ArticleChemical research in toxicology2013
Reactive intermediates produced from the metabolism of the vanilloid ring of capsaicinoids by p450 enzymes.
Article in Chemical research in toxicology, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 48 citations in OpenAlex.
- Bioactive Properties, Bioavailability Profiles, and Clinical Evidence of the Potential Benefits of Black Pepper (Molecules (Basel, Switzerland) · 2023Review
- Capsaicin binds the N-terminus of Hsp90, induces lysosomal degradation of Hsp70, and enhances the anti-tumor effects of 17-AAG (Tanespimycin).Scientific reports · 2023Article
- A chemical probe unravels the reactive proteome of health-associated catechols.Chemical science · 2023Article
- Review
- The Effects of Capsaicin on Gastrointestinal Cancers.Molecules (Basel, Switzerland) · 2020Review
- Metabolic Forest: Predicting the Diverse Structures of Drug Metabolites.Journal of chemical information and modeling · 2020Article
- Capsaicin: Effects on the Pathogenesis of Hepatocellular Carcinoma.Molecules (Basel, Switzerland) · 2019Review
- Formation and biological targets of botanical o-quinones.Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association · 2018Review
- Thiol Reactivity of Curcumin and Its Oxidation Products.Chemical research in toxicology · 2018Article
- Computational Approach to Structural Alerts: Furans, Phenols, Nitroaromatics, and Thiophenes.Chemical research in toxicology · 2017Article
- Extraction, bioavailability, and bioefficacy of capsaicinoids.Journal of food and drug analysis · 2017Review
- Regioselective Enzymatic β-Carboxylation ofAdvanced synthesis & catalysis · 2015Article
- Bioavailability of capsaicin and its implications for drug delivery.Journal of controlled release : official journal of the Controlled Release Society · 2014Review
- Quinone Methide Bioactivation Pathway: Contribution to Toxicity and/or Cytoprotection?Current organic chemistry · 2014Article
- Unusual cytochrome p450 enzymes and reactions.The Journal of biological chemistry · 2013Review
Corrections and comments
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Authors and funding
8 authors at 4 institutions in 1 country.
Funding
Abstract
This study characterized electrophilic and radical products derived from the metabolism of capsaicin by cytochrome P450 and peroxidase enzymes. Multiple glutathione and β-mercaptoethanol conjugates (a.k.a., adducts), derived from the trapping of quinone methide and quinone intermediates of capsaicin, its analogue nonivamide, and O-demethylated and aromatic hydroxylated metabolites thereof, were produced by human liver microsomes and individual recombinant human P450 enzymes. Conjugates derived from concomitant dehydrogenation of the alkyl terminus of capsaicin were also characterized. Modifications to the 4-OH substituent of the vanilloid ring of capsaicinoids largely prevented the formation of electrophilic intermediates, consistent with the proposed structures and mechanisms of formation for the various conjugates. 5,5'-Dicapsaicin, presumably arising from the bimolecular coupling of free radical intermediates was also characterized. Finally, the analysis of hepatic glutathione conjugates and urinary N-acetylcysteine conjugates from mice dosed with capsaicin confirmed the formation of glutathione conjugates of O-demethylated quinone methide and 5-OH-capsaicin in vivo. These data demonstrated that capsaicin and structurally similar analogues are converted to reactive intermediates by certain P450 enzymes, which may partially explain conflicting reports related to the cytotoxic, pro-carcinogenic, and chemoprotective effects of capsaicinoids in different cells and/or organ systems.
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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.