High-water-solubility cumin aldehyde inclusion compound and preparation method thereof
The encapsulation of cinnamaldehyde in water-soluble calixarene addresses the solubility and bioavailability issues of cinnamaldehyde, enhancing its effectiveness against Root cancer-inducing bacteria and facilitating industrial production.
Patent Information
- Application Number
- CN202510470342.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-04-15
- Publication Date
- 2025-07-15
AI Technical Summary
The water solubility of Kuminaldehyde is poor and has low bioavailability, which leads to its poor effect when dealing with Agrobacterium tumefaciens, affecting plant growth and forming coronaviruses.
The kumming aldehyde is embedded in a water-soluble column [5] aromatic hydrocarbon. By preparing a highly water-soluble kumming aldehyde inclusion compound, it includes the inclusion process of the water-soluble column [5] aromatic hydrocarbon and kumming aldehyde. The specific steps include dissolution, grinding, centrifugation, freeze-drying, etc.
It improves the water solubility and bioavailability of Kumingaldehyde, reduces the use of Kumingaldehyde, reduces the cost, and avoids toxic side effects, and has broad market prospects.
Smart Images
Figure CN120304407A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to the technical field of agrochemistry, and particularly to a high-water-solubility cumin aldehyde clathrate and a preparation method thereof. Background Art
[0002] Agrobacterium tumefaciens is a soil-borne bacterium famous for its DNA transfer ability and is widely used in plant transformation. Although there has always been interest in the efficacy of Agrobacterium tumefaciens, overuse of Agrobacterium tumefaciens can mainly infect plant tissues, leading to abnormal plant growth, inhibiting normal root development, affecting the plant's ability to absorb nutrients and water, and forming tumors. After being infected with this bacterium, a series of reactions will be triggered in the plant, leading to the synthesis of a very common compound - crown gall, which in turn causes the transformed cells to become cancerous and ultimately leads to the formation of crown gall tumors. The occurrence of crown gall will lead to a reduction in a variety of cash crops, having a negative impact on agricultural output value.
[0003] Research has found that cumin aldehyde has significant antibacterial effects and can be used to treat Agrobacterium tumefaciens. However, cumin aldehyde has poor water solubility and low bioavailability, and cannot be well absorbed by plants and play its role. Summary of the Invention
[0004] To solve the problems mentioned in the background art and improve the water solubility of cumin aldehyde, the purpose of the present invention is to provide a high-water-solubility cumin aldehyde clathrate.
[0005] To achieve the above goal, the technical solution of the present invention is as follows:
[0006] A high-water-solubility cumin aldehyde clathrate, comprising cumin aldehyde and water-soluble pillar[5]arene, wherein the cumin aldehyde is embedded in the water-soluble pillar[5]arene.
[0007] The purpose of the present invention also includes a preparation method of the high-water-solubility cumin aldehyde clathrate, and the preparation method includes the following steps:
[0008] S1: Add cumin aldehyde to an appropriate amount of ethanol and dissolve it fully. Then, drop the cumin aldehyde-ethanol solution into water-soluble pillar[5]arene and grind it fully until the mixture is completely dry. Among them, the molar ratio of cumin aldehyde to water-soluble pillar[5]arene is 1:1;
[0009] S2: Use absolute ethanol to repeatedly rinse the obtained dry mixture to remove the unincorporated cumin aldehyde;
[0010] S3: Add an appropriate amount of distilled water to the dry mixture to dissolve it, and then perform high-speed centrifugation and freeze-drying to obtain a water-soluble pillar[5]arene-cumin aldehyde clathrate.
[0011] Further, in the step S1, cumin aldehyde is fully dissolved in the ethanol solution by ultrasonic dispersion.
[0012] Further, the water-soluble pillar[5]arene is prepared by the following method:
[0013] A1: Dissolve hydroquinone in an acetone solution under a nitrogen atmosphere. Add 1,2-dibromoethane and anhydrous potassium carbonate to the hydroquinone-acetone mixture, stir at 62°C for 24 hours, filter by suction to collect the filtrate, and rotary evaporate to dryness;
[0014] A2: Extract the organic layer in the filtrate with water and dichloromethane, then wash with hydrochloric acid and sodium hydroxide respectively, crystallize and filter by suction to obtain the filter cake, and obtain product A;
[0015] A3: Weigh a certain amount of product A and dissolve it in a dichloromethane solution under a nitrogen atmosphere. Add paraformaldehyde and stir at room temperature for 20 minutes, then add boron trifluoride diethyl ether, react for 3 hours. When the raw materials are reacted completely, add methanol to terminate the reaction, filter by suction to collect the filter cake, and perform column chromatography to obtain product B;
[0016] A4: Weigh a certain amount of product B and dissolve it in an ethanol solution, stir at room temperature for 5 minutes. Under ice bath conditions, add a trimethylamine ethanol solution to the product B-ethanol solution, reflux in an 80°C water bath for 15 hours, rotary evaporate to remove the solvent, then add 10 mL of distilled water, filter by suction, extract, clarify, filter, rotary evaporate to remove the water, and vacuum dry at 65°C to obtain the water-soluble pillar[5]arene.
[0017] The beneficial effects of the present invention are as follows: A water-soluble pillar[5]arene-kumin aldehyde inclusion compound is designed, which greatly improves the problems of poor water solubility and low bioavailability of kumin aldehyde, enables kumin aldehyde to be better absorbed and play its role, and can reduce the input amount of kumin aldehyde so as to save costs; the kumin aldehyde-water-soluble pillar[5]arene inclusion compound has good biological safety, can effectively avoid potential hazards and side effects of kumin aldehyde drug molecules, and has a broad market prospect; moreover, the preparation method of the kumin aldehyde-water-soluble pillar[5]arene inclusion compound in the present invention has a simple process flow and is easy to industrialize production. Description of the Drawings
[0018] Figure 1 It is a comparative schematic diagram of Agrobacterium tumefaciens before and after the pillar[5]arene-kumin aldehyde inclusion compound is used for corn root hairs. Detailed Embodiments
[0019] Next, the technical solutions of the present invention will be clearly and completely described in conjunction with the embodiments of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art belong to the protection scope of the present invention.
[0020] The preparation process of water-soluble column [5] aromatic hydrocarbon-cumaldehyde inclusion complex is as follows: First, water-soluble column [5] aromatic hydrocarbon is prepared, and the steps are as follows: 9.9 g of hydroquinone is dissolved in 60 mL of acetone solution under nitrogen atmosphere, 30 mL of 1,2-dibromoethane and 37.3 g of anhydrous K2CO3 are added, and stirred at 62°C for 24 hours, and the filtrate is collected by suction filtration and rotary evaporation to dry. The organic layer in the filtrate is extracted with 150 mL of water and 150 mL of dichloromethane, and then washed with 100 mL of 0.5 mol / L HCl and 100 mL of 0.5 mol / L sodium hydroxide, respectively, and the filter cake is obtained by recrystallization and suction filtration to obtain product A. Under nitrogen atmosphere, 3.3 g of product A was dissolved in 120 mL of dichloromethane solution, 0.38 g of paraformaldehyde was added and stirred at room temperature for 20 minutes, then 1.45 mL of boron trifluoride ether was added and reacted for 3 hours. After the reaction of the raw materials was completed, methanol was added to terminate the reaction, the filter cake was collected by suction filtration, and column chromatography was performed to obtain B. 0.8 g of product B was dissolved in 40 mL of ethanol solution, stirred at room temperature for 5 minutes, 5.63 mL of trimethylamine ethanol solution was added to the product B-ethanol mixture in an ice bath, refluxed in an 80°C water bath for 15 hours, and the solvent was removed by rotary evaporation. Then 10 mL of distilled water was added, suction filtered, extracted, clarified, filtered, and water was removed by rotary evaporation. It was then vacuum dried at 65°C for 48 hours to obtain water-soluble column [5] aromatic hydrocarbons. Secondly, a water-soluble column [5] aromatic hydrocarbon-cumaldehyde inclusion complex is prepared by wet grinding, and the steps are as follows: 1.2 g of water-soluble column [5] aromatic hydrocarbon and 0.15 g of cumaldehyde are weighed according to a molar ratio of 1:1 between the water-soluble column [5] aromatic hydrocarbon and the cumaldehyde, and the cumaldehyde is added to 2 mL of ethanol and fully dissolved by ultrasonic dispersion. Subsequently, the cumaldehyde ethanol solution is gradually added dropwise to a mortar containing the water-soluble column [5] aromatic hydrocarbon and fully ground for about 40 minutes until the mixture is completely dry. The obtained dry mixture is then repeatedly rinsed 3 times with anhydrous ethanol to remove the cumaldehyde not included, and then an appropriate amount of distilled water is added to dissolve it, and high-speed centrifugation and freeze-drying are performed to obtain a water-soluble column [5] aromatic hydrocarbon-cumaldehyde inclusion complex.
[0021] Figure 1 Schematic diagram of the comparison of the effect of column [5] aromatic hydrocarbon-cumaldehyde inclusion complex on Agrobacterium tumefaciens before and after application in corn roots.
[0022] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. All modifications, equivalent substitutions, improvements, etc. within the spirit and principles of the present invention should be included in the protection scope of the present invention.
Claims
1. A highly water-soluble cumin aldehyde clathrate, characterized in that, It comprises cuminaldehyde and water-soluble column [5] aromatic hydrocarbon, wherein the cuminaldehyde is embedded in the water-soluble column [5] aromatic hydrocarbon.
2. A preparation method of a high-water-solubility cumin aldehyde inclusion compound, characterized in that, The steps include: S1: adding cumaldehyde to an appropriate amount of ethanol to fully dissolve, then dropping the cumaldehyde-ethanol solution into the water-soluble column [5] aromatic hydrocarbon and grinding the mixture until the mixture is completely dry, wherein the molar ratio of cumaldehyde to the water-soluble column [5] aromatic hydrocarbon is 1:1; S2: repeatedly washing the obtained dry mixture with anhydrous ethanol to remove the uncontained cumaldehyde; S3: Add an appropriate amount of distilled water to the dry mixture to dissolve it, then centrifuge at high speed and freeze-dry to obtain a water-soluble column [5] aromatic hydrocarbon-cumaldehyde inclusion complex.
3. The preparation method according to claim 2, characterized in that, In the step S1, cuminaldehyde is fully dissolved in the ethanol solution by ultrasonic dispersion.
4. The preparation method according to claim 2 or 3, characterized in that, The water-soluble column [5] aromatic hydrocarbon is prepared by the following method: A1: Dissolve hydroquinone in acetone solution under nitrogen atmosphere, add 1,2-dibromoethane and anhydrous potassium carbonate to the hydroquinone-acetone mixture, stir at 62°C for 24 hours, collect the filtrate by suction, and dry it by rotary evaporation; A2: The organic layer in the filtrate is extracted with water and dichloromethane, then washed with hydrochloric acid and sodium hydroxide respectively, recrystallized and filtered to obtain a filter cake to obtain product A; A3: Weigh a certain amount of product A and dissolve it in a dichloromethane solution under a nitrogen atmosphere, add paraformaldehyde and stir at room temperature for 20 minutes, then add boron trifluoride etherate and react for 3 hours. When the reaction of the raw materials is complete, add methanol to terminate the reaction, collect the filter cake by suction, and obtain product B by column chromatography; A4: Weigh a certain amount of product B and dissolve it in ethanol solution. Stir at room temperature for 5 minutes. Add trimethylamine ethanol solution to the product B-ethanol solution under ice bath conditions. Reflux in an 80°C water bath for 15 hours. Remove the solvent by rotary evaporation. Add 10 mL of distilled water, filter, extract, clarify, filter, remove water by rotary evaporation, and vacuum dry at 65°C to obtain water-soluble columnar [5] aromatic hydrocarbons.