Synthesis, Antimicrobial, and Antioxidant Activities of Chalcogen-Containing Nitrone Derivatives from (R)-citronellal.
Synthesis, Antimicrobial, and Antioxidant Activities of Chalcogen-Containing Nitrone Derivatives from (R)-citronellal.
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DOI：
10.3390/medicines4020039
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发表时间：
2017-06-10
期刊：
影响因子：
--
通讯作者：
Jacob RG
中科院分区：
文献类型：
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作者：
Ferraz MC;Mano RA;Oliveira DH;Maia DSV;Silva WP;Savegnago L;Lenardão EJ;Jacob RG
背景：香茅和香茅挥发油的主要成分分别为(R)-香茅醛和柠檬醛。有机醇类化合物可以提高天然产物的生物活性。方法：以(R)-香茅醛和柠檬醛为原料，合成了几种含硫的硝酮类化合物，并对其抑菌和抗氧化活性进行了评价。用纸片扩散法评价其抗菌活性，用DPPH(1，1-二苯基-2-苦基肼)、ABTS(2，2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic酸和铁离子还原抗氧化力试验评价其体外抗氧化性能。结果：在抑菌试验中，(E)-N，3，7-trimethyl-3-(phenylthio)oct-6-en-1-imine氧化物5c在21.5 mm(大肠杆菌O157：H7)和(E)-N，3，7-三甲基-6-烯-1-亚胺氧化物5d(E.coliO157：H7)和(E)-N，3，7-三甲基-6-烯-1-亚胺氧化物5d(E.ColiO157：H7)和(E)-N，3，7-三甲基-6-烯-1-亚胺氧化物5d在22.5 mm(大肠杆菌O157：H7)和31.0 mm(单核细胞增生性李斯特菌)之间出现晕圈。(E)-N，3，7-Trimethyl-2-(phenylthio)oct-6-en-1-imine氧化物5a对蜡样芽孢杆菌的最低抑菌浓度为0.48 mM，对大肠杆菌O157：H7的最小杀菌浓度为0.52 mM。在抗氧化剂测定中，5c、5d和10((E)-3，7-二甲基-2-(苯基硒)辛基-6-烯醛)分别在DPPH、ABTS和FRAP测定中活性最高。结论：硝酮中苯硫基的存在提高了纸片扩散试验中对革兰氏阳性和革兰氏阴性食源性致病菌的抗菌活性和体外抗氧化活性。
Background: The main constituents of Cymbopogonnardus (L) Rendle and C. citratus (DC) Stapfessential oils are (R)-citronellal and citral, respectively. Organochalcogen compounds can boost the biological activities of natural products. Methods: Several chalcogen-containing nitrones derived from (R)-citronellal and citral were prepared and evaluated for their antimicrobial and antioxidant activities. The antimicrobial activity was evaluated by the disc diffusion test and the antioxidant properties were evaluated in vitro by DPPH (1,1-diphenyl-2-picryl-hydrazyl), ABTS (2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid), and FRAP (ferric ion reducing antioxidant power) assays. Results: In the antimicrobial assay, (E)-N,3,7-trimethyl-3-(phenylthio)oct-6-en-1-imine oxide 5c exhibited halos between 21.5 mm (Escherichia coli O157:H7) and 26.0 mm (Listeria monocytogenes), while (E)-N,3,7-trimethyloct-6-en-1-imine oxide 5d presented halos between 22.5 mm (E. coli O157:H7) and 31.0 mm (L. monocytogenes). (E)-N,3,7-Trimethyl-2-(phenylthio)oct-6-en-1-imine oxide 5a showed the lowest minimal inhibitory concentration (MIC) value against Bacillus cereus (0.48 mM), and 5c was the most potent bactericide, with a minimal bactericidal concentration (MBC) of 0.52 mM for E. coli O157:H7. In the antioxidant assays, 5c, 5d, and 10 ((E)-3,7-dimethyl-2-(phenylselanyl)oct-6-enal oxime) were the most actives in the DPPH, ABTS, and FRAP assays, respectively. Conclusions: The presence of a phenylthio group in the nitrone increases its antimicrobial activity against Gram-positive and Gram-negative foodborne pathogens in the disk diffusion test and the antioxidant activity in vitro.