Advanced search
Publication Cover
Bioscience, Biotechnology, and Biochemistry Volume 70, 2006 - Issue 2
Journal homepage
265
Views
8
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of Naturally Derived Bioactive Compounds of Agricultural Interest

Hiromasa KIYOTALaboratory of Applied Bioorganic Chemistry, Division of Bioscience & Biotechnology for Future Bioindustries, Graduate School of Agricultural Science, Tohoku University
Pages 317-324 | Published online: 22 May 2014

  • 1) Wolf, F. A., and Foster, 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-methylarylfran 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-dimethyldeca-2,6,8-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).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.