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Published on May 8, 2008; 10.1104/pp.108.118372

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Received February 25, 2008
Accepted May 6, 2008

A Pathogenic Fungi Diphenyl Ether Phytotoxin Targets Plant Enoyl (Acyl Carrier Protein) Reductase

Franck E. Dayan *, Daneel Ferreira , Yan-Hong Wang , Ikhlas A. Khan , John A. McInroy , and Zhiqiang Pan

Natural Products Utilization Research Unit, United States Department of Agriculture, Agricultural Research Services, P.O. Box 8048, University, MS 38677, USA. Fax 662-915-1035; Department of Pharmacognosy, School of Pharmacy, The University of Mississipipi, University, MS 38677; National Center for Natural Products Research, Research Institute of Pharmaceutical Science, School of Pharmacy, The University of Mississipipi, University, MS 38677; Department of Entomology and Plant Pathology, 209 LSB, Auburn University, AL 36849

* Corresponding author; email: fdayan{at}olemiss.edu.

Cyperin is a natural diphenyl ether phytotoxin produced by several fungal plant pathogens. At high concentrations, this metabolite inhibits protoporphyrinogen oxidase, a key enzyme in porphyrin synthesis. However, unlike its herbicide structural analogues, the mode of action of cyperin is not light-dependent, causing loss of membrane integrity in the dark. We report that this natural diphenyl ether inhibits Arabidopsis thaliana enoyl (acyl carrier protein) reductase (ENR). This enzyme is also sensitive to triclosan, a synthetic antimicrobial diphenyl ether. While cyperin was much less potent than triclosan on this target site, their ability to cause light-independent disruption of membrane integrity and inhibition of ENR are similar at their respective phytotoxic concentrations. The sequence of ENR is highly conserved within higher plants and a homology model of A. thaliana ENR was derived from the crystal structure of the protein from Brassica napus. Cyperin mimicked the binding of triclosan in the binding pocket of ENR. Both molecules were stabilized by the {pi}-{pi} stacking interaction between one of their phenyl rings and the nicotinamide ring of the NAD+. Furthermore, the side chain of tyrosine is involved in hydrogen bonding with a phenolic hydroxy group of cyperin. Therefore, cyperin may contribute to the virulence of the pathogens by inhibiting ENR and destabilizing the membrane integrity of the cells surrounding the point of infection.






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