Strategies for the discovery of bioactive phytochemicals

Phytochemicals as Bioactive Agents

Volumn , Issue , 2000, Pages 1-20

  Duke, Stephen O ^a   Rimando, Agnes M ^a   Dayan, Franck E ^a   Canel, Camilo ^a   Wedge, David E ^a   Tellez, Mario R ^a   Schrader, Kevin K ^a   Weston, Leslie A ^b   Smillie, Troy J ^a   Paul, Rex N ^c   Duke, Mary V ^c  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b Department of Population Medicine and Diagnostic Sciences   (United States)

^c AGRICULTURAL RESEARCH SERVICE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOACTIVITY;

19TH CENTURY; 20TH CENTURY; ACTIVE INGREDIENTS; PEST MANAGEMENT; PHYTOCHEMICALS; PLANT COMPOUNDS; PYRETHROIDS;

SALICYLIC ACID;

EID: 84889964523     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (74)

1. Albert, K., Braumann, U., Tseng, L-H., Nicholson, G., Bayer, E., Spraul, M., Hofmann, M., Dowle, C., and Chippendale, M. 1994. Online Coupling of Supercritical-Fluid Chromatography and Proton High-Field Nuclear-Magnetic-Resonance Spectroscopy. Anal. Chem 66:3042-3026.
2. Albert, K. 1995. On-Line Use of NMR Detection in Separation Chemistry. J. Chromatogr. A 703: 123–147.
3. Albert, K., Schlotterbeck, G., Braumann, U., Handel, H., Spraul, M., and Krack, G. 1995. Structure Determination of Vitamin A Acetate Isomers through Coupled HPLC and ‘H NMR Spectroscopy. Angew. Chem. Int. Ed. Engl.34:1014-1016.
4. Ayers, S.W., Isaac, G.G., Krupa, D.M., Crosby, K.E., L etendre, L.J., and Stonard, R.J. 1989. Herbicidal Compounds from Microorganisms. Pestic. Sci. 27:221-223.
5. Brockmoller, J., Reum, T., Bauer, S., Kerb, R., and Hiibner, W.D. 1997. Hypericin and Pseudohy-pericin: Pharmacokinetics and Effects on Photosensitivity in Humans. Pharmacopsychiat. 30(Suppl):94-101.
6. Buckingham, J. and Thompson, S. 1997. The Dictionary of Natural Products and Other Information Sources for Natural Products Scientists. In Phytochemical Diversiry. A Source of New Industrial Products, S. Wrigley, M. Hayes, R. Thomas, and E. Chrystal, Eds., Royal Soc. Chem., Cambridge, UK, pp. 53–67.
7. Carlson, T.J., Cooper, R., King, S.R., and Rozhon, E.J. 1997. Modem Science and Traditional Healing. In Phytochemical Diversity. A Source of New Industrial Products, S. Wrigley, M. Hayes, R. Thomas, and E. Chrystal, Royal Soc. Chem., Cambridge, UK, pp. 84–95.
8. Choudhary, M.I. and Atta-ur-Rahman. 1997. Bioactivity-Guided Isolation of Phytochemicals from Medicinal Plants. In Phytochemical Diversify. A Source of New Industrial Products. S. Wrigley, M. Hayes, R. Thomas, and E. Chrystal, Eds., Royal Soc. Chem., Cambridge, UK, pp. 41–52.
9. Clayton, E., Taylor, S., Wright, B., and Wilson, I.D. 1998. The Application of High Performance Liquid Chromatography, Coupled to Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry (HPLC-NMR-MS), to the Characterization of Ibuprofen Metabolites from Human Urine. Chromatographia 47:264-270.
10. Corley, D.G., and Durley, R.C. 1994. Strategies for Database Dereplication of Natural Products. J. Nut. Prod. 57:1484-1490.
11. Cui, B., Chai, H., Constant, H.L., Santisuk, T., Reutrakul, V., Beecher, C.W.W., Farnsworth, N.R., Cordell, G.A., Pezzuto, J.M., and Kinghorn, A.D. 1998. Limonoids from Azadirachta excelcia. Phytochemistry 47: 1283–1287.
12. Curtis, J.D. and Lersten, N.R. 1990. Internal Secretory Structures in Hypericum (Clusiaceae): H. perforarum L. and H. balearicum. New Phytol. 1l4:571-580.
13. Czarnota, M.A., Weston, L.A., and Dayan, F.E. 1998. The Use of Molecular Modeling Studies to Predict the Activity of Sorgoleone. Weed Sci. Soc. Amer. Abstr. 38:52.
14. Dayan, F.E., Hernandez, A., Allen, S.N., Moraes, R.M., Vroman, J.A., Avery, M.A., and Duke, S.O. 1999. Comparative Phytotoxicity of Artemisinin and Several Sesquiterpene Analogues. Phytochemistry 50:607-614.
15. Decosterd, L., Gustafson, K.R., Cardellina, J.H., 11, Cragg, G.M., and Boyd, M.R. 1994. The Differential Cytotoxicity of Cardenolides from Thevetia ahouia. Phytotherapy Res. 8:74-77.
16. Duke, M.V., Paul, R.N., Elsohly, H.K., Sturtz, G., and Duke, S.O. 1994. Localization of Artemisinin and Artemisitene in Foliar Tissues of Glanded and Glandless Biotypes of Artemisia annua. Internat. J. Plant Sci. 155:365-373.
17. Duke, S.O. 1994. Commentary: Glandular Trichomes-A Focal Point of Chemical and Structural Interactions. Internat. J. Plant Sci. 155:617-620.
18. Duke, S.O. 1991. Plant Terpenoids as Pesticides. In Toxicology of Plant and Fungal Compounds. Handbook of Natural Toxins, Vol. 6., R.F. Keeler and A.T. Tu, Eds., Marcel Dekker, New York, pp. 269–296.
19. Duke, S.O. and Paul, R.N. 1993. Development and Fine Structure of the Glandular Trichomes of Artemisia annua L. Internat. J. Plant Sci. 154: 107–118.
20. Duke, S.O., Paul, R.N., and Lee, S.M. 1988. Terpenoids from the Genus Artemisia as Potential Pesticides. Amer. Chem. Soc. Symp. Ser. 38O:318-334.
21. Duke, S.O., Vaughn, KC., Croorn, E.M., Jr., and Elsohly, H.N. 1987. Artemisinin, a Constituent of Annual Wormwood (Artemesia annu), Is a Selective Phytotoxin. Weed Sci. 35:499-505.
22. Einhellig, F.A. and Rasmussen, J.A. 1989. Prior Cropping with Grain Sorghum Inhibits Weeds. J. Chem. Ecol. 15:951-960.
23. Einhellig, F.A., Rasmussen, J.A., Hejl, A., and Souza, I.F. 1993. Effects of Root Exudate Sorgoleone on Photosynthesis. J. Chem. Ecol. 19:369-375.
24. Ferreira, J.F.S. and Duke, S.O. 1997. Approaches for Maximizing Biosynthesis of Medicinal Plant Secondary Metabolites. AgBiotech News and Information 9:309N-316N.
25. Ferreira, J.F.S. and Janick, J. 1995. Floral Morphology of Artemisia annua with Special Reference to Trichomes. Int. J. Plant Sci. 156(6):807-815.
26. Fields, P.G., Arnason, J.T., Philoghe, B.J.R., and Aucoin, R.R. 1991. Phototoxins as Insecticides and Natural Plant Defenses. Mem. Ent. Soc. Can. 159:29-38.
27. Forney, D.R. and Foy, C.L. 1985. Phytotoxicity of Products from Rhizospheres of a Sorghum-Sudangrass Hybrid (S. bicolor X S. sudanase). Weed Sci. 33:597-604.
28. Forney, D.R., Foy, C.L., and Wolf, D.D. 1985. Weed Suppressin in No-Till Alfalfa (Medicago sativa) by Prior Cropping of Summer Annual Grasses. Weed Sci. 33:490-497.
29. Fujita, T. 1995. Quantitative Structure-Activity Analysis and Database-Aided Bioisosteric Structural Transformation Procedure as Methodologies of Agrochemical Design, Amer. Chem. Soc. Symp. Ser. 606: 13–34.
30. Giese, A.C. 1980. Hypericism. Photochem. Photobiol. Rev. 5:229-255.
31. Gonzalez, V., Nimbal, C.I., Weston, L.A., and Cheniae, G.M. 1997. Inhibition of Photosystem II Electron Transfer Reaction by Sorgoleone, a Natural Product. J. Agric. Food Chem. 45:1415-1421.
32. Grayson, B.T., Williams. K.S. Freehauf, P.A., Pease, R.R. Ziesel, W.T., Sereno, R.N., and Reinsfelder, R.E. 1987. The Physical and Chemical Properties of the Herbicide Cinmethylin (SD 95481). Pestic. Sci. 21:143-153.
33. Gu, Z., Zhou, D. and Wu, J. 1997. Screening for Annonaceous Acetogenins in Bioactive Plant Extracts by Liquid Chrornatographyhlass Spectrometry. J. Nut. Prod. 60:242-248.
34. Hedin, P.A., Hollingworth, R.M., Masler, E.P., Miyarnoto, J., and Thompson, D.G. (Eds.) 1997. Phytochemicals for Pest Control, Amer. Chem. Soc. Symp. Ser., 658:372.
35. Holt, R.M., Newman, M.J., Pullen, F.S., Richards, D.S., and Swanson, A.G. 1997. High Performance Liquid ChromatographyINMR Spectrometry/mass Spectrometry: Further Advances in Hyphenated Technology. J. Mass. Spectrom. 32:64-70.
36. Hook, D.J., Pack, F.J., Yacobucci, J.J., and Guss, J. 1997. Approaches to Automating the Dereplication of Bioactive Natural Products-The Key Step in High Throughput Screening of Biactive Materials from Natural Sources. J. Biomolec. Screening 2:145-152.
37. Iwabuchi, H., Kitazawa, E., Kobayashi, N., Watanabe, H., Kanai, M., and Nakamura, K. 1994. Studies on Drug Metabolism Using Liquid Chromatographyhlass Spectrometry: Comparison of Three Liquid Chromatographid Mass Spectrometric Interfaces. Bid. Mass Spectrom. 23:540-546.
38. Johnson, S., Morgan, E.D., Wilson, I.D., Spraul, M., and Hofmann, M. 1994. Photo-Isomerization of Azadirachtin Studied by High Performance Liquid Chromatography Coupled to High Field Proton NMR Spectroscopy. J. Chem. Soc. Perkin Trans. 1:1499-1502.
39. Kimura, H., Harris, M.S., Sakamoto, T., Gopalakrishna, R., Gundimeda, U., Cui, J.Z., Spee, C., Hinton, D.R., and Ryan, S.J. 1997. Hypericin Inhibits Choroidal Endothelial Cell Proliferation and Cord Formation in vitro. Current Eye Res. 16:967-972.
40. Klayman, D.L. 1985. Qinghaosu (Artemisinin): an Antimalarial Drug from China. Science. 228: 1049–1055.
41. Knox, J.P. and Dodge, A.D. 1985. Isolation and Activity of the Photodynamic Pigment Hypericin. Plant Cell Environ. 9: 19–25.
42. Knox, J.P., Samuels, R.I., and Dodge, A.D. 1987. Photodynamic Action of Hypericin. Amer. Chem. Soc. Symp. Ser. 339:265-270.
43. Koren, H., Schenk, G.M., Jindra, R.H., Alth, G., Ebermann, R., Kubin, A., Koderhold, G., and Kreitner, M. 1996. Hypericin in Phototherapy. J. Photochem. Photobiol. 36B: 113–119.
44. Lavie, G., Mazur, Y., Prince, A.M., Pascual, D., Liebes, L., Levin, B., and Meruelo, D. 1995. Hypericin as an Inactivator of Infectious Viruses in Blood Components. Transfusion. 35:392-400.
45. Likhiwitayawuid, K., Angerhofer, C.K., Cordell, G.A., and Pezzuto, J.M. 1993. Cytotoxic and Antimalarial Bisbenzylisoquinoline Alkaloids from Stephania erecta. J. Nut. Prod. 56:30-38.
46. Lindon, J.C., Nicholson, J.K., and Wilson, I.D. 1995. The Development and Application of Coupled HPLC-NMR Spectroscopy. Adv. Chromatogr. 36:315-382.
47. Lindon, J.C., Nicholson, J.K., and Wilson, I.D. 1997. Directly Coupled HPLC-NMR and Its Application to Drug Metabolism. Drug Metab. Rev. 29:705-746.
48. Lydon, J. and Duke, S.O. 1989. The Potential of Pesticides from Plants. In Herbs, Spices, and Medicinal Plants: Recent Advances in Botany, Horticulture, und Pharmacology, Vol. 4, L.E. Craker and J.E. Simon, Oryx Press, Phoenix, AZ, pp. 1–41.
49. Miiller, G. and Giera, H. 1998. Protein Secondary Structure Templates Derived from Bioactive Natural Products. J. Computer-Aided Molec. Design. 12:l-6.
50. Netzley, D.H. and Butler, L.G. 1986. Roots of Sorghum Exude Hydrophobic Droplets Containing Biologically Active Components. Crop Sci. 26:776-778.
51. Nimbal, C.I., Yerkes, C.N., Weston, L.A., and Weller, S.C. 1996. Herbicidal Activity and Site of Action of the Natural Product Sorgoleone. Pestic. Biochem. PhysioL 54:73-83.
52. Olofsdotter, M., (Ed) 1998. Allelopathy in Rice. Intern. Rice Res. Inst., Manila, 154 pp.
53. Pachlatko, J.P. 1998. Natural Products in Crop Production. Chimia. 52:29-47.
54. Putnam, A.R. and DeFrank, J. 1983. Use of Phytotoxic Plant Residues for Selective Weed Control. Crop Protect. 2: 173–181.
55. Rimando, A.M., Dayan, F.E., Czarnota, M.A., Weston, L.A., and Duke, S.O. 1998. A New Photosytem 11 Electron Transfer Inhibitor from Sorghum bicolor (L.). J. Nut. Products. 61:927-930.
56. Robbers, J.E., Speedie, M.K., and Tyler, V.E. 1996. Pharmacognosy and Pharmacobiotechnology. Williarns and Wilkins, Baltimore, 337 pp.
57. Scarfe, G.B., Wilson, I.D., Spraul, M., Hoffmann, M., Braumann, U., Lindon, J.C., and Nicholson, J.K. 1997. Application of Directly Coupled High Performance Liquid Chromatography-Nuclear Magnetic Resonance-Mass Spectrometry to the Detection and Characterization of the Metabolites lites of 2-Bromo-4-trifluoromethylaniline in Rat Urine. Anal. Chem. 34:37-39.
58. Shockcor, J.P., Unger, S.E., Wilson, I.A., Foxall, P.J.D., Nicholson, J.K., and Lindon, J.C. 1996. Combined HPLC, NMR Spectroscopy, and Ion-Trap Mass Spectrometry with Application to the Detection and Characterization of Xenobiotics and Endogenous Metabolites in Human Urine. Anal. Chem. 68:4431-4435.
59. Schrader, K.K., de Regt, M.Q., Tidwell, P.D., Tucker, C.S., and Duke, S.O. 1998. Selective Growth Inhibition of the Musty-Odor Producing Cyanobacterium Oscillatoria cf. chalybea by Natural Compounds. Bull. Environ. Toxicol. 60:651-658.
60. Schrader, K.K., de Regt, M.Q., Tucker, C.S., and Duke, S.O. 1997. A Rapid Bioassay for Selective Algicides. Weed Technol. 11:767-774.
61. Shu, Y.-Z. 1998. Recent Natural Products Based Drug Development: A Pharmaceutical Industry Perspective. J. Nat. Prod. 61:1053-1071.
62. Siuzdak, G. 1994. The Emergence of Mass Spectrometry in Biochemical Research. Proc. Natl. Acad. Sci. U.S.A. 91: 11290–11297.
63. Spraul, M., Braumann, U., Renault, J.H., Thepenier, P., and Nuzillad, J.M. 1997. Nuclear Magnetic Resonance Monitoring of Centrifugal Partition Chromatography in pH-Zone-Refining Mode. J. Chromatogr. A. 766:255-260.
64. Spring, O., Buschmann, H., Vogler, B., Schilling, E.E., Spraul, M., and Hoffmann, M. 1995. Sesquiterpene Lactone Chemistry of Zaluzania grayana from On-Line LC-NMR Measurements. Phytochemistry. 39:609-612.
65. Strobel, G.A., Hess, W.M., Ford, E., Sidhu, R.S., and Yang, X. 1996. Taxol from Fungal Endophytes and the Issue of Biodiversity. J. Industrial Microbiol. Biotechnol. 17:417-423.
66. Tellez, M.R., Canel, C., Rimando, A.M., and Duke, S.O. 1999. Differential Accumulation of Isoprenoids in Glanded and Glandless Artemisia annua. Submitted to Phytochemistry.
67. Upton, R., Graff, A., Williamson, E., Bunting, D., Gatherum, D.M., Walker, E.B., Butterweck, V., Liefliinder-Wulf, U., Nahrstedt, A., Wall, A., Winterhoff, H., Cott, J., Marquis, M.C., Shumake, R.L., Stansbury, J., and Petrone, C., 1997. St. John’s Wort (Hypericum peforatum). In American Herbal Pharmacopoeia and Therapeutic Compendium. R. Upton, Ed., American Herbal Pharmacopoeia, Santa Cruz, CA, 32 pp.
68. Vogler, B., Klaiber, I., Roos, G., Walter, C.U., Hiller, W., Sandor, P., and Kraus, W. 1998. Combination of LC-MS and LC-NMR as a Tool for the Structure Determination of Natural Products. J. Nat. Prod. 61: 175–178.
69. Wedge, D.E. and Kuhajek, J.M. 1998. A Microbioassay for Fungicide Discovery. SAAS Bulletin Biochem. Biotech. 11: 1–7.
70. Wedge, D.E. and Kuhajek, J.M. 1999. A Natural Product Fungicide Discovery Protocol Using Bioautography and Microtiter Assays. Phytopathology. Abstract, in press.
71. Weston, L.A., Nimbal, C.I., and Jeandet, P. 1998. Allelopathic Potential of Grain Sorghum (S. bicolor (L.) Moench) and Related Species. In Principles and Practices of Plant Ecology, Inderjit and C.L. Foy, Eds., CRC Press, New York, pp. 467–477.
72. Whitney, J.L., Kerns, E.H., Rourick, R.A., Hail, M.E., Volk, K.J., Fink, S.W., and Lee, MS. 1998. Accelerated Structure Profiling Using Automated LC-MS and Robotics. Pharm. Technol. May, 76–82.
73. Wu, N., Peck, T.L., Webb, A.G., Magin, R.L., and Sweedler, J.V. 1994. Nanoliter Volume Sample Cells for ’H-NMR Application to Online Detection in Capillary Electrophoresis. J. Am. Chem. Soc. 116:7929-7930.
74. Zhou, S. and Hamburger, M. 1996. Application of Liquid Chromatography-Atmospheric Pressure Ionization Mass Spectrometry in Natural Product Analysis. Evaluation and Optimization of Electrospray and Heated Nebulizer Interfaces. J. Chrom. 755:189-204.