ArticleThe Journal of biological chemistry2015
Unraveling curcumin degradation: autoxidation proceeds through spiroepoxide and vinylether intermediates en route to the main bicyclopentadione.
Article in The Journal of biological chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 64 papers.
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Who cites it
64 citing papers in PubMed, 161 citations in OpenAlex.
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- Insights into the Structural Patterns in Human Glioblastoma Cell Line SF268 Activity and ADMET Prediction of Curcumin Derivatives.Pharmaceutics · 2025Article
- Triple-Loaded Nanoemulsions Incorporating Coffee Extract for the Photoprotection of Curcumin and Capsaicin: Experimental and Computational Evaluation.Pharmaceutics · 2025Article
- Curcumin: A Magical Small Molecule with a Large Role in Active-Intelligent Degradable Food Packaging.International journal of molecular sciences · 2025Review
- Synergistic power of functional foods and exercise in colorectal cancer control: targeting metabolism, mitochondrial function, redox homeostasis, exercise performance, neuroimmune signaling, and brain-gut axis crosstalk.Frontiers in nutrition · 2025Review
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- Dry Heating of Curcumin in the Presence of Basic Salts Yields Anti-inflammatory Dimerization Products.ACS omega · 2024Article
- Conjugates of 3,5-Bis(arylidene)-4-piperidone and Sesquiterpene Lactones Have an Antitumor Effect via Resetting the Metabolic Phenotype of Cancer Cells.Molecules (Basel, Switzerland) · 2024Article
- Enhancement of Solubility, Stability, Cellular Uptake, and Bioactivity of Curcumin by Polyvinyl Alcohol.International journal of molecular sciences · 2024Article
- Curcumin Supplementation and Human Disease: A Scoping Review of Clinical Trials.International journal of molecular sciences · 2023Article
- Development of a Slow-Degrading Polymerized Curcumin Coating for Intracortical Microelectrodes.ACS applied bio materials · 2023Article
- Curcumin a Natural Phenol and Its Therapeutic Role in Cancer and Photodynamic Therapy: A Review.Pharmaceutics · 2023Review
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- Efficacy of the monocarbonyl curcumin analog C66 in the reduction of diabetes-associated cardiovascular and kidney complications.Molecular medicine (Cambridge, Mass.) · 2022Review
- Selected Plant-Derived Polyphenols as Potential Therapeutic Agents for Peripheral Artery Disease: Molecular Mechanisms, Efficacy and Safety.Molecules (Basel, Switzerland) · 2022Review
- Environmentally Safe Photodynamic Control ofMolecules (Basel, Switzerland) · 2022Article
- Regulation of Gene Expression through Food-Curcumin as a Sirtuin Activity Modulator.Plants (Basel, Switzerland) · 2022Review
- Curcumin activates G protein-coupled receptor 97 (GPR97) in a manner different from glucocorticoid.Biochemical and biophysical research communications · 2022Article
4 more citing papers are in PubMed but not listed here.
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
Abstract
Curcumin is a dietary anti-inflammatory and chemopreventive agent consisting of two methoxyphenol rings connected by a conjugated heptadienedione chain. Curcumin is unstable at physiological pH and rapidly degrades in an autoxidation reaction to a major bicyclopentadione product in which the 7-carbon chain has undergone oxygenation and double cyclization. Early degradation products (but not the final bicyclopentadione) mediate topoisomerase poisoning and possibly many other activities of curcumin, but it is not known how many and what autoxidation products are formed, nor their mechanism of formation. Here, using [(14)C2]curcumin as a tracer, seven novel autoxidation products, including two reaction intermediates, were isolated and identified using one- and two-dimensional NMR and mass spectrometry. The unusual spiroepoxide and vinylether reaction intermediates are precursors to the final bicyclopentadione product. A mechanism for the autoxidation of curcumin is proposed that accounts for the addition and exchange of oxygen that have been determined using (18)O2 and H2(18)O. Several of the by-products are formed from an endoperoxide intermediate via reactions that are well precedented in lipid peroxidation. The electrophilic spiroepoxide intermediate formed a stable adduct with N-acetylcysteine, suggesting that oxidative transformation is required for biological effects mediated by covalent adduction to protein thiols. The spontaneous autoxidation distinguishes curcumin among natural polyphenolic compounds of therapeutic interest; the formation of chemically diverse reactive and electrophilic products provides a novel paradigm for understanding the polypharmacological effects of curcumin.
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