The DOI matches its Crossref record; 7 of the 7 references it cites were found in a registry or an index.
Free Radical Scavenging and Antioxidative Activity of Caffeic Acid Amide and Ester Analogues: Structure−Activity Relationship
Abstract
The structure-activity relationships of synthetic caffeic acid amide and ester analogues as potential antioxidants and free radical scavengers have been investigated. The 2,2-diphenyl-1-picrylhydrazyl radical (DPPH.) scavenging activity of the test compounds was N-trans-caffeoyl-L-cysteine methyl ester (5) > N-trans-caffeoyldopamine (4) > N-trans-caffeoyltyramine (3) > N-trans-caffeoyl-beta-phenethylamine (2) > Trolox C (8) > caffeic acid phenethyl ester (1) > caffeic acid (6) > ferulic acid (7). This established that the radical scavenging activity of the compounds increased with increasing numbers of hydroxyl groups or catechol moieties and also with the presence of other hydrogen-donating groups (-NH, -SH). The antioxidative activity of the compounds was also investigated in an emulsified linoleic acid oxidation system accelerated by 2,2'-azobis(2-amidinopropane) dihydrochloride. The order was 1 > 2 > 4 > 3 > or = 5 > 6 > 8 > 7. Therefore, in the emulsion system, the antioxidative activity of the test compounds depends not only on the hydroxyl groups or catechol rings but also on the partition coefficient (log P) or hydrophobicity of the compounds. This supports the concept that hydrophobic antioxidants tend to exhibit better antioxidative activity in an emulsion system.
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Cites
Antioxidant Determinations by the Use of a Stable Free Radical
BLOIS, M. S. (1958) · Nature · doi:10.1038/1811199a0 · Cited by 12,994
Caffeic acid phenethyl ester as a lipoxygenase inhibitor with antioxidant properties
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Comparative Study of Selected Coupling Reagents in Dipeptide Synthesis
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[4] Generation of iron(IV) and iron(V) complexes in aqueous solutions
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Antimelanogenic and Antioxidant Properties of Gallic Acid
Kim, Y.-J. (2007) · Biological and Pharmaceutical Bulletin · doi:10.1248/bpb.30.1052 · Cited by 340
Phenolamides: Bridging polyamines to the phenolic metabolism
Bassard, J.-E., Ullmann, P., Bernier, F., & Werck-Reichhart, D. (2010) · Phytochemistry · doi:10.1016/j.phytochem.2010.08.003 · Cited by 300
Goel, A., Halami, P. M., & Tamang, J. P. (2020) · Frontiers in Microbiology · doi:10.3389/fmicb.2020.00040 · Cited by 125
dos S. Baião, D., da Silva, D. V. T., & Paschoalin, V. M. F. (2020) · Antioxidants · doi:10.3390/antiox9100960 · Cited by 102
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Metadata
- Authors
- Son, S., & Lewis, B. A.
- Venue
- Journal of Agricultural and Food Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2001-12-21
- Volume
- 50
- Issue
- 3
- Pages
- 468-472
- ISSN
- 0021-8561 (ISSN-L)
- 1520-5118
- OpenAlex
- W2045023739
- Cited by
- 508
- References
- 7
- FWCI
- 7.76
- Type
- journal article
- Language
- en
- Open access
- closed
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