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Molecules 2014, 19(8), 12486-12499; doi:10.3390/molecules190812486

Caffeic Acid Inhibits the Formation of 7-Carboxyheptyl Radicals from Oleic Acid under Flavin Mononucleotide Photosensitization by Scavenging Singlet Oxygen and Quenching the Excited State of Flavin Mononucleotide

Department of Chemistry, Wakayama Medical University, 580 Mikazura, Wakayama 641-0011, Japan
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Author to whom correspondence should be addressed.
Received: 21 April 2014 / Revised: 21 July 2014 / Accepted: 11 August 2014 / Published: 18 August 2014
(This article belongs to the Section Medicinal Chemistry)
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Abstract

We examined the effects of caffeic acid (CA) and related compounds on 7-carboxyheptyl radical formation. This analysis was performed using a standard D2O reaction mixture containing 4.3 mM oleic acid, 25 μM flavin mononucleotide (FMN), 160 mM phosphate buffer (pH 7.4), 10 mM cholic acid, 100 mM α-(4-pyridyl-1-oxide)-N-tert-butylnitrone, and 1 mM Fe(SO4)2(NH4)2 during irradiation with 7.8 J/cm2 at 436 nm. 7-Carboxyheptyl radical formation was inhibited by CA, catechol, gallic acid, chlorogenic acid, ferulic acid, noradrenalin, 2-hydroxybenzoic acid, 3-hydroxybenzoic acid, and 4-hydroxybenzoic acid. Quinic acid, benzoic acid, and p-anisic acid had no effect on radical formation. These results suggest that a phenol moiety is essential for these inhibitory effects. The fluorescence intensity of FMN decreased by 69% ± 2% after CA addition, suggesting that CA quenches the singlet excited state of FMN. When 1 mM CA was added to a standard reaction mixture containing 25 μM FMN, 140 mM phosphate buffer (pH 7.4), and 10 mM 4-oxo-2,2,6,6-tetramethylpiperidine, the electron spin resonance signal of 4-oxo-2,2,6,6-tetramethylpiperidinooxy disappeared. This finding suggests that singlet oxygen was scavenged completely by CA. Therefore, CA appears to inhibit 7-carboxyheptyl radical formation by scavenging singlet oxygen and quenching the excited state of FMN. View Full-Text
Keywords: caffeic acid; FMN; oleic acid; photosensitization reaction; 7-carboxyheptyl radical; singlet oxygen; phenol; spin trapping; HPLC-ESR caffeic acid; FMN; oleic acid; photosensitization reaction; 7-carboxyheptyl radical; singlet oxygen; phenol; spin trapping; HPLC-ESR
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Asano, M.; Iwahashi, H. Caffeic Acid Inhibits the Formation of 7-Carboxyheptyl Radicals from Oleic Acid under Flavin Mononucleotide Photosensitization by Scavenging Singlet Oxygen and Quenching the Excited State of Flavin Mononucleotide. Molecules 2014, 19, 12486-12499.

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