Photosynthetic Electron Transport Inhibition by Pyrimidines and Pyridines Substituted with Benzylamino, Methyl and Trifluoromethyl Groups

2001 ◽  
Vol 56 (3-4) ◽  
pp. 203-210
Author(s):  
Shinpei Ohki ◽  
Hideomi Takahashi ◽  
Nobuhiro Kuboyama ◽  
Kazuya Koizumi ◽  
Hitoshi Kohno ◽  
...  
Keyword(s):  
Electron Transport ◽  
Spinacia Oleracea ◽  
Chenopodium Album ◽  
Photosynthetic Electron Transport ◽  
Herbicidal Activity ◽  
Trifluoromethyl Group ◽  
Wild Type ◽  
Ring Nitrogen ◽  
Group 2 ◽  
Trifluoromethyl Groups

AbstractThe decrease of the number of ring nitrogen atoms of 2-benzylamino-4-methyl-6-trifluoro-methyl-1,3,5-triazines on herbicidal activity and inhibition of photosynthetic electron trans­ port (PET) was assayed using thylakoids from Spinacia oleracea or atrazine-resistant Chenopodium album. Three 2-benzylamino-4-methyl-6-trifluoromethyl-1,3,5-triazines, nine pyrimidines with a benzylamino-, methyl-and trifluoromethyl-group, 2-benzylamino-6-methyl-4-trifluoromethyl-pyridine and N-benzyl-3-methyl-5-trifluoromethylaniline were synthesized and assayed. 2-(4-Bromobenzylamino)-4-methyl-6-trifluoromethylpyrimidine exhibited the highest PET inhibitory activity against Spinacia oleracea thylakoids of all compounds tested. The 2-benzylaminopyrimidines and 2-methylpyrimidines having a 4-halobenzylamino group exhibited higher PET inhibition than atrazine and 2-trifluoromethylpyrimidines against Spinacia oleracea thylakoids. These PET inhibitory active compounds also exhibited a strong and similar inhibition both against atrazine-resistant Chenopodium album thylakoids as well as against thylakoids from wild-type Chenopodium. The herbicidal activity of 4-(4-bromoben-zylamino)-2-methyl-6-trifluoromethylpyrimidine was equivalent to that of known herbicides like simetryne, simazine or atrazine.

Cyanoacrylate Inhibitors of Photosynthetic Electron Transport in Atrazine Susceptible and Atrazine Resistant Brassica Chloroplasts

1987 ◽  
Vol 42 (6) ◽  
pp. 670-673 ◽  
Author(s):  
John N. Phillips ◽  
John L. Huppatz
Keyword(s):  
Electron Transport ◽  
Inhibitory Activity ◽  
Photosynthetic Electron Transport ◽  
Resistant Mutant ◽  
Herbicidal Activity ◽  
Optical Isomers ◽  
Wild Type ◽  
Specific Receptor ◽  
Receptor Sites ◽  
Alkyl Moiety

Comparison of the p/50 values for a series of cyanoacrylate derivatives in chloroplasts isolated from atrazinc susccptiblc (wild type) and atrazine resistant (mutant) Brassica napus biotvpes reveal that the degree and direction of discrimination can vary from being 200- fold more active against the wild type to 10-fold more active against the mutant. There appears to be a direct correlation between the level of inhibitory activity in thylakoids isolated from “susceptible” chloroplasts and the level of discrimination between “susceptible” and “resistant” chloroplasts - a correlation which can be improved by allowing for variations in molecular hydrophobicity. Studies with optically active ethoxyethyl-3-alkyl-2-cyano-3-α-methylbenzylamino acrylates suggest that there are specific receptor sites present in both “susceptible” and “resistant” chloroplasts for both the a-methylbenzyl chiral centre and the 3-alkyl moiety. There is a direct relationship between photosynthetic electron transport inhibitory activity and herbicidal activity of optical isomers.

scholarly journals Photosynthetic Electron Transport Inhibition by 2-Substituted 4-Alkyl-6-benzylamino-1,3,5-triazines with Thylakoids from Wild-Type and Atrazine-Resistant Chenopodium album

2002 ◽  
Vol 57 (11-12) ◽  
pp. 1009-1015 ◽  
Author(s):  
Ruiko Okano ◽  
Aiko Ohki ◽  
Shinpei Ohki ◽  
Hitoshi Kohno ◽  
Jack J. S. van Rensen ◽  
...  
Keyword(s):  
Electron Transport ◽  
Chenopodium Album ◽  
Photosynthetic Electron Transport ◽  
Resistance Ratio ◽  
Triazine Herbicides ◽  
Inhibition Assay ◽  
Wild Type ◽  
Amino Groups ◽  
Triazine Derivatives ◽  
Derivatives Of

The effect of 2-benzylamino-1,3,5-triazines on photosynthetic electron transport (PET) was measured with thylakoids isolated from atrazine-resistant, wild-type Chenopodium album, and spinach to find novel 1,3,5-triazine herbicides bearing a strong PET inhibition. The PET inhibition assay with Chenopodium (wild-type and resistant), yielded a resistance ratio (R/ W = I50 (resistant)/I50 (wild-type)) of 324 for atrazine while for benzylamino-1,3,5-triazine derivatives of diamino-1,3,5-triazines a R/W of 11 to 160 was found. The compounds having a benzylamino group at one of the amino groups in the diamino-1,3,5-triazines have a resistant ratio down to one half to 1/30 of the atrazine value. The average resistance ratio of 21 benzylamino derivatives of monoamino-1,3,5-triazines was found to be about 4.0. The inhibition of 21 benzylamino-1,3,5-triazines assayed with atrazine-resistant Chenopodium thylakoids, indicated by pI50 (R) -values, correlated well with the PET inhibition pI50 (W) of wildtype thylakoids from Chenopodium.

scholarly journals TIP family aquaporins play role in chloroplast osmoregulation and photosynthesis

2020 ◽  
Author(s):  
Azeez Beebo ◽  
Ahmad Zia ◽  
Christopher R. Kinzel ◽  
Andrei Herdean ◽  
Karim Bouhidel ◽  
...  
Keyword(s):  
Electron Transport ◽  
Oxygen Evolution ◽  
Photosynthetic Electron Transport ◽  
Chloroplast Envelope ◽  
Photosynthetic Oxygen Evolution ◽  
Wild Type ◽  
Thylakoid Lumen ◽  
Photosynthetic Oxygen ◽  
Osmotic Treatment ◽  
Envelope Membranes

SUMMARYPhotosynthetic oxygen evolution by photosystem II requires water supply into the chloroplast to reach the thylakoid lumen. A rapid water flow is also required into the chloroplast for optimal oxygen evolution and to overcome osmotic stress. The mechanisms governing water transport in chloroplasts are largely unexplored. Previous proteomics indicated the presence of three aquaporins from the tonoplast intrinsic protein (TIP) family, TIP1;1, TIP1;2 and TIP2;1, in chloroplast membranes of Arabidopsis thaliana. Here we revisited their location and studied their role in chloroplasts. Localization experiments indicated that TIP2;1 resides in the thylakoid, whereas TIP1;2 is present in both thylakoid and envelope membranes. Mutants lacking TIP1;2 and/or TIP2;1 did not display a macroscopic phenotype when grown under standard conditions. The mutant chloroplasts and thylakoids underwent less volume changes than the corresponding wild type preparations upon osmotic treatment and in the light. Significantly reduced rates of photosynthetic electron transport were obtained in the mutant leaves, with implications on the CO2 fixation rates. However, electron transport rates did not significantly differ between mutants and wild type when isolated thylakoids were examined. Less acidification of the thylakoid lumen was measured in mutants thylakoids, resulting in a slower induction of delta pH-dependent photoprotective mechanisms. These results identify TIP1;2 and TIP2;1 as chloroplast proteins and highlight their importance for osmoregulation and optimal photosynthesis. A third aquaporin, TIP1;1, is present in the chloroplast envelope, and may play role in photosynthesis under excessive light conditions, as based on the weak photosynthetic phenotype of its mutant.

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

Weed Science ◽  
1970 ◽  
Vol 18 (3) ◽  
pp. 419-426 ◽  
Author(s):  
D. E. Moreland ◽  
W. J. Blackmon
Keyword(s):  
Electron Transport ◽  
Oxygen Uptake ◽  
Electron Donor ◽  
Spinacia Oleracea ◽  
Herbicidal Activity ◽  
Oxygen Utilization ◽  
White Potato ◽  
Ferricyanide Reduction ◽  
Cyclic Photophosphorylation ◽  
Limited Oxygen

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.

Photoautotrophic Cultured Plant Cells: A Novel System to Survey New Photosynthetic Electron Transport Inhibitors

1991 ◽  
Vol 46 (7-8) ◽  
pp. 563-568 ◽  
Author(s):  
Fumihiko Sato ◽  
Yasuyuki Yamada ◽  
Sang Soo Kwak ◽  
Katsunori Ichinose ◽  
Mitsuhiro Kishida ◽  
...  
Keyword(s):  
Electron Transport ◽  
Cultured Cells ◽  
Plant Cells ◽  
Photosynthetic Electron Transport ◽  
Herbicidal Activity ◽  
Marchantia Polymorpha ◽  
Hill Reaction ◽  
Transport Inhibitors ◽  
Comparison Of The Results ◽  
The Hill

Abstract The responses of photoautotrophic (PA) cultured cells of tobacco (Nicotiana tabacum cv. Samsun NN) and liverwort (Marchantia polymorpha L.) to thirty-eight cyclohexanedione derivatives were surveyed. Each derivative was also tested for inhibitory activity on photosynthetic electron transport (PET), using isolated thylakoids, and herbicidal activity, using seed­ lings and mature plants. Comparison of the results from the different assays showed that the responses of PA cells to each com pound correlated more closely with the responses of seed­ lings and mature plants than did the results of the Hill reaction assays. Our findings suggest that PA cultured cells would be a suitable screening material for identifying potential herbicides with PET-inhibiting activity.

Metribuzin-Resistant Mutants of Chlamydomonas reinhardii

1984 ◽  
Vol 39 (5) ◽  
pp. 437-439 ◽  
Author(s):  
N. Pucheu ◽  
W. Oettmeier ◽  
U. Heisterkamp ◽  
K. Masson ◽  
G.F. Wildner
Keyword(s):  
Electron Transport ◽  
Photosynthetic Electron Transport ◽  
Wild Type ◽  
Binding Studies ◽  
Molecular Weight Range ◽  
Chlamydomonas Reinhardii ◽  
Thylakoid Membrane Proteins ◽  
Mutant Strains ◽  
Resistant Mutants

Herbicide resistance in Chlamydomonas reinhardii cells was induced by mutagenesis with 5-fluorodeoxyuridine and ethylmethanesulfonate. Four mutant strains were isolated and analyzed for resistance against DCMU-type or phenolic inhibitors of photosynthetic electron transport. The mutants were different in both the extent and the pattern of their resistance: the R/S value, i.e. the ratio of I50 values of the inhibition of photosynthetic electron transport in isolated resistant and susceptible thylakoids, varied for metribuzin from 10 000 to 36. The mutant MZ-1 was resistant against metribuzin, atrazine and DCMU, whereas the mutant MZ-2 showed resistance mainly against metribuzin and atrazine. The mutant MZ-3 was similar to MZ-1, but showed a lesser extent of resistance against DCMU. The mutant MZ-4 showed resistance against metribuzin, but not against atrazine. These results demonstrate that the resistance against one herbicide of the DCMU-type (metribuzin) must not be accompanied by similar resistance against te other inhibitors. Binding studies with radioactively labeled herbicides, [14C]metribuzin, [14C]atrazine and [3H]DCMU, and isolated thylakoids supported these observations. Phosphorylation of thylakoid membrane proteins was studied with wild-type cells and resistant mutants under in vivo conditions in the light. The 32P-labeled main proteins bands were in the molecular weight range of 10-14 kDa, 26-29 kDa, 32-35 kDa and 46-48 kDa. The pattern and the extent of incorporation of 32P were similar for the mutants and the wild-type cells.

scholarly journals The effects of high concentrations of salts on photosynthetic electron transport in spinach (Spinacia oleracea) chloroplasts

1982 ◽  
Vol 204 (3) ◽  
pp. 705-712 ◽  
Author(s):  
A C Stewart
Keyword(s):  
Electron Transport ◽  
Photosystem Ii ◽  
Photosystem I ◽  
Spinacia Oleracea ◽  
Photosynthetic Electron Transport ◽  
Potassium Citrate ◽  
O2 Evolution ◽  
Hofmeister Series ◽  
Reaction Centre ◽  
High Concentrations

1. Photosynthetic electron transport from water to lipophilic Photosystem II acceptors was stimulated 3-5-fold by high concentrations (greater than or equal to 1 M) of salts containing anions such as citrate, succinate and phosphate that are high in the Hofmeister series. 2. In trypsin-treated chloroplasts, K3Fe(CN)6 reduction insensitive to 3-(3,4-dichlorophenyl)-1,1-dimethylurea was strongly stimulated by high concentrations of potassium citrate, but there was much less stimulation of 2,6-dichloroindophenol reduction in Tris-treated chloroplasts supplied with 1,5-diphenylcarbazide as artificial donor. The results suggest that the main site of action of citrate was the O2-evolving complex of Photosystem II. 3. Photosystem I partial reactions were also stimulated by intermediate concentrations of citrate (up to 2-fold stimulation by 0.6-0.8 M-citrate), but were inhibited at the highest concentrations. The observed stimulation may have been caused by stabilizaton of plastocyanin that was complexed with the Photosystem I reaction centre, 4. At 1 M, potassium citrate protected O2 evolution against denaturation by heat or by the chaotropic agent NaNO3. 5. It is suggested that anions high in the Hofmeister series stimulated and stabilized electron transport by enhancing water structure around the protein complexes in the thylakoid membrane.

scholarly journals Preparation and Photosynthesis-Inhibiting Activity of Novel Dihalogenated 3-Hydroxynaphthalene-2-carboxanilides

Proceedings ◽  
2019 ◽  
Vol 41 (1) ◽  
pp. 30
Author(s):  
Jiri Kos ◽  
Tomas Gonec ◽  
Tomas Strharsky ◽  
Michal Oravec ◽  
Josef Jampilek
Keyword(s):  
Electron Transport ◽  
Photosystem Ii ◽  
Spinacia Oleracea ◽  
Photosynthetic Electron Transport ◽  
Microwave Assisted Synthesis ◽  
Inhibiting Activity ◽  
Microwave Assisted ◽  
Spinacia Oleracea L ◽  
Wide Range

In this study, a series of nine 3-hydroxynaphthalene-2-carboxanilides, disubstituted on the anilide ring by fluorine, chlorine and bromine in various positions, was prepared by microwave-assisted synthesis and characterized. The compounds were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The PET-inhibiting activity of the compounds was within a wide range, but rather moderate; the highest activity within the series of the compounds was observed for N-(3,5-difluorophenyl)-3-hydroxynaphthalene-2-carboxamide (IC50 = 9.8 µM). The compounds were found to inhibit PET in photosystem II.

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