Abstract
Free-radical-scavenging capacity antioxidant and membrane-protective properties of natural and related synthetic allylpolyalkoxybenzenes with different numbers of alkoxy/methoxy groups in the aromatic ring were evaluated using several in vitro models. These included the DPPH assay, inhibition of lipid peroxidation products accumulation, inhibition of H2O2-induced hemolysis, and oxidation of oxyhemoglobin. A synthetic protocol for the synthesis of natural nothoapiol (9) from a parsley seed metabolite, apiol (7), was developed. A structure−activity relationship study revealed that both the methylenedioxy fragment and methoxy groups in the aromatic ring are favorable for antioxidant activity. Hydroxyapiol (14), containing a hydroxy group in the aromatic core, was identified as the most potent compound. The pentaalkoxy-substituted nothoapiol (9) showed antioxidant activity in mouse brain homogenates, whereas in mouse erythrocytes it exhibited a marked pro-oxidant effect. Despite their low free-radical-scavenging capacity, allylpolyalkoxybenzenes can contribute to the total antioxidant potencies of plant essential oils. © 2019 American Chemical Society and American Society of Pharmacognosy.
| Original language | English |
|---|---|
| Pages (from-to) | 1451-1458 |
| Journal | Journal of Natural Products |
| Volume | 82 |
| Issue number | 6 |
| Online published | 18 Jun 2019 |
| DOIs | |
| Publication status | Published - 28 Jun 2019 |
| Externally published | Yes |
Funding
This work was carried out with the financial support of the Russian Science Foundation (grant no. 18-13-00044). The study of antioxidant and membrane-protective properties of the compounds was conducted by O.G.S. with the financial support of the state assignment (project no. AAAA-A18-118011120004-5).