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CN-116283569-B - Preparation process of curcumin esterified derivative

CN116283569BCN 116283569 BCN116283569 BCN 116283569BCN-116283569-B

Abstract

The invention relates to a preparation process of curcumin esterified derivative. The borneol and succinic anhydride are subjected to esterification reaction to prepare borneol succinate, and curcumin and borneol succinate are subjected to esterification reaction to prepare curcumin borneol succinate. Compared with the original curcumin, the curcumin borneol succinate prepared by the invention has stronger antioxidant capacity, maintains the original biological activity of curcumin, and can be added into various dosage forms or multifunctional foods. In addition, the preparation process has the advantages of simple flow, short period, low cost, easy expansion and easy industrialization.

Inventors

  • YU HUIMIN
  • WANG JUNTING
  • SUN YAN
  • SHI GUOYANG
  • ZHANG HANSHUO

Assignees

  • 于慧敏

Dates

Publication Date
20260512
Application Date
20230221

Claims (10)

  1. 1. The preparation process of the curcumin esterified derivative is characterized by comprising the following steps of: (1) Dissolving succinic anhydride, a certain amount of catalyst 4-dimethylaminopyridine DMAP and triethylamine in a solvent, stirring and refluxing at a certain temperature, wherein the feeding ratio is based on the addition amount of the succinic anhydride, and the molar ratio of succinic anhydride to DMAP to triethylamine=1:0.1:0.1-1:3:3; (2) Dissolving a certain amount of borneol in the solvent and dropwise adding the borneol into the reaction liquid in the step (1) for reacting for a period of time; (3) Washing the reaction liquid in the step (2) to be neutral by washing liquid in sequence; (4) Adding a desiccant into the reaction liquid in the step (3) for drying, and performing rotary evaporation and vacuum drying to obtain borneol succinate; (5) Dissolving curcumin and a certain amount of catalyst 4-dimethylaminopyridine DMAP and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride EDC in a solvent, stirring and refluxing at a certain temperature, wherein the feeding proportion takes the additive amount of the curcumin as a reference, and the molar ratio is that curcumin is DMAP, EDC=1:0.1:0.1-1:3:3; (6) Dissolving a certain amount of borneol succinate obtained in the step (4) in a solvent, dropwise adding the solvent into the reaction liquid in the step (5), and reacting for 12-48 hours at 35-60 ℃, wherein the molar ratio of the borneol succinate to the curcumin is 1:1-1:3; (7) Washing the reaction solution in the step (6) to be neutral by washing liquid in sequence; (8) Adding a drying agent into the reaction liquid obtained in the step (7) for drying, and performing rotary evaporation and vacuum drying to obtain a crude product of curcumin borneol succinate; (9) And (3) separating the crude product obtained in the step (8) through a silica gel column to obtain a pure product of curcumin borneol succinate.
  2. 2. The process for preparing an esterified derivative of curcumin according to claim 1, wherein the molar ratio of the borneol to the succinic anhydride in the step (1) to the step (2) is 1:0.1-1:3.
  3. 3. The process for preparing esterified derivatives of curcumin according to claim 1, wherein the reaction solvent in the step (1) and the step (2) is dichloromethane.
  4. 4. The process for preparing an esterified derivative of curcumin according to claim 1, wherein the reaction temperature of the borneol and the succinic anhydride in the step (1) and the step (2) is 25-60 ℃ and the reaction time is 12-48 h.
  5. 5. The process for preparing esterified derivatives of curcumin according to claim 1, wherein the reaction solvent in the step (5) and the step (6) is dichloromethane.
  6. 6. The process for preparing the esterified derivative of curcumin according to claim 1, wherein the silica gel used in the silica gel column in the step (9) is 100-500 meshes, and the mobile phase is petroleum ether, namely ethyl acetate=1:2-2:1.
  7. 7. The process for preparing an esterified derivative of curcumin according to claim 1, wherein the obtained borneol succinate has characteristic peaks at 1744 cm -1 and 2900 cm -1 in infrared spectrum.
  8. 8. The process for preparing an esterified derivative of curcumin according to claim 1, wherein the borneol succinate 1 H nuclear magnetic resonance spectrum obtained has characteristic peaks at 2.23: 2.23 ppm and 4.8: 4.8 ppm.
  9. 9. The process for preparing esterified derivatives of curcumin according to claim 2, characterized in that the obtained infrared spectrum of borneol succinate of curcumin has characteristic peaks at 1250 cm -1 and 1730 cm -1 .
  10. 10. The process for preparing esterified derivatives of curcumin according to claim 2, characterized in that the obtained borneol succinate 1 H nuclear magnetic resonance spectrum has characteristic peaks at 3.8 ppm and 6.7 ppm.

Description

Preparation process of curcumin esterified derivative Technical Field The invention relates to the technical field of chemical synthesis and improvement of oxidation resistance of natural products, and mainly relates to a preparation process of curcumin esterified derivatives, which provides a curcumin esterified product, namely curcumin borneol succinate, and improves the oxidation resistance of curcumin. Background Curcumin was first isolated in 1870 from turmeric as a low relative molecular weight polyphenol, which was orange-yellow crystalline powder with slightly bitter taste and insoluble in water. With the increasing depth of research on curcumin, it has been found that curcumin has wide pharmacological activities of anti-inflammatory, antioxidant, lipid regulating, antiviral, anti-infective, anti-tumor, anticoagulative, anti-hepatic fibrosis, anti-atherosclerosis and the like, and has low toxicity and small adverse reaction. In view of the fact that the modern medical research discovers that the occurrence of a plurality of diseases of human bodies is related to the participation of free radical formation and inflammatory reaction, the antioxidant activity and the anti-inflammatory effect of curcumin have attracted extensive attention of domestic and foreign scholars. Borneol, also called borneol, etc. is obtained by steam distillation and recrystallization of the stems and leaves of blumea balsamifera of Compositae or the branches and leaves of borneol camphor of Lauraceae. The chemical component is 2-alcohol, and the chemical formula is C 10Ｈ18 O. Also useful are turpentines obtained by a series of chemical processes. It can be used for inducing resuscitation, dispelling pathogenic fire, removing nebula, improving eyesight, relieving swelling and pain, clearing heat and toxic materials, and removing pathogenic fire and toxic materials. For treating mammary gland caking, apoplexy, vomiting, fever, coma, convulsion, epilepsy, phlegm, deafness due to qi-obstruction, pharyngitis, aphtha, otitis media, carbuncle, hemorrhoid, nebula, enterobiasis, etc. Disclosure of Invention Based on the facts, the curcumin structure is modified by the borneol, so that the antioxidant capacity of the curcumin is remarkably improved on the basis of keeping the original activity. And the curcumin esterified derivative is fully characterized. The process has the advantages of simple operation, short preparation period, low cost, easy expansion and easy industrialization. In order to achieve the above object, the present invention provides the following technical solutions: The invention provides a preparation process of a curcumin esterified derivative, which comprises the following steps: (1) Succinic anhydride and a certain amount of catalyst are dissolved in a solvent, and the mixture is stirred and refluxed at a certain temperature. (2) Dissolving a certain amount of borneol in the solvent and dropwise adding the solution into the reaction solution in the step (1) for reacting for a period of time. (3) And (3) washing the reaction liquid in the step (2) to be neutral by washing liquid in sequence. (4) And (3) adding a drying agent into the reaction liquid in the step (3) for drying, and performing rotary evaporation and vacuum drying to obtain the borneol succinate. (5) Curcumin and a certain amount of catalyst are dissolved in a solvent, and the mixture is stirred and refluxed at a certain temperature. (6) Dissolving a certain amount of borneol succinate obtained in the step (4) in a solvent, dropwise adding the solvent into the reaction solution in the step (5), and reacting for a period of time. (7) And (3) washing the reaction solution in the step (6) to be neutral by washing liquid in sequence. (8) And (3) adding a drying agent into the reaction liquid obtained in the step (7) for drying, and performing rotary evaporation and vacuum drying to obtain a crude product of curcumin borneol succinate. (9) And (3) separating the crude product obtained in the step (8) through a silica gel column to obtain a pure product of curcumin borneol succinate. Preferably, the molar ratio of the borneol in the step (1) to the borneol in the step (2) to the succinic anhydride is 1:0.1-1:3. Preferably, the reaction solvent of the step (1) and the step (2) is dichloromethane. Preferably, the catalyst of the step (1) is 4-Dimethylaminopyridine (DMAP) and triethylamine. The feeding proportion is based on the addition amount of succinic anhydride, and the molar ratio of succinic anhydride to DMAP to triethylamine=1:0.1:0.1-1:3:3. Preferably, the reaction temperature of the borneol and the succinic anhydride in the step (1) and the step (2) is 25-60 ℃ and the reaction time is 12-48 hours. Preferably, the washing liquid in the step (3) and the washing liquid in the step (4) are dilute hydrochloric acid and pure water in sequence of 0.1 mol/mL. The desiccant is anhydrous sodium sulfate. Preferably, the molar ratio of the borneol succinate i