., Avery, M.A., Rimando, A.M. 2008. Design, Synthesis, Biological Evaluation and Docking Studies of Pterostilbene Analogs Inside PPARa. Bioorganic and Medicinal Chemistry. 16:3800-3808.

Remsberg, C.M., Yanez, J.A., Ohgami, Y., Vega-Villa, K.R., Rimando, A.M., Davies, N.M. 2008. Pharmacometrics of Pterostilbene: Pre-Clinical Pharmacokinetics and Metabolism, Anti-Cancer, Anti-Inflammatory, Anti-Oxidant, and Analgesic Activity. Phytotherapy Research. 22(2):169-179.

Cantrell, C.L., Duke, S.O., Fronczek, F.R., Osbrink, W.L., Mamonov, L.K., Vassilyev, J.I., Wedge, D.E., Dayan, F.E. 2007. Phytotoxic Eremophilanes from Ligularia macrophylla. Journal of Agricultural and Food Chemistry. v. 55:10656-10663.

Cantrell, C.L., Case, B.P., Mena, E., Kniffin, T.M., Duke, S.O., Wedge, D.E. 2008. Isolation and Identification of Antifungal Fatty Acids from the Basidiomycete Gomphus floccosus. Journal of Agricultural and Food Chemistry. 56:5062-5068.

Chen, J., Cantrell, C.L., Duke, S.O., Allen, M.L. 2008. Repellency of Callicarpenal and Intermedeol Against Workers of Imported Fire Ants. Journal of Economic Entomology.101(2):265-271 (2008).

Last Modified: 4/20/2014
Footer Content Back to Top of Page