Nematicidal alkaloids and related compounds produced by the fungus penicillium cf. Simplicissimum

Bioscience, Biotechnology and Biochemistry

Volumn 64, Issue 12, 2000, Pages 2559-2568

  Kusano, Miyako ^a   Koshino, Hiroyuki ^b   Uzawa, Jun ^b   Fujioka, Shozo ^b   Kawano, Tsuyoshi ^a   Kimura, Yasuo ^a  

^a TOTTORI UNIVERSITY   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

Dihydroquinolinones; Nematicidal activity; Penicillium cf. simplicissimum; Peniprequinolone

Indexed keywords

ALKALOID; ANTINEMATODAL AGENT; BENZODIAZEPINE DERIVATIVE; CYCLOPENIN; PENIGEQUINOLONE A; PENIPREQUINOLONE; QUINOLONE DERIVATIVE;

ANIMAL; ARTICLE; CAENORHABDITIS ELEGANS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; DRUG SENSITIVITY; ISOLATION AND PURIFICATION; METABOLISM; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARASITOLOGY; PENICILLIUM; PLANT ROOT; RICE;

ALKALOIDS; ANIMALS; ANTINEMATODAL AGENTS; BENZODIAZEPINONES; CAENORHABDITIS ELEGANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORYZA SATIVA; PARASITIC SENSITIVITY TESTS; PENICILLIUM; PLANT ROOTS; QUINOLONES;

EID: 0034567580     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.64.2559     Document Type: Article

References (25)

1. Kimura, Y., Kusano, M., Koshino, H., Uzawa, J., Fujioka, S., and Tani, K., Penigequinolones A and B, pollen-growth inhibitors produced byPénicilliumsp. No. 410.Tetrahedron Lett.,37, 4961-4964 (1996).
2. Hayashi, H., Nakatani, T., Inoue, Y., Nakayama, M., and Nozaki, H., New dihydroquinolinone toxic toArtemia salinaproduced byPénicilliumsp. NTC-47.Biosci. Biotechnol. Biochem.,61,914-916 (1997).
3. Mohammed, Y. S. and Luckner, M., The structure of cyclopenin and cyclopenol, metabolic products fromPénicillium cyclopiumWestling andPénicillium viridicatumWestling.Tetrahedron Lett.,28,1953-1958 (1963).
4. MacCamish, M. and White, J. D., Mass spectra of cyclopenin and viridicatin.Organic Mass Spectrometry,4,241-248 (1970).
5. Nover, L. and Luckner, M., Mixed functional oxygenations during the biosynthesis of cyclopenin and cyclopenol, benzodiazepine alkaloids ofPénicillium cyclopiumWestling.FEBS Lett.,3, 292-296 (1969).
6. Sayed, E., Aboutabl, A., Azzouny, A. E., Winter, K., and Luckner, M., Stereochemical aspects of the conversion of cyclopeptine into dehydrocyclopeptine by cyclopeptine dehydrogenase fromPénicillium cyclopium. Phytochemistry,15,1925-1928 (1976).
7. Cole, R. J. and Cox, R. EL, Pénicilliumtoxins, in “Handbook of toxic fungal metabolites”, eds. Academic Press, London, pp. 849-852.
8. Kursberg, L. R., Studies on the culturing and parasitism of plant-parasitic nematodes, in particularDitylenchus dipsaciandAphelenchoides ritzemabosion alfalfa tissues.Nematologica,6,181-200 (1961).
9. Kursberg, L. R., In “Experimental methods for soil microorganisms” (in Japanese), eds. Dojo Biseibutu Kenkyukai You-kendo Press, Tokyo, pp. 146-157 (1975).
10. Saigusa, T., In “Nematodes” (in Japanese) 2nd ed., Rural Culture Association Press, Tokyo, pp. 107-113 (1993).
11. Kimura, Y., Mori, M., Hyeson, S., Suzuki, A., and Mitsui, Y., A rapid and simple method for assay of nematicidal activity and application to measuring the activities of dicarboxylic esters.Agric. Biol. Chem.,45,249-251 (1981).
12. Stadler, M. and Anke, H., Lachnumon and lachnumol, new metabolites with nematicidal and antimicrobial activities from the ascomyceteLachnum papyraceum(KARST.) KARST.46,961-966 (1993).
13. Wood, W. B., In “The nematodeCaenorahabditis elegans”, Cold Spring Harbor Press, pp. 587-593 (1988).
14. Kimura, Y., Tani, K., Kojima, A., Sotoma, G., Okada, K., and Shimada, A., Cyc/o-(L-tryptophyl-L-phenylalanyl), a plant growth regulator produced by the fungusPénicilliumsp.Phytochemistry,42,665-669 (1996).
15. Kimura, Y., Suzuki, A., Tamura, S., Mori, K., Oda, M. and Matui, M., Biological activity of pestalotins on the elongation growth of rice seedlings.Plant Cell Physiol,18,1177-1179 (1977).
16. 13C chemical shifts of some model olefins. Org. Magn. Reson.,8,426-431 (1976).
17. Hurd, H. E. and John, B. K., Gradient-enhanced proton-detected heteronuclear multiple-quantum coherence spectroscopy.J. Magn. Reson.,91,648-653 (1991).
18. Willker, W., Leibfritz, D., Kerssebaum, R., and Ber-mel, W., Gradient selection in inverse heteronuclear correlation spectroscopy.Magn. Reson. Chem.,31,287-297 (1993).
19. Luckner, M. and Mothes, K., On the biosynthesis of 2,3-dihydroxy-4-phenyl-quinoline (viridicatin).Tetrahedron Lett.,23,1035-1039 (1962).
20. Birkinshaw, J. H., Lucker, M., Mohammed, Y. S., Mothes, K., and Sticking, C. E., Studies in the biochemistry of micro-organisms 114.Biochem. J.,89,196-202 (1963).
21. Taniguchi, M. and Satomura, Y., Isolation of viridicatin fromPénicillium crustosum, and physiological activity of viridicatin and its 3-carboxymethylene derivative on microorganisms and plants.Agric. Biol. Chem.,34,506-510 (1970).
22. Framm, J., Nover, L., Azzouny, A. E., Richter, H., Winter, K., Werner, S., and Luckner, M., Cyclope-nin und dehydrocyclopeptin, Zwischenprodukte der biosynthese von alkaloiden der cyclopenin-viridicatin-gruppe beiPénicillium cyclopium Westling.Eur. J. Biochem.,37,78-85 (1973).
23. Voigt, S. and Luckner M., Dehydrocyclopeptine epoxidase fromPénicillium cyclopium. Phytochemistry,16,1651-1655 (1977).
24. Mayer, A., Anke, H., and Sterner, O., Omphalotin, a new cyclic peptide with potent nematicidal activity fromOmphalotus olearius1.Natural Product Lett.,10, 25-32 (1997).
25. Kimura, Y., Nakahara, S., and Fujioka, S., Aspy-rone, a nematicidal compound isolated from the fungus, Aspergillus melleus. Biosci. Biotechnol. Biochem.,60, 1375-1376 (1996).