Ophiobolin A. A natural product inhibitor of calmodulin

J Biol Chem. 1984 Mar 10;259(5):2742-7.

Abstract

Ophiobolin A, a fungal metabolite and a phytotoxin which can stimulate the net leakage of electrolytes and glucose from maize seedling roots (Tipton, C. L., Paulsen, P. V., and Betts, R. E. (1977) Plant Physiol. 59, 907-910) was found to be a potent inhibitor of calmodulin-activated cyclic nucleotide phosphodiesterase. The physiologically less active analogue, 3-anhydro-ophiobolin A, was found to be less inhibitory than ophiobolin A in the phosphodiesterase assay. The direct interaction between ophiobolin A and calmodulin has been demonstrated by changes in fluorescence of the protein and by the effect of ophiobolin A on calmodulin activity upon preincubation. Addition of ophiobolin A to calmodulin solutions resulted in an instantaneous quenching of the intrinsic tyrosine fluorescence followed by a time-dependent quenching. The instantaneous quenching is probably due to the inner filtering effect of ophiobolin A. The time-dependent fluorescence quenching was correlated with a time-dependent inhibition of calmodulin upon preincubation with ophiobolin A. The inhibition of calmodulin by ophiobolin A could not be reversed by dialysis, dilution, nor denaturation by urea in the presence of methanol followed by renaturation, and was much more pronounced in solutions containing Ca2+ than in those containing EGTA. Ophiobolin A also was shown to inhibit spinach calmodulin. The results of the present study suggest that calmodulin may be one of the target proteins of the phytotoxic action of ophiobolin A and that the interaction of ophiobolin A with calmodulin may involve a covalent modification of the protein by the fungal metabolite.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2',3'-Cyclic-Nucleotide Phosphodiesterases / metabolism*
  • Animals
  • Brain
  • Calcium / pharmacology
  • Calmodulin / antagonists & inhibitors*
  • Cattle
  • Enzyme Activation
  • Helminthosporium
  • Kinetics
  • Phosphoric Diester Hydrolases / metabolism*
  • Sesterterpenes
  • Spectrometry, Fluorescence
  • Terpenes / isolation & purification
  • Terpenes / pharmacology*
  • Trypsin / pharmacology

Substances

  • Calmodulin
  • Sesterterpenes
  • Terpenes
  • ophiobolin A
  • 2',3'-Cyclic-Nucleotide Phosphodiesterases
  • Phosphoric Diester Hydrolases
  • Trypsin
  • Calcium