文章摘要
金桂勇,程东旭,杜佳,陈芝飞,赵森森,万帅,赵铭钦,张晓平,席高磊.香豆素-3-羧酸类化合物的绿色合成及抗氧化性能测定[J].精细化工,2021,(8):0
香豆素-3-羧酸类化合物的绿色合成及抗氧化性能测定
Green synthesis and antioxidation activities of coumarin-3-carboxylic acids
投稿时间:2021-02-24  修订日期:2021-04-21
DOI:
中文关键词: 香豆素-3-羧酸  无催化剂  绿色合成  抗氧化  自由基
英文关键词: coumarin-3-carboxylic acids  catalyst-free  green synthesis  antioxidant  free radical
基金项目:国家自然科学基金项目(21801064)
作者单位E-mail
金桂勇 河南农业大学烟草学院 jinguiyong0303@sina.com 
程东旭 河南中烟工业有限责任公司技术中心  
杜佳 河南中烟工业有限责任公司技术中心  
陈芝飞 河南中烟工业有限责任公司技术中心  
赵森森 河南中烟工业有限责任公司技术中心  
万帅 河南中烟工业有限责任公司技术中心  
赵铭钦 河南农业大学烟草学院  
张晓平 河南农业大学烟草学院 xiaoping078@163.com 
席高磊 河南中烟工业有限责任公司技术中心  
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中文摘要:
      为优化香豆素-3-羧酸类化合物的合成方法,并考察其抗氧化性能。以水为反应介质,在无催化剂条件下加热促使水杨醛类化合物与米氏酸发生反应,合成了18种香豆素-3-羧酸类化合物。利用1HNMR和13CNMR对合成产物结构进行表征;并通过抑制HO•、还原型谷胱甘肽自由基(GS•)和2,2′-偶氮二异丁基脒二盐酸盐(AAPH)氧化DNA反应对其抗氧化活性进行检测,进而探究取代基种类和位置对香豆素-3-羧酸类化合物抗氧化性能的影响。结果表明:该合成方法绿色高效,具有很好的普适性,目标化合物的产率为54.3%~95.6%;18种化合物均能够抑制HO•、GS•和AAPH氧化DNA,其相对空白硫代巴比妥酸活性物质(TBARS)吸光度百分数(TBARS百分数)分别可达69.42%~93.39%、75.23%~99.45%和66.62%~97.72%;在抑制HO•、GS•和AAPH氧化DNA反应中,羟基取代化合物(化合物XV~XVIII)的TBARS百分数分别为69.42%~77.67%、75.23%~82.87%和66.62%~75.08%,远小于连其他取代基的香豆素-3-羧酸类化合物(化合物I~XIV),与水溶性维生素E的TBARS百分数相当,是一类潜在的抗氧化剂。
英文摘要:
      In order to optimize the synthesis methods of coumarin-3-carboxylic acids and investigate their antioxidant properties, eighteen coumarin-3-carboxylic compounds were obtained via the reaction of meldrum’s acid and various salicylaldehydes without catalyst in water. The structures of the obtained compounds were confirmed by 1HNMR and 13CNMR, and the antioxidant activities were evaluated by inhibiting DNA oxidation reaction by hydroxyl radical (HO•), reductive glutathione radical (GS•) and 2,2′-azobis(2-methylpropionamidine) dihydrochloride (AAPH), aiming at exploring antioxidant abilities of different types and positions of the substitutes. The results showed that this approach is green and efficiently, and can tolerate substrates with diverse functional groups. The yields of the eighteen coumarin-3-carboxylic compounds were with ranged from 54.3% to 95.6%. All the compounds exhibited strong activities to protect DNA against oxidation induced by HO•, GS• and AAPH. The absorbance percentages of thiobarbituric acid reactive substances (TBARS) were 69.42%~93.39%, 75.23%~99.45% and 66.62%~97.72%, respectively. In reaction of inhibiting HO•, GS• and AAPH induced oxidation of DNA, the TBARS percentages of hydroxyl substituted compounds (compounds XV ~ XVIII) were 69.42% ~ 77.67%, 75.23% ~ 82.87% and 66.62% ~ 75.08%, respectively. The TBARS percentages of hydroxyl substituted compounds were far less than the other coumarin-3-carboxylic compounds (compounds I ~ XIV). The results indicated that hydroxyl substituted coumarin-3-carboxylic acids showed similar TBARS percentages to water-soluble vitamin E, and can be used as potential antioxidants.
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