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A comparative study of the radical-scavenging activity of the phenolcarboxylic acids caffeic acid, p-coumaric acid, chlorogenic acid and ferulic acid, with or without 2-mercaptoethanol, a thiol, using the induction period method.
Molecules. 2008 Oct 15; 13(10):2488-99.M

Abstract

Phenolcarboxylic acid antioxidants do not act in vivo as radical-scavengers in isolation, but rather together with GSH (glutathione), a coantioxidant, they constitute an intricate antioxidant network. Caffeic acid, p-coumaric acid, ferulic acid and chlorogenic acid with or without 2-mercaptoethanol (ME), as a substitute for GSH, was investigated by the induction period (IP) method for polymerization of methyl methacrylate (MMA) initiated by thermal decomposition of 2,2'-azobisisobutyronitrile (AIBN, a source of alkyl radicals, R(.)) and benzoyl peroxide (BPO, a source of peroxy radicals, PhCOO(.)) using differential scanning calorimetry (DSC). Upon PhCOO(.)radical scavenging, the stoichiometric factors (n, number of free radical trapped by one mole of antioxidant) for caffeic acid, ferulic acid, p-coumaric acid and chlorogenic acid were 2.4, 1.8, 1.7 and 0.9, whereas upon R(.) radical scavenging, the corresponding values were 1.3, 1.2, 1.0 and 0.8, respectively. Antioxidants with n values close to 2 suggest the stepwise formation of semiquinone radicals and quinones. By contrast, those with n values close to 1 suggest the formation of dimers after single-electron oxidation, possibly due to recombination of corresponding aryloxy radicals. The ratio of the rate constant of inhibition to that of propagation (k(inh)/k(p)) declined in the order chlorogenic acid > p-coumaric acid > ferulic acid > caffeic acid. The ratio of the observed IP for the phenolcarboxylic acid/2-mercapto-ethanol (ME) mixture (1:1 molar ratio) (A) to the calculated IP (the simple sum of phenol acid antioxidant and ME) (B) was investigated. Upon R(.) scavenging, the caffeic acid or p-coumaric acid/ME mixture was A/B > 1, particularly the former was 1.2, suggesting a synergic effect. By contrast, upon PhCOO(.) scavenging, the corresponding mixture was A/B < 1, particularly the latter was 0.7, suggesting an antagonistic effect. Upon both radicals scavenging, the A/B for the ferulic acid or chlorogenic acid/ME mixture was approximately 1. The reported beneficial antioxidant, anti-inflammatory and anticancer effects of caffeic acid and p-coumaric acid may be related to their prooxidant-antioxidant balance in the presence of GSH.

Authors+Show Affiliations

Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, Kanda-surugadai, Chiyoda-ku, Tokyo 101-0062, Japan. y-kadoma.fm@tmd.ac.jpNo affiliation info available

Pub Type(s)

Comparative Study
Journal Article

Language

eng

PubMed ID

18923340

Citation

Kadoma, Yoshinori, and Seiichiro Fujisawa. "A Comparative Study of the Radical-scavenging Activity of the Phenolcarboxylic Acids Caffeic Acid, P-coumaric Acid, Chlorogenic Acid and Ferulic Acid, With or Without 2-mercaptoethanol, a Thiol, Using the Induction Period Method." Molecules (Basel, Switzerland), vol. 13, no. 10, 2008, pp. 2488-99.
Kadoma Y, Fujisawa S. A comparative study of the radical-scavenging activity of the phenolcarboxylic acids caffeic acid, p-coumaric acid, chlorogenic acid and ferulic acid, with or without 2-mercaptoethanol, a thiol, using the induction period method. Molecules. 2008;13(10):2488-99.
Kadoma, Y., & Fujisawa, S. (2008). A comparative study of the radical-scavenging activity of the phenolcarboxylic acids caffeic acid, p-coumaric acid, chlorogenic acid and ferulic acid, with or without 2-mercaptoethanol, a thiol, using the induction period method. Molecules (Basel, Switzerland), 13(10), 2488-99. https://doi.org/10.3390/molecules13102488
Kadoma Y, Fujisawa S. A Comparative Study of the Radical-scavenging Activity of the Phenolcarboxylic Acids Caffeic Acid, P-coumaric Acid, Chlorogenic Acid and Ferulic Acid, With or Without 2-mercaptoethanol, a Thiol, Using the Induction Period Method. Molecules. 2008 Oct 15;13(10):2488-99. PubMed PMID: 18923340.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A comparative study of the radical-scavenging activity of the phenolcarboxylic acids caffeic acid, p-coumaric acid, chlorogenic acid and ferulic acid, with or without 2-mercaptoethanol, a thiol, using the induction period method. AU - Kadoma,Yoshinori, AU - Fujisawa,Seiichiro, Y1 - 2008/10/15/ PY - 2008/09/01/received PY - 2008/10/07/revised PY - 2008/10/09/accepted PY - 2008/10/17/pubmed PY - 2008/12/17/medline PY - 2008/10/17/entrez SP - 2488 EP - 99 JF - Molecules (Basel, Switzerland) JO - Molecules VL - 13 IS - 10 N2 - Phenolcarboxylic acid antioxidants do not act in vivo as radical-scavengers in isolation, but rather together with GSH (glutathione), a coantioxidant, they constitute an intricate antioxidant network. Caffeic acid, p-coumaric acid, ferulic acid and chlorogenic acid with or without 2-mercaptoethanol (ME), as a substitute for GSH, was investigated by the induction period (IP) method for polymerization of methyl methacrylate (MMA) initiated by thermal decomposition of 2,2'-azobisisobutyronitrile (AIBN, a source of alkyl radicals, R(.)) and benzoyl peroxide (BPO, a source of peroxy radicals, PhCOO(.)) using differential scanning calorimetry (DSC). Upon PhCOO(.)radical scavenging, the stoichiometric factors (n, number of free radical trapped by one mole of antioxidant) for caffeic acid, ferulic acid, p-coumaric acid and chlorogenic acid were 2.4, 1.8, 1.7 and 0.9, whereas upon R(.) radical scavenging, the corresponding values were 1.3, 1.2, 1.0 and 0.8, respectively. Antioxidants with n values close to 2 suggest the stepwise formation of semiquinone radicals and quinones. By contrast, those with n values close to 1 suggest the formation of dimers after single-electron oxidation, possibly due to recombination of corresponding aryloxy radicals. The ratio of the rate constant of inhibition to that of propagation (k(inh)/k(p)) declined in the order chlorogenic acid > p-coumaric acid > ferulic acid > caffeic acid. The ratio of the observed IP for the phenolcarboxylic acid/2-mercapto-ethanol (ME) mixture (1:1 molar ratio) (A) to the calculated IP (the simple sum of phenol acid antioxidant and ME) (B) was investigated. Upon R(.) scavenging, the caffeic acid or p-coumaric acid/ME mixture was A/B > 1, particularly the former was 1.2, suggesting a synergic effect. By contrast, upon PhCOO(.) scavenging, the corresponding mixture was A/B < 1, particularly the latter was 0.7, suggesting an antagonistic effect. Upon both radicals scavenging, the A/B for the ferulic acid or chlorogenic acid/ME mixture was approximately 1. The reported beneficial antioxidant, anti-inflammatory and anticancer effects of caffeic acid and p-coumaric acid may be related to their prooxidant-antioxidant balance in the presence of GSH. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/18923340/A_comparative_study_of_the_radical_scavenging_activity_of_the_phenolcarboxylic_acids_caffeic_acid_p_coumaric_acid_chlorogenic_acid_and_ferulic_acid_with_or_without_2_mercaptoethanol_a_thiol_using_the_induction_period_method_ L2 - https://www.mdpi.com/resolver?pii=13102488 DB - PRIME DP - Unbound Medicine ER -