Medizinische Universität Graz Austria/Österreich - Forschungsportal - Medical University of Graz
Gewählte Publikation:
SHR Neuro Krebs Kardio Lipid Stoffw Microb
Greilberger, J; Feigl, G; Greilberger, M; Bystrianska, S; Greilberger, M.
5-Hydroxymethylfurfural: A Particularly Harmful Molecule Inducing Toxic Lipids and Proteins?
MOLECULES. 2025; 30(19):
Doi: 10.3390/molecules30193897
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- Führende Autor*innen der Med Uni Graz
- Greilberger Joachim
- Co-Autor*innen der Med Uni Graz
- Feigl Georg
- Greilberger Michaela
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- Abstract:
- Introduction: 5-HMF is a molecule found in carbohydrate-rich foods that is associated not only with cancer and anaphylactic reactions, but also with anti-oxidant properties. Questions arose as to whether 5-HMF exhibited a catalytic effect in relation to lipid peroxidation and lipoprotein oxidation in presence of metals and/or radicals. Methods: Peroxynitrite (ONOO-)-induced chemiluminescence and ONOO- nitration of tyrosine residues on BSA using anti-nitro-tyrosine-antibodies were used to measure the protection of 5-HMF against peroxides or nitration compared to vitamin C (VitC). The reductive potential of 5-HMF or VitC on Cu2+ or Fe3 was estimated using the bicinchoninic acid (BCA) or Fenton-complex method. Human plasma was used to measure the generation of malondialdehyde (MDA), 4-hydroxynonenal (HNE), and total thiols after Fe2+/H2O2 oxidation in the presence of different concentrations of 5-HMF or VitC. Finally, Cu2+ oxidation of LDL after 4 h was carried out with 5-HMF or VitC, measuring the concentration of MDA in LDL with the thiobarbituric assay (TBARS). Results: VitC was 4-fold more effective than 5-HMF in scavenging ONOO- to nearly 91.5% at 4 mM, with the exception of 0.16 mM, where the reduction of ONOO- by VitC was 3.3-fold weaker compared to 0.16 mM 5-HMF. VitC or 5-HMF at a concentration of 6 mM inhibited the nitration of tyrosine residues on BSA to nearly 90% with a similar course. While 5-HMF reduced free Fe3+ in presence of phenanthroline, forming Fe2+ (phenantroleine)3 [Fe2+(phe)3] or complexed Cu2+(BCA)4 to Cu+(BCA)4 weakly, VitC was 7- to 19-fold effective in doing so over all the used concentrations (0-25 mM). A Fe2+-H2O2 solution mixed with human plasma showed a 6-10 times higher optical density (OD) of MDA or HNE in the presence of 5-HMF compared to VitC. The level of thiols was significantly decreased in the presence of higher VitC levels (1 mM: 198.4 ± 7.7 µM; 2 mM: 160.0 ± 13.4 µM) compared to equal 5-HMF amounts (2562 ± 7.8 µM or 242.4 ± 2.5 µM), whereas the usage of lower levels at 0.25 µM 5-HMF resulted in a significant decrease in thiols (272.4 ± 4.0 µM) compared to VitC (312.3 ± 19.7 µM). Both VitC and 5-HMF accelerated copper-mediated oxidation of LDL equally: while the TBARS levels from 4 h oxidized LDL reached 137.7 ± 12.3 nmol/mg, it was 1.7-fold higher using 6 mM VitC (259.9 ± 10.4 nmol/mg) or 6 mM 5-HMF (239.3 ± 10.2 nmol/mg). Conclusions: 5-HMF appeared to have more pro-oxidative potential compared to VitC by causing lipid peroxidation as well as protein oxidation.
- Find related publications in this database (using NLM MeSH Indexing)
- Humans - administration & dosage
- Furaldehyde - analogs & derivatives, chemistry, adverse effects, pharmacology
- Lipid Peroxidation - drug effects
- Oxidation-Reduction - drug effects
- Copper - chemistry
- Hydrogen Peroxide - chemistry
- Malondialdehyde - administration & dosage
- Ascorbic Acid - chemistry, pharmacology
- Peroxynitrous Acid - chemistry
- Antioxidants - pharmacology, chemistry
- Iron - chemistry
- Find related publications in this database (Keywords)
- vitamin C (VitC)
- 5-Hydroxy-methyl-furfural (5-HMF)
- Malondialdehyde (MDA)
- 4-Hydroxynonenal (HNE)
- thiobarbituric acid reacting substances (TBARS)
- Fenton reaction
- lipid peroxidation
- atherosclerosis