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Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids

Significance Statement

Microorganism infection is a continue threat to human health. About the control the infection, using antimicrobial agent is one of the effective options. Now, natural antimicrobial agents are focused extensively because they are low-toxic and safe. Cinnamaldehyde is a natural antimicrobial substance, which is extracted from bark of  Cinnamomum genus trees. Cinnamaldehyde possesses good bioactivity and could inhibit the growing of many kinds of fungi and bacteria. Cinnamaldehyde is categorized as Generally Recognized as Safe (GRAS) by the U.S. Food and Drug Administration. However, Cinnamaldehyde has several drawbacks, such as its strong odor, high volatility and water insolubility, which limited its application.

In our research, cinnamaldehyde was modified by amino acids to synthesize a new class of Schiff base compounds. Bioactivity results indicated that the Schiff base compounds remarkably inhibited the growth of the tested bacteria and fungi, and they have broad-spectrum antimicrobial activity. Compared with control compounds, i.e. Ciprofloxacin and Fluconazole, most of the Schiff base compounds exhibited better bioactivity than the two control compounds.

The key finding of this study is that, the new class of cinnamaldehyde Schiff base compounds, which could be easily synthesized, have great bioactivity, low-toxicity, low odor and good water solubility. Therefore, cinnamaldehyde Schiff base compounds were potential to be antibacterial agents or food preservatives.

Moreover, the further analysis on antimicrobial activity and chemical structure were conducted in our research. Results from the structure-activity relationship suggest that both p-Cl of benzene ring from cinnamaldehyde and the number of –COOK from amino acid salts significantly contributed to their antimicrobial activity.

Our research results provided an alternative option for exploring of new antimicrobial agents. 

Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids.. Global Medical Discovery

About The Author

Prof. Shujun Li received her Bachelor Degree in Forest Products Chemical Processing from Northeast Forestry University, China in 1995. She received her Master Degree in 1998, also in the same major, and received her Ph. D in 2001, majored in wood science and technology.

Currently, she serves as a full Professor of Forest Products Chemical Processing Department at Northeast Forestry University, Harbin, China. Her research interests include biomass conversion and application in a high-value way. 

 

About The Author

Miss Hui Wang received her bachelor degree in 2013 from Lanzhou University of Technology, Lanzhou, China. She is now a doctoral candidate at Northeast Forestry University, and her current research is synthesis of cinnamaldehyde derivatives and its bioactivity. 

Journal Reference

Bioorg Med Chem Lett. 2016 Feb 1;26(3):809-13.

Wang H1, Yuan H1, Li S2, Li Z1, Jiang M1. 

Show Affiliations
  1. Key Laboratory of Bio-Based Material Science and Technology of the Ministry of Education, Northeast Forestry University, Harbin 150040, China.
  2. Key Laboratory of Bio-Based Material Science and Technology of the Ministry of Education, Northeast Forestry University, Harbin 150040, China. Electronic address: [email protected]

Abstract

The purpose of this study was to synthesize hydrophilic cinnamaldehyde Schiff base compounds and investigate those bioactivity. A total of 24Schiff base compounds were synthesized using a simple approach with 3 cinnamaldehyde derivates and 8 amino acids as raw materials. The structures of synthesized compounds were confirmed using FTIR, (1)HNMR, HRMS purity and melting point. The antimicrobial activities of newcompounds were evaluated with fluconazole and ciprofloxacin as the control against Aspergillus niger, Penicillium citrinum, Escherichia coli and Staphylococcus aureus.

Findings show that major compounds exhibited significant bioactivity. Results from the structure-activity relationship suggest that both -p-Cl on benzene ring of cinnamaldehyde and the number of -COOK of amino acid salts significantly contributed to antimicrobialactivity.

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