The biology of ophiobolins

doi:10.1016/S0024-3205(00)00668-8

Life Sciences

Volume 67, Issue 7, 7 July 2000, Pages 733-742

https://doi.org/10.1016/S0024-3205(00)00668-8 Get rights and content

Abstract

This review article aims at summarizing the research findings on the biological aspects of ophiobolins, phytotoxins produced by the pathogenic fungi Bipolaris species, which usually infect rice, maize and sorghum. The topics covered include the organisms that produce the various ophiobolins, the structural variations of ophiobolins, the biological actions of ophiobolins in plants, animals and microorganisms, and the mode of action and the possible use of ophiobolin A as a calmodulin antagonist.

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A stereoselective synthetic entry point to the 5–8–5 carbocyclic core of the ophiobolins was developed. This strategy exploits the chiral tertiary alcohol of ophiobolin A to guide assmebly of the 5–8–5 scaffold in a single step via a photoinitiated cycloisomerization. Mechanistic insights into the origin of stereocontrol in this reaction are described, as are efforts to elaborate the resultant fused 5–8–5 ring system to the pharmacophore of ophiobolin A.
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The biology of ophiobolins