ArticlePloS one2014
Improvement of pro-oxidant capacity of protocatechuic acid by esterification.
Article in PloS one, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed, 55 citations in OpenAlex.
- Antioxidant, pro-oxidant, cytotoxic and antimicrobial properties of selected plant phenolic compounds and resulting structure-activity relationships.Scientific reports · 2026Article
- Preventive Effect of Protocatechuic Acid Ethyl Ester against Doxorubicin-Induced Toxicity in Cardiomyocytes.International journal of preventive medicine · 2026Article
- Antioxidant Metabolism Pathways in Vitamins, Polyphenols, and Selenium: Parallels and Divergences.International journal of molecular sciences · 2024Review
- A Concise Profile of Gallic Acid-From Its Natural Sources through Biological Properties and Chemical Methods of Determination.Molecules (Basel, Switzerland) · 2023Review
- Fe(III) and Cu(II) Complexes of Chlorogenic Acid: Spectroscopic, Thermal, Anti-/Pro-Oxidant, and Cytotoxic Studies.Materials (Basel, Switzerland) · 2022Article
- Orientin Enhances Colistin-Mediated Bacterial Lethality through Oxidative Stress Involvement.Evidence-based complementary and alternative medicine : eCAM · 2022Article
- Natural Cinnamic Acid Derivatives: A Comprehensive Study on Structural, Anti/Pro-Oxidant, and Environmental Impacts.Materials (Basel, Switzerland) · 2021Article
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- Crystal Structure, Spectroscopic Characterization, Antioxidant and Cytotoxic Activity of New Mg(II) and Mn(II)/Na(I) Complexes of Isoferulic Acid.Materials (Basel, Switzerland) · 2021Article
- Development of a caffeic acid-phthalimide hybrid compound for NADPH oxidase inhibition.RSC advances · 2021Article
- Involvement of PTEN and FOXO3a Proteins in the Protective Activity of Protocatechuic Acid Against Cisplatin-Induced Ovarian Toxicity in Mice.Reproductive sciences (Thousand Oaks, Calif.) · 2021Article
- Phenolic content, chemical composition and anti-/pro-oxidant activity of Gold Milenium and Papierowka apple peel extracts.Scientific reports · 2020Article
- Roles and action mechanisms of herbs added to the emulsion on its lipid oxidation.Food science and biotechnology · 2020Review
- Zn(II) Complex of Plant Phenolic Chlorogenic Acid: Antioxidant, Antimicrobial and Structural Studies.Materials (Basel, Switzerland) · 2020Article
- Protein-Protected Gold Nanocluster-Based Biosensor for Determining the Prooxidant Activity of Natural Antioxidant Compounds.ACS omega · 2019Article
- Design of Antibacterial Agents: Alkyl Dihydroxybenzoates againstInternational journal of molecular sciences · 2018Article
- The Study of Anti-/Pro-Oxidant, Lipophilic, Microbial and Spectroscopic Properties of New Alkali Metal Salts of 5-O-Caffeoylquinic Acid.International journal of molecular sciences · 2018Article
- Possible Mechanisms of the Prevention of Doxorubicin Toxicity by Cichoric Acid-Antioxidant Nutrient.Nutrients · 2018Article
- Involvement of oxidative stress in protocatechuic acid-mediated bacterial lethality.MicrobiologyOpen · 2017Article
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Authors and funding
9 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Pro-oxidant effects of phenolic compounds are usually correlated to the one-electron redox potential of the phenoxyl radicals. Here we demonstrated that, besides their oxidizability, hydrophobicity can also be a decisive factor. We found that esterification of protocatechuic acid (P0) provoked a profound influence in its pro-oxidant capacity. The esters bearing alkyl chains containing two (P2), four (P4) and seven (P7) carbons, but not the acid precursor (P0), were able to exacerbate the oxidation of trolox, α-tocopherol and rifampicin. This effect was also dependent on the catechol moiety, since neither gallic acid nor butyl gallate showed any pro-oxidant effects. A comparison was also made with apocynin, which is well-characterized regarding its pro-oxidant properties. P7 was more efficient than apocynin regarding co-oxidation of trolox. However, P7 was not able to co-oxidize glutathione and NADH, which are targets of the apocynin radical. A correlation was found between pro-oxidant capacity and the stability of the radicals, as suggested by the intensity of the peak current in the differential pulse voltammetry experiments. In conclusion, taking into account that hydroquinone and related moieties are frequently found in biomolecules and quinone-based chemotherapeutics, our demonstration that esters of protocatechuic acid are specific and potent co-catalysts in their oxidations may be very relevant as a pathway to exacerbate redox cycling reactions, which are usually involved in their biological and pharmacological mechanisms of action.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.