Method for extracting alkaloid compounds in fructus evodiae

Abstract

The invention belongs to the technical field of extraction of active ingredients of traditional Chinese medicines and natural medicines, and particularly relates to a method for extracting alkaloid compounds in fructus evodiae. The extraction method comprises the following steps: mixing evodia rutaecarpa powder and a deep-eutectic solvent, and carrying out ultrasonic extraction to obtain the alkaloid compound, the eutectic solvent comprises a hydrogen bond acceptor and a hydrogen bond donor; the hydrogen bond receptor is menthol; the hydrogen bond donor is formic acid. According to the method disclosed by the invention, the eutecticevaporate solvent is used for extracting the fructus evodiae powder under the assistance of ultrasonic waves, the extraction rate of alkaloid compounds is high, and the evodiamine, the rutaecarpin, the 1-methyl-2-nonylquinoline-4 (1H)-ketone, the 1-methyl-2-undecyl-4 (1H)-quinolone, the evodiamine, the 1-methyl-2-[(6Z, 9Z)-6, 7, 8-tetramethyl-1, 3, 4, 5, 6-tetramethyl-1, 3, 5-tetramethyl-1, 3, 5-tetramethyl-1, 3, 5-tetramethyl-1, 3, 5-tetramethyl-1, 3 The compound is composed of seven target compounds, i.e., 2, 3, 4, 6, 7, 9-pentadecadiene]-4 (1H)-quinolone and dihydroevodia rutaecarpin.

Description

Technical Field

[0001] This invention belongs to the field of extraction technology of active ingredients of traditional Chinese medicine and natural drugs, and specifically relates to a method for extracting alkaloid compounds from Evodia rutaecarpa. Background Technology

[0002] Evodia rutaecarpa is a plant belonging to the genus Tetradium in the family Rutaceae. Tetradium ruticarpum The dried, nearly mature fruit of *A. Jussieu* TG Hartley, also known as *Evodia rutaecarpa*, is pungent, bitter, and hot in nature, with slight toxicity. It possesses properties of dispelling cold and relieving pain, suppressing nausea and vomiting, and tonifying yang and stopping diarrhea. It is primarily used to treat Jueyin headache, cold hernia abdominal pain, and cold-damp beriberi. *Evodia rutaecarpa* is a commonly used traditional Chinese medicine with a long history of use, first recorded in the *Shennong Bencao Jing* (Shennong's Classic of Materia Medica). It is one of the famous "Three Seeds and One Shell" (gardenia, plantain, *Evodia rutaecarpa*, and *Citrus aurantium*) medicinal materials of Jiangxi Province, and also one of the "Ten Flavors of Jiangxi" medicinal materials. Modern pharmacological studies have shown that it has anti-inflammatory, anti-ulcer, anti-tumor, antibacterial, analgesic, and antihypertensive effects. It is widely used in clinical prescriptions and compound preparations, such as Hua Tuo Zaizao Wan, Wu Zhu Yu Tang, and Zuo Jin Wan, all famous and classic Chinese medicines and prescriptions containing *Evodia rutaecarpa*. Among them, Wu Zhu Yu Tang is often used clinically to treat inflammatory diseases such as acute and chronic gastritis, peptic ulcers, chronic prostatitis and eczema.

[0003] The chemical components of Evodia rutaecarpa mainly include alkaloids, bitter substances, flavonoids, and volatile oils. Among them, alkaloids and limonene compounds are the main active ingredients and also the main anti-inflammatory active substances. Alkaloids can be mainly divided into indole alkaloids and quinolone alkaloids according to their structural type. Currently, various traditional extraction methods are used to extract alkaloids from Evodia rutaecarpa, such as decoction, percolation, and Soxhlet extraction, but these methods suffer from low extraction rates. Summary of the Invention

[0004] In view of this, the purpose of this invention is to provide a method for extracting alkaloids from Evodia rutaecarpa. The extraction method provided by this invention achieves a high extraction rate of alkaloids from Evodia rutaecarpa.

[0005] This invention provides a method for extracting alkaloids from Evodia rutaecarpa, comprising the following steps: Evodia rutaecarpa powder was mixed with a eutectic solvent and subjected to ultrasonic extraction to obtain alkaloid compounds; the alkaloid compounds include one or more of the following: evodiamine, evodiamine alkaloid, 1-methyl-2-nonylquinoline-4(1H)-one, 1-methyl-2-undecyl-4(1H)-quinolone, evodiamine alkaloid, 1-methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone, and dihydroevodiamine alkaloid; The eutectic solvent includes a hydrogen bond acceptor and a hydrogen bond donor; the hydrogen bond acceptor is menthol; and the hydrogen bond donor is formic acid.

[0006] Preferably, the molar ratio of the hydrogen bond acceptor to the hydrogen bond donor is 1:1 to 6.

[0007] Preferably, the power of the ultrasonic extraction is 180~480W.

[0008] Preferably, the temperature for ultrasonic extraction is 20~70℃.

[0009] Preferably, the ultrasonic extraction time is 20-120 min.

[0010] Preferably, the mass ratio of the Evodia rutaecarpa powder to the volume ratio of the eutectic solvent is 1g:10~35mL.

[0011] Preferably, the molar ratio of the hydrogen bond acceptor to the hydrogen bond donor is 1:2; the ultrasonic extraction power is 300W, the temperature is 30℃, and the time is 40min; the mass ratio of the Evodia rutaecarpa powder to the volume ratio of the eutectic solvent is 1g:20mL.

[0012] Preferably, the ultrasonic extraction further includes: solid-liquid separation of the obtained mixture; the solid-liquid separation is centrifugation, the centrifugation speed is 8000~12000 rpm, and the time is 5~20 min.

[0013] Preferably, the method for preparing the eutectic solvent includes the following steps: mixing and heating a hydrogen bond acceptor and a hydrogen bond donor to obtain a eutectic solvent; the mixing and heating temperature is 80~95℃ and the time is 90~180min.

[0014] Preferably, the eutectic solvent further includes water, and the volume fraction of water in the eutectic solvent is 10-30%.

[0015] Compared with the prior art, the present invention has the following beneficial effects: This invention provides a method for extracting alkaloids from Evodia rutaecarpa, comprising the following steps: mixing Evodia rutaecarpa powder with a eutectic solvent and performing ultrasonic extraction to obtain alkaloids; the alkaloids include one or more of evodiamine, evodiamine alkaloid, 1-methyl-2-nonylquinoline-4(1H)-one, 1-methyl-2-undecyl-4(1H)-quinolone, evodiamine alkaloid, 1-methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone, and dihydroevodiamine alkaloid; the eutectic solvent comprises a hydrogen bond acceptor and a hydrogen bond donor; the hydrogen bond acceptor is menthol; and the hydrogen bond donor is formic acid.

[0016] This invention employs a eutectic solvent supplemented with ultrasound to extract Evodia rutaecarpa powder. The strong hydrogen bonding between the eutectic solvent and the target compounds facilitates extraction. This invention achieves a high extraction rate of alkaloids from Evodia rutaecarpa powder and can extract multiple alkaloids in a single extraction, including evodiamine, evodiamine alkaloid, 1-methyl-2-nonylquinoline-4(1H)-one, 1-methyl-2-undecyl-4(1H)-quinolone, evodiamine alkaloid, 1-methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone, and dihydroevodiamine alkaloid. Compared to traditional organic solvents, this invention utilizes a eutectic solvent, which significantly improves the extraction rate of alkaloids from Evodia rutaecarpa.

[0017] Moreover, the eutectic solvent of the present invention has the advantages of being degradable, low-cost, non-toxic and harmless, which is of great significance for the green extraction of active ingredients of traditional Chinese medicine and natural drugs. Attached Figure Description

[0018] To more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the drawings used in the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0019] Figure 1 This is the standard curve of the evodiamine standard in Example 1; Figure 2 This is the standard curve of the Evodia rutaecarpa alkaloid standard in Example 1; Figure 3 This is the standard curve of the 1-methyl-2-nonylquinoline-4(1H)-one standard in Example 1; Figure 4 This is the standard curve of the 1-methyl-2-undecyl-4(1H)-quinolone standard in Example 1; Figure 5 This is the standard curve chromatogram of the Evodia rutaecarpa standard in Example 1; Figure 6 This is the standard curve of the 1-methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone standard in Example 1; Figure 7 This is the standard curve of the dihydroevodiamine standard in Example 1; Figure 8 The figure shows the extraction rate of seven target compounds by eutectic solvents synthesized with different molar ratios of hydrogen bond acceptors and hydrogen bond donors in Example 2. Figure 9The extraction rates of the seven target compounds under different ultrasonic powers in Example 2 are shown in the graph. Figure 10 The extraction rates of the seven target compounds at different extraction temperatures in Example 2 are shown in the graph. Figure 11 The extraction rates of the seven target compounds under different ultrasonic times in Example 2 are shown in the graph. Figure 12 This is a characterization graph of the extraction rates of the seven target compounds under different liquid-to-solid ratios in Example 2. Detailed Implementation

[0020] This invention provides a method for extracting alkaloids from Evodia rutaecarpa, comprising the following steps: Evodia rutaecarpa powder was mixed with a eutectic solvent and subjected to ultrasonic extraction to obtain alkaloid compounds; the alkaloid compounds include one or more of the following: evodiamine, evodiamine alkaloid, 1-methyl-2-nonylquinoline-4(1H)-one, 1-methyl-2-undecyl-4(1H)-quinolone, evodiamine alkaloid, 1-methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone, and dihydroevodiamine alkaloid; The eutectic solvent includes a hydrogen bond acceptor and a hydrogen bond donor; the hydrogen bond acceptor is menthol; and the hydrogen bond donor is formic acid.

[0021] Unless otherwise specified, all materials and equipment used in this invention are commercially available products in the field.

[0022] In this invention, the particle size of the Evodia rutaecarpa powder is preferably 30-50 mesh.

[0023] In this invention, the method for preparing the eutectic solvent preferably includes the following steps: mixing and heating a hydrogen bond acceptor and a hydrogen bond donor to obtain a eutectic solvent; the mixing and heating temperature is preferably 80~95℃, specifically 85℃, and the time is preferably 90~180min, specifically 90min; the mixing and heating process is preferably accompanied by stirring, and the obtained eutectic solvent is a clear liquid.

[0024] In this invention, the eutectic solvent preferably further includes water, and the volume fraction of water in the eutectic solvent is preferably 10-30%, specifically 20%.

[0025] Compared to eutectic solvents composed of other hydrogen bond acceptors (such as choline chloride, betaine, and citric acid) and hydrogen bond donors (polyols, organic acids, sugars, phenols, and amines), this invention uses menthol as the hydrogen bond acceptor and formic acid as the hydrogen bond donor to form a eutectic solvent, resulting in high extraction efficiency for alkaloids. The polyols include one or more of ethylene glycol, 1,2-propanediol, glycerol, tert-butanol, 1,3-butanediol, and xylitol; the organic acids include one or more of hydroxysuccinic acid, acetopropionic acid, lactic acid, p-toluenesulfonic acid, and pyruvic acid; the sugars include fructose and / or glucose; the phenols include 1,3-benzenediol; and the amines include urea.

[0026] In this invention, the molar ratio of the hydrogen bond acceptor to the hydrogen bond donor is preferably 1:1 to 6, specifically 1:1, 1:2, 1:3, 1:4, 1:5, or 1:6. With this molar ratio, formic acid can form more hydrogen bond networks and bind better to alkaloids without diluting the hydrophobic microenvironment of menthol. This results in a high partition coefficient of the target compound in the organic phase, thereby improving the extraction rate of alkaloid compounds.

[0027] In this invention, the preferred solid-liquid ratio (mass of Evodia rutaecarpa powder to volume of the eutectic solvent) is 1g:10~35mL, specifically 1g:10mL, 1g:15mL, 1g:20mL, 1g:25mL, 1g:30mL, or 1g:35mL. This solid-liquid ratio results in a high extraction rate for alkaloid compounds.

[0028] In this invention, the ultrasonic extraction process preferably includes soaking the system obtained by mixing Evodia rutaecarpa powder and a eutectic solvent overnight.

[0029] In this invention, the preferred power for ultrasonic extraction is 180-480W, specifically 180W, 240W, 300W, 360W, 420W, or 480W; the preferred temperature for ultrasonic extraction is 20-70℃, specifically 20℃, 30℃, 40℃, 50℃, 60℃, or 70℃; and the preferred extraction time is 20-120min, specifically 20min, 30min, 40min, 60min, 80min, or 120min. The power, temperature, and time of ultrasonic extraction described in this invention result in a high extraction rate for alkaloid compounds.

[0030] In this invention, the ultrasonic extraction preferably further includes: solid-liquid separation of the obtained mixture, and removal of the eutectic solvent (DES) from the obtained extract to obtain alkaloid compounds. The solid-liquid separation is preferably centrifugation, with a centrifugation speed preferably between 8000 and 12000 rpm, specifically 10000 rpm, and a centrifugation time preferably between 5 and 20 minutes, specifically 10 minutes; the removal of the eutectic solvent (DES) is preferably performed using a macroporous adsorption resin.

[0031] In this invention, the method for determining the content of alkaloid compounds in the extract preferably includes the following steps: The extract was diluted with methanol and filtered through a membrane for liquid chromatography detection. The content of alkaloid compounds was determined based on the obtained peak area and a predetermined standard curve. The conditions for the liquid chromatography detection included: column: Waters XBridge® C18 column; flow rate: 1 mL / min; mobile phase A: methanol; mobile phase B: water and diethylamine; gradient elution program: 0–30 min, mobile phase A volume fraction increased from 50% to 78%; 30–70 min, mobile phase A volume fraction increased from 78% to 100%; detection wavelength: 210 nm; column temperature: 30 °C; injection volume: 10 μL.

[0032] In this invention, the dilution factor is preferably 6 times; the pore size of the filter membrane is preferably 0.22 μm. The specifications of the Waters XBridge® C18 column are preferably 5 μm, 250 mm × 4.6 mm ID; the volume concentration of diethylamine in the mobile phase B is preferably 0.015%. The determination method of this invention can simultaneously separate and detect seven alkaloid components in Evodia rutaecarpa, including evodiamine, evodiamine alkaloid, 1-methyl-2-nonylquinoline-4(1H)-one, 1-methyl-2-undecyl-4(1H)-quinolone, evodiamine alkaloid, 1-methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone and dihydroevodiamine alkaloid.

[0033] This invention is the first to use a designed and synthesized hydrophobic eutectic solvent (DES) for the extraction of alkaloids from Evodia rutaecarpa, which is more efficient and environmentally friendly than traditional solvents, and has a high extraction rate.

[0034] To further illustrate the present invention, the extraction method of alkaloid compounds from Evodia rutaecarpa provided by the present invention will be described in detail below with reference to the accompanying drawings and embodiments, but these should not be construed as limiting the scope of protection of the present invention.

[0035] Example 1 1. Standard curves of 7 target compounds (1) Preparation of standard solutions Accurately weigh 0.20 mg of 1-methyl-2-nonylquinoline-4(1H)-one and add methanol to prepare a standard solution with a concentration of 0.10 mg / mL of 1-methyl-2-nonylquinoline-4(1H)-one.

[0036] (2) Preparation of mixed standard solutions Accurately weigh 0.80 mg of evodiamine, 0.34 mg of evodiamine alkaloid, 0.22 mg of 1-methyl-2-undecyl-4(1H)-quinolone, 0.27 mg of evodiamine alkaloid, 0.18 mg of 1-methyl-2-[(6Z,9Z)-6,9-pentadecanadiene]-4(1H)-quinolone and 0.24 mg of dihydroevodiamine alkaloid, and dissolve in methanol to prepare a mixed standard solution of evodiamine alkaloid 0.40 mg / mL, evodiamine alkaloid 0.17 mg / mL, 1-methyl-2-undecyl-4(1H)-quinolone 0.11 mg / mL, evodiamine alkaloid 0.135 mg / mL, 1-methyl-2-[(6Z,9Z)-6,9-pentadecanadiene]-4(1H)-quinolone 0.09 mg / mL and dihydroevodiamine alkaloid 0.12 mg / mL.

[0037] (3) Chromatographic conditions for HPLC-PDA content determination Chromatographic column: Waters XBridge® C18 column (5 μm, 250 mm × 4.6 mm ID); flow rate: 1 mL / min; mobile phase A: methanol; mobile phase B: water and diethylamine (diethylamine volume concentration: 0.015%); gradient elution program: 0–30 min, mobile phase A volume fraction increased from 50% to 78%; 30–70 min, mobile phase A volume fraction increased from 78% to 100%; detection wavelength: 210 nm; column temperature: 30 ℃; injection volume: 10 μL.

[0038] (4) Linearity range study of HPLC-PDA content determination The single standard solution in (1) and the mixed standard solution in (2) were halved to obtain single and mixed standard solutions with gradient concentrations, which were then determined according to the chromatographic conditions in (3). Linear regression was performed with the peak area of ​​the chromatographic peak as the ordinate (y) and the concentration of each component in the single and mixed standards as the abscissa (x), yielding the regression equation. The results are shown in Table 1. The standard curves of the seven target compounds are shown below. Figures 1-7 As shown.

[0039] Table 1. Results of linear relationship investigation for the 7 target compounds.

[0040] 2. Green and efficient extraction of alkaloids from Evodia rutaecarpa using a eutectic solvent, including the following steps: Accurately weigh the Evodia rutaecarpa powder, add a eutectic solvent, vortex, soak overnight, and then ultrasonically extract for a period of time at a certain temperature and ultrasonic power. After centrifuging the mixture at 10,000 rpm for 10 min, take the supernatant, dilute it 6 times with methanol, and filter it through a 0.22 μm microporous membrane to obtain the Evodia rutaecarpa powder extract to be tested.

[0041] (1) Preparation of choline chloride-ethylene glycol, choline chloride-1,2-propanediol, choline chloride-glycerol, choline chloride-xylitol, choline chloride-hydroxysuccinic acid, choline chloride-acetylpropionic acid, choline chloride-lactic acid, choline chloride-p-toluenesulfonic acid, choline chloride-1,3-benzenediol, choline chloride-urea, choline chloride-fructose, choline chloride-glucose, betaine-ethylene glycol, betaine-acetylphenyl acid, betaine-lactic acid, betaine-xylitol, betaine-glycerol, betaine-glucose, citric acid-glycerol, citric acid-ethylene glycol, menthol-formic acid, menthol-pyruvic acid, menthol-lactic acid, menthol-glycerol, menthol-acetyl The study included 35 eutectic solvents: propionic acid, menthol-1,3-butanediol, menthol-tert-butanol, choline chloride-ethylene glycol-lactic acid, choline chloride-hydroxysuccinic acid-urea, betaine-glycerol-glucose, betaine-lactic acid-glycerol, menthol-levulinic acid-1,3-butanediol, menthol-levulinic acid-tert-butanol, menthol-1,3-butanediol-tert-butanol, and menthol-levulinic acid-1,3-butanediol-tert-butanol. Among them, DES1~DES20 were binary hydrophilic, DES21~DES27 were binary hydrophobic, DES28~DES31 were ternary hydrophilic, and DES32~DES35 were multi-component hydrophobic. Hydrogen bond acceptor (HBA) and hydrogen bond donor (HBD) were mixed with water according to the proportions in Table 2, and heated in an oil bath at 85°C for 1.5 h until clear. During heating, the mixture was stirred continuously to ensure that the solution was mixed evenly.

[0042] Table 2. Types of eutectic solvents used for extraction.

[0043] (2) Screening of eutectic solvents The extraction rates of seven target compounds from Evodia rutaecarpa using different types of eutectic solvents were investigated to select the optimal eutectic solvent. 0.1 g of Evodia rutaecarpa powder was weighed and placed in a 7 mL centrifuge tube. Thirty-five different eutectic solvents and traditional solvents (water, ethyl acetate, and methanol) were added at a liquid-to-solid ratio of 20 mL / g, mixed thoroughly, and left to stand overnight. The mixture was then ultrasonically extracted at 30 °C (240 W) for 30 min. The mixture was centrifuged at 10,000 rpm for 10 min, and the supernatant (extract) was collected. This extract was diluted 6-fold with chromatographic grade methanol and filtered through a 0.22 μm microporous membrane. Finally, HPLC was used to quantify each extract, and the extraction rate (mg of target compound extracted per g of Evodia rutaecarpa powder) was calculated. The results are shown in Table 3.

[0044] Table 3 Extraction rates of seven target compounds from Evodia rutaecarpa using different eutectic solvents

[0045] DES-21 forms weak interactions such as hydrogen bonds with alkaloids in Evodia rutaecarpa, resulting in lower binding energies and easier extraction of more alkaloid components. The seven target compounds—evodiamine, evodiamine alkaloid, 1-methyl-2-nonylquinoline-4(1H)-one, 1-methyl-2-undecyl-4(1H)-quinolone, evodiamine neoalkaloid, 1-methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone, and dihydroevodiamine neoalkaloid—achieved the highest total extraction rate of 68.64 mg / g in the eutectic solvent DES-21 (menthol:formic acid). Furthermore, the extraction rates of all seven target compounds using DES-21 were higher than those using traditional solvents (water, methanol, ethyl acetate).

[0046] In the ultrasound-assisted extraction method, the total extraction rate of the seven target components in Evodia rutaecarpa by DES-21 was higher than that by using water, methanol, and ethyl acetate as solvents. Therefore, DES-21 was selected as the optimal extraction solvent for subsequent experiments.

[0047] Example 2 1. A eutectic solvent (DES-21) was used, and the molar ratio of hydrogen bond acceptor to hydrogen bond donor was 1:1, 1:2, 1:3, 1:4, 1:5, and 1:6, respectively. The remaining steps and conditions were the same as in Example 1.

[0048] Figure 8The extraction rates of seven target compounds are characterized by eutectic solvents (DES-21) synthesized with different molar ratios of hydrogen bond acceptors and hydrogen bond donors. EVOD, RUT, NQL, UQL, EVOC, PDQL, DHCP, and TA represent evodiamine, evodiamine alkaloid, 1-methyl-2-nonylquinoline-4(1H)-one, 1-methyl-2-undecyl-4(1H)-quinolone, evodiamine alkaloid, 1-methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone, dihydroevodiamine alkaloid, and total alkaloids, respectively.

[0049] Depend on Figure 8 It was found that under the condition that the molar ratio of hydrogen bond acceptor (menthol) to hydrogen bond donor (formic acid) was 1:1 to 6, all seven target compounds showed good extraction efficiency. Among them, the extraction efficiency was 67.08 mg / g when the molar ratio was 1:1, 73.48 mg / g when the molar ratio was 1:2, 71.86 mg / g when the molar ratio was 1:3, 71.90 mg / g when the molar ratio was 1:4, 70.82 mg / g when the molar ratio was 1:5, and 69.70 mg / g when the molar ratio was 1:6. The extraction efficiency was the highest when the molar ratio was 1:2.

[0050] 2. A eutectic solvent (DES-21) was used, with a hydrogen bond acceptor to hydrogen bond donor molar ratio of 1:2. The ultrasonic powers were 180 W, 240 W, 300 W, 360 W, 420 W, and 480 W, respectively. The remaining steps and conditions were the same as in Example 1.

[0051] Figure 9 The extraction rates of seven target compounds are characterized by different ultrasonic powers. (Source: [Insert source here]) Figure 9 It can be seen that under the conditions of extraction power of 180~480 W, all seven target compounds showed good extraction effects. Specifically, the extraction efficiency was 67.83 mg / g at an ultrasonic power of 180 W, 70.02 mg / g at an ultrasonic power of 240 W, 70.84 mg / g at an ultrasonic power of 300 W, 70.63 mg / g at an ultrasonic power of 360 W, 70.68 mg / g at an ultrasonic power of 420 W, and 70.68 mg / g at an ultrasonic power of 480 W. The extraction efficiency was the highest when the ultrasonic power was 300 W.

[0052] 3. A eutectic solvent (DES-21) was used, with a hydrogen bond acceptor to hydrogen bond donor molar ratio of 1:2, an ultrasonic power of 300W, and extraction temperatures of 20℃, 30℃, 40℃, 50℃, 60℃, and 70℃, respectively. The remaining steps and conditions were the same as in Example 1.

[0053] Figure 10 This is a characterization graph showing the extraction rates of seven target compounds at different extraction temperatures. (Source: [Insert graph here]) Figure 10 It can be seen that under extraction temperatures ranging from 20 to 70℃, all seven target compounds exhibited good extraction effects. Specifically, the extraction efficiency was 72.06 mg / g at an ultrasonic temperature of 20℃, 72.69 mg / g at 30℃, 71.60 mg / g at 40℃, 72.24 mg / g at 50℃, 71.34 mg / g at 60℃, and 71.90 mg / g at 70℃. The highest extraction efficiency was observed at an extraction temperature of 30℃.

[0054] 4. A eutectic solvent (DES-21) was used, with a hydrogen bond acceptor to hydrogen bond donor molar ratio of 1:2, an ultrasonic power of 300W, an extraction temperature of 30℃, and extraction times of 20 min, 40 min, 60 min, 80 min, 100 min, and 120 min, respectively. The remaining steps and conditions were the same as in Example 1.

[0055] Figure 11 This is a characterization graph showing the extraction rates of seven target compounds at different ultrasound durations. (Source: [Insert graph here]) Figure 11 It can be seen that under the conditions of ultrasonic time of 20-120 min, all seven target compounds showed good extraction effects. Specifically, the extraction efficiency was 71.94 mg / g when the ultrasonic time was 20 min, 75.08 mg / g when the ultrasonic time was 40 min, 74.80 mg / g when the ultrasonic time was 60 min, 74.86 mg / g when the ultrasonic time was 80 min, 74.86 mg / g when the ultrasonic time was 100 min, and 73.88 mg / g when the ultrasonic time was 120 min. The extraction efficiency was the highest when the extraction time was 40 min.

[0056] 5. A eutectic solvent (DES-21) was used, with a hydrogen bond acceptor to hydrogen bond donor molar ratio of 1:2, an ultrasonic power of 300W, an extraction temperature of 30℃, an extraction time of 40 min, and liquid-solid ratios of 10 mL / g, 15 mL / g, 20 mL / g, 25 mL / g, 30 mL / g, and 35 mL / g, respectively. The remaining steps and conditions were the same as in Example 1.

[0057] Figure 12 The extraction rates of seven target compounds at different liquid-to-solid ratios are characterized. Figure 12 It can be seen that under the conditions of a eutectic solvent and a liquid-to-solid ratio of Evodia rutaecarpa powder of 10–35 mL / g, all seven target compounds showed good extraction effects. Specifically, the extraction efficiency was 67.17 mg / g at a liquid-to-solid ratio of 10 mL / g, 67.63 mg / g at a liquid-to-solid ratio of 15 mL / g, 71.32 mg / g at a liquid-to-solid ratio of 20 mL / g, 67.93 mg / g at a liquid-to-solid ratio of 25 mL / g, 66.17 mg / g at a liquid-to-solid ratio of 10 mL / g, and 68.02 mg / g at a liquid-to-solid ratio of 10 mL / g. The extraction efficiency was the highest when the liquid-to-solid ratio was 20 mL / g.

[0058] As can be seen from the above data, the eutectic solvent provided by this invention can significantly improve the extraction efficiency of seven target compounds (evodiamine, evodiamine alkaloid, 1-methyl-2-nonylquinoline-4(1H)-one, 1-methyl-2-undecyl-4(1H)-quinolone, evodiamine neoalkaloid, 1-methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone, and dihydroevodiamine neoalkaloid) from Evodia rutaecarpa powder compared with traditional organic solvents. This invention employs a eutectic solvent and ultrasound-assisted extraction method to extract Evodia rutaecarpa powder. Due to the strong hydrogen bonding between the eutectic solvent and the target extracts, the extraction of the target extracts is facilitated. Simultaneously, the ultrasound-assisted extraction conditions are optimized, thereby improving the extraction rate of the seven target compounds from Evodia rutaecarpa powder.

[0059] Although the above embodiments have provided a detailed description of the present invention, they are only some embodiments of the present invention, not all embodiments. People can obtain other embodiments based on the present invention without creative effort, and these embodiments all fall within the protection scope of the present invention.

Claims

1. A method for extracting alkaloid compounds from Evodia rutaecarpa, characterized in that, Includes the following steps: Evodia rutaecarpa powder was mixed with a eutectic solvent and subjected to ultrasonic extraction to obtain alkaloid compounds; the alkaloid compounds include one or more of the following: evodiamine, evodiamine alkaloid, 1-methyl-2-nonylquinoline-4(1H)-one, 1-methyl-2-undecyl-4(1H)-quinolone, evodiamine alkaloid, 1-methyl-2-[(6Z,9Z)-6,9-pentadecadiene]-4(1H)-quinolone, and dihydroevodiamine alkaloid; The eutectic solvent includes a hydrogen bond acceptor and a hydrogen bond donor; the hydrogen bond acceptor is menthol; and the hydrogen bond donor is formic acid.

2. The extraction method according to claim 1, characterized in that, The molar ratio of the hydrogen bond acceptor to the hydrogen bond donor is 1:1 to 6.

3. The extraction method according to claim 1, characterized in that, The power of the ultrasonic extraction is 180~480W.

4. The extraction method according to claim 1 or 3, characterized in that, The temperature for ultrasonic extraction is 20~70℃.

5. The extraction method according to claim 4, characterized in that, The ultrasonic extraction time is 20~120 min.

6. The extraction method according to claim 1, characterized in that, The mass ratio of the Evodia rutaecarpa powder to the volume ratio of the eutectic solvent is 1g:10~35mL.

7. The extraction method according to claim 1, characterized in that, The molar ratio of hydrogen bond acceptor to hydrogen bond donor is 1:2; the ultrasonic extraction power is 300W, the temperature is 30℃, and the time is 40min; the mass ratio of Evodia rutaecarpa powder to the volume ratio of eutectic solvent is 1g:20mL.

8. The extraction method according to claim 1, characterized in that, The ultrasonic extraction process further includes: solid-liquid separation of the obtained mixture; the solid-liquid separation is performed by centrifugation, the centrifugation speed is 8000~12000 rpm, and the time is 5~20 min.

9. The extraction method according to claim 1, characterized in that, The method for preparing the eutectic solvent includes the following steps: mixing and heating a hydrogen bond acceptor and a hydrogen bond donor to obtain a eutectic solvent; the temperature of the mixing and heating is 80~95℃ and the time is 90~180min.

10. The extraction method according to claim 1, characterized in that, The eutectic solvent also includes water, and the volume fraction of water in the eutectic solvent is 10-30%.

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