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Bioscience, Biotechnology, and Biochemistry Volume 62, 1998 - Issue 10
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Original Articles

Solanapyrones, Phytotoxins Produced by Alternaria solani: Biosynthesis and Isolation of Minor Components

Hideaki OIKAWADepartment of Bioscience and Chemistry, Faculty of Agriculture, Hokkaido University
,
Tomohiro YOKOTADepartment of Bioscience and Chemistry, Faculty of Agriculture, Hokkaido University
,
Chiaki SAKANODepartment of Bioscience and Chemistry, Faculty of Agriculture, Hokkaido University
,
Yuichi SUZUKIDepartment of Bioscience and Chemistry, Faculty of Agriculture, Hokkaido University
,
Akira NAYADepartment of Bioscience and Chemistry, Faculty of Agriculture, Hokkaido University
&
Akitami ICHIHARADepartment of Bioscience and Chemistry, Faculty of Agriculture, Hokkaido University
Pages 2016-2022 | Received 01 Jun 1998, Published online: 22 May 2014

  • 1) Ichihara, A. and Oikawa, H., Biosynthesis of Phytotoxins from Alternaria solani. Biosci. Biotech. Biochem., 61, 12-18 (1997).
  • 2) Ichihara, A., Tazaki, H., and Sakamura, S., Solanapyrones A, B and C, Phytotoxic Metabolites from the Fungus Alternaria solani. Tetrahedron Lett., 24, 5373-5376 (1983).
  • 3) Ichihara, A., Miki, M., and Sakamura, S., Absolute Configuration of (-)-Solanapyrone A. Tetrahedron Lett., 26, 2453-2454 (1985).
  • 4) Alam, S. S., Bilton, J. M., Slawin, M. Z., Williams, D. J., Sheppard, R. N., and Strange, R. M., Chickpea Blight: Production of the Phytotoxins Solanapyrone A and C by Ascochyta rabiei. Phytochemistry, 28, 2627-2630 (1989).
  • 5) Oikawa, H., Suzuki, Y., Naya, A., Katayama, K., and Ichihara, A., First Direct Evidence in Biological Diels-Alder Reaction of Incorporation of Diene-Dienophile Precursors in the Biosynthesis of Solanapyrones. J. Am. Chem. Soc., 116, 3605-3606 (1994).
  • 6) Oikawa, H., Katayama, K., Suzuki, Y., and Ichihara, A., Enzymatic Activity Catalyzing Exo-selective Diels-Alder Reaction in Solanapyrone Biosynthesis. J. Chem. Soc. Chem. Commun., 1321-1322 (1995).
  • 7) Oikawa, H., Yokota, T., Ichihara, A., and Sakamura, S., Structure and Absolute Configuration of Solanapyrone D: A New Clue to the Occurrence of Biological Diels-Alder Reactions. J. Chem. Soc. Chem. Commun., 1284-1285 (1989).
  • 8) Oikawa, H., Yokota, T., Abe, T., Ichihara, A., Sakamura, S., Yoshizawa, Y., and Vederas, J. C., Biosynthesis of Solanapyrone A, a Phytotoxin of Alternaria solani. J. Chem. Soc. Chem. Commun., 1282-1284 (1989).
  • 9) Ichihara, A., Miki, M., Tazaki, H., and Sakamura, S., Synthesis of (±)-Solanapyrone A. Tetrahedron Lett., 28, 1175-1178 (1987).
  • 10) Tominaga, Y., Ushirogochi, A., Matsuda, Y., and Kobayashi, G., Synthesis and Reaction of 6-Aryl- and 6-Styryl-3-cyano-4-methylthio-2H-pyran-2-ones. Chem. Pharm. Bull., 32, 3384-3395 (1984).
  • 11) Tominaga, Y., Ushirogochi, A., and Matsuda, Y., Synthesis and Reaction of 6-Substituted 3-Methoxycarbonyl-4-methylthio-2H-pyran-2-one. J. Heterocyclic Chem., 24, 1557-1567 (1987).

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