Angiotensin-converting enzyme inhibitory effects by plant phenolic compounds: a study of structure activity relationships
- Author
- Nadin Al Shukor (UGent) , John Van Camp (UGent) , Bryan Gonzales (UGent) , Dorien Staljanssens (UGent) , Karin Struijs (UGent) , Moises João Zotti, Katleen Raes (UGent) and Guy Smagghe (UGent)
- Organization
- Abstract
- In this study, 22 phenolic compounds were investigated to inhibit the angiotensin-converting enzyme (ACE). Tannic acid showed the highest activity (IC50 = 230 mu M). The IC50 values obtained for phenolic acids and flavonoids ranged between 0.41 and 9.3 mM. QSAR analysis confirmed that the numbers of hydroxyl groups on the benzene ring play an important role for activity of phenolic compounds and that substitution of hydroxyl groups by methoxy groups decreased activity. Docking studies indicated that phenolic acids and flavonoids inhibit ACE via interaction with the zinc ion and this interaction is stabilized by other interactions with amino acids in the active site. Other compounds, such as resveratrol and pyrogallol, may inhibit ACE via interactions with amino acids at the active site, thereby blocking the catalytic activity of ACE. These structure function relationships are useful for designing new ACE inhibitors and potential blood-pressure-lowering compounds based on phenolic compounds.
- Keywords
- PEPTIDES, INTESTINE, BRADYKININ, POLYPHENOLS, BIOAVAILABILITY, HYPERTENSION, FLAVONOIDS, PROTEIN, PERFORMANCE LIQUID-CHROMATOGRAPHY, hypertension, angiotensin-converting enzyme, phenolic compounds, structure-activity relationship, molecular docking, TANNINS
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-4405057
- MLA
- Al Shukor, Nadin, et al. “Angiotensin-Converting Enzyme Inhibitory Effects by Plant Phenolic Compounds: A Study of Structure Activity Relationships.” JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 61, no. 48, 2013, pp. 11832–39, doi:10.1021/jf404641v.
- APA
- Al Shukor, N., Van Camp, J., Gonzales, G., Staljanssens, D., Struijs, K., Zotti, M. J., … Smagghe, G. (2013). Angiotensin-converting enzyme inhibitory effects by plant phenolic compounds: a study of structure activity relationships. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 61(48), 11832–11839. https://doi.org/10.1021/jf404641v
- Chicago author-date
- Al Shukor, Nadin, John Van Camp, Gerard Gonzales, Dorien Staljanssens, Karin Struijs, Moises João Zotti, Katleen Raes, and Guy Smagghe. 2013. “Angiotensin-Converting Enzyme Inhibitory Effects by Plant Phenolic Compounds: A Study of Structure Activity Relationships.” JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 61 (48): 11832–39. https://doi.org/10.1021/jf404641v.
- Chicago author-date (all authors)
- Al Shukor, Nadin, John Van Camp, Gerard Gonzales, Dorien Staljanssens, Karin Struijs, Moises João Zotti, Katleen Raes, and Guy Smagghe. 2013. “Angiotensin-Converting Enzyme Inhibitory Effects by Plant Phenolic Compounds: A Study of Structure Activity Relationships.” JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 61 (48): 11832–11839. doi:10.1021/jf404641v.
- Vancouver
- 1.Al Shukor N, Van Camp J, Gonzales G, Staljanssens D, Struijs K, Zotti MJ, et al. Angiotensin-converting enzyme inhibitory effects by plant phenolic compounds: a study of structure activity relationships. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. 2013;61(48):11832–9.
- IEEE
- [1]N. Al Shukor et al., “Angiotensin-converting enzyme inhibitory effects by plant phenolic compounds: a study of structure activity relationships,” JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 61, no. 48, pp. 11832–11839, 2013.
@article{4405057,
abstract = {{In this study, 22 phenolic compounds were investigated to inhibit the angiotensin-converting enzyme (ACE). Tannic acid showed the highest activity (IC50 = 230 mu M). The IC50 values obtained for phenolic acids and flavonoids ranged between 0.41 and 9.3 mM. QSAR analysis confirmed that the numbers of hydroxyl groups on the benzene ring play an important role for activity of phenolic compounds and that substitution of hydroxyl groups by methoxy groups decreased activity. Docking studies indicated that phenolic acids and flavonoids inhibit ACE via interaction with the zinc ion and this interaction is stabilized by other interactions with amino acids in the active site. Other compounds, such as resveratrol and pyrogallol, may inhibit ACE via interactions with amino acids at the active site, thereby blocking the catalytic activity of ACE. These structure function relationships are useful for designing new ACE inhibitors and potential blood-pressure-lowering compounds based on phenolic compounds.}},
author = {{Al Shukor, Nadin and Van Camp, John and Gonzales, Bryan and Staljanssens, Dorien and Struijs, Karin and Zotti, Moises João and Raes, Katleen and Smagghe, Guy}},
issn = {{0021-8561}},
journal = {{JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY}},
keywords = {{PEPTIDES,INTESTINE,BRADYKININ,POLYPHENOLS,BIOAVAILABILITY,HYPERTENSION,FLAVONOIDS,PROTEIN,PERFORMANCE LIQUID-CHROMATOGRAPHY,hypertension,angiotensin-converting enzyme,phenolic compounds,structure-activity relationship,molecular docking,TANNINS}},
language = {{eng}},
number = {{48}},
pages = {{11832--11839}},
title = {{Angiotensin-converting enzyme inhibitory effects by plant phenolic compounds: a study of structure activity relationships}},
url = {{http://doi.org/10.1021/jf404641v}},
volume = {{61}},
year = {{2013}},
}
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