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首页> 美国卫生研究院文献>Molecules >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
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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

机译：咖啡酸通过清除单线态氧并淬灭黄素单核苷酸的激发态抑制黄素单核苷酸光敏作用下油酸中7-羧庚基自由基的形成。

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摘要

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.
机译：我们检查了咖啡酸（CA）和相关化合物对7-羧基庚基自由基形成的影响。使用包含4.3 mM油酸，25μM黄素单核苷酸（FMN），160 mM磷酸盐缓冲液（pH 7.4），10 mM胆酸，100 mMα-（4-吡啶基-1-氧化物）的标准D2O反应混合物进行分析）-N-叔丁基硝酮和1 mM Fe（SO4）2（NH4）2在436 nm波长下以7.8 J / cm 2 照射。 CA，邻苯二酚，没食子酸，绿原酸，阿魏酸，去甲肾上腺素，2-羟基苯甲酸，3-羟基苯甲酸和4-羟基苯甲酸可抑制7-羧基庚基的形成。奎宁酸，苯甲酸和对茴香酸对自由基的形成没有影响。这些结果表明，酚部分对于这些抑制作用是必不可少的。加入CA后，FMN的荧光强度降低了69％±2％，这表明CA终止了FMN的单线激发态。当将1 mM CA添加到包含25μMFMN，140 mM磷酸盐缓冲液（pH 7.4）和10 mM 4-oxo-2,2,6,6-四甲基哌啶的标准反应混合物中时，电子自旋共振信号为4-氧代2,2,6,6-四甲基哌啶子氧基消失了。这个发现表明单重态氧被CA完全清除了。因此，CA似乎通过清除单线态氧并淬灭FMN的激发态来抑制7-羧基庚基自由基的形成。

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