Radical-scavenging Activity of Natural Methoxyphenols vs. Synthetic Ones using the Induction Period Method

Kadoma, Yoshinori; Atsumi, Toshiko; Okada, Naoya; Ishihara, Mariko; Yokoe, Ichiro; Fujisawa, Seiichiro

doi:10.3390/12020130

Cited by 16 publications

(17 citation statements)

References 9 publications

(6 reference statements)

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“…The induction period (IP) and initial rate of polymerization in the presence (Rp inh ) or absence (Rp con ) of a phenolcarboxylic acid and ME were determined by the method previously reported [ 10 ]. In brief, the experimental resin consisted of MMA and AIBN (or BPO) with or without additives.…”

Section: Methodsmentioning

confidence: 99%

“…In the case of [MMA] = 9.4 M and [AIBN or BPO] = 0.1 M at 70°C, the induction period method using DTBM gave the rate of initiation, R i , at 70°C. The R i values of AIBN and BPO were 5.66 x 10 -6 Ms -1 and 2.28 x 10 -6 Ms -1 , respectively [ 10 ].…”

Section: Methodsmentioning

confidence: 99%

“…Also, we previously used differential scanning calorimetry (DSC) and the induction period method for polymerization of methyl methacrylate (MMA) initiated by thermal decomposition of 2,2'-azobisisobutyronitrile (AIBN) in order to investigate the radical scavenging activity of ferulic acid and related compounds under nearly anaerobic conditions, and found that ferulic acid scavenged radicals derived from AIBN [ 9 ]. This induction period method using the AIBN- and benzoyl peroxide (BPO)-MMA systems has proved to be reliable for evaluating the activity of phenolic compounds [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

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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

Kadoma

Fujisawa

2008

Molecules

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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 (kinh/kp) 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.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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

Kadoma

Fujisawa

2008

Molecules

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“…We previously synthesized the reaction products of isoeugenol with ethanethiol, thiophenol, 2-mercaptothiazoline or 2-mercapto-1-methylimidazole in the presence of Lewis acid. Reaction products of isoeugenol bearing a SH group may tend to form via its radical-scavenging process because oxidation of isoeugenol produces a reactive benzyl radical as an intermediate (23). These findings suggest a possible interaction between biological macromolecules such as protein and DNA and isoeugenol, possibly resulting in allergens (24).…”

Section: Resultsmentioning

confidence: 89%

Expression of Cyclooxygenase-2, Nitric Oxide Synthase 2 and Heme Oxygenase-1 mRNA Induced by Bis-Eugenol in RAW264.7 Cells and their Antioxidant Activity Determined Using the Induction Period Method

Murakami

Kawata

Fujisawa

2018

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Abstract. Background Conclusion: Most eugenol-related compounds had proinflammatory activity at high concentrations. However, they had also anti-inflammatory activity at lower concentrations. Eugenol-related compounds may exert antioxidant and anti-inflammatory activity in LPS-stimulated RAW264.7 cells possibly by inhibiting the activation of nuclear factor-kappa B (Nf-ĸB), whereas bis-eugenol requires induction of HO-1 expression. bis-Eugenol as well as curcumin, may have anti-inflammatory and anticancer therapeutic applications.Eugenol-related compounds are known to have antioxidant, anti-inflammatory, antiviral, antifungal, antibacterial, anticancer, antidiabetic and neuroprotective properties (1-3). We have previously shown that the biphenols curcumin, biseugenol, magnolol and honokiol exert antioxidant effects and also inhibit the up-regulation of cyclooxygenase-2 (Cox-2) mRNA expression elicited by lipopolysaccharide (LPS) and Porphyromonas gingivalis fimbriae (PGF) (4, 5). We have also shown that the prooxidant activity of eugenol, isoeugenol and curcumin is inhibited by visible light irradiation and treatment with horseradish peroxidase, suggesting that these compounds elicit production of intracellular reactive oxygen species (ROS) under prooxidative conditions (6-8). Interestingly, low and physiological levels of ROS are required for normal physiological activity in cells, whereas high levels of ROS promote cytotoxicity, apoptosis, and inflammatory activity. A high level of ROS modulates a number of cell signaling pathways, and regulates the expression of multiple genes such as Cox-2 and nitric oxide synthase (Nos) 2 in vitro and in vivo 819

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“…It's used in perfumes, soaps, detergents, air purifiers and as a flavoring agent in cosmetics and food products. In addition, isoeugenol has a propenyl moiety and beneficial properties such as antioxidants and anti-inflammatory [13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

In Vitro Antifungal Effect of Isoeugenol Against <em>Penicillium citrinum</em> Strains

Ferreira

Dantas

Silva

et al. 2017

Proceedings of MOL2NET 2017, International Conference on Multidisciplinary Sciences, 3rd Edition

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Graphical AbstractAbstract.Human mycoses have controversial treatment, since the available antifungal drugs besides favoring the appearance of resistant isolates, can present great toxicity to the human organism. This fact has driven the search for more efficient, safe and natural therapeutic alternatives with the objective of reversing this scenario of resistance presented by pathogenic fungi, for this, new natural and effective alternatives, such as the use of plant extracts, natural compounds and semisynthetic, have been extensively investigated for the development of new drugs. In view of this scenario, this study aims to evaluate the antifungal activity of isoeugenol in vitro against strains of Penicillium citrinum. For this, the broth microdilution technique was used to determine the Minimum Inhibitory Concentration (MIC) and Minimum Fungicide Concentration (MFC) of isoeugenol and voriconazole. The concentrations by which the strains were submitted, 1024 μg/mL to 0.5 μg/mL, were obtained by means of serial dilution at a ratio of two, so that in the first row of the plate is the highest concentration and in the last , the lowest concentration. Finally, 10 μL of the fungal inoculum of each isolate was added to the wells, where each strain was placed on a plate MOL2NET, 2017, 3, doi:10.3390/mol2net-03-xxxx 2 column. MIC was defined as the lowest concentration capable of inhibiting fungal growth visually verified by maintaining the original coloration of the medium. After reading the MIC, aliquots of 20 μL of the supernatant from the wells where complete inhibition of fungal growth in the microdilution plates were observed were plated on Sabouraud dextrose agar plates. Plates were incubated, and MFC was considered the lowest concentration at which growth was less than 3 colonies. The assays were performed in triplicate and the geometric mean was calculated. The CIM of isoeugenol varied between 256 and 32 μg/mL, being the highest MIC value for the LM-21 strain and the lowest value for the LM-02, LM-03, LM-08, LM-155, LM-157 and LM-161. The MIC range of voriconazole was 0.5 to 256 μg/mL. The MFC of isoeugenol varied between 64-512 μg/mL and for voriconazole it was 2 μg/mL and above 1024 μg/mL. In this way, we can conclude that isoeugenol presented an antifungal effect, which enables it as a potential antifungal drug, requiring complementary tests that clarify the mechanism of action involved in its antimicrobial activity.

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Radical-scavenging Activity of Natural Methoxyphenols vs. Synthetic Ones using the Induction Period Method

Cited by 16 publications

References 9 publications

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

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

Expression of Cyclooxygenase-2, Nitric Oxide Synthase 2 and Heme Oxygenase-1 mRNA Induced by Bis-Eugenol in RAW264.7 Cells and their Antioxidant Activity Determined Using the Induction Period Method

In Vitro Antifungal Effect of Isoeugenol Against <em>Penicillium citrinum</em> Strains

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