Inhibition of O<sub>2</sub> Consumption Resistant to Cyanide and Its Development by <i>N</i>-Propyl Gallate and Salicylhydroxamic Acid

Janes, Harry W.; Wiest, Steven C.

doi:10.1104/pp.70.3.853

Cited by 13 publications

(6 citation statements)

References 7 publications

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“…2). This result was consistent with previous kinetic studies which indicated that gallate esters and hydroxamates inhibit the alternative pathway in a mutually exclusive fashion (14,25). The similarities of the results obtained when SHAM was used in place of unlabeled butyl gallate in the binding studies (Fig.…”

Section: Resultssupporting

confidence: 82%

Binding of Butyl Gallate to Isolated Mung Bean Mitochondria

Siedow

Bickett²

1983

Plant Physiol.

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The binding of radioactively labeled butyl gailate to sucrose gradientpurified mung bean ( Vigna radiata L.) mitochondria was studied. propyl gallate and the hydroxamic acids inhibit the alternative pathway at the same (or at least spatially very similar) site. The structural features required for inhibition of the alternative pathway by propyl gallate have also been determined (24). Additional compounds which inhibit the alternative pathway at site(s) other than the site which is sensitive to gallates and hydroxamates have also been reported (7,11,20).Studies using the binding of radioactively labeled herbicides to isolated chloroplasts have proved remarkably successful in helping characterize the component known as 'B' on the photosynthetic electron transfer chain (15,16, 28). While binding studies using labeled inhibitors with animal mitochondria have also been reported (4, 12), almost no such experiments have appeared using isolated mitochondria from higher plants. In the present report, we synthesized a radioactive analog of propyl gallate, [14CJbutyl gallate, and studied its binding to isolated, purified mung bean mitochondria. The results serve to confirm independently several earlier observations obtained from kinetic studies ofpropyl gallate inhibition of the alternative pathway and allow, for the first time, an estimate of the absolute amount of alternative oxidase present in plant (in this case, mung bean) mitochondria.The cyanide-resistant, alternative pathway represents one of the most intensively studied aspects of the plant mitochondrial electron transfer chain yet many of the basic questions regarding the nature of the pathway remain unanswered. It is generally accepted that the cyanide-resistant electron flux to O2 involves a mitochondrial-associated oxidase, and that electrons branch off the main, cyanide-sensitive pathway onto the alternative pathway at the level of the ubiquinone pool (5, 17, 23). Several lines of evidence indicate that the alternative oxidase functions as a pdiphenol:oxygen oxidoreductase (2, 13). However, the nature of the oxidase remains to be elucidated, and in no case is the absolute amount of alternative oxidase present in the mitochondrial membrane known.Whereas progress toward characterization of the alternative oxidase has proceeded somewhat slowly, recent years have seen the appearance of a number of compounds which specifically inhibit electron transfer through the alternative pathway in isolated mitochondria, specificity being defined by a lack of effect on cyanide-sensitive electron transfer. In 1971, Schonbaum et al. (22) reported that aryl-substituted hydroxamic acids could completely inhibit the alternative pathway at concentrations which were without effect on the main pathway. More recently, Siedow and Girvin (25) found that the antioxidant n-propyl gallate could inhibit the alternative pathway, and kinetic studies showed that ' This investigation was supported by National Institute of General Medical Sciences Grant GM 26095 to J. N. Siedow. MATER...

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Section: Resultssupporting

confidence: 82%

Binding of Butyl Gallate to Isolated Mung Bean Mitochondria

Siedow

Bickett²

1983

Plant Physiol.

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“…Inhibitor potency is an important parameter for drug development projects. Derivatives of salicylic acid and of gallic acid are well-known AOX inhibitors [48][49][50] , but are only effective against M. perniciosa at millimolar concentrations 5,7 . We have also recently shown that another AOX inhibitor, N-(3-bromophenyl)-3-fluorobenzamide, has a protective effect in plants against WBD at 200 µM even in the absence of a main respiration inhibitor 7 .…”

Section: Discussionmentioning

confidence: 99%

“…Points represent two independent measurements and the continuous lines are the best fit for a 4-parameter sigmoid function. EC50 = 166 µM (GMP), 918 µM (AMP) and ca. 6.5 mM (ADP).…”

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confidence: 99%

Biochemical characterization and inhibition of the alternative oxidase enzyme from the fungal phytopathogen Moniliophthora perniciosa

et al. 2020

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Moniliophthora perniciosa is a fungal pathogen and causal agent of the witches' broom disease of cocoa, a threat to the chocolate industry and to the economic and social security in cocoaplanting countries. The membrane-bound enzyme alternative oxidase (MpAOX) is crucial for pathogen survival; however a lack of information on the biochemical properties of MpAOX hinders the development of novel fungicides. In this study, we purified and characterised recombinant MpAOX in dose-response assays with activators and inhibitors, followed by a kinetic characterization both in an aqueous environment and in physiologically-relevant proteoliposomes. We present structure-activity relationships of AOX inhibitors such as colletochlorin B and analogues which, aided by an MpAOX structural model, indicates key residues for protein-inhibitor interaction. We also discuss the importance of the correct hydrophobic environment for MpAOX enzymatic activity. We envisage that such results will guide the future development of AOX-targeting antifungal agents against M. perniciosa, an important outcome for the chocolate industry.

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“…Gallate esters have been shown to exhibit antimicrobial activity; in several cases, propyl gallate may serve as an effective alternative to salicylhydroxamic acid, which is a likely developmental toxicant . Salicylhydroxamic acid works by specifically blocking the activity of alternative oxidase (AOX) in pecan scab and in ethylene-treated tubers …”

Section: Introductionmentioning

confidence: 99%

“…49 Salicylhydroxamic acid works by specifically blocking the activity of alternative oxidase (AOX) in pecan scab 50 and in ethylene-treated tubers. 51 We tested all of these compounds for activity against Aspergillus brasiliensis (mold) and Pseudomonas aeruginosa (Gram negative bacteria)representative microorganisms that the health and personal care product industries use for evaluating preservative efficacy 52,53 over a range of alkyl chain lengths to observe variability in antimicrobial activity, as a function of chain length. Of note, A. brasiliensis has recently been found as a causative agent of keratitis, 54 while P. aeruginosa can cause disease in humans, 55 thus emphasizing the importance and relevance of testing these microbes.…”

Section: ■ Introductionmentioning

confidence: 99%

Design and Testing of Safer, More Effective Preservatives for Consumer Products

Buckley

Hart‐Cooper

Kim

et al. 2017

ACS Sustainable Chem. Eng.

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Preservatives deter microbial growth, providing crucial functions of safety and durability in composite materials, formulated products, and food packaging. Concern for human health and the environmental impact of some preservatives has led to regulatory restrictions and public pressure to remove individual classes of compounds, such as parabens and chromated copper arsenate, from consumer products. Bans do not address the need for safe, effective alternative preservatives, which are critical for both product performance (including lifespan and therefore life cycle metrics) and consumer safety. In this work, we studied both the safety and efficacy of a series of phenolic preservatives and compared them to common preservatives found in personal care products and building materials. We quantified antimicrobial activity against Aspergillus brasiliensis (mold) and Pseudomonas aeruginosa (Gram negative bacteria), and we conducted a hazard assessment, complemented by computational modeling, to evaluate the human and environmental health impacts of these chemicals. We found that octyl gallate demonstrates better antimicrobial activity and comparable or lower hazards, compared to current-use preservatives. Therefore, octyl gallate may serve as a viable small-molecule preservative, particularly in conjunction with low concentrations of other preservatives that act through complementary mechanisms.

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Inhibition of O₂ Consumption Resistant to Cyanide and Its Development by N-Propyl Gallate and Salicylhydroxamic Acid

Cited by 13 publications

References 7 publications

Binding of Butyl Gallate to Isolated Mung Bean Mitochondria

Binding of Butyl Gallate to Isolated Mung Bean Mitochondria

Biochemical characterization and inhibition of the alternative oxidase enzyme from the fungal phytopathogen Moniliophthora perniciosa

Design and Testing of Safer, More Effective Preservatives for Consumer Products

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Inhibition of O2 Consumption Resistant to Cyanide and Its Development by N-Propyl Gallate and Salicylhydroxamic Acid

Cited by 13 publications

References 7 publications

Binding of Butyl Gallate to Isolated Mung Bean Mitochondria

Binding of Butyl Gallate to Isolated Mung Bean Mitochondria

Biochemical characterization and inhibition of the alternative oxidase enzyme from the fungal phytopathogen Moniliophthora perniciosa

Design and Testing of Safer, More Effective Preservatives for Consumer Products

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Product

Resources

About

Inhibition of O₂ Consumption Resistant to Cyanide and Its Development by N-Propyl Gallate and Salicylhydroxamic Acid