Position: Home > Articles > Synthesis of Halogenated Curcumin Derivatives and Its Photodynamic Inactivation Effect on Vibrio parahaemolyticus
FOOD SCIENCE
2024
(16)
19-24
卤代姜黄素衍生物的合成及其对副溶血性弧菌的光动力灭活作用
作 者：
李雨薇;赵淑怡;洪高博;张宾;焦龙;张晓晔
单 位：
;浙江海洋大学食品与药学学院
关键词：
卤代姜黄素;光动力灭活;重原子效应;系间窜越;副溶血性弧菌
摘 要：
为提升姜黄素(curcumin,Cur)的光动力灭活(photodynamic inactivation,PDI)效果,合成新型卤代姜黄素衍生物(X-cur,X=F、Cl、Br).通过测定X-cur的紫外-可见吸收光谱和荧光光谱,对比X-cur的单线态氧(1O2)生成能力并辅助激发态理论计算结果,分析筛选出具有PDI潜力的姜黄素衍生物.结果表明:随着非金属重原子卤素相对分子质量的增加,其自旋耦合作用逐渐增强,导致Br-cur具有最小的单重激发态(S1)和三重激发态(T3)能级差ΔEst(S1-T3)(0.140 eV)和最大的自旋轨道耦合值(0.642262 cm-1),说明Br-cur最容易发生系间窜越过程进入到T3;此外,Br-cur相比于Cur和其他卤代姜黄素具有最小的S1和基态(S0)间能级差(3.260 eV);以上两因素导致Br-cur极易被光激发且具有最高的1O2生成能力;在对水产品中典型食源性致病菌副溶血性弧菌(Vibrio parahaemolyticus)的PDI实验中,Br-cur的PDI作用依赖于其使用浓度和光照时间,且PDI效果显著高于Cur对照组,是极具应用潜力的新型PDI光敏剂.
译 名：
Synthesis of Halogenated Curcumin Derivatives and Its Photodynamic Inactivation Effect on Vibrio parahaemolyticus
单 位：
Key Laboratory of Health Risk Factors for Seafood of Zhejiang Province,College of Food Science and Pharmacy,Zhejiang Ocean University,Zhoushan 316022,China;Pisa Marine Graduate School,Zhejiang Ocean University,Zhoushan 316022,China;State Key Laboratory of Fine Chemicals,Dalian University of Technology,Dalian 116024,China;School of Naval Architecture and Maritime,Zhejiang Ocean University,Zhoushan 316022,China
关键词：
halogenated curcumin%photodynamic inactivation%heavy-atom effect%intersystem crossing%Vibrio parahaemolyticus
摘 要：
In order to enhance the photodynamic inactivation(PDI)effect of curcumin,a novel class of halogenated curcumin derivatives X-cur(X=F,Cl or Br)was synthesized and screened for its potential for PDI by ultraviolet-visible(UV-Vis)absorption and fluorescence spectroscopy,singlet oxygen(1O2)generation capacity and theoretical calculations of excited states.The results demonstrated that as the relative molecular mass of the nonmetallic heavy atom halogen increased,the spin-spin coupling effect was gradually strengthened,so the smallest energy level difference(ΔEst(S_(1-T3)))between singlet excited state(S1)and triplet excited state(T3)(0.140 eV)and the highest spin-orbit coupling value(0.642262 cm-1)were observed in Br-cur.This finding suggested that Br-cur was most likely to undergo transition into triplet state through intersystem crossing.Furthermore,compared to curcumin and other halogenated curcumins,Br-cur exhibited the smallest energy level difference(3.260 eV)between its S1and ground state(S0).Due to the aforementioned factors,Br-cur was highly prone to photooxidation and had the highest1O2generation capacity.Br-cur had a PDI effect on Vibrio parahaemolyticus,a prevalent foodborne pathogen in aquatic products,which depended on its concentration and light exposure duration and was significantly higher than that of curcumin.Thus,Br-cur has great potential for application as a novel PDI agent.
