Journal
PHYTOCHEMISTRY
Volume 103, Issue -, Pages 178-187Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2014.03.010
Keywords
Grey alder (Alnus incana) bark; Diarylheptanoids; Antioxidants; DPPH-; ABTS(+); Superoxide; ORAC; Molecular modeling; O-H bond dissociation enthalpies; Ionization potentials; Electron transfer; Structure-activity relationship
Categories
Funding
- European Social Fund within the project Support for Doctoral Studies at University of Latvia
- Latvian budget (Government Program) [564/2012]
- Conseil Regional du Limousin
- COST action [CM0804]
- Operational Program Research and Development for Innovations
- European Regional Development Fund [CZ.1.05/2.1.00/03.0058]
- Ministry of Education, Youth and Sports of the Czech Republic
- Operational Program Education for Competitiveness - European Social Fund [CZ.1.07/2.3.00/ 20.0017, CZ.1.07/2.3.00/20.0058]
- Grant Agency of the Czech Republic [P208/12/G016]
Ask authors/readers for more resources
A series of diarylheptanoids, namely 1,7-bis-(3,4-dihydroxyphenyl)-heptan-3-one-5-O-D-xylopyranoside (oregonin), 1,7-bis-(3,4-dihydroxyphenyl)-3-hydroxyheptane-5-O-beta-D-xylopyranoside and 1,7-bis(4-hydroxyphenyl)-heptane-3-one-5-O-beta-D-glucopyranoside (platyphylloside), were isolated from the bark of alder family trees, a species widely spread over in Europe. As antioxidants, these natural polyphenols have a promising potential in various fields of application, but their redox reactivity is insufficiently characterized. In this work, their antioxidant activity is described using assays based on DPPH and ABTS(center dot+) radical scavenging, oxygen anion radicals (0) quenching. The standardized ORAC assay was also achieved, which measures the capacity to protect fluorescent molecules against oxidative degradation. The measured antioxidant activity was higher than that of the well-known antioxidant and biologically active diarylheptanoid curcumin. Molecular modeling was used to rationalize the differences in activity and the mechanisms of action. Thermodynamic descriptors mainly O-H bond dissociation enthalpies (BDEs) establish a clear structure-activity relationship. (c) 2014 Elsevier Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available