Antioxidant Activity of Natural Allylpolyalkoxybenzene Plant Essential Oil Constituents
Alexander V. Samet
1
,
Vyacheslav V Rusak
1
,
Eduard M Chartov
1
,
Andrey B Myshlyavtsev
1
,
Daniil A Rusanov
1
,
Marina Semenova
3
,
Victor Semenov
1
Publication type: Journal Article
Publication date: 2019-06-18
scimago Q1
wos Q1
SJR: 0.629
CiteScore: 6.5
Impact factor: 3.6
ISSN: 01633864, 15206025
PubMed ID:
31244145
Organic Chemistry
Drug Discovery
Pharmacology
Pharmaceutical Science
Molecular Medicine
Complementary and alternative medicine
Analytical Chemistry
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.
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Metrics
37
Total citations:
37
Citations from 2025:
2
(5.41%)
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GOST
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Samet A. V. et al. Antioxidant Activity of Natural Allylpolyalkoxybenzene Plant Essential Oil Constituents // Journal of Natural Products. 2019. Vol. 82. No. 6. pp. 1451-1458.
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Samet A. V., Shevchenko O. G., Rusak V. V., Chartov E. M., Myshlyavtsev A. B., Rusanov D. A., Semenova M., Semenov V. Antioxidant Activity of Natural Allylpolyalkoxybenzene Plant Essential Oil Constituents // Journal of Natural Products. 2019. Vol. 82. No. 6. pp. 1451-1458.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.jnatprod.8b00878
UR - https://doi.org/10.1021/acs.jnatprod.8b00878
TI - Antioxidant Activity of Natural Allylpolyalkoxybenzene Plant Essential Oil Constituents
T2 - Journal of Natural Products
AU - Samet, Alexander V.
AU - Shevchenko, Oksana G.
AU - Rusak, Vyacheslav V
AU - Chartov, Eduard M
AU - Myshlyavtsev, Andrey B
AU - Rusanov, Daniil A
AU - Semenova, Marina
AU - Semenov, Victor
PY - 2019
DA - 2019/06/18
PB - American Chemical Society (ACS)
SP - 1451-1458
IS - 6
VL - 82
PMID - 31244145
SN - 0163-3864
SN - 1520-6025
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2019_Samet,
author = {Alexander V. Samet and Oksana G. Shevchenko and Vyacheslav V Rusak and Eduard M Chartov and Andrey B Myshlyavtsev and Daniil A Rusanov and Marina Semenova and Victor Semenov},
title = {Antioxidant Activity of Natural Allylpolyalkoxybenzene Plant Essential Oil Constituents},
journal = {Journal of Natural Products},
year = {2019},
volume = {82},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.jnatprod.8b00878},
number = {6},
pages = {1451--1458},
doi = {10.1021/acs.jnatprod.8b00878}
}
Cite this
MLA
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Samet, Alexander V., et al. “Antioxidant Activity of Natural Allylpolyalkoxybenzene Plant Essential Oil Constituents.” Journal of Natural Products, vol. 82, no. 6, Jun. 2019, pp. 1451-1458. https://doi.org/10.1021/acs.jnatprod.8b00878.
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