ArticleMolecules (Basel, Switzerland)2021
Pharmacokinetics-Driven Evaluation of the Antioxidant Activity of Curcuminoids and Their Major Reduced Metabolites-A Medicinal Chemistry Approach.
Article in Molecules (Basel, Switzerland), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 21 citations in OpenAlex.
- Curcumin's Protective Effects Against HMolecules (Basel, Switzerland) · 2026Review
- Curcumin in Atherogenic Dyslipidemia: Linking Preclinical Mechanistic Insights to Clinical Outcomes.Nutrients · 2026Review
- Behavioral and Biochemical Evaluation of a Curcumin-Loaded Nano-Liposomal Formulation in a Scopolamine-Induced Mouse Model of Cognitive Impairment.Biomolecules & therapeutics · 2026Article
- Oxidative Stress in Diabetic Cardiomyopathy: Molecular Mechanisms, Current Treatment and Therapeutic Potential of Plant Antioxidants.Antioxidants (Basel, Switzerland) · 2026Review
- Anti-Leukemic Properties of Curcumin on Acute Lymphoblastic Leukemia: A Systematic Review.Biology · 2026Review
- Metabolomics analysis of mechanism of improving quality of Schisandrae chinensis fructus by NO combining with high-temperature stress.PloS one · 2025Article
- Targeted Screening of Curcumin Derivatives as Pancreatic Lipase Inhibitors Using Computer-Aided Drug Design.ACS omega · 2024Article
- Positive Tetrahydrocurcumin-Associated Brain-Related Metabolomic Implications.Molecules (Basel, Switzerland) · 2023Review
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
Abstract
Curcuminoids are the main bioactive components of the well-known Asian spice and traditional medicine turmeric. Curcuminoids have poor chemical stability and bioavailability; in vivo they are rapidly metabolized to a set of bioreduced derivatives and/or glucuronide and sulfate conjugates. The reduced curcuminoid metabolites were also reported to exert various bioactivities in vitro and in vivo. In this work, we aimed to perform a comparative evaluation of curcuminoids and their hydrogenated metabolites from a medicinal chemistry point of view, by determining a set of key pharmacokinetic parameters and evaluating antioxidant potential in relation to such properties.Reduced metabolites were prepared from curcumin and demethoxycurcumin through continuous-flow hydrogenation. As selected pharmacokinetic parameters, kinetic solubility, chemical stability, metabolic stability in human liver microsomes, and parallel artificial membrane permeability assay (PAMPA)-based gastrointestinal and blood-brain barrier permeability were determined. Experimentally determined logP for hydrocurcumins in octanol-water and toluene-water systems provided valuable data on the tendency for intramolecular hydrogen bonding by these compounds. Drug likeness of the compounds were further evaluated by a in silico calculations. Antioxidant properties in diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and oxygen radical absorbance capacity (ORAC) assays were comparatively evaluated through the determination of ligand lipophilic efficiency (LLE). Our results showed dramatically increased water solubility and chemical stability for the reduced metabolites as compared to their corresponding parent compound. Hexahydrocurcumin was found the best candidate for drug development based on a complex pharmacokinetical comparison and high LLE values for its antioxidant properties. Development of tetrahydrocurcumin and tetrahydro-demethoxycurcumin would be limited by their very poor metabolic stability, therefore such an effort would rely on formulations bypassing first-pass metabolism.
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Registered trials
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