Stimulation of h efflux and inhibition of photosynthesis by esters of carboxylic acids.

Suspensions of mechanically isolated Asparagus sprengeri Regel mesophyll cells were used to investigate the influence of various carboxyester compounds on rates of net H(+) efflux in the dark or light and photosynthetic O(2) production. Addition of 0.15 to 1.5 millimolar malathion, alpha-naphthyl acetate, phenyl acetate, or p-nitrophenyl acetate stimulated H(+) efflux and inhibited photosynthesis within 1 minute. In contrast, the more polar esters methyl acetoacetate or ethyl p-aminobenzoate had little or no effect on either of these two processes. A 0.15 millimolar concentration of alpha-naphthylacetate stimulated the normal rate of H(+) efflux, 0.77 nanomoles H(+) per 10(6) cells per minute by 750% and inhibited photosynthesis by 100%. The four active carboxyester compounds also stimulated H(+) efflux after the normal rate of H(+) efflux was eliminated with 0.01 milligrams per milliliter oligomycin or 100% N(2). Oligomycin reduced the ATP level by 70%. Incubation of cells with malathion, alpha-naphthyl acetate, or p-nitrophenyl acetate resulted in the generation of the respective hydrolysis products ethanol, alpha-naphthol, and p-nitrophenol. It is proposed that inhibition of photosynthesis and stimulation of H(+) efflux result when nonpolar carboxyester compounds enter the cell and generate acidic carboxyl groups when hydrolyzed by esterase enzymes.