Hostname: page-component-78c5997874-m6dg7 Total loading time: 0 Render date: 2024-11-02T22:02:36.626Z Has data issue: false hasContentIssue false
  • English
  • Français

Effects of 3,5-dibromo-4-hydroxybenzaldehyde O-(2,4-dinitrophenyl)oxime on Reactions of Mitochondria and Chloroplasts

Published online by Cambridge University Press:  12 June 2017

D. E. Moreland  and
W. J. Blackmon
D. E. Moreland
Affiliation:
Crops Research Division, Agr. Res. Serv., U. S. Dep. of Agr., Crop Science Department, North Carolina State University, Raleigh, North Carolina
W. J. Blackmon
Affiliation:
Crop Science Department, North Carolina State University, Raleigh, North Carolina
Get access Rights & Permissions [Opens in a new window]

Abstract

The effects of 3,5-dibromo-4-hydroxybenzaldehyde O-(2,4-dinitrophenyl)oxime (hereinafter referred to as C-9122), 3,5-dibromo-4-hydroxybenzonitrile (bromoxynil), 3,5-dibromo-4-hydroxybenzaldoxime (hereinafter referred to as bromoxime), and 2,4-dinitrophenol (hereinafter referred to as DNP) on phosphorylation and electron transport were measured in mitochondria isolated from white potato tubers (Solarium tuberosum L.) and in chloroplasts from spinach leaves (Spinacia oleracea L.). Mitochondrial oxygen utilization was monitored polarographically. All four chemicals stimulated ADP-limited oxygen utilization, inhibited non-ADP-limited oxygen uptake, and relieved oligomycin-inhibited oxygen uptake. C-9122 produced responses at lower molar concentrations than did bromoxynil, bromoxime, and DNP. The I50 value for inhibition of state 3 respiration by C-9122 was 2.7 × 10−6 M.

In chloroplasts, C-9122, bromoxime, and DNP inhibited photoreduction and coupled photophosphorylation with water as the electron donor, and with ferricyanide and NADP as electron acceptors. Cyclic photophosphorylation, with phenazine methosulfate as the electron mediator under an argon gas phase, also was inhibited. With ascorbate-2,6-dichlorophenolindophenol (hereinafter referred to as DPIP) as the electron donor, phosphorylation coupled to NADP reduction was inhibited, but not the reduction of NADP. C-9122 was the strongest inhibitor, and bromoxime was the weakest inhibitor of the several reactions. The I50 value for inhibition of the coupled ferricyanide reduction was 4.6 × 10−6 M for C-9122. C-9122 appeared to act in two different ways by (a) inhibiting electron transport at or near photosystem II and the oxygen evolution pathway, and (b) interfering with energy transfer and the generation of ATP. Bromoxynil inhibited photoreduction and photophosphorylation reactions in which water served as the electron donor; but it was a very poor inhibitor of both cyclic photophosphorylation, and photophosphorylation coupled to NADP reduction with ascorbate-DPIP serving as the electron donor. Because of the pivotal role of ATP in cellular metabolism, it is conceivable that interference with ATP generation could be a major (but not necessarily the only) mechanism through which the herbicidal activity of C-9122 is expressed.

Type
Research Article
Information
Weed Science , Volume 18 , Issue 3 , May 1970 , pp. 419 - 426
Copyright
Copyright © 1970 Weed Science Society of America 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Literature Cited

1. Arnon, D. I. 1949. Copper enzymes in isolated chloroplasts. Polyphenoloxidase in Beta vulgaris . Plant Physiol. 24:1–15.Google Scholar
2. Avron, M. 1960. Photophosphorylation by Swiss-chard chloroplasts. Biochim. Biophys. Acta 40:257–272.Google Scholar
3. Baltscheffsky, H. 1963. Inhibition of photophosphorylation in isolated spinach chloroplasts by lower aliphatic straight-chain alcohols. Acta Chem. Scand. 17:S308–S312.Google Scholar
4. Büchel, K. H., Draper, W., Trebst, A., and Pistorius, E. 1966. Zur Hemmung photosynthetischer Reaktionen in isolierten Chloroplasten durch Herbizide des Benzimidazol-Typs und deren Struktur-Aktivitäts-Beziehung unter Berücksichtigung des Verteilungskoeffizienten und des pKa-Wertes. Z. Naturforsch. 21b:243–254.Google Scholar
5. Chance, B. and Williams, G. R. 1955. Respiratory enzymes in oxidative phosphorylation. III. The steady state. J. Biol. Chem. 217:409–427.Google Scholar
6. Chance, B., Williams, G. R., and Hollunger, G. 1963. Inhibition of electron and energy transfer in mitochondria. III. Spectroscopic and respiratory effects of uncoupling agents. J. Biol. Chem. 278:439–444.Google Scholar
7. Desmoras, J. and Jacquet, P. 1964. Études préliminaires sur le mode d'action de deux produits a activité herbicide de contact: le DNBP et l'ioxynil. Mededel. Landbouwhogeschool Opzoekingssta. Staat Gent 29:633–643.Google Scholar
8. Ferrari, T. E. and Moreland, D. E. 1969. Effects of 3,5-dihalogenated-4-hydroxybenzonitriles on the activity of mitochondria from white potato tubers. Plant Physiol. 44:429–434.Google Scholar
9. Friend, J. and Olsson, R. 1967. Inhibition of photosynthetic electron transport by ioxynil. Nature 214:942–943.CrossRefGoogle Scholar
10. Green, D. E. and MacLennan, D. H. 1969. Structure and function of the mitochondrial cristael membrane. Bioscience 19:213–222.Google Scholar
11. Gromet-Elhanan, Z. 1968. The inhibition of photoreactions of chloroplasts by ioxynil. Biochem. Biophys. Res. Commun. 30:28–31.Google Scholar
12. Gromet-Elhanan, Z. 1968. Energy-transfer inhibitors and electron transport inhibitors in chloroplasts. Arch. Biochem. Biophys. 123:447–456.Google Scholar
13. Hall, D. O. and Palmer, J. M. 1969. Mitochondrial research today. Nature 221:717–723.Google Scholar
14. Hanson, J. B. and Hodges, T. K. 1967. Energy-linked reactions of plant mitochondria, p. 65–98. In Sanadi, D. R. (ed.) Current Topics in Bioenergetics. Vol. 2. Academic Press, New York.Google Scholar
15. Ikuma, H. and Bonner, W. D. Jr. 1967. Properties of higher plant mitochondria. II. Effects of DNP, m-Cl-CCP, and oligomycin on respiration of mung bean mitochondria. Plant Physiol. 42:1400–1406.Google Scholar
16. Kahn, J. S. 1964. Construction of a simple and sensitive Clark-type electrode for measurement of oxygen consumption. Anal. Biochem. 9:389–391.Google Scholar
17. Katoh, S. and Pietro, A. San 1966. Inhibitory effect of salicylaldoxime on chloroplast photooxidation-reduction reactions. Biochem. Biophys. Res. Commun. 24:903–908.Google Scholar
18. Kerr, M. W. and Wain, R. L. 1964. The uncoupling of oxidative phosphorylation in pea shoot mitochondria by 3,5-diiodo-4-hydroxybenzonitrile (ioxynil) and related compounds. Ann. Appl. Biol. 54:441–446.Google Scholar
19. Kerr, M. W. and Wain, R. L. 1964. Inhibition of the ferricyanide-Hill reaction of isolated bean leaf chloroplasts by 3,5-diiodo-4-hydroxybenzonitrile (ioxynil) and related compounds. Ann. Appl. Biol. 54:447–450.Google Scholar
20. Krogmann, D. W., Jagendorf, A. T., and Avron, M. 1959. Uncouplers of spinach chloroplast photosynthetic phosphorylation. Plant Physiol. 34:272–277.Google Scholar
21. Lardy, H. A., Connelly, J. L., and Johnson, D. 1964. Antibiotics as tools for metabolic studies. II. Inhibition of phosphoryl transfer in mitochondria by oligomycin and aurovertin. Biochemistry 3:1961–1968.Google Scholar
22. McKenzie, H. A. and Wallace, H. S. 1954. The Kjeldahl determination of nitrogen: A critical study of digestion conditions—temperature, catalyst, and oxidizing agent. Australian J. Chem. 7:55–70.Google Scholar
23. Neumann, J. and Jagendorf, A. T. 1964. Dinitrophenol as an uncoupler of photosynthetic phosphorylation. Biochem. Biophys. Res. Commun. 16:562–567.Google Scholar
24. Parker, V. H. 1965. Uncouplers of rat-liver mitochondrial oxidative phosphorylation. Biochem. J. 97:658–662.Google Scholar
25. Paton, D. and Smith, J. E. 1965. The effect of 4-hydroxy-3,5-diiodobenzonitrile on CO2 fixation, ATP formation and NADP reduction in chloroplasts of Vicia faba L. Weed Res. 5:75–77.Google Scholar
26. Paton, D. and Smith, J. E. 1967. The effect of 4-hydroxy-3,5-diiodobenzonitrile (ioxynil) on respiratory electron transport in Vicia faba L. Can. J. Biochem. 45:1891–1899.CrossRefGoogle ScholarPubMed
27. Renger, G., Vater, J., and Witt, H. T. 1967. Effect of salicylaldoxime on the complete electron transport system of photosynthesis and on the isolated reaction cycle II. Biochem. Biophys. Res. Commun. 26:477–480.Google Scholar
28. Slater, E. C. 1963. Uncouplers and inhibitors of oxidative phosphorylation, p. 503–516. In Hochster, R. M. and Quastel, J. H. (ed.) Metabolic Inhibitors. Vol. 2. Academic Press, New York.Google Scholar
29. Taussky, H. H. and Shorr, E. 1953. A microcolorimetric method for the determination of inorganic phosphorous. J. Biol. Chem. 202:675–685.Google Scholar
30. Trebst, A. 1963. Zur Hemmung photosynthetischer Reaktionen in isolierten Chloroplasten durch Salicylaldoxim. Z. Naturforsch. 18b:817–821.Google Scholar
31. Weinbach, E. C. and Garbus, J. 1969. Mechanism of action of reagents that uncouple oxidative phosphorylation. Nature 221:1016–1018.Google Scholar
32. Wentworth, V. and Brady, O. L. 1920. The isomerism of the oximes. Part IX. 2:4-Dinitrobenzaldoxime and bromosubstituted hydroxy- and methoxy-benzaldoximes. J. Chem. Soc. 117:1040–1045.CrossRefGoogle Scholar
33. Witt, H. T., Döring, G., Rumberg, B., Schmidt-Mende, P., Siggel, U., and Stiehl, H. H. 1967. Electron transport in photosynthesis. Brookhaven Symp. Biol. 19:161–167.Google Scholar