New insights into the antioxidant activity and cytotoxicity of arzanol and effect of methylation on its biological properties
| Autor: | Antonella Rosa, Giovanni Appendino, Mariella Nieddu, Angela Atzeri |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
Male Nitrilotriacetic Acid Antioxidant Cell Survival medicine.medical_treatment Cell Phloroglucinol medicine.disease_cause 01 natural sciences Biochemistry Ferric Compounds Methylation Antioxidants HeLa Lipid peroxidation 03 medical and health sciences chemistry.chemical_compound Structure-Activity Relationship Cell Line Tumor Drug Discovery medicine Animals Humans Viability assay Rats Wistar Cytotoxicity Molecular Biology Helichrysum biology 010405 organic chemistry Chemistry Plant Extracts Organic Chemistry Cell Biology biology.organism_classification 0104 chemical sciences Rats Oxidative Stress 030104 developmental biology medicine.anatomical_structure Cholesterol Pyrones Cancer cell Lipid Peroxidation Oxidation-Reduction Oxidative stress |
| Zdroj: | Chemistry and physics of lipids. 205 |
| ISSN: | 1873-2941 |
| Popis: | The heterodimeric phloroglucinyl pyrone arzanol (Arz) has raised considerable interest because of its antiviral, anti-inflammatory, and antioxidant activity. We have investigated the effect of methylation of the pyrone moiety on the antioxidant activity and cytotoxicity of Arz. This manoeuvre, that left the polyphenolic moiety unscathed, was nevertheless detrimental for antioxidant activity in both the cholesterol thermal degradation- and the Cu2+-induced liposome oxidation assays, providing evidence of structure-activity relationships that go beyond the preservation of the polyphenolic pharmacophore. The antioxidant activity of Arz was retained also in the Fe-NTA model of in vivo oxidative stress, with protective effect on the oxidative degradation of plasmatic lipids, unsaturated fatty acids and cholesterol. Both Arz and methylarzanol (Me-Arz) were devoid of toxic effect on colonic differentiated Caco-2 cells up to 100μM, but significantly reduced cancer Caco-2 cell viability at lower dosages. Arz could also selectively reduce viability of other cancer cell lines, [murine melanoma cells (B16F10 cells), human cervical carcinoma cells (HeLa cells)], suggesting that it can act as a selective modulator of cell processes typical of cancer cells. Taken together, our results qualify Arz as a lead structure for further in vivo investigation of its pharmacological potential. |
| Databáze: | OpenAIRE |
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