ArticleThe Journal of biological chemistry2011
Autoxidative and cyclooxygenase-2 catalyzed transformation of the dietary chemopreventive agent curcumin.
Article in The Journal of biological chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 52 papers.
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Who cites it
52 citing papers in PubMed, 152 citations in OpenAlex.
- Triple-Loaded Nanoemulsions Incorporating Coffee Extract for the Photoprotection of Curcumin and Capsaicin: Experimental and Computational Evaluation.Pharmaceutics · 2025Article
- Curcumin: A Natural Warrior Against Inflammatory Liver Diseases.Nutrients · 2025Review
- Advancements in curcuminoid formulations: An update on bioavailability enhancement strategies curcuminoid bioavailability and formulations.Open life sciences · 2025Review
- Curcumin-Loaded Liposomes in Gel Protect the Skin of Mice against Oxidative Stress from Photodamage Induced by UV Irradiation.Gels (Basel, Switzerland) · 2024Article
- Dry Heating of Curcumin in the Presence of Basic Salts Yields Anti-inflammatory Dimerization Products.ACS omega · 2024Article
- Dietary Effect of Curcumin on Amino Acid, Fatty Acid, and Volatile Compound Profiles of Chicken Meat.Foods (Basel, Switzerland) · 2024Article
- Design and Development of a Polymeric-Based Curcumin Nanoparticle for Drug Delivery Enhancement and Potential Incorporation into Nerve Conduits.Molecules (Basel, Switzerland) · 2024Article
- A Critical Appraisal of the Protective Activity of Polyphenolic Antioxidants against Iatrogenic Effects of Anticancer Chemotherapeutics.Antioxidants (Basel, Switzerland) · 2024Review
- Development of a Slow-Degrading Polymerized Curcumin Coating for Intracortical Microelectrodes.ACS applied bio materials · 2023Article
- Structure-activity relationship of dibenzylideneacetone analogs against the neglected disease pathogen, Trypanosoma brucei.Bioorganic & medicinal chemistry letters · 2023Article
- Lysine-targeting inhibition of amyloid β oligomerization by a green perilla-derived metastable chalconeRSC chemical biology · 2022Article
- Curcumin activates G protein-coupled receptor 97 (GPR97) in a manner different from glucocorticoid.Biochemical and biophysical research communications · 2022Article
- Identification of G protein-coupled receptor 55 (GPR55) as a target of curcumin.NPJ science of food · 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
- Binding of quercetin and curcumin to human serum albumin in aqueous dimethyl sulfoxide and in aqueous ethanol.Journal of thermal analysis and calorimetry · 2022Article
- Toxic Feedback Loop Involving Iron, Reactive Oxygen Species, α-Synuclein and Neuromelanin in Parkinson's Disease and Intervention with Turmeric.Molecular neurobiology · 2021Review
- 1,5-Benzodiazepin-2(3H)-ones: In Vitro Evaluation as Antiparkinsonian Agents.Antioxidants (Basel, Switzerland) · 2021Article
- Dietary Curcumin Improves Energy Metabolism, Brain Monoamines, Carcass Traits, Muscle Oxidative Stability and Fatty Acid Profile in Heat-Stressed Broiler Chickens.Antioxidants (Basel, Switzerland) · 2021Article
- Review
- Fabrication of Caseinate Stabilized Thymol Nanosuspensions via the pH-Driven Method: Enhancement in Water Solubility of Thymol.Foods (Basel, Switzerland) · 2021Article
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Authors and funding
6 authors at 3 institutions in 2 countries.
Funding
Abstract
The efficacy of the diphenol curcumin as a cancer chemopreventive agent is limited by its chemical and metabolic instability. Non-enzymatic degradation has been described to yield vanillin, ferulic acid, and feruloylmethane through cleavage of the heptadienone chain connecting the phenolic rings. Here we provide evidence for an alternative mechanism, resulting in autoxidative cyclization of the heptadienone moiety as a major pathway of degradation. Autoxidative transformation of curcumin was pH-dependent with the highest rate at pH 8 (2.2 μM/min) and associated with stoichiometric uptake of O(2). Oxidation was also catalyzed by recombinant cyclooxygenase-2 (COX-2) (50 nm; 7.5 μM/min), and the rate was increased ≈10-fold by the addition of 300 μM H(2)O(2). The COX-2 catalyzed transformation was inhibited by acetaminophen but not indomethacin, suggesting catalysis occurred by the peroxidase activity. We propose a mechanism of enzymatic or autoxidative hydrogen abstraction from a phenolic hydroxyl to give a quinone methide and a delocalized radical in the heptadienone chain that undergoes 5-exo cyclization and oxygenation. Hydration of the quinone methide (measured by the incorporation of O-18 from H(2)(18)O) and rearrangement under loss of water gives the final dioxygenated bicyclopentadione product. When curcumin was added to RAW264.7 cells, the bicyclopentadione was increased 1.8-fold in cells activated by LPS; vanillin and other putative cleavage products were negligible. Oxidation to a reactive quinone methide is the mechanistic basis of many phenolic anti-cancer drugs. It is possible, therefore, that oxidative transformation of curcumin, a prominent but previously unrecognized reaction, contributes to its cancer chemopreventive activity.
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