Curcumin derivative with high photosensitive bactericidal activity, preparation method and photodynamic sterilization and fresh-keeping method for fresh shrimps

Abstract

The invention relates to the field of aquatic product processing and storage, and discloses a curcumin derivative with high photosensitive bactericidal activity, a preparation method and a photodynamic sterilization and fresh-keeping method for fresh shrimps in order to overcome the defects that the existing preservation effect is poor, the safety of the existing preservation technology is uncontrollable, and the texture and flavor are damaged. A substituent group containing a nitroxide free radical is introduced to a curcumin phenolic hydroxyl group structure, so that the photosensitive characteristic of the curcumin derivative can be improved, and the capability of generating reactive oxygen species (ROS) with cytotoxicity is improved under a certain condition, thereby causing wide oxidative damage to bacterial cells. And moreover, the generation of active oxygen can be completed only by irradiation of an LED lamp, the sterilization and fresh-keeping process is simple and easy to operate, safe and pollution-free, the fresh-keeping time of the shrimps can be prolonged, the fresh-keeping effect is excellent, and the practical value is very high.

Description

technical field

[0001] The invention relates to the field of aquatic product processing and storage, in particular to a curcumin derivative with high photosensitivity and bactericidal activity, a preparation method, and a method for photodynamic sterilization and preservation of fresh shrimp. Background technique

[0002] Photodynamic sterilization is a new type of cold sterilization technology, which has the advantages of non-toxicity and no drug resistance. When the photosensitizer is irradiated with visible light, cytotoxic reactive oxygen species (ROS) are generated, which in turn causes extensive oxidative damage to bacterial cells. At present, the sterilization methods of aquatic products mainly include: traditional heat treatment sterilization technology, cold sterilization technology such as irradiation and low temperature plasma, and the preparation of curcumin derivatives based on high photosensitivity sterilization performance and its application in fresh shrimp p...

Examples

Embodiment 1

[0057] Synthesis of curcumin derivative II with high photosensitivity and bactericidal activity, wherein the structural formula of curcumin derivative II is as follows:

[0058]

[0059] , the reaction equation is as figure 1 shown.

[0060] At room temperature, N 2 Under protective conditions, accurately weighed 1 mmol of curcumin and 3 mmol of 4-dimethylaminopyridine were dissolved in a reaction flask with 15 mL of N,N-dimethylformamide, and stirred at room temperature for 1 h, during which 1 mmol of 1-dimethylaminopyridine was added every 20 min. Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, and finally 2 mmol of 3-carboxy-2,2,5, dissolved in 5 mL of N,N-dimethylformamide, was added. 5-tetramethylpyrrolidine-1-oxyl radical, and continue to stir the reaction for 12h. After the reaction, the curcumin derivative II with high photosensitivity and bactericidal activity was obtained through extraction and column chromatography purification, such as: figure 2 As...

Embodiment 2

[0062] At room temperature, N 2 Under protective conditions, accurately weighed 1 mmol of curcumin and 1 mmol of 4-dimethylaminopyridine were dissolved in a reaction flask with 15 mL of N,N-dimethylformamide, and stirred at room temperature for 1 h, during which 0.5 mmol of 1 mmol was added every 30 min. -Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, and finally 3 mmol of 3-carboxy-2,2,5 dissolved in 5 mL of N,N-dimethylformamide was added , 5-tetramethylpyrrolidine-1-oxyl radical, and continue to stir the reaction for 12h. After the reaction, the curcumin derivative II with high photosensitivity and bactericidal activity was obtained by extraction and purification by column chromatography.

Embodiment 3

[0064] The curcumin derivative II of embodiment 1 is applied to the method for the photodynamic sterilization and preservation of fresh shrimp, and the concrete steps are as follows:

[0065] 1) Prepare 10 μM Curcumin Derivative II aqueous solution and fill it in a light-proof watering can;

[0066] 2) Select fresh and complete, brightly colored and uniformly sized Penaeus vannamei, immerse it in ice water and freeze it to death quickly, use sterile saline to wash and drain the surface moisture;

[0067] 3) using the spraying method, the prepared curcumin derivative II aqueous solution in step 1) is sprayed in sufficient amount and uniformly on the surface of the fresh shrimp prepared in step 2), and let stand in the dark for 5min;

[0068] 4) The fresh shrimp prepared in step 3) is placed under a blue LED matrix with a light power of 30W for irradiation for 120s, and the irradiation wavelength is 400nm to complete the process of photodynamic sterilization and preservation.

technical field

[0001] The invention relates to the field of aquatic product processing and storage, in particular to a curcumin derivative with high photosensitivity and bactericidal activity, a preparation method, and a method for photodynamic sterilization and preservation of fresh shrimp. Background technique

[0002] Photodynamic sterilization is a new type of cold sterilization technology, which has the advantages of non-toxicity and no drug resistance. When the photosensitizer is irradiated with visible light, cytotoxic reactive oxygen species (ROS) are generated, which in turn causes extensive oxidative damage to bacterial cells. At present, the sterilization methods of aquatic products mainly include: traditional heat treatment sterilization technology, cold sterilization technology such as irradiation and low temperature plasma, and the preparation of curcumin derivatives based on high photosensitivity sterilization performance and its application in fresh shrimp p...

Examples

Embodiment 1

[0057] Synthesis of curcumin derivative II with high photosensitivity and bactericidal activity, wherein the structural formula of curcumin derivative II is as follows:

[0058]

[0059] , the reaction equation is as figure 1 shown.

[0060] At room temperature, N 2 Under protective conditions, accurately weighed 1 mmol of curcumin and 3 mmol of 4-dimethylaminopyridine were dissolved in a reaction flask with 15 mL of N,N-dimethylformamide, and stirred at room temperature for 1 h, during which 1 mmol of 1-dimethylaminopyridine was added every 20 min. Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, and finally 2 mmol of 3-carboxy-2,2,5, dissolved in 5 mL of N,N-dimethylformamide, was added. 5-tetramethylpyrrolidine-1-oxyl radical, and continue to stir the reaction for 12h. After the reaction, the curcumin derivative II with high photosensitivity and bactericidal activity was obtained through extraction and column chromatography purification, such as: figure 2 As...

Embodiment 2

[0062] At room temperature, N 2 Under protective conditions, accurately weighed 1 mmol of curcumin and 1 mmol of 4-dimethylaminopyridine were dissolved in a reaction flask with 15 mL of N,N-dimethylformamide, and stirred at room temperature for 1 h, during which 0.5 mmol of 1 mmol was added every 30 min. -Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, and finally 3 mmol of 3-carboxy-2,2,5 dissolved in 5 mL of N,N-dimethylformamide was added , 5-tetramethylpyrrolidine-1-oxyl radical, and continue to stir the reaction for 12h. After the reaction, the curcumin derivative II with high photosensitivity and bactericidal activity was obtained by extraction and purification by column chromatography.

Embodiment 3

[0064] The curcumin derivative II of embodiment 1 is applied to the method for the photodynamic sterilization and preservation of fresh shrimp, and the concrete steps are as follows:

[0065] 1) Prepare 10 μM Curcumin Derivative II aqueous solution and fill it in a light-proof watering can;

[0066] 2) Select fresh and complete, brightly colored and uniformly sized Penaeus vannamei, immerse it in ice water and freeze it to death quickly, use sterile saline to wash and drain the surface moisture;

[0067] 3) using the spraying method, the prepared curcumin derivative II aqueous solution in step 1) is sprayed in sufficient amount and uniformly on the surface of the fresh shrimp prepared in step 2), and let stand in the dark for 5min;

[0068] 4) The fresh shrimp prepared in step 3) is placed under a blue LED matrix with a light power of 30W for irradiation for 120s, and the irradiation wavelength is 400nm to complete the process of photodynamic sterilization and preservation.

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