食品科学 ›› 2024, Vol. 45 ›› Issue (16): 19-24.doi: 10.7506/spkx1002-6630-20230831-235

• 基础研究 • 上一篇    下一篇

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

李雨薇,赵淑怡,洪高博,张宾,焦龙,张晓晔   

  1. (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)
  • 出版日期:2024-08-25 发布日期:2024-08-06
  • 基金资助:
    浙江省基础公益研究计划项目(LQ22C200011)

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

LI Yuwei, ZHAO Shuyi, HONG Gaobo, ZHANG Bin, JIAO Long, ZHANG Xiaoye   

  1. (1. Key Laboratory of Health Risk Factors for Seafood of Zhejiang Province, College of Food Science and Pharmacy, Zhejiang Ocean University, Zhoushan 316022, China; 2. Pisa Marine Graduate School, Zhejiang Ocean University, Zhoushan 316022, China; 3. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China; 4. School of Naval Architecture and Maritime, Zhejiang Ocean University, Zhoushan 316022, China)
  • Online:2024-08-25 Published:2024-08-06

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(0.642 262 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。

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

Abstract: 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(S1-T3)) between singlet excited state (S1) and triplet excited state (T3) (0.140 eV) and the highest spin-orbit coupling value (0.642 262 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 S1 and ground state (S0) . Due to the aforementioned factors, Br-cur was highly prone to photooxidation and had the highest 1O2 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.

Key words: halogenated curcumin; photodynamic inactivation; heavy-atom effect; intersystem crossing; Vibrio parahaemolyticus

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