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  

Synthesis of Halogenated Curcumin Derivatives and Its Photodynamic Inactivation Effect on Vibrio parahaemolyticus

作　　者：李雨薇 赵淑怡 洪高博 张宾 焦龙 张晓晔 LI Yuwei;ZHAO Shuyi;HONG Gaobo;ZHANG Bin;JIAO Long;ZHANG Xiaoye(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)

机构地区：[1]浙江海洋大学食品与药学学院,浙江省海产品健康危害因素关键技术研究重点实验室,浙江舟山316022 [2]浙江海洋大学比萨海洋研究生学院,浙江舟山316022 [3]大连理工大学精细化工国家重点实验室,辽宁大连116024 [4]浙江海洋大学船舶与海运学院,浙江舟山316022

出　　处：《食品科学》2024年第16期19-24,共6页Food Science

基　　金：浙江省基础公益研究计划项目(LQ22C200011)。

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(^(1)O_(2))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(S_(1))和三重激发态(T_(3))能级差ΔE_(st(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T_(3);此外,Br-cur相比于Cur和其他卤代姜黄素具有最小的S_(1)和基态(S_(0))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^(1)O_(2)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。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(^(1)O_(2))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(Δ_(Est(S_(1)-T_(3))))between singlet excited state(S_(1))and triplet excited state(T_(3))(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 S_(1)and ground state(S_(0)).Due to the aforementioned factors,Br-cur was highly prone to photooxidation and had the highest^(1)O_(2)generation 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.

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 

分 类 号：TS254.4[轻工技术与工程—水产品加工及贮藏工程]