Solanapyrones, Phytotoxins Produced byAlternaria solani: Biosynthesis and Isolation of Minor Components
- 1 January 1998
- journal article
- Published by Taylor & Francis in Bioscience, Biotechnology, and Biochemistry
- Vol. 62 (10) , 2016-2022
- https://doi.org/10.1271/bbb.62.2016
Abstract
Two minor components of solanapyrones D and E, phytotoxins from Alternaria solani, were isolated. The absolute stereochemistry of D and the optical purity of solanapyrones A and D were determined by chemical transformation and measurement of the CD spectrum. In addition, complete signal assignment of the (1)H- and (13)C-NMR spectra of solanapyrones A and D, and their solution conformations were studied. Feeding experiments with various isotopically labeled acetates and methionine established the biosynthetic pathway of solanapyrones. The phytotoxicity of solanapyrones on lettuce seedlings is discussed.Keywords
This publication has 11 references indexed in Scilit:
- Biosynthesis of Phytotoxins fromAlternaria solaniBioscience, Biotechnology, and Biochemistry, 1997
- Enzymatic activity catalysing exo-selective Diels–Alder reaction in solanapyrone biosynthesisJournal of the Chemical Society, Chemical Communications, 1995
- First Direct Evidence in Biological Diels-Alder Reaction of Incorporation of Diene-Dienophile Precursors in the Biosynthesis of SolanapyronesJournal of the American Chemical Society, 1994
- Chickpea blight: Production of the phytotoxins solanapyrones A and C by Ascochyta rabieiPhytochemistry, 1989
- Structure and absolute configuration of solanapyrone D: a new clue to the occurrence of biological Diels–Alder reactionsJournal of the Chemical Society, Chemical Communications, 1989
- Biosynthesis of solanapyrone A, a phytotoxin of Alternaria solaniJournal of the Chemical Society, Chemical Communications, 1989
- Synthesis of (±)-solanapyrone ATetrahedron Letters, 1987
- Absolute configuration of (−)-solanapyrone ATetrahedron Letters, 1985
- Synthesis and reactions of 6-aryl- and 6-styryl-3-cyano-4-methylthio-2H-pyran-2-ones.CHEMICAL & PHARMACEUTICAL BULLETIN, 1984
- Solanapyrones A, B and C, phytotoxic metabolites from the fungus Alternaria solaniTetrahedron Letters, 1983