We have shown that major phenols that are present in mango had synergistic or antagonistic interactions, which lead to changes in the antioxidant capacity [2]. However, vanillic acid exhibited poor activity. In this paper, we used 1H NMR to analyze the interactions and mechanisms that are present in major phenolic acids found in mango (gallic, protocatechuic, chlorogenic and vanillic acids) and papaya (caffeic, ferulic and p-coumaric acids), and the DPPH radical was used to evaluate the effect of the antioxidant mixtures. 6 Centro de Investigación en Alimentación y Desarrollo (CIAD), A.C. Carretera a Ejido La Victoria Km 0.6, Hermosillo Sonora, 83000, México. The number and the position of the hydroxyl groups in the structure of the phenols determine the capacity to donate an electron or a hydrogen atom.
However, no new signals were detected with NMR, indicating that no quinone was formed. We observed the interaction between the phenolic acids alone and when they are combined. All of the solutions changed color from purple to brown, indicating that the neutralization of DPPH occurred. The NMR spectrometer is operated under the support of the Secretaría de Educación Pública, México (SES-SEP, programs No. For more information about PLOS Subject Areas, click Many studies of the application of NMR to identify phenolic acids in different extracts have been reported [13,14]. D Box 131, Cheongryang, Seoul 130-650, Korea, Department of Biotechnology, Chung-Ang University, An-Sung 456-756, Korea, and …

The ability of the phenolic acid to neutralize the DPPH radical decreases in the following order in mango: gallic > chlorogenic > protocatechuic > vanillic. Chemical Product Kojic acid (KA) and vanillic acid (VA) were also identified from EAE as bioactive metabolic products of fungi and yeasts. View the GISSMO record for this entry. Additionally, changes in the signals of all of the protons of the non-aromatic ring were observed as a consequence of the quinone formation.  |  The signals of the chlorogenic acid-quinone protons are at 6.74(H1), 6.46(H4), 7.65(H5) ppm, whereas the H6 signal appears at 7.43 ppm and the H7 signal is at 6.78 ppm. Generally, the presence of hydroxyl substituents increases the antioxidant capacity. O Commercial standards of caffeic, ferulic, p-coumaric, chlorogenic, gallic, protocatechuic and vanillic acids (Sigma-Aldrich, Toluca, México) and a stable free radical, 1,1-diphenyl-2-picrylhydrazyl (DPPH), were used for all experiments. Functional effects of Japanese style fermented soy sauce (shoyu) and its components. If the viewer is not showing any spectra or is slow, try updating to the latest version of your The interactions were found to occur via hydrogen bonds between the -OH … This behavior was observed in previous studies that evaluated the antioxidant capacity of these acids using UV-Vis [2]. Epub 2014 Aug 11. The hydroxyl and carboxylic protons have broad signals in the upper spectra, which are indicative of the interaction with other -OH groups that are possibly water remnants [23] that are found between 9 and 11 ppm. Quantitative metabolomics services for biomarker discovery and validation. The spectrum of chlorogenic acid was more complex because of its chemical structure (Fig 3). National Center for Biotechnology Information, Unable to load your collection due to an error, Unable to load your delegates due to an error. The results suggest a parallel between this bioconversion reaction and the beta-oxidation of fatty acids. All of the mixtures were allowed to stand for 3 min at room temperature, and after the purple color of the DPPH faded, they were subjected to 1H NMR analysis. broad scope, and wide readership – a perfect fit for your research every time. e0140242. A similar behavior was observed with the -COOH group. Example 2163-42-0 15186-48-8 13463-67-7 57-55-6 107-43-7 56-81-5 Current Page: Home › Compound Encyclopedia › 121-34-6 Recommended Suppliersmore. Structure Q Partners

40 MHz Only two broad peaks were observed (protons 15 and 16) that correspond to the carboxylic and hydroxyl groups at position of C5 in the non-aromatic group. 9, Home doi: 10.1093/nar/gkn810. -, Lead Time: Thus, we assume that chlorogenic acid is the first compound to react in this mixture. The gallic acid spectrum shows the characteristic hydroxyl protons at 8.85 and 9.19 ppm and the acid group at 12.15 ppm. This site needs JavaScript to work properly.

Therefore, chlorogenic acid is now a quinone derivative, leading to changes in the unsaturated cinnamic arm and the displacement of protons in the non-aromatic ring. [. The protocatechuic, chlorogenic and caffeic acids exhibited the SET mechanism for neutralization of the DPPH radical. Yes

vanillic acid 121-34-6 NMR spectrum, vanillic acid H-NMR spectral analysis, vanillic acid C-NMR spectral analysis ect. Table 2 displays the results obtained for the mixtures of phenolic acids that are present in mango, and it also shows which compound is responsible for the DPPH color change, according to the observed changes in the 1H NMR spectra. Upon reaction with DPPH, peak 15 sharpens, which is due to the hydroxyl group. N According to the results, these two mechanisms are Hydrogen Atom Transfer (HAT) and Single Electron Transfer (SET). 5 There are two mechanisms for the antioxidant neutralization of the DPPH radical using the phenolic acids: Hydrogen Atom Transfer (HAT) and Single Electron Transfer (SET). Such interactions appear to occur via hydrogen bonding between the -OH and -COOH groups.

For the mixture of gallic, protocatechuic and vanillic acids, the first compound in the neutralization of DPPH was gallic acid. Vanillic acid: Spectrum type: 1H NMR Spectrum: Spectrum View. Compound Vanillic acid methyl ester with free spectra: 6 NMR, 5 FTIR, 2 Raman, and 2 UV-Vis. This potential has been attributed to their acidic chemical structure, which possesses hydroxyl groups in different positions. This site uses cookies.

Click through the PLOS taxonomy to find articles in your field. Suppliers Products To zoom into a region, draw a box around it. J Biosci Bioeng. Compound Vanillic acid methyl ester with free spectra: 6 NMR, 5 FTIR, 2 Raman, and 2 UV-Vis. Fig 5 shows the spectra of the individual and the ternary mixture of chlorogenic, gallic and vanillic acids after reacting them with the DPPH radical. COVID-19 is an emerging, rapidly evolving situation. Moreover, within the acids found in papaya, the abilities to neutralize the DPPH decrease in the following order: caffeic > p-coumaric > ferulic.
The detailed peak assignments of vanillic acid moieties carbons are based on previous studies in literature, where they are in well accordance with the ones found in the studies of Gioia and Huang et al.

This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. HHS No, Is the Subject Area "Antioxidants" applicable to this article? We found that ferulic and vanillic acids did not present a color change after contact with the DPPH radical for several hours. Biosci Biotechnol Biochem. 14 Day, Lead Time: 200 MHz 400 MHz The identification of antioxidants in dark soy sauce. About Us Aldrich-H36001; Vanillic acid 0.97; CAS No. 8 https://doi.org/10.1371/journal.pone.0140242.g005. 2020 Feb 20;10(2):75. doi: 10.3390/metabo10020075. In this paper, we used 1 H NMR to analyze the interactions and mechanisms that are present in major phenolic acids found in mango (gallic, protocatechuic, chlorogenic and vanillic acids) and papaya (caffeic, ferulic and p-coumaric acids), and the DPPH radical was used to evaluate the effect of the antioxidant mixtures. http://spectrabase.com/spectrum/BM8tsCi4z7F

Yes No, Is the Subject Area "Protons" applicable to this article? NMR-STAR file: bmse000614.str NMR-STAR interactive viewer Mol file: bmse000614.mol All files for bmse000614 Time Domain Data: bmse000614.zip. 2005 Sep;100(3):227-34. doi: 10.1263/jbb.100.227. Solutions were prepared at a concentration of 5 mM in DMSO-d6 for each phenolic acid or mixture of phenolic acids using a ratio of 1:1 and 0.5 mL of this solution was placed into a NMR quartz tube to collect the spectra.  |  Charisiadis et al. Discover a faster, simpler path to publishing in a high-quality journal. 700 MHz The addition of DPPH was performed using a 1:1 ratio with respect to the concentration of the solution of the phenolic acids, either individually or as mixtures. 2007 Apr;41(4):479-88. doi: 10.1080/10715760601110871. Wang H, Jenner AM, Lee CY, Shui G, Tang SY, Whiteman M, Wenk MR, Halliwell B. Nuclear magnetic resonance (NMR) is a sophisticated and powerful analytical method that has found a variety of applications, such as the identification of structures and molecular interactions.

HAT refers to the loss of a proton to the radical and to the stabilization of the charge by nearby groups.

The signals labeled with an asterisk are attributed to the °DPPH radical. The benefits of phenolic acids on human health are very often ascribed to their potential to counteract free radicals to provide antioxidant protection. The capacity of the phenolic acids that are present in mango to neutralize the DPPH decreases in the following order: chlorogenic > gallic > protocatechuic > vanillic. It is a flavouring and scent agent that produces a pleasant, creamy odour. The phenolic acids present in mango and papaya exhibit a good antioxidant activity. Compound Type Concentration; vanillic acid: Solute: 100mM: D2O: Solvent: 100%: sodium phosphate: Buffer: 50mM: sodium azide: Cytocide: 500uM: DSS: Reference: 500uM (accessed Nov 12, 2020).

Moreover, the antioxidant activity of phenolic acids is generally governed by their chemical structures; the activity improves as the number of hydroxyl (OH) and methoxy groups increase, and the number of OH groups is more important.