ArticleProceedings of the National Academy of Sciences of the United States of America2008
Long-chain carboxychromanols, metabolites of vitamin E, are potent inhibitors of cyclooxygenases.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 86 papers, 1 of them a synthesis that pooled it.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
86 citing papers in PubMed, 1 synthesis or guideline pooled it, 179 citations in OpenAlex.
- Pooled it
- Vitamin E, γ-tocopherol, reduces airway neutrophil recruitment after inhaled endotoxin challenge in rats and in healthy volunteers.Free radical biology & medicine · 2013Trial
- The effects of different forms of vitamin E on gut microbiota, mechanisms, and implications in disease prevention.The Journal of nutritional biochemistry · 2026Review
- Micronutrient Deficiencies in Obese Patients and Risk of Postoperative Fistula: A Forgotten Link in Bariatric and Metabolic Surgery.Nutrients · 2026Review
- The interplay mechanisms between gut microbiota and ferroptosis in inflammatory bowel disease.Frontiers in immunology · 2026Review
- Review
- Nutritional Support of Chronic Obstructive Pulmonary Disease.Nutrients · 2025Review
- Combining vitamin E metabolite 13'-carboxychromanol and a lactic acid bacterium synergistically mitigates colitis and colitis-associated dysbiosis in mice.Free radical biology & medicine · 2025Article
- Composite dietary antioxidant index and HPV infection from single and mixed associations to SHAP-interpreted machine learning predictions.Frontiers in nutrition · 2025Article
- Selection of sciatic nerve injury models: implications for pathogenesis and treatment.Frontiers in neurology · 2025Review
- Nutritional interventions for osteoarthritis: targeting the metabolism-inflammation-oxidative stress axis-clinical evidence and translational practice.Frontiers in nutrition · 2025Review
- The Role of Vitamin E Isoforms and Metabolites in Cancer Prevention: Mechanistic Insights into Sphingolipid Metabolism Modulation.Nutrients · 2024Review
- Association Between Dietary Intake After Roux-en-Y Gastric Bypass Surgery and Antioxidant/inflammatory Status: A 6-Month Pilot Prospective Cohort Study.Obesity surgery · 2024Article
- Post-diagnostic multivitamin supplement use and colorectal cancer survival: A prospective cohort study.Cancer · 2024Article
- Tocotrienol suppresses colitis-associated cancer progression through TLR4 signaling in a mouse model of colorectal cancer.Current research in toxicology · 2024Article
- Restorative Effect of MicroalgaeInternational journal of molecular sciences · 2023Article
- Antioxidant and Anti-Tumor Effects of Dietary Vitamins A, C, and E.Antioxidants (Basel, Switzerland) · 2023Review
- Role of Oxidative Stress in Peyronie's Disease: Biochemical Evidence and Experiences of Treatment with Antioxidants.International journal of molecular sciences · 2022Review
- Tocotrienol in the Treatment of Topical Wounds: Recent Updates.Pharmaceutics · 2022Review
- Vitamin E (Alpha-Tocopherol) Metabolism and Nutrition in Chronic Kidney Disease.Antioxidants (Basel, Switzerland) · 2022Review
26 more citing papers are in PubMed but not listed here.
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
6 authors at 2 institutions in 1 country.
Funding
Abstract
Cyclooxygenase (COX-1/COX-2)-catalyzed eicosanoid formation plays a key role in inflammation-associated diseases. Natural forms of vitamin E are recently shown to be metabolized to long-chain carboxychromanols and their sulfated counterparts. Here we find that vitamin E forms differentially inhibit COX-2-catalyzed prostaglandin E(2) in IL-1beta-stimulated A549 cells without affecting COX-2 expression, showing the relative potency of gamma-tocotrienol approximately delta-tocopherol > gamma-tocopherol >> alpha- or beta-tocopherol. The cellular inhibition is partially diminished by sesamin, which blocks the metabolism of vitamin E, suggesting that their metabolites may be inhibitory. Consistently, conditioned media enriched with long-chain carboxychromanols, but not their sulfated counterparts or vitamin E, reduce COX-2 activity in COX-preinduced cells with 5 microM arachidonic acid as substrate. Under this condition, 9'- or 13'-carboxychromanol, the vitamin E metabolites that contain a chromanol linked with a 9- or 13-carbon-length carboxylated side chain, inhibits COX-2 with an IC(50) of 6 or 4 microM, respectively. But 13'-carboxychromanol inhibits purified COX-1 and COX-2 much more potently than shorter side-chain analogs or vitamin E forms by competitively inhibiting their cyclooxygenase activity with K(i) of 3.9 and 10.7 microM, respectively, without affecting the peroxidase activity. Computer simulation consistently indicates that 13'-carboxychromanol binds more strongly than 9'-carboxychromanol to the substrate-binding site of COX-1. Therefore, long-chain carboxychromanols, including 13'-carboxychromanol, are novel cyclooxygenase inhibitors, may serve as anti-inflammation and anticancer agents, and may contribute to the beneficial effects of certain forms of vitamin E.
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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.