scholarly journals 735 PB 029 SORGOLEONE: A PHOTOSYSTEM II INHIBITOR PRODUCED BY SORGHUM BICOLOR

HortScience ◽  
1994 ◽  
Vol 29 (5) ◽  
pp. 538c-538
Author(s):  
Leslie A. Weston ◽  
Verónica M. Gonzalez

Sorgoleone, the oxidized quinone form of a hydrophobic p-benzoquinone was first isolated from Sorghum root exudates. Sorgoleone is a potent inhibitor of growth in several annual weed species and causes tissue bleaching at concentrations of <25 μ M. These investigations were designed to determine if soreoleone's allelopathic activity was related to an inhibition of photosynthetic electron transport. The effect of sorgoleone versus DCMU (diuron) on inhibition of O2 evolution by broken wheat thylakoids, and in oxygenevolving PSII membranes containing QA and QB primary and secondary electron acceptors in PSII was determined. Sorgoleone was a potent inhibitor of O2 evolution in this system with ∼ 0.04 and 0.78 μ M concentrations required for 50 and 100% inhibition as compared to -0.11 and 2.0 μ M DCMU, respectively. Sorgoleone caused no significant inhibition of PSI mediated photooxidation of ascorbate/dichlorophenolindophenol, establishing that the locus of inhibition by sorgoleone was within the PSII complex. The effect of trypsin treatment of chloroplasts and PSII membranes on sensitivity to inhibition by DCMU and sorgoleone was examined. The comparison of DCMU and sorgoleone upon the formation and decay of flash-induced chlorophyll a variable fluorescence indicates that sorgoleone specifically inhibited the oxidation of QA by QB.

Weed Science ◽  
2009 ◽  
Vol 57 (6) ◽  
pp. 579-583 ◽  
Author(s):  
Franck E. Dayan ◽  
Maria L. B. Trindade ◽  
Edivaldo D. Velini

Amicarbazone is a new triazolinone herbicide with a broad spectrum of weed control. The phenotypic responses of sensitive plants exposed to amicarbazone include chlorosis, stunted growth, tissue necrosis, and death. Its efficacy as both a foliar- and root-applied herbicide suggests that absorption and translocation of this compound is very rapid. This new herbicide is a potent inhibitor of photosynthetic electron transport, inducing chlorophyll fluorescence and interrupting oxygen evolution ostensibly via binding to the QB domain of photosystem II (PSII) in a manner similar to the triazines and the triazinones classes of herbicides. As a result, its efficacy is susceptible to the most common form of resistance to PSII inhibitors. Nonetheless, amicarbazone has a good selectivity profile and is a more potent herbicide than atrazine, which enables its use at lower rates than those of traditional photosynthetic inhibitors.


1984 ◽  
Vol 39 (5) ◽  
pp. 374-377 ◽  
Author(s):  
J. J. S. van Rensen

The reactivation of the Hill reaction in CO2-depleted broken chloroplasts by various concentrations of bicarbonate was measured in the absence and in the presence of photosystem II herbicides. It appears that these herbicides decrease the apparent affinity of the thylakoid membrane for bicarbonate. Different characteristics of bicarbonate binding were observed in chloroplasts of triazine-resistant Amaranthus hybridus compared to the triazine-sensitive biotype. It is concluded that photosystem II herbicides, bicarbonate and formate interact with each other in their binding to the Qв-protein and their interference with photosynthetic electron transport.


Weed Science ◽  
1983 ◽  
Vol 31 (5) ◽  
pp. 693-699 ◽  
Author(s):  
Blaik P. Halling ◽  
Richard Behrens

Experiments were conducted with isolated protoplasts of wild oat (Avena fatuaL. # AVEFA) and isolated chloroplasts of wild oat and wheat (Triticum aestivumL.), to determine if the methyl sulfate salt of difenzoquat (1,2-dimethyl-3,5-diphenyl-1H-pyrazolium) might influence photoreactions in these species. Difenzoquat did not affect CO2fixation, uncoupled electron transport, or proton uptake. At concentrations of 0.5 mM and 1 mM, difenzoquat caused a slight, but statistically significant, inhibition of photophosphorylation. Experiments assaying coupled electron transport indicated that inhibition of photophosphorylation occurred not through uncoupling, but by an energy-transfer inhibition. This same effect was observed in isolated mitocondria of both species, with about 50% inhibition of state 3 respiration rates occurring with 10 μM difenzoquat. However, no important differentials were observed in the relative susceptibilities of wheat and wild oat mitochondria. Difenzoquat also functioned as a weak autooxidizing electron acceptor in photosynthetic electron transport. Therefore, difenzoquat-induced leaf chlorosis and necrosis may result from a bipyridilium-type electron acceptor activity if sufficient herbicide is absorbed.


1991 ◽  
Vol 46 (1-2) ◽  
pp. 93-98 ◽  
Author(s):  
Helen G. McFadden ◽  
Donald C. Craig ◽  
John L. Huppatz ◽  
John N. Phillips

Abstract X-ray crystallographic data for the highly potent cyanoacrylate photosynthetic electron transport inhibitor, (Z)-ethoxyethyl 3-(4-chlorobenzylamino)-2-cyano-4-methylpent-2-enoate, are presented. This compound has a particularly high affinity for the photosystem II (PS II) herbicide receptor with a p I50 value of 9.5 (in the Hill reaction under uncoupled condi­tions with a chlorophyll concentration of 0.1 μg/ml). Data regarding the structure of small li­gands, such as this potent cyanoacrylate, which bind to the site with high affinity may be used to provide the basis for modelling studies of PS II/herbicide complexes. The X-ray data presented confirm the Z-stereochemistry of active cyanoacrylates and demonstrate the pres­ence of a planar core stabilized by an intramolecular hydrogen bond between the ester car­bonyl oxygen and a benzylamino hydrogen atom. In order to assess the importance of the benzylamino -NH -group in this type of cyanoacrylate, analogues containing a methylene group in its place were synthesized and found to be 100-and 1000-fold less active as Hill inhibitors.


2020 ◽  
Vol 117 (26) ◽  
pp. 15354-15362 ◽  
Author(s):  
Ricarda Höhner ◽  
Mathias Pribil ◽  
Miroslava Herbstová ◽  
Laura Susanna Lopez ◽  
Hans-Henning Kunz ◽  
...  

In photosynthetic electron transport, large multiprotein complexes are connected by small diffusible electron carriers, the mobility of which is challenged by macromolecular crowding. For thylakoid membranes of higher plants, a long-standing question has been which of the two mobile electron carriers, plastoquinone or plastocyanin, mediates electron transport from stacked grana thylakoids where photosystem II (PSII) is localized to distant unstacked regions of the thylakoids that harbor PSI. Here, we confirm that plastocyanin is the long-range electron carrier by employing mutants with different grana diameters. Furthermore, our results explain why higher plants have a narrow range of grana diameters since a larger diffusion distance for plastocyanin would jeopardize the efficiency of electron transport. In the light of recent findings that the lumen of thylakoids, which forms the diffusion space of plastocyanin, undergoes dynamic swelling/shrinkage, this study demonstrates that plastocyanin diffusion is a crucial regulatory element of plant photosynthetic electron transport.


1980 ◽  
Vol 35 (3-4) ◽  
pp. 293-297 ◽  
Author(s):  
P. V. Sane ◽  
Udo Johanningmeier

Abstract Low concentrations (10 µM) of tetranitromethane inhibit noncyclic electron transport in spinach chloroplasts. A study of different partial electron transport reactions shows that tetranitromethane primarily interferes with the electron flow from water to PS II. At higher concentrations the oxidation of plastohydroquinone is also inhibited. Because diphenyl carbazide but not Mn2+ ions can donate electrons efficiently to PS II in the presence of tetranitromethane it is suggested that it blocks the donor side of PS II prior to donation of electrons by diphenyl carbazide. The pH dependence of the inhibition by this protein modifying reagent may indicate that a functional-SH group is essential for a protein, which mediates electron transport between the water splitting complex and the reaction center of PS II.


1990 ◽  
Vol 45 (5) ◽  
pp. 343-347 ◽  
Author(s):  
John N. Phillips

Cyanoacrylate thiolate salts such as the sodium salt of ethoxyethyl-3-p-chlorobenzylthio-2-cyano-3-mercapto acrylate have been shown to be relatively slow binding, potent inhibitors of photosynthetic electron transport, that are equally active against thylakoids isolated from atrazine-susceptible and atrazine-resistant Brassica napus seedlings. It has been suggested that their mode of binding involves the substituted benzyl group interacting with the membrane lipids and the thiolate ion interacting in the region of the histidine215 residue of the D1 peptide, close to the non-heme Fe centre. This, together with their slow rate of binding, has led to the thiolate salts being classified as phenol type inhibitors.


1975 ◽  
Vol 30 (3-4) ◽  
pp. 183-189 ◽  
Author(s):  
G. Schäfer ◽  
A. Trebst ◽  
K. H. Büchel

Abstract 2-anilino-1,3,4-thiadiazoles carrying various substituents in the 5-position as well as in the benzene-ring were synthesized. The compounds were tested with rat-liver-mitochondria and with spinach-chloroplasts and revealed to be potent uncouplers of both, oxidative and photosynthetic phosphorylation, with p I50-values rangeing from 6.79 to 4.05. At higher concentration all compounds are inhibitors of the Hillreaction. In mitochondria a fair correlation exists between pKa of the acidic NH-group and the uncoupling activity; a maximum is obtained around pKa= 6 .8 , whereas in chloroplasts activity is shifted to more acid pKa-values. The compounds meet the requirements for uncouplers according to the chemi-osmotic theory, being lipophilic weak acids. N-methylation causes total loss of activity in mitochondrial oxidative phosphorylation. The inhibitory action on photosynthetic electron transport is located within photosystem II. This latter activity is almost independent of substituent effects in contrast to uncoupling of either respiratory- or photo-phosphorylation


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