Abstract
Two fungal metabolites, cochliospicin A from a strain (D-5) of Cochliobolus spicifer, a pathogen of leaf spot disease in Gramineae, and sorokinianin from a strain (OB-25-1) of Bipolaris sorokiniana, a pathogen causing spot blotch or foot and root rot diseases of wheat and other grasses, were isolated and characterized. The deduced chemical structure of cochliospicin A indicates that it is composed of two parts: a polyketide origin portion structurally related to spiciferinone, a phytotoxin of C. spicifer and a C3 portion. Sorokinianin is assumed to be composed of a helminthosporol-type sesquiterpene portion and a C3 portion. Although they have in common β-hydroxy-γ-lactone C3 unit portion, sorokinianin shows phytotoxicity, wheras cochliospicin A does not. To clarify the biosynthetic origin of sorokinianin, we conducted two experiments: a [1,2-13C2] sodium acetate feeding experiment; and a replacement culture experiment with the candidates for the C3 unit precursor, together with prehelminthosporol, the major metabolite of strain OB-25-1. The results of these experiments suggest that sorokinianin is synthesized from prehelminthosporol by reactions that include the addition of a member of the TCA cycle, decarboxylation and lactonization.
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Nakajima, H. (1998). Structures and Biosyntheses of Phytotoxins in Cochliobolus Spicifer and Bipolaris Sorokiniana: C3 Unit Addition Reaction in Phytotoxin Biosyntheses. In: Kohmoto, K., Yoder, O.C. (eds) Molecular Genetics of Host-Specific Toxins in Plant Disease. Developments in Plant Pathology, vol 13. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-5218-1_8
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DOI: https://doi.org/10.1007/978-94-011-5218-1_8
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