ArticleChemical research in toxicology2018
Thiol Reactivity of Curcumin and Its Oxidation Products.
Article in Chemical research in toxicology, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 36 citations in OpenAlex.
- Curcumin Between Pleiotropic Potential and Translational Constraints.International journal of molecular sciences · 2026Review
- Synthetic Cyclic CAntioxidants (Basel, Switzerland) · 2025Article
- Dry Heating of Curcumin in the Presence of Basic Salts Yields Anti-inflammatory Dimerization Products.ACS omega · 2024Article
- Oil soluble iron: Curcumin derivatives and their complex.Food chemistry · 2024Article
- Interaction of Thiol Antioxidants with α,β-Unsaturated Ketone Moiety: Its Implication for Stability and Bioactivity of Curcuminoids.Molecules (Basel, Switzerland) · 2023Article
- Curcumin partly prevents ISG15 activation via ubiquitin-activating enzyme E1-like protein and decreases ISGylation.Biochemical and biophysical research communications · 2022Article
- Oxidative Products of Curcumin Rather Than Curcumin Bind toMolecules (Basel, Switzerland) · 2022Article
- Curcumin Inhibition of TGFβ signaling in bone metastatic breast cancer cells and the possible role of oxidative metabolites.The Journal of nutritional biochemistry · 2022Article
- Perspective on Improving the Relevance, Rigor, and Reproducibility of Botanical Clinical Trials: Lessons Learned From Turmeric Trials.Frontiers in nutrition · 2021Review
- The Diarylheptanoid Curcumin Induces MYC Inhibition and Cross-Links This Oncoprotein to the Coactivator TRRAP.Frontiers in oncology · 2021Article
- Curcumin Oxidation Is Required for Inhibition ofFrontiers in cellular and infection microbiology · 2021Article
- Mechanistic Differences in the Inhibition of NF-κB by Turmeric and Its Curcuminoid Constituents.Journal of agricultural and food chemistry · 2020Article
- Targeting Cytokine Release Through the Differential Modulation of Nrf2 and NF-κB Pathways by Electrophilic/Non-Electrophilic Compounds.Frontiers in pharmacology · 2020Article
- Curcumin induces secretion of glucagon-like peptide-1 through an oxidation-dependent mechanism.Biochimie · 2019Article
- Liposomal Curcumin Enhances the Effect of Naproxen in a Rat Model of Migraine.Medical science monitor : international medical journal of experimental and clinical research · 2019Article
- Article
- A Curcumin Degradation Product, 7-Norcyclopentadione, Formed by Aryl Migration and Loss of a Carbon from the Heptadienedione Chain.Journal of natural products · 2018Article
- Stability and anti-inflammatory activity of the reduction-resistant curcumin analog, 2,6-dimethyl-curcumin.Organic & biomolecular chemistry · 2018Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The polypharmacological effects of the turmeric compound curcumin may be partly mediated by covalent adduction to cellular protein. Covalent binding to small molecule and protein thiols is thought to occur through a Michael-type addition at the enone moiety of the heptadienedione chain connecting the two methoxyphenol rings of curcumin. Here we show that curcumin forms the predicted thiol-Michael adducts with three model thiols, glutathione, N-acetylcysteine, and β-mercaptoethanol. More abundant, however, are respective thiol adducts of the dioxygenated spiroepoxide intermediate of curcumin autoxidation. Two electrophilic sites at the quinone-like ring of the spiroepoxide are identified. Addition of β-mercaptoethanol at the 5'-position of the ring gives a 1,7-dihydroxycyclopentadione-5' thioether, and addition at the 1'-position results in cleavage of the aromatic ring from the molecule, forming methoxyphenol-thioether and a tentatively identified cyclopentadione aldehyde. The curcuminoids demethoxy- and bisdemethoxycurcumin do not form all of the possible thioether adducts, corresponding with their increased stability toward autoxidation. RAW264.7 macrophage-like cells activated with phorbol ester form curcumin-glutathionyl and the 1,7-dihydroxycyclopentadione-5'-glutathionyl adducts. These studies indicate that the enone of the parent compound is not the only functional electrophile in curcumin, and that its oxidation products provide additional electrophilic sites. This suggests that protein binding by curcumin may involve oxidative activation into reactive quinone methide and spiroepoxide electrophiles.
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