The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids
- PMID: 12083758
- DOI: 10.1016/s0006-291x(02)00618-6
The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids
Abstract
Phloretin is a dihydrochalcone flavonoid that displays a potent antioxidant activity in peroxynitrite scavenging and the inhibition of lipid peroxidation. Comparison with structurally related compounds revealed that the antioxidant pharmacophore of phloretin is 2,6-dihydroxyacetophenone. The potent activity of 2,6-dihydroxyacetophenone is due to stabilisation of its radical via tautomerisation. The antioxidant pharmacophore in the dihydrochalcone phloretin, i.e., the 2,6-dihydroxyacetophenone group, is different from the antioxidant pharmacophores previously reported in flavonoids.
(c) 2002 Elsevier Science (USA).
Similar articles
-
Dihydrochalcones: evaluation as novel radical scavenging antioxidants.J Agric Food Chem. 2003 May 21;51(11):3309-12. doi: 10.1021/jf0341060. J Agric Food Chem. 2003. PMID: 12744659
-
Hydrogen bond formation as basis for radical scavenging activity: a structure-activity study of C-methylated dihydrochalcones from Myrica gale and structurally related acetophenones.Free Radic Biol Med. 1997;22(1-2):307-11. doi: 10.1016/s0891-5849(96)00277-8. Free Radic Biol Med. 1997. PMID: 8958155
-
Inhibition of peroxynitrite-mediated LDL oxidation by prenylated flavonoids: the alpha,beta-unsaturated keto functionality of 2'-hydroxychalcones as a novel antioxidant pharmacophore.Chem Res Toxicol. 2003 Oct;16(10):1277-86. doi: 10.1021/tx020100d. Chem Res Toxicol. 2003. PMID: 14565769
-
Free radical scavenging and antioxidant activity of plant flavonoids.Adv Exp Med Biol. 1994;366:351-76. doi: 10.1007/978-1-4615-1833-4_25. Adv Exp Med Biol. 1994. PMID: 7771265 Review. No abstract available.
-
Screening methods for antioxidants-a review.Mini Rev Med Chem. 2006 Mar;6(3):305-12. doi: 10.2174/138955706776073448. Mini Rev Med Chem. 2006. PMID: 16515469 Review.
Cited by
-
Cardioprotective effect of ritonavir, an antiviral drug, in isoproterenol induced myocardial necrosis: a new therapeutic implication.J Transl Med. 2013 Mar 26;11:80. doi: 10.1186/1479-5876-11-80. J Transl Med. 2013. PMID: 23531330 Free PMC article.
-
Cryotolerance of Stallion Spermatozoa Relies on Aquaglyceroporins rather than Orthodox Aquaporins.Biology (Basel). 2019 Nov 12;8(4):85. doi: 10.3390/biology8040085. Biology (Basel). 2019. PMID: 31726707 Free PMC article.
-
Quercetin, Morin, Luteolin, and Phloretin Are Dietary Flavonoid Inhibitors of Monocarboxylate Transporter 6.Mol Pharm. 2017 Sep 5;14(9):2930-2936. doi: 10.1021/acs.molpharmaceut.7b00264. Epub 2017 May 31. Mol Pharm. 2017. PMID: 28513167 Free PMC article.
-
Effects of phlorizin on diabetic retinopathy according to isobaric tags for relative and absolute quantification-based proteomics in db/db mice.Mol Vis. 2013 Apr 5;19:812-21. Print 2013. Mol Vis. 2013. PMID: 23592918 Free PMC article.
-
Membrane transport of singlet oxygen monitored by dipole potential measurements.Biophys J. 2009 Jan;96(1):77-85. doi: 10.1529/biophysj.108.135145. Biophys J. 2009. PMID: 18931253 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
Medical