RESEARCH PAPER |
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Synthesis, Bacteriostatic and Anti-alga Capability of Monomers and Polymers Containing Capsaicin |
Xiaochun ZHANG,Liangmin YU,Xiaohui JIANG
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Key Laboratory of Marine Chemistry Theory and Technology of Ministry of Education, Ocean University of China,Qingdao 266100 |
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Abstract Four compounds (4-hydroxy-2-methyl-5-methylthio benzyl acrylamide (A), 2-hydroxy-4-acrylamide methyl-5-methylthio-6-methyl benzyl acrylamide (B), 3-acrylamide methyl-2-hydroxy benzamide (C), 1-acrylamide methyl-2-naphthol (D)) containing capsaicin moieties were synthesized with substituted aromatic and N-methylol acrylamide by Friedel-Crafts alkylation reaction, and their structures were characterized by infrared spectroscopy (IR) and hydrogen nuclear magnetic spectra ( 1H NMR). The results of antibacterial test showed that the best inhibitory activity can be observed on Staphylococcus aureus and Escherichia coli with compound D, reaching the minimum inhibitory concentration (MIC) of 0.187 5 mg/mL. Moreover, the inhibitory activity of D on the two tested algae performed the best. The resins synthesized with four compounds as functional monomers were verified to have great inhibitory activity on tested algae. Besides, the best inhibitory activity is obtained on resin comprised of compound D, which has the inhibition rate of over 50% after 72 h.
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Published: 25 January 2018
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Structures of target products
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NO. | Capsaicin monomer added | Content of capsaicin | Resin properties | R0 | — | 0% | Colorless transparent viscous liquid | RA | A | 5% | Light yellow transparent viscous liquid | RB | B | 5% | Light yellow transparent viscous liquid | RC | C | 5% | Light yellow transparent viscous liquid | RD | D | 5% | Red brown transparent viscous liquid |
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Synthesis of acrylic resin with different capsaicin derivative structure
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IR and 1H NMR of A
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IR of the resins
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Tested compounds | A | B | C | D | Escherichia coli | 0.375 0 | 0.375 0 | 0.375 0 | 0.187 5 | Staphylococcus aureus | 0.187 5 | 0.187 5 | 0.375 0 | 0.187 5 |
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MIC of tested compounds with two kinds of bacteria (unit:mg/mL)
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Inhibitory effect of the tested compounds on Escherichia coli
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Inhibitory effect of the tested compounds on Staphylococcus aureus
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Effects of the subjects on the growth curve of the Phaeodactylum tricornutum Bohlin
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Effects of the subjects on the growth curve of the Nitzschia closterium
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Time h | Phaeodactylum tricornutum Bohlin | Nitzschia closterium | RA | RB | RC | RD | RA | RB | RC | RD | 24 | 27.2 | 30.5 | 10.2 | 30.5 | 25.9 | 30.3 | 8.7 | 43.3 | 48 | 32.5 | 34.2 | 15.4 | 51.3 | 29.3 | 36.1 | 13.8 | 48.2 | 72 | 39.5 | 46.0 | 26.0 | 61.8 | 31.7 | 38.7 | 16.9 | 52.3 |
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Inhibitory rate of resin on algae(%)
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Working curve of (a) the Phaeodactylum tricornutum Bohlin and (b) the Nitzschia closterium
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