Synthesis of naturally derived bioactive compounds of agricultural interest

Bioscience, Biotechnology and Biochemistry

Volumn 70, Issue 2, 2006, Pages 317-324

  Kiyota, Hiromasa ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Glutarimide; Marine antifeedant; Natural product; Phytotoxin; Synthesis

Indexed keywords

AGRICULTURE; ALCOHOLS; ANTIBIOTICS; SYNTHESIS (CHEMICAL); TOXIC MATERIALS;

GLUTARIMIDE; MARINE ANTIFEEDANT; NATURAL PRODUCT; PHYTOTOXIN;

BIOMATERIALS;

ACTIKETAL; AGRICULTURAL CHEMICAL; ANTIINFECTIVE AGENT; BIOLOGICAL PRODUCT; GIZZEROSINE; IMIDAZOLE DERIVATIVE; PIPERIDONE DERIVATIVE;

ANIMAL; CHEMISTRY; PLANT DISEASE; REVIEW; SYNTHESIS;

AGROCHEMICALS; ANIMALS; ANTI-BACTERIAL AGENTS; BIOLOGICAL PRODUCTS; IMIDAZOLES; PIPERIDONES; PLANT DISEASES;

NICOTIANA TABACUM;

EID: 33344477621     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.70.317     Document Type: Review

References (52)

1. Wolf, F. A., and Fostr, A. C., Bacterial leaf spot of tobacco. Science, 46, 361-362 (1917).
2. Woolley, D. W., Shaffner, G., and Braun, A. C., Studies on the structure of the phytopathogenic toxin of Pseudomonas tabaci. J. Biol. Chem., 215, 485-493 (1955) and references cited therein.
3. Stewart, W. W., Isolation and proof of structure of wildfire toxin. Nature, 229, 174-178 (1971).
4. Uchytil, T. F., and Durbin, R. D., Hydrolysis of tabtoxins by plant and bacterial enzymes. Experientia, 36, 301-302 (1980).
5. Taylor, P. A., Schnoes, H. K., and Durbin, R. D., Characterization of chlorosis-inducing toxins from a plant pathogenic Pseudomonas sp. Biochim. Biophys. Acta, 286, 107-117 (1972).
6. Durbin, R. D., Uchytil, T. F., Steele, J. A., and Ribeiro, R. de L. D., Tabtoxinine-β-lactam from Pseudomonas tabaci. Phytochemistry, 17, 147 (1978).
7. Langston-Unkefer, P. J., Robinson, A. C., Knight, T. J., and Durbin, R. D., Inactivation of pea seed glutamine synthetase by the toxin, tabtoxinine-β-lactam. J. Biol. Chem., 262, 1608-1613 (1987) and references cited therein.
8. He, H., Ding, Y., Bartlam, M., Sun, F., Le, Y., Qin, X., Tang, H., Zhang, R., Joachimiak, A., Liu, J., Zhao, N., and Rao, Z., Crystal structure of tabtoxin resistance protein complexed with acetyl coenzyme A reveals the mechanism for β-lactam acetylation. J. Mol. Biol., 325, 1019-1030 (2003) and references cited therein.
9. Baldwin, J. E., Otsuka, M., and Wallace, P. M., Synthetic studies of tabtoxin. Synthesis of a naturally occurring inhibitor of glutamine synthetase, tabtoxinine-β-lactam, and analogues. Tetrahedron, 42, 3097-3110 (1986).
10. Baldwin, J. E., Bailey, P. D., Gallacher, G., Otsuka, M., Singleton, K. A., and Wallace, P. M., Stereospecific synthesis of tabtoxin. Tetrahedron, 40, 3695-3707 (1984).
11. Doll, R. E., Li, C-S., Novelli, R., Kruse, L. I., and Eggleston, D., Enantioselective synthesis of (-)-tabtoxinine β-lactam. J. Org. Chem., 57, 128-132 (1992).
12. Adlington, R. M., Baldwin, J. E., Basak, A., and Kozyrod, R. P., Applications of radical addition reactions to the synthesis of a C-glucoside and a functionalised amino-acid. J. Chem. Soc., Chem. Commun., 944-945 (1983).
13. Baldwin, J. E., Adlington, R. M., Birch, D. J., Crawford, J. A., and Sweeney, J. B., Radical reactions in synthesis: carbon-carbon bond formation from 2-substituted allyl trialkyl stannanes. J. Chem. Soc., Chem. Commun., 1339-1340 (1986).
14. Li, G., Chang, H.-T., and Sharpless, K. B., Catalytic asymmetric aminohydroxylation (AA) of olefins. Angew. Chem. Int. Ed. Engl., 35, 451-454 (1996).
15. Kolb, H. C., Van Nioeuwenhze, M. S., and Sharpless, K. B., Catalytic asymmetric dihydroxylation. Chem. Rev., 94, 2483-2547 (1994).
16. Knochel, P., and Singer, R. D., Preparation and reactions of polyfunctional organozinc reagents in organic synthesis. Chem. Rev., 93, 2117-2188 (1993).
17. Miller, M. J., Mattingly, P. G., Morrison, M. A., and Kerwin Jr., J. F., Synthesis of β-lactams from substituted hydroxamic acids. J. Am. Chem. Soc., 102, 7026-7032 (1980).
18. Kiyota, H., Takai, T., Saitoh, M., Nakayama, O., Oritani, T., and Kuwahara, S., Facile synthesis of tabtoxinine-β-lactam and its (3′R)-isomer. Tetrahedron Lett., 45, 8191-8194 (1994).
19. Umetsu, N., Kaji, J., and Tamari, K., Investigation on the toxin production by several blast fungus strains and isolation of tenuazonic acid as a novel toxin. Agric. Biol. Chem., 36, 859-866 (1972) and references cited therein.
20. Iwasaki, S., Nozoe, S., Okuda, S., Sato, Z., and Kozawa, T., Isolation and structural elucidation of a phytotoxic substance produced by Pyricularia oryzae Cavara. Tetrahedron Lett., 3977-3980 (1969).
21. Nukina, M., Sassa, T., Ikeda, M., Umezawa, T., and Tasaki, H., Pyriculariol, a new phytotoxic metabolite of Pyricularia oryzae Cavara. Agric. Biol. Chem., 45, 2161-2162 (1981).
22. Suzuki, M., Sugiyama, T., Watanabe, M., Murayama, T., and Yamashita, K., Synthesis and absolute configuration of pyriculol. Agric. Biol. Chem., 51, 1121-1127 (1987).
23. Kim, J.-C., Min, J.-Y., Kim, H.-T., Cho, K.-Y., and Yu, S.-H., Pyricuol, a new phytotoxin from Magnaporthe grisea. Biosci. Biotechnol. Biochem., 62, 173-174 (1998).
24. Still, W. C., and Mitra, A., Stereoselective synthesis of Z-trisubstituted olefins via [2,3]-sigmatropic rearrangement. Preference for a pseudoaxially substituted transition state. J. Am. Chem. Soc., 100, 1927-1928 (1987).
25. Kiyota, H., Ueda, R., Oritani, T., and Kuwahara, S., First synthesis of (±)-pyricuol, a plant pathogen isolated from rice blast disease fungus Magnaporthe grisea. Synlett, 219-220 (2003).
26. Chackalamannil, S., Davies, R. J., Wang, Y., Asberom, T., Doller, D., Wong, J., and Leone, D., Total synthesis of (+)-himbacine and (+)-himbeline. J. Org. Chem., 64, 1932-1940 (1999).
27. Nakamura, Y., Kiyota, H., Ueda, R., and Kuwahara, S., Synthesis to determine the absolute configuration of (-)-pyricuol, a phytotoxin isolated from rice blast disease fungus, Magnaporthe grisea. Tetrahedron Lett., 46, 7107-7109 (2005).
28. Sonoda, T., Osada, H., Uzawa, J., and Isono, K., Actiketal, a new member of the glutarimide antibiotics. J. Antibiot., 44, 160-163 (1991).
29. Highet, R. J., and Prelog, V., Stoffwechselprodukte von Actinomyceten 18. Actiphenol. Helv. Chim. Acta, 42, 1523-1526 (1959).
30. Stoermer, R., and Göhl, F., Synthese des Cumarans (Hydrocumarons) und seiner Homologen. Chem. Ber., 36, 2873-2877 (1903).
31. Kasahara, A., Izumi, T., Yodono, M., Saito, R., Takeda, T., and Sugawara, T., Arylation and vinylation reactions of benzo[b]furan via organopalladium intermediates. Bull. Chem. Soc. Jpn., 46, 1220-1225 (1973).
32. Matsuda, F., Kawasaki, M., and Terashima, S., Efficient synthesis and antitumor activity of an enantiomeric pair of the sesbanimide AB-ring system. Tetrahedron Lett., 26, 4639-4642 (1985).
33. Ishii, H., Ishikawa, T., Takeda, S., Ueki, S., and Suzuki, M., Cesium fluoride-mediated Claisen rearrangement of aryl propargyl ether. Exclusive formation of 2-methyl-arylfran and its availability as a masked salicylaldehyde. Chem. Pharm. Bull., 40, 1148-1153 (1992).
34. Kiyota, H., Shimizu, Y., and Oritani, T., Synthesis of actiketal, a glutarimide antibiotic. Tetrahedron Lett., 41, 5887-5890 (2000).
35. Kiyota, H., Shimizu, Y., and Oritani, T., Synthesis of actiketal, an unique benzofuran glutarimide antibiotic from Streptomyces pulveraceus subsp. epiderstagenes. J. Pesticide Sci., 25, 93-95 (2001).
36. Johnson, D. C., and Pinedo, C., Gizzard erosion and ulceration in Peru broilers. Avian Diseases, 15, 835-837 (1971).
37. Okazaki, T., Noguchi, T., Igarashi, K., Sakagami, Y., Seto, H., Mori, K., Naito, H., Masumura, T., and Sugahara, M., Gizzerosine, a new toxic substance in fish meal, causes severe gizzard erosion in chicks. Agric. Biol. Chem., 47, 2949-2952 (1983).
38. Mori, K., Sugai, T., Maeda, Y., Okazaki, T., Noguchi, T., and Naito, H., Synthesis of the racemic and optically active forms of gizzerosine, the inducer of gizzard erosion in chicks. Tetrahedron, 41, 5307-5311 (1985).
39. Dunn, M. J., Jackson, R. F. W., Pietruszka, J., and Turner, D., Synthesis of enantiomerically pure unsaturated α-amino acids using serine-derived zinc/copper reagents. J. Org. Chem., 60, 2210-2215 (1995).
40. Lombard, M., Girotti, R., Morganti, S., and Trombini, C., A new protocol for the acetoxyallylation of aldehydes mediated by indium in THF. Org. Lett., 3, 2981-2983 (2001).
41. Shimasaki, Y., Kiyota, H., Sato, M., and Kuwahara, S., Facile synthesis of (S)-gizzerosine, a potent inducer of gizzard erosion in chicks, using successive zinc-mediated and palladium-catalyzed coupling reactions. Synthesis, 3191-3192 (2005).
42. McClintock, J. B., and Janssen, J., Pteropod abduction as a chemical defense in a pelagic antarctic amphipod. Nature, 346, 462-464 (1990).
43. Bryan, P. J., Yoshida, W. Y., McClintock, J. B., and Baker, B. J., Ecological role for pteroenone, a novel antifeedant from the conspicuous antarctic pteropod Clione antarctica (Gymnosomata: Gastropoda). Marine Biology, 122, 271-277 (1995).
44. Yoshida, W. Y., Bryan, P. J., Baker, B. J., and McClintock, J. B., Pteroenone: a defensive metabolite of the abducted antarctic pteropod Clione antarctica. J. Org. Chem., 60, 780-782 (1995).
45. Evans, D. A., Tedrow, J. S., Shaw, J. T., and Downey, C. W., Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones. J. Am. Chem. Soc., 124, 392-393 (2002).
46. Mori, K., and Amaike, M., Pheromone synthesis. Part 166. Synthesis of (2E,5R,6E,8E)-5,7-dimethyldeca2,6,8-trien-4-one, the major component of the sex pheromone of the Israeli pine blast scale and its antipode. J. Chem. Soc., Perkin Trans. 1, 2727-2733 (1994).
47. Nakamura, Y., Kiyota, H., Baker, B. J., and Kuwahara, S., First synthesis of (+)-pteroenone: a defensive metabolite of the abducted antarctic pteropod Clione antarctica. Synlett, 635-636 (2005).
48. Nakamura, Y., Kiyota, H., and Kuwahara, S., Synthesis of pteroenone and its stereoisomer, a marine antifeedant isolated from Clione antarctica. Abstracts of Papers: Annual Meeting of Japan Society for Bioscience, Biotechnology, and Agrochemistry, Sapporo, March 28-30, p. 188 (2005).
49. González, N., Rodríguez, J., and Jiménez, C., Didemniserinolipids A-C, unprecedented serinolipids from the tunicate Didemnum sp. J. Org. Chem., 64, 5705-5707 (1999).
50. Dixon, D. J., Foster, A. C., and Ley, S. V., A short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicilin. Org. Lett., 2, 123-125 (2000).
51. Lidströme, P., Tierney, J., Wathey, B., and Westman, J., Microwave assisted organic synthesis - a review. Tetrahedron, 57, 9225-9283 (2001).
52. Kiyota, H., Dixon, D. J., Luscombe, C. K., Hettstedt, S., and Ley, S. V., Syntheses and structure revision of didemniserinolipid B, a marine natural product from a tunicate, Didemnum sp. Org. Lett., 4, 3223-3226 (2002).