Interference of l,2,3,4-Tetramethoxy-5-(2-propenyl)benzene with Photosynthetic Electron Transport

1998 ◽  
Vol 53 (1-2) ◽  
pp. 55-59 ◽  
Author(s):  
A. Jimenez ◽  
R. Mata ◽  
B. Lotina-Hennsen ◽  
A. L. Anaya

AbstractThe effect of 1,2,3,4-tetramethoxy-5-(2-propenyl)benzene, the major phytogrowth-inhibitory agent isolated from the leaves, stem bark and wood of Malmea depressa (Annonaceae), on several photosynthetic activities has been investigated using freshly lysed spinach chloroplasts. The results indicate that this compound inhibits proton-uptake, ATP synthesis and electron flow (basal, phosphorylating and uncoupled) in a concentration dependent manner, therefore acting as a Hill reaction inhibitor. Uncoupled electron transport through photosystem I from reduced dichlorophenol-indophenol to methylviologen is unaffected by this compound. On the other hand, uncoupled electron transport through photosystem II from water to dichlorophenol-indophenol, from water to silicomolibdate and from diphenylcarbazide to dichlorophenol-indophenol is inhibited by this phenylpropanoid, suggesting that the site of inhibition is located in the span from P680 to QA.

2000 ◽  
Vol 55 (7-8) ◽  
pp. 631-637 ◽  
Author(s):  
Carlos Céspedes ◽  
Lahoucine Achnine ◽  
Julio Alarcón ◽  
José Becerra ◽  
Blas Lotina-Hennsen

Abstract The effects of 9β-benzoyloxy-la, 2α, 6β, 8α, 15-pentaacetoxy-dihydro-β-agarofuran and 9β furoyloxy-1α, 6β, 8α-triacetoxy-dihydro-β-agarofuran, major phytogrowth inhibitors isolated from the aerial parts of Maytenus disticha (Celastraceae) and seeds of Maytenus boaria (Celastaraceae), respectively, on different photosynthetic activities of isolated spinach chloroplasts have been investigated. Photophosphorylation and electron transport (basal, phosphorylating and uncoupled) were inhibited in a concentration dependent manner by both compounds, therefore acting as Hill reaction inhibitors. The site of action of these natural compounds was located in the span from P680 to QA. 9β-benzoyloxy-1,2,6,8,15-pentaacetoxydihydro-β-agarofuran was one order of magnitude more potent (I50 = 2.6 μм) than 9β-furoyloxy-1,6,8,-triacetoxydihydro-β-agarofuran, suggesting that the substitution at C-9 and the acetoxy groups at carbons 2 and 15 are important structural requirements for the displayed inhibitory activity.


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.


1994 ◽  
Vol 72 (2) ◽  
pp. 177-181 ◽  
Author(s):  
Ernesto Bernal-Morales ◽  
Alfonso Romo De Vivar ◽  
Bertha Sanchez ◽  
Martha Aguilar ◽  
Blas Lotina-Hennsen

The inhibition of ATP synthesis, proton uptake, and electron transport (basal, phosphorylating, and uncoupled) from water to methylviologen by ivalin (a naturally occurring sesquiterpene lactone in Zaluzania triloba and Iva microcephala) indicates that it acts as electron transport inhibitor. Since photosystem I and electron transport from DPC to QA were not affected, while the electron flow of uncoupled photosystem II from H2O to DAD and from water to silicomolybdate was inhibited, we concluded that the site of inhibition of ivalin is located at the oxygen evolution level. Key words: oxygen evolution, ivalin, photosynthesis, sesquiterpene lactone.


1996 ◽  
Vol 51 (3-4) ◽  
pp. 179-184 ◽  
Author(s):  
Surendra Chandra Sabat

Abstract The inhibitory effects of copper ion (Cu2+) on the photosynthetic electron transport func­tion was investigated both in NaCl washed (depleted in 17 and 23 kDa polypeptides) and native (unwashed) photosystem II membrane preparations from spinach (Beta vulgaris) chlo-roplasts. Copper in the range of 2.0 to 15 μᴍ strongly inhibited the electron flow from water to 2,6-dichlorobenzoquinone in NaCl washed particles in a concentration dependent manner. Com plete inhibition was noticed at 15 μᴍ Cu2+. Oppositely in native membranes, 15 μᴍ C u2+ inhibited only 10-12% of control activity. It was found that calcium ion (Ca2+) significantly reduced the Cu2+ inhibition of electron transport activity. The Ca2+ supported prevention of Cu2+ toxicity was specific to Ca2+. Further analysis indicated that both Cu2+ and Ca2+ act competitively. Since Ca2+ is known to have stimulating/stabilizing effect at the donor side of photosystem II, it is therefore suggested that Cu2+ in NaCl washed particles exerts its inhibi­tory effect(s) at the oxidizing side of photosystem stimulates/stabilizes the oxygen evolution.


1973 ◽  
Vol 28 (1-2) ◽  
pp. 36-44 ◽  
Author(s):  
Alfons Radunz ◽  
Georg H. Schmid

An antiserum to lutein inhibits photosynthetic electron transport between water and potassium ferricyanide in diloroplasts from green Nicotiana tabacum var. John William’s Breadleaf. However, electron transport between diphenylcarbazide and potassium ferricyanide is not impaired. From this it is concluded that the photochemically active carotenoid should feed its electrons into the photosynthetic electron transport chain before the site from which diphenyl-carbazide donates electrons. The inhibition of the ferricyanide Hill reaction in diloroplasts by antibodies to lutein depends on the accessibility of the carotenoid antigen in the thylakoid membrane. In fresh preparations the accessibility is greater in diloroplasts in which photo- synthetic electron transport is coupled to photophosphorylation. Concomitantly the antiserum to lutein agglutinates only such chloroplast preparations in which the Hill reaction is impaired by the antiserum. An antiserum to plastoquinone inhibits ferricyanide photoreduction of diloroplasts regardless whether driven by water or diphenylcarbazide as the electron donors. Typical photosystem-I-reactions are not influenced by the antiserum. In a certain type of chloroplast preparations the antiserum does not inhibit PMS-mediated photophosphorylation inferring that plastoquinone, eventually involved in this reaction, is either not accessible to antibodies, or that this cyclic electron flow does not necessarily pass through plastoquinone.


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.


1972 ◽  
Vol 27 (4) ◽  
pp. 445-455 ◽  
Author(s):  
Heinrich Strotmann ◽  
Christa Von Gösseln

Photosystem I related phosphorylation of isolated chloroplasts was investigated with special reference to the stoichiometry between ATP production and electron transprt (ATP: 2e⊖). The system studied contained DCMU to inhibit electron flow from photosystem II, ascorbate and DPIP to supply electrons to photosystem I, and methylviologen as electron acceptor. The following results were obtained:1. Basal electron transport is stimulated by the addition of the phosphorylating system, indicating that phosphorylation is really coupled to non-cyclic electron flow. The ratio ATP: 2e⊖ is 1, when the increase of electron flow obtained by the addition of ADP and phosphate is correlated to phosphorylation. This ratio is constant upon varying several parameters including DPIP concentration and light intensity.2. In the absence of methylviologen a DPIP catalyzed cyclic phosphorylation takes place (cf. I. c.7, 11, 12). Phosphorylation is not increased by the addition of methylviologen, indicating that both, the cyclic DPIP mediated and the non-cyclic system are coupled to the same phosphorylation site and limited by the same reaction step.3. In the absence of oxygen a methylviologen supported cyclic phosphorylation occurs. Comparing optimum rates, phosphorylation under these conditions is about twice as high as in the noncyclic system. Therefore we conclude that two phosphorylation sites are involved in methylviologen catalyzed cyclic electron transport. This system is sensitive against trypsin treatment of the chloroplasts, whereas the linear system is not.4. The two cyclic systems as well as the non-cyclic system are coupled to reversible proton uptake. Furthermore the linear system exhibits an irreversible uptake of hydrogen ions, which is stoichiometric to electron flow. From the reversible and the irreversible components of the pH changes the ratio of the proton pump to electron transprt can be calculated. Under steady state conditions the ration H⨁ : e⊖ approaches 1.


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.


2019 ◽  
Vol 14 (1) ◽  
pp. 1934578X1901400
Author(s):  
Lilia Cherigo ◽  
Sergio Martínez-Luis

In our continuous search for α-glucosidase inhibitors, three active pentacyclic triterpenes were isolated from stem bark samples of the Panamanian mangrove Pelliciera rhizophorae Triana & Planchon. These compounds were identified by both spectroscopic and spectrometric analysis. Of the isolated compounds, only betulinic acid has been previously isolated from P. rhizophorae leaves while both betulin (IC50 2.09 μM) and lupeol (IC50 0.58 μM) were isolated from this plant for the first time. All three pentacyclic triterpenes inhibited the α-glucosidase enzyme in a concentration-dependent manner, and their inhibitory activity was higher than that of the antidiabetic drug acarbose (IC50 241.6 μM). Kinetic analysis established that betulin and lupeol acted as competitive inhibitors. Finally, docking analysis suggested that all three triterpenes bind at the same site as acarbose does in the human intestinal α-glucosidase (PDB: 3TOP). This work contributes further evidence similar to previous studies that point out that the aerial parts of P. rhizophorae might be potential agents in controlling hyperglycemia in diabetic persons.


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