Title

Synthesis and Characterization of p-Coumaric Acid Derivatives and Determination of Radical Scavenging Potential

Poster Number

14A

Lead Author Major

Biochemistry

Lead Author Status

Senior

Format

Poster Presentation

Faculty Mentor Name

Andreas Franz

Faculty Mentor Email

afranz@pacific.edu

Faculty Mentor Department

Chemistry

Graduate Student Mentor Name

Cate Simmermaker

Graduate Student Mentor Email

c_simmermaker@u.pacific.edu

Graduate Student Mentor Department

Chemistry

Abstract/Artist Statement

Polyphenols have previously been studied and their biological properties evaluated, concluding that they are potent antimicrobial, antiviral, and antioxidant agents, the last being the most crucial to this research1. The aim of this research is to synthesize and characterize p-coumaric acid-amino acid conjugate derivatives and determine radical scavenging by 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) assay. Amino acids have been linked to synergistic effects and the combination of resonance assistance and amino acid assistance could lead to more efficacious properties. These compounds were synthesized through a 4-step scheme: acetylation, chlorination, amidation, and deprotection. Coumaric acid is a polyphenol of the hydroxycinnimates family commonly found in nut, beans, tomatoes, carrots, wine and vinegar. Antioxidants, compounds that protect the body and cells from free radicals, quench those unstable molecules characterized by an unpaired valence shell electron, that damage cells and are generated by sun exposure, stress, and as part of the natural aging process by inhibiting oxidation, which results in damaging biological chain reactions2. Previous research shows both cinnamic acids and hydroxycinnamic acids contain antioxidant properties3. Antioxidant potential can be determined through DPPH assay. DPPH is a stable free radical with a purple-red color, and will change via reduction to a clear-yellow color. This color change can be tracked by UV/Vis spectroscopy at 515nm. The current DPPH rankings of some hydroxycinnamic acids from strongest to weakest are as followed: caffeic acid, sinapic acid, ferulic acid, p-coumaric acid. Because of the antioxidant properties found in polyphenols, synthetic derivatization of p-coumaric acid with possible resonance enhancing properties can prove significant for the study of structure activity relationships (SARs) in the field of antioxidants.

References

  1. Rajan P., Vedernikova I., Cos P., Berghe D.V., Augustyns K., Haemers A., Synthesis and Evaluation of Caffeic Acid Amides as Antioxidants, Bioorg. Med. Chem. Lett., 11, 215-217 (2001)
  2. Fu J., Cheng K., Zhang Z., Fang R., Zhu H., Synthesis, structure and structure-activity relationship analysis of caffeic acid amides as potential antimicrobials, Eur. J. Med. Chem., 45, 2638- 2643 (2010)
  3. Gaspar A., Garrido E.M., Esteves M., Quezada E., Milhazes N., Garrido J., Borges F., New insights into the antioxidant activity of hydroxycinnamic acids: Synthesis and physicochemical characterization of novel halogenated derivatives, Eur. J. Med. Chem., 44, 2092 – 2099 (2009)

Location

DeRosa University Center Ballroom

Start Date

27-4-2018 12:30 PM

End Date

27-4-2018 2:30 PM

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Apr 27th, 12:30 PM Apr 27th, 2:30 PM

Synthesis and Characterization of p-Coumaric Acid Derivatives and Determination of Radical Scavenging Potential

DeRosa University Center Ballroom

Polyphenols have previously been studied and their biological properties evaluated, concluding that they are potent antimicrobial, antiviral, and antioxidant agents, the last being the most crucial to this research1. The aim of this research is to synthesize and characterize p-coumaric acid-amino acid conjugate derivatives and determine radical scavenging by 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) assay. Amino acids have been linked to synergistic effects and the combination of resonance assistance and amino acid assistance could lead to more efficacious properties. These compounds were synthesized through a 4-step scheme: acetylation, chlorination, amidation, and deprotection. Coumaric acid is a polyphenol of the hydroxycinnimates family commonly found in nut, beans, tomatoes, carrots, wine and vinegar. Antioxidants, compounds that protect the body and cells from free radicals, quench those unstable molecules characterized by an unpaired valence shell electron, that damage cells and are generated by sun exposure, stress, and as part of the natural aging process by inhibiting oxidation, which results in damaging biological chain reactions2. Previous research shows both cinnamic acids and hydroxycinnamic acids contain antioxidant properties3. Antioxidant potential can be determined through DPPH assay. DPPH is a stable free radical with a purple-red color, and will change via reduction to a clear-yellow color. This color change can be tracked by UV/Vis spectroscopy at 515nm. The current DPPH rankings of some hydroxycinnamic acids from strongest to weakest are as followed: caffeic acid, sinapic acid, ferulic acid, p-coumaric acid. Because of the antioxidant properties found in polyphenols, synthetic derivatization of p-coumaric acid with possible resonance enhancing properties can prove significant for the study of structure activity relationships (SARs) in the field of antioxidants.

References

  1. Rajan P., Vedernikova I., Cos P., Berghe D.V., Augustyns K., Haemers A., Synthesis and Evaluation of Caffeic Acid Amides as Antioxidants, Bioorg. Med. Chem. Lett., 11, 215-217 (2001)
  2. Fu J., Cheng K., Zhang Z., Fang R., Zhu H., Synthesis, structure and structure-activity relationship analysis of caffeic acid amides as potential antimicrobials, Eur. J. Med. Chem., 45, 2638- 2643 (2010)
  3. Gaspar A., Garrido E.M., Esteves M., Quezada E., Milhazes N., Garrido J., Borges F., New insights into the antioxidant activity of hydroxycinnamic acids: Synthesis and physicochemical characterization of novel halogenated derivatives, Eur. J. Med. Chem., 44, 2092 – 2099 (2009)