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Hydroxyl group abundance and lipid environment determine the cytotoxic activity of polyphenols.

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Τίτλος: Hydroxyl group abundance and lipid environment determine the cytotoxic activity of polyphenols.
Συγγραφείς: Aguilar-Carrillo AB; Tecnológico Nacional de México/ITS de Ciudad Hidalgo, Av. Ing. Carlos Rojas Gutiérrez #2120, Ciudad Hidalgo, Michoacán, 61100, Mexico. Electronic address: bethsy.aguila.c@gmail.com., Garduño-Valdovinos SA; Tecnológico Nacional de México/ITS de Ciudad Hidalgo, Av. Ing. Carlos Rojas Gutiérrez #2120, Ciudad Hidalgo, Michoacán, 61100, Mexico. Electronic address: gardunosofia8@gmail.com., Nava GM; Facultad de Química, Universidad Autónoma de Querétaro, Cerro de Las Campanas, Santiago de Querétaro, Qro., 76010, Mexico. Electronic address: gerardomnava@gmail.com., Sánchez-Quezada V; Facultad de Química, Universidad Autónoma de Querétaro, Cerro de Las Campanas, Santiago de Querétaro, Qro., 76010, Mexico. Electronic address: vanessa.sanchez@uaq.mx., Madrigal-Perez LA; Facultad de Química, Universidad Autónoma de Querétaro, Cerro de Las Campanas, Santiago de Querétaro, Qro., 76010, Mexico. Electronic address: luis.madrigal@uaq.mx.
Πηγή: Biochemical and biophysical research communications [Biochem Biophys Res Commun] 2026 Oct 08; Vol. 834, pp. 154442. Date of Electronic Publication: 2026 Aug 13.
Τύπος έκδοσης: Journal Article
Γλώσσα: English
Στοιχεία περιοδικού: Publisher: Elsevier Country of Publication: United States NLM ID: 0372516 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1090-2104 (Electronic) Linking ISSN: 0006291X NLM ISO Abbreviation: Biochem Biophys Res Commun Subsets: MEDLINE
Imprint Name(s): Publication: <2002- >: San Diego, CA : Elsevier
Original Publication: New York, Academic Press.
Ιατρικοί όροι (MeSH): Polyphenols*/chemistry , Polyphenols*/toxicity , Saccharomyces cerevisiae*/drug effects, Quercetin/chemistry ; Quercetin/toxicity ; Fatty Acids/chemistry ; Gallic Acid/chemistry ; Gallic Acid/toxicity ; Flavanones/chemistry ; Flavanones/toxicity ; Stilbenes/chemistry ; Stilbenes/toxicity ; Resveratrol ; Hydroxylation
Περίληψη: Polyphenols are plant secondary metabolites that contribute to defense against biotic and abiotic stressors. Their aromatic rings confer lipophilic properties, whereas hydroxyl groups determine their redox activity, suggesting that both structural features may influence their interaction with mitochondrial membranes and oxidative phosphorylation. However, the contribution of hydroxyl groups and a lipophilic environment to the biological activity of polyphenols remains poorly understood. This study investigated the effects of polyphenol structure and lipid environment on toxicity using Saccharomyces cerevisiae as a model organism. Four polyphenols with different numbers of hydroxyl groups and structural features (quercetin, naringenin, resveratrol, and gallic acid) were evaluated in the presence of different fatty acids to assess the influence of a lipophilic environment. The presence of fatty acids increased the observed cytotoxicity of polyphenols under our experimental conditions. Although these findings are consistent with enhanced activity in a lipophilic environment, our experimental design does not distinguish whether this effect results from increased interaction of polyphenols with cells, altered cellular susceptibility, or other mechanisms. Additionally, among the compounds tested, quercetin, which contains five hydroxyl groups, exhibited the highest toxicity, indicating a positive association between hydroxyl group abundance and biological activity. These findings indicate that both the lipid environment and the number of hydroxyl groups are important determinants of polyphenol toxicity. The enhanced activity of polyphenols in lipid as solvents provides new insights into their mechanism of action and may facilitate the development of technologies that exploit their biological properties.
(Copyright © 2026 Elsevier Inc. All rights reserved.)
Competing Interests: Declaration of competing interest The authors declare the following financial interests/personal relationships which may be considered as potential competing interests:Luis Alberto Madrigal-Perez reports financial support, administrative support, equipment, drugs, or supplies, statistical analysis, and writing assistance were provided by National Technology of Mexico. Luis Alberto Madrigal-Perez reports financial support, administrative support, equipment, drugs, or supplies, statistical analysis, and writing assistance were provided by Institute of Science Technology and Innovation of the State of Michoacan de Ocampo. If there are other authors, they declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Contributed Indexing: Keywords: Bioavailability; Hydroxyl groups; Hydroxylation; Polyphenols; Redox potential
Substance Nomenclature: 0 (Polyphenols)
9IKM0I5T1E (Quercetin)
0 (Fatty Acids)
HN5425SBF2 (naringenin)
632XD903SP (Gallic Acid)
Q369O8926L (Resveratrol)
0 (Flavanones)
0 (Stilbenes)
Entry Date(s): Date Created: 20260821 Date Completed: 20260909 Latest Revision: 20260909
Update Code: 20260910
DOI: 10.1016/j.bbrc.2026.154442
PMID: 42628327
Βάση Δεδομένων: MEDLINE
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– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: Polyphenols are plant secondary metabolites that contribute to defense against biotic and abiotic stressors. Their aromatic rings confer lipophilic properties, whereas hydroxyl groups determine their redox activity, suggesting that both structural features may influence their interaction with mitochondrial membranes and oxidative phosphorylation. However, the contribution of hydroxyl groups and a lipophilic environment to the biological activity of polyphenols remains poorly understood. This study investigated the effects of polyphenol structure and lipid environment on toxicity using Saccharomyces cerevisiae as a model organism. Four polyphenols with different numbers of hydroxyl groups and structural features (quercetin, naringenin, resveratrol, and gallic acid) were evaluated in the presence of different fatty acids to assess the influence of a lipophilic environment. The presence of fatty acids increased the observed cytotoxicity of polyphenols under our experimental conditions. Although these findings are consistent with enhanced activity in a lipophilic environment, our experimental design does not distinguish whether this effect results from increased interaction of polyphenols with cells, altered cellular susceptibility, or other mechanisms. Additionally, among the compounds tested, quercetin, which contains five hydroxyl groups, exhibited the highest toxicity, indicating a positive association between hydroxyl group abundance and biological activity. These findings indicate that both the lipid environment and the number of hydroxyl groups are important determinants of polyphenol toxicity. The enhanced activity of polyphenols in lipid as solvents provides new insights into their mechanism of action and may facilitate the development of technologies that exploit their biological properties.&lt;br /&gt; (Copyright &#169; 2026 Elsevier Inc. All rights reserved.)
– Name: Abstract
  Label: Competing Interests
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  Data: Declaration of competing interest The authors declare the following financial interests/personal relationships which may be considered as potential competing interests:Luis Alberto Madrigal-Perez reports financial support, administrative support, equipment, drugs, or supplies, statistical analysis, and writing assistance were provided by National Technology of Mexico. Luis Alberto Madrigal-Perez reports financial support, administrative support, equipment, drugs, or supplies, statistical analysis, and writing assistance were provided by Institute of Science Technology and Innovation of the State of Michoacan de Ocampo. If there are other authors, they declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
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  Data: 0 (Polyphenols)&lt;br /&gt;9IKM0I5T1E (Quercetin)&lt;br /&gt;0 (Fatty Acids)&lt;br /&gt;HN5425SBF2 (naringenin)&lt;br /&gt;632XD903SP (Gallic Acid)&lt;br /&gt;Q369O8926L (Resveratrol)&lt;br /&gt;0 (Flavanones)&lt;br /&gt;0 (Stilbenes)
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        Value: 10.1016/j.bbrc.2026.154442
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      – Code: eng
        Text: English
    PhysicalDescription:
      Pagination:
        StartPage: 154442
    Subjects:
      – SubjectFull: Quercetin chemistry
        Type: general
      – SubjectFull: Quercetin toxicity
        Type: general
      – SubjectFull: Fatty Acids chemistry
        Type: general
      – SubjectFull: Gallic Acid chemistry
        Type: general
      – SubjectFull: Gallic Acid toxicity
        Type: general
      – SubjectFull: Flavanones chemistry
        Type: general
      – SubjectFull: Flavanones toxicity
        Type: general
      – SubjectFull: Stilbenes chemistry
        Type: general
      – SubjectFull: Stilbenes toxicity
        Type: general
      – SubjectFull: Resveratrol
        Type: general
      – SubjectFull: Hydroxylation
        Type: general
      – SubjectFull: Polyphenols chemistry
        Type: general
      – SubjectFull: Polyphenols toxicity
        Type: general
      – SubjectFull: Saccharomyces cerevisiae drug effects
        Type: general
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      – TitleFull: Hydroxyl group abundance and lipid environment determine the cytotoxic activity of polyphenols.
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              Text: 2026 Oct 08
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