Natural Antioxidant, Chlorogenic Acid, Protects Against DNA Breakage Caused by Monochloramine

Shibata, Hitoshi; Sakamoto, Yuji; Oka, Mikiko; Kono, Yasuhisa

doi:10.1271/bbb.63.1295

Cited by 90 publications

(47 citation statements)

References 22 publications

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“…The most widely occurring chlorogenic acid in dietary plants and medicinal herbs is 5-O-caffeoylquinic acid [(1S,3R,4R,5R)-3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexanecarboxylic acid; 5-CQA] (Clifford, 2000). It has received much attention in recent years due to its multiple pharmacological properties, such as anti-inflammatory, antioxidant, analgesic, antipyretic, and anticarcinogenic effects (Shibata et al, 1999;Jiang et al, 2000;dos Santos et al, 2006). Some Chinese herbal injections, such as Shuang-Huang-Lian, Yin-ZhiHuang, Qing-Kai-Ling, Mai-Luo-Ning, and Xiao-Ai-Ping, are widely used in China to treat common colds, upper respiratory tract infections, cardiovascular diseases, and cancer.…”

Section: Introductionmentioning

confidence: 99%

Identification of the ortho-Benzoquinone Intermediate of 5-O-Caffeoylquinic Acid In Vitro and In Vivo: Comparison of Bioactivation under Normal and Pathological Situations

Xie¹,

Zhong²,

Chen³

2012

Drug Metab Dispos

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ABSTRACT:5-O-Caffeoylquinic acid (5-CQA) is one of the major bioactive ingredients in some Chinese herbal injections. Occasional anaphylaxis has been reported for these injections during their clinical use, possibly caused by reactive metabolites of 5-CQA. This study aimed at characterizing the bioactivation pathway(s) of 5-CQA and the metabolic enzyme(s) involved. After incubating 5-CQA with GSH and NADPH-supplemented human liver microsomes, two types of GSH conjugates were characterized: one was M1-1 from the 1,4-addition of GSH to ortho-benzoquinone intermediate; the other was M2-1 and M2-2 from the 1,4-addition of GSH directly to the ␣,␤-unsaturated carbonyl group of the parent. The formation of M1-1 was cytochrome P450 (P450)-mediated, with 3A4 and 2E1 as the principal catalyzing enzymes, whereas the formation of M2-1 and M2-2 was independent of NADPH and could be accelerated by cytosolic glutathione transferase. In the presence of cumene hydroperoxide, M1-1 formation increased 6-fold, indicating that 5-CQA can also be bioactivated by P450 peroxidase under oxidizing conditions. Furthermore, M1-1 could be formed by myeloperoxidase in activated human leukocytes, implying that 5-CQA bioactivation is more likely to occur under inflammatory conditions. This finding was supported by experiments on lipopolysaccharideinduced inflammatory rats, where a greater amount of M1-1 was detected. In S-adenosyl methionine-and GSH-supplemented human S9 incubations, M1-1 formation decreased by 80% but increased after tolcapone-inhibited catechol-O-methyltransferase (COMT) activity. In summary, the high reactivities of the orthobenzoquinone metabolite and ␣,␤-unsaturated carbonyl group of 5-CQA to nucleophiles have been demonstrated. Different pathological situations and COMT activities in patients may alter the bioactivation extent of 5-CQA.

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Section: Introductionmentioning

confidence: 99%

Identification of the ortho-Benzoquinone Intermediate of 5-O-Caffeoylquinic Acid In Vitro and In Vivo: Comparison of Bioactivation under Normal and Pathological Situations

Xie¹,

Zhong²,

Chen³

2012

Drug Metab Dispos

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“…CGA, like other catechol derivatives, was a excellent antioxidant, possessing powerful radical scavenging property in a variety of vitro model systems (Guglielmetti et al 2008), because the one-electron oxidation product of CGA formed by the reaction with free radicals is rapidly broken down to further products that cannot generate any free radicals (Shibata et al 1999). However, there was a report in the literature that CGA exhibited prooxidative property and induced dna damage under certain conditions as well as other catechol derivatives (Miura et al 2000).…”

Section: Introductionmentioning

confidence: 99%

Oxidative damage to DNA by 1,10-phenanthroline/l-threonine copper (II) complexes with chlorogenic acid

Wang

Zhang

et al. 2009

Biometals

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The oxidative DNA damage by copper (II) complexes in the presence of chlorogenic acid was explored using agarose gel electrophoresis. The extent of pBR322 DNA damage was enhanced significantly with increasing concentration of [Cu-phen-Thr] complex and incubation time. A fluorescence quenching activity of calf thymus DNA-EB was observed more remarkably with chlorogenic acid than without chlorogenic acid. The fluorescence measurements suggested that [Cu-phen-Thr] complex not only can bind to DNA by intercalation but also can damage the double strand DNA in the presence of chlorogenic acid. Further, 8-hydroxy-2'-deoxyguanosine, a biomarker of DNA oxidative damage was determined by electrochemical method. The control experiments revealed that the structure of copper (II) complexes affected capability of complex to DNA damage. The planar structure copper (II) complex showed high efficiency to DNA damage. The chlorogenic acid as biological reductant could improve copper (II) complex to DNA damage. A mechanism on [Cu-phen-Thr] complex to DNA damage in the presence of chlorogenic acid was proposed.

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“…The molecular formula is C 16 H 18 O 9 (12). It has been reported that CGA has strong anti-inflammatory (13), antioxidative (14,15), antihypertensive (16), antitumor (17,18), and analgesic and antipyretic (19,20) effects. In addition, CGA could inhibit lipopolysaccharide (LPS)-induced microglial activation and improve the survival of dopaminergic neurons (21).…”

mentioning

confidence: 99%

Antischistosomiasis Liver Fibrosis Effects of Chlorogenic Acid through IL-13/miR-21/Smad7 Signaling Interactions In Vivo and In Vitro

Wang

Yang

Xue

et al. 2017

Antimicrob Agents Chemother

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Natural Antioxidant, Chlorogenic Acid, Protects Against DNA Breakage Caused by Monochloramine

Cited by 90 publications

References 22 publications

Identification of the ortho-Benzoquinone Intermediate of 5-O-Caffeoylquinic Acid In Vitro and In Vivo: Comparison of Bioactivation under Normal and Pathological Situations

Identification of the ortho-Benzoquinone Intermediate of 5-O-Caffeoylquinic Acid In Vitro and In Vivo: Comparison of Bioactivation under Normal and Pathological Situations

Oxidative damage to DNA by 1,10-phenanthroline/l-threonine copper (II) complexes with chlorogenic acid

Antischistosomiasis Liver Fibrosis Effects of Chlorogenic Acid through IL-13/miR-21/Smad7 Signaling Interactions In Vivo and In Vitro

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