Activity of Quinones on Colletotrichum species

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 13, 2003, Pages 3824-3828

  Meazza, Giovanni ^a   Dayan, Franck E ^b   Wedge, David E ^b  

^a Isagro Ricerca Srl   (Italy)

^b NATURAL PRODUCTS UTILIZATION RESEARCH UNIT   (United States)

Author keywords

Antifungal activity; Benzoquinone; Fungicide; Naphthoquinone; Natural products; Triketone

Indexed keywords

1,2 NAPHTHOQUINONE; 1,4 BENZOQUINONE; 1,4 NAPHTHOQUINONE; ANTHRAQUINONE; FUNGICIDE; QUINONE DERIVATIVE;

AGRICULTURE; ANTIFUNGAL ACTIVITY; ARTICLE; COLLETOTRICHUM; COLLETOTRICHUM ACUTATUM; COLLETOTRICHUM FRAGARIAE; COLLETOTRICHUM GLOEOSPORIOIDES; DRUG SENSITIVITY; FUNGUS; PLANT DISEASE;

COLLETOTRICHUM; COLLETOTRICHUM FRAGARIAE; FUNGI; GLOMERELLA ACUTATA; GLOMERELLA CINGULATA;

EID: 0038454772     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0343229     Document Type: Article

References (42)

1. Dayan, F. E. Natural pesticides. In Encyclopedia of Pest Management; Pimentel, D., Ed.; Marcel Dekker: New York, 2002; pp 521-525.
2. Kirst, H. A.; Michel, K. H.; Mynderase, J. S.; Chio, E. H.; Yao, R. C.; Nakasukasa, W. M.; Boeck, L. D.; Occlowitz, J. L.; Paschal, J. W.; Deeter, J. B.; Thompson, G. D. In Synthesis and Chemistry of Agrochemicals III; Baker, D. R., Fenyes, J. G., Steffens, J. J., Eds.; ACS Symposium Series No. 504; Amercian Chemical Society: Washington DC, 1992; pp 214-225.
3. McChesney, J. D. Biological and chemical diversity and the search for new pharmaceuticals and other bioactive natural products. In Human Medicinal Agents from Plants; Kinghorn, A. D., Balandrin, M. F., Eds.; ACS Symposium Series 534; American Chemical Society: Washington, DC, 1993; pp 38-47.
4. Wedge, D. E.; Camper, N. D. Connections between agrochemicals and pharmaceuticals. In Biologically Active Natural Products: Agrochemicals and Pharmaceuticals; Cutler, H. G., Cutler, S. J., Eds.; CRC Press: Boca Raton, FL, 2000; pp 1-15.
5. Strack, D. Phenolic metabolism. In Plant Biochemisty; Dey, P. E., Harborne, J. B., Eds.; Academic Press: San Diego, CA, 1997; pp 387-416.
6. Maloy, O. C. Fungicide Development and Use. In Plant Disease Control; John Wiley and Sons: New York, 1993; pp 163-180.
7. Meister, R. T. Crop Protection. In Farm Chemicals Handbook; Meister Publishing Co.: Willoughby, OH, 2000; Vol. 86, pp C1-414.
8. Freeman, S.; Katan, T.; Shabi, E. Characterization of Colletotrichum species responsible for anthracnose diseases of various fruits. Plant Dis. 1998, 82, 596-607.
9. Wedge, D. E.; Riley, M. B.; Tainter, F. H. Phytotoxicity of Discula destructiva culture filtrates to Cornus spp. and the relationship to disease symptomology. Plant Dis. 1999, 83, 377-380.
10. Maas, J. L., Ed. Compendium of Strawberry Diseases, 2nd ed.; APS Press: St. Paul, MN, 1998.
11. Maas, J. L.; Palm, M. E. Occurrence of anthracnose irregular leafspot, caused by Colletotrichum acutatum, on strawberry in Maryland, Adv. Strawberry Res. 1997, 16, 68-70.
12. Howard, C. M.; Maas, J. L.; Chandler, C. L.; Albreghts, E. A. Anthracnose of strawberry caused by the Colletotrichum complex in Florida. Plant Dis. 1992, 76, 976-981.
13. Smith, B. J. Anthracnose Crown Rot. In Compendium of Strawberry Diseases, 2nd ed.; Maas, J. L., Ed.; American Phytopathological Society: St. Paul, MN, 1998; pp 46-48.
14. Smith, B. J. Anthracnose Fruit Rot (Black Spot). In Compendium of Strawberry Diseases, 2nd ed.; Maas, J, L., Ed.; American Phytopathological Society: St. Paul, MN, 1998; pp 31-33.
15. Smith, B. J. Anthracnose Leaf Spot and Irregular Leaf Spot. In Compendium of Strawberry Diseases. 2nd ed.; Maas, J. L., Ed.; American Phytopathological Society: St. Paul, MN, 1998; pp 24-25.
16. Wedge, D. E.; Nagle, D. G. A new 2D-TLC bioautography method for the discovery of novel antifungal agents to control plant pathogens. J. Nat. Prod. 2000, 63, 1050-1054.
17. Wedge, D. E.; Galindo, J. C. G.; Marcias, F. A. Fungicidal activity of natural and synthetic sesquiterpene lactone analogues. Phytochemistry, 2000, 53, 747-757.
18. Smith, B. J.; Black, L. L. Morphological, cultural, and pathogenic variation among Colletotrichum species isolated from strawberry. Plant Dis. 1990, 74, 69-76.
19. Espinel-Ingrof, A.; Kerkering, T. M. Spectrophotometric method of inoculum preparation for the in vitro susceptibility testing of filamentous fungi. J. Clin. Microbiol. 1991, 29, 393-394.
20. Wedge, D. E.; Kuhajek, J. M. A microbioassay for fungicide discovery. SAAS Bull. Biochem. Biotechnol. 1998, 11, 1-7.
21. Homans, A. L.; Fuchs, A. Direct bioautography on thin-layer chromatography as a method for detecting fungitoxic substances. J. Chromatogr. 1970, 51, 327-329.
22. Osborne, A. E.; Chase, B. R.; Lunness, P.; Scott, P. R.; Daniels, M. J. An oat species lacking avenacin is susceptible to infection by Gaeumannomyces graminis var. tritici. Physiol. Mol. Plant Pathol. 1994, 45, 457-467.
23. Katzung, B. G. Principles-Introduction. In Basic and Clinical Pharmacology; Katzung, B. G., Ed.; Appleton-Lange: 1998; p 5.
24. Wedge, D. E.; Smith, B. J. A microtiter assay shows effectiveness of a natural fungicide for control of Collerotrichum spp. Phytopathology 2000, 90, S83.
25. LaMondia, J. A. In vitro evaluation of fungicides against Colletotrichum acutatum isolates from strawberry. Adv. Strawberry Res. 1993, 12, 34-37.
26. Smith, B. J.; Black, L. L. In vitro fungicide studies show the occurrence of benomyl-resistant Colletotrichum spp. strawberry. Adv. Strawberry Res. 1993, 12, 42-48.
27. Sasaki, K.; Abe, H.; Yoshizaki, F. In vitro antifungal activity of naphthoquinone derivatives. Biol. Pharm. Bull. 2002, 25, 669-670.
28. Brigham, L. A.; Michaels, P. J.; Flores, H. E. Cell-specific production and antimicrobial activity of naphthoquinones in roots of Lithospermum erythrorhizon. Plant Physiol. 1999, 119, 417-428.
29. Binutu, O. A.; Adesogan, K. E.; Okogun, J. I. Antibacterial and antifungal compounds from Kigelia pinnata. Planta Med. 1996, 62, 352-353.
30. Meister, R. T.; Berg, G. L.; Sine, C.; Meister, S.; Poplyk, J. Farm Chemicals Handbook, 70th ed.; Meister Publishing Co.: Willoughby, OH, 1984.
31. Dayan, F. E. Octan-1-ol/water partition coefficients of p-benzo and p-naphthoquinones corrected for pH effect. J. Chem. Res. 2002, 10, 518-519.
32. Schultz, T. W.; Bearden, A. P. Structure-toxicity relationships for selected naphthoquinones to Tetrahymena pyriformis. Bull. Environ. Contam. Toxicol. 1998, 6, 405-410.
33. Jewess, P. J.; Higgins, J.; Berry, K. J.; Moss, S. R.; Boogaard, A. B.; Khambay, B. P. S. Herbicidal action of 2-hydroxy-3-alkyl-1,4-naphthoquinones. Pest Manage. Sci. 2002, 58, 234-242.
34. Jewess, P. J.; Chamberlain, K.; Boogaard, A. B.; Devonshire, A. L.; Khambay, B. P. S. Insecticidal 2-hydroxy-3-alkyl-1,4-naphthoquinones: correlation of inhibition of ubiquinol cytochrome c oxidoreductase (complex III) with insecticidal activity. Pest Manage. Sci. 2002, 58, 243-247.
35. Khambay, B. P. S.; Batty, D.; Beddie, D.; Denholm, I.; Cahill, M. R. A new group of plant-derived naphthoquinone pesticides. Pestic. Sci. 1997, 50, 291-296.
36. Khambay, B. P. S.; Jewess, P. The potential of natural naphthoquinones as the basis for a new class of pest control agents - an overview of research at IACR-Rothamsted. Crop Protect. 2000, 19, 597-601,
37. Kozubek, A.; Tyman, J. H. P. Resorcinolic lipids, the natural nonisoprenoid phenolic amphiphiles and their biological activity. Chem. Res. 1999, 99, 1-25.
38. Meazza, G.; Scheffler, B. E.; Tellez, M. R.; Rimando, A. M.; Nanayakkara, N. P. D.; Khan, I. A.; Abourashed, E. A.; Romagni, J. G.; Duke, S. O.; Dayan, F. E. The inhibitory activity of natural products on plant p-hydroxyphenylpyruvate dioxygenase. Phytochemistty 2002, 59, 281-288.
39. Sankaram, A. V. B.; Srinivasan, T. N.; Indulkar, A. S. Fungicidal activity of some naturally occurring naphthaquinones. Pestic. Sci. 1975, 6, 165-168.
40. Spencer, G. F.; Tjarks, L. W.; England, R. E.; Seest, E. P. The effect of naturally occurring naphthoquinones on velvetleaf (Abutilon theophrasti) germination. J. Nat. Prod. 1986, 49, 530-533.
41. Kawai, K. Interaction of mycotoxins with biomembranes. Inhibition of mitochondrial respiratory chain by quinone mycotoxin. Maku 1987, 12, 304-312.
42. Jahn, M.; Burth, U.; Lyr, H. Positive physiological side effects regarding plant growth and yield. In Modern Fungicides and Antifungal Compounds; Lyr, H., Rssell, P. E., Sisler, H. D., Eds.; Intercept: Andover, 1996; pp 263-271.