A phenolic glycoside compound and its preparation method and application

Abstract

The present invention discloses a phenolic glycoside compound, a new chemical component discovered in the leaves of Illicium verum. The present invention also structurally identified the compound isolated by the above method through physicochemical properties and modern spectroscopic methods. The present invention also evaluated the activity of the compound using an LPS-induced RAW 264.7 cell inflammation model and other activity screening systems. The compound was found to have a certain protective effect on the mouse macrophage cell line RAW 264.7, significantly inhibiting the release of PGE2, demonstrating a strong anti-inflammatory effect.

Description

Technical Field

[0001] The present invention relates to the field of medical technology, and in particular to a new compound, a preparation method and an application thereof. Background Art

[0002] Red Star Anise (Illicium dunnianum Tutcher) is a member of the genus Illicium in the family Magnoliaceae. Illicium is an aromatic evergreen tree or shrub. There are 34 species worldwide, 28 of which are found in my country, with two varieties. Most are found in eastern and southeastern Asia, with a few found in southeastern North America and Central and South America. Red Star Anise is endemic to China, found in Guangxi, Fujian, Guizhou, Hunan, and Guangdong. It grows along rivers, along valleys, in mountain forests, on moist slopes, and in rocky crevices at altitudes of 400-1000 meters. Its fruit resembles red fennel, but is small and typically consists of 7-8 fruits, sometimes 13. It has a distinct, slightly curved, subtended tip. The fruit stalk is slender but the stalk is short. The seeds are small and easily distinguishable. Bitter and pungent in flavor, with a warm nature, its roots and bark are commonly used in folk medicine for their ability to dissipate blood stasis, reduce swelling, dispel wind and dampness, and relieve pain. They are applied externally to treat rheumatic bone pain, traumatic injuries, and contusions and fractures. They are toxic, with shikitoxin and neoshikitoxin isolated from the roots as convulsant components. Pharmacological studies have shown that the alcohol extract of Illicium safflower leaves has central and peripheral analgesic effects, demonstrating effective analgesic and detumescent properties for various pain conditions and acute soft tissue injuries.

[0003] Safflower star anise is a plant endemic to my country. As a folk medicine, it is often used to treat rheumatic bone pain, traumatic injuries, contusions and fractures. It has not yet been included in the Chinese Pharmacopoeia, but safflower star anise leaves are one of the ingredients of the traditional Chinese medicine Jinhong tablets. Jinhong tablets have the effects of soothing the liver and relieving depression, regulating qi and activating blood circulation, and harmonizing the stomach and relieving pain. Clinically, it is mainly used to treat chronic superficial gastritis and liver-stomach disharmony, with definite and significant efficacy. However, at present, there is little research on the chemical composition of safflower star anise leaves or Jinhong tablets, and it is impossible to fully elucidate the chemical composition of Jinhong tablets, which limits the in-depth study of the pharmacological substances and their mechanisms of action of Jinhong tablets, and it is also impossible to improve its quality control standards. Therefore, an in-depth study of the active ingredients in safflower star anise leaves is conducted. Summary of the Invention

[0004] The present invention aims to conduct a more in-depth study on the active components in the leaves of Carthamus tinctorius and to discover the active components.

[0005] In view of this, the present invention provides a phenolic glycoside compound or a pharmaceutically acceptable salt, solvate, tautomer, stereoisomer, prodrug molecule, or metabolite thereof, wherein the compound has the following structure, as shown in Formula I:

[0006]

[0007] Another object of the present invention is to provide a method for preparing the above-mentioned compound, characterized in that it comprises:

[0008] A) Extract the leaves of Carthamus tinctorius with 40-60% ethanol under reflux, and remove the solvent to obtain a total extract;

[0009] B) the total extract is dissolved in water, and separated by macroporous adsorption resin column chromatography, eluting with water, 25-35% ethanol, 45-55% ethanol, and 90-100% ethanol in sequence, collecting each eluate, and concentrating under reduced pressure to obtain a water elution fraction, a 25-35% ethanol elution fraction, a 45-55% ethanol elution fraction, and a 90-100% ethanol elution fraction; each gradient elution is 4 column volumes (the same below);

[0010] C) The 45-55% ethanol elution fraction was separated by silica gel column chromatography and gradient elution with dichloromethane-methanol to obtain 15 fractions, 3A-3O. Fraction 3G was separated by ODS column chromatography with a methanol-water gradient elution to obtain 9 fractions, 3G1-3G9. Fraction 3G9 was separated by semi-preparative liquid phase separation.

[0011] Specifically, the Illicium verum leaves may be dried leaves of Illicium verum.

[0012] Furthermore, the step A) comprises: taking dried safflower star anise leaves, refluxing and extracting them with 3-5 times the amount of 40-60% ethanol for 1-3 times, each time for 1-3 hours, combining the extracts, and removing the solvent under reduced pressure to obtain the total extract.

[0013] Preferably, the step B) comprises: eluting with water, 30% ethanol, 50% ethanol, and 95% ethanol in sequence, collecting each eluate, and concentrating under reduced pressure until there is no alcohol smell, thereby obtaining a water elution fraction, a 30% ethanol elution fraction, a 50% ethanol elution fraction, and a 95% ethanol elution fraction.

[0014] Optionally, the dichloromethane-methanol gradient elution in step C) is performed at a volume ratio of 100:0 to 0:100; the methanol-water gradient elution is performed at a volume ratio of 15:85 to 100:0.

[0015] Optionally, the dichloromethane-methanol gradient elution in step C) is performed at a volume ratio of 100:0 to 0:100; the methanol-water gradient elution is performed at a volume ratio of 15-30:85-70 to 100:0.

[0016] Specifically, the dichloromethane-methanol gradient elution in the step C) is performed with a volume ratio of 100:0; 95:5; 90:10; 85:15; 80:20; 70:30 to 60:40, 0:100; and the methanol-water gradient elution is performed with a volume ratio of 30:70; 40:60; 50:50; 70:30 to 100:0.

[0017] Specifically, the macroporous adsorption resin includes one or more of D101 macroporous adsorption resin, HP-20 macroporous adsorption resin, HPD-100 macroporous adsorption resin, HPD-100A macroporous adsorption resin or HPD-300 macroporous adsorption resin.

[0018] Furthermore, the conditions of the semi-preparative liquid chromatography include:

[0019] Specification is C 18 ,5μm,10×250mm Phenomenex Gemini column; volume ratio of mobile phase: 15~25:85~75:0.05-0.5 acetonitrile-water-formic acid, detection wavelength is 240-260nm, flow rate is 2-4mL / min.

[0020] Preferably, the step A) is to extract with 50% ethanol under reflux twice, each time for 2 hours;

[0021] The mobile phase for the compound of the present invention is acetonitrile-water-formic acid in a volume ratio of 20:80:0.1, the detection wavelength is 254 nm, and the flow rate is 3 mL / min.

[0022] Another object of the present invention is to provide the use of the above-mentioned compound or its pharmaceutically acceptable salt, solvate, tautomer, stereoisomer, prodrug molecule, metabolite in the preparation of anti-inflammatory drugs.

[0023] The present invention also provides a drug for treating inflammation, which comprises the above-mentioned phenolic glycoside compound or a pharmaceutically acceptable salt, solvate, tautomer, stereoisomer, prodrug molecule, or metabolite thereof.

[0024] Furthermore, the drug contains a therapeutically effective amount of the above-mentioned phenolic glycoside compound or a pharmaceutically acceptable salt, solvate, tautomer, stereoisomer, prodrug molecule, metabolite thereof, and one or more pharmaceutically acceptable carriers.

[0025] Specifically, the drug can be any dosage form described in pharmacy, including tablets, capsules, soft capsules, gels, oral preparations, suspensions, granules, patches, ointments, pills, powders, injections, infusions, freeze-dried injections, intravenous emulsions, liposome injections, suppositories, sustained-release preparations or controlled-release preparations.

[0026] Furthermore, the pharmaceutically acceptable carrier refers to conventional pharmaceutical carriers in the pharmaceutical field, such as diluents, excipients, and water; fillers such as starch, sucrose, lactose, and microcrystalline cellulose; binders such as cellulose derivatives, alginates, gelatin, and polyvinylpyrrolidone; wetting agents such as glycerin; disintegrants such as sodium carboxymethyl starch, hydroxypropyl cellulose, cross-linked carboxymethyl cellulose, agar, calcium carbonate, and sodium bicarbonate; absorption enhancers such as quaternary ammonium compounds; surfactants such as cetyl alcohol and sodium lauryl sulfate; adsorption carriers such as kaolin and bentonite; lubricants such as talc, calcium and magnesium stearate, micronized silica gel, and polyethylene glycol. Other adjuvants such as flavoring agents and sweeteners may also be added to the composition.

[0027] The phenolic glycoside compounds described in the present invention are new chemical components discovered by researchers in the leaves of Carthamus tinctorius. It was found that the compounds are stable in all batches of Carthamus tinctorius leaves. The inventors used physical and chemical properties and modern spectroscopic methods (MS, 1 H-NMR, 13 C-NMR, etc.), the compound isolated by the above method was structurally identified and confirmed to be a novel compound represented by the structure of Formula (I). The present invention also evaluated its activity using an LPS-induced RAW 264.7 cell inflammation model and other activity screening systems. It was found that the compound had a certain protective effect on the mouse macrophage cell line RAW 264.7, significantly inhibiting the release of PGE2, demonstrating a strong anti-inflammatory effect. This compound has promising research and development prospects. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] Figure 1 HR-ESI-Q-TOF-MS spectrum of compound 1 of the present invention;

[0029] Figure 2 is the UV spectrum of compound 1 of the present invention;

[0030] Figure 3 is the IR spectrum of compound 1 of the present invention;

[0031] Figure 4 Compound 1 of the present invention 1 H-NMR spectrum

[0032] Figure 5 Compound 1 of the present invention 13 C-NMR spectrum;

[0033] Figure 6 DEPT-135 spectrum of compound 1 of the present invention;

[0034] Figure 7 is H of compound 1 of the present invention 1 -H 1 COSY spectrum;

[0035] Figure 8 is the HSQC spectrum of compound 1 of the present invention;

[0036] Figure 9 is the HMBC spectrum of compound 1 of the present invention;

[0037] Figure 10 is the NOESY spectrum of compound 1 of the present invention;

[0038] Figure 11 The experimental and calculated CD spectra of compound 1 of the present invention;

[0039] Figure 12 The main compound of the present invention 1 1 H- 1 Correlation diagram of H COSY, HMBC and NOESY. DETAILED DESCRIPTION

[0040] The following is a detailed description based on the experimental examples.

[0041] It is particularly important to note that similar substitutions and modifications made to the present invention will be obvious to those skilled in the art and are considered to be included in the present invention. It is obvious that relevant persons can modify or appropriately change and combine the methods and applications described herein to implement and apply the technology of the present invention without departing from the content, spirit, and scope of the present invention. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments.

[0042] Unless otherwise specified, the present invention was carried out under conventional conditions or those recommended by the manufacturer. The raw materials or excipients, as well as the reagents or instruments used, for which the manufacturer is not specified, are all conventional products that can be purchased commercially.

[0043] Example 1 Preparation of the compound of the present invention

[0044] (1) Take the dried leaves of Carthamus tinctorius, extract them with 40% ethanol under reflux twice, each time for 2 hours, combine the extracts, remove the solvent under reduced pressure, and obtain the total extract. The total extract is dissolved in water and separated by HP-20 macroporous adsorption resin column chromatography, eluting with water, 25% ethanol, 45% ethanol, and 90% ethanol in sequence, with each gradient elution of 4 column volumes (the same below). Collect each eluate separately, and concentrate under reduced pressure until there is no alcohol smell, to obtain the water elution fraction, the 25% ethanol elution fraction, the 45% ethanol elution fraction, and the 90% ethanol elution fraction;

[0045] (2) The 45% ethanol elution fraction of step (1) was separated by silica gel column chromatography and eluted with dichloromethane-methanol gradient (95:5; 90:10; 85:15; 80:20; 70:30 to 60:40, 0:100, v / v) to obtain 15 fractions (3A-3O). Fraction 3G was subjected to ODS column chromatography with methanol-water gradient elution (15:85; 40:60; 45:55 to 100:0, v / v) to obtain 9 fractions, 3G1-3G9. Fraction 3G9 was subjected to semi-preparative liquid chromatography to obtain the compound of the present invention.

[0046] Wherein, the semi-preparative liquid chromatography conditions in step (2) are as follows: semi-preparative chromatography column: Phenomenex Gemini (C 18 , 5μm, 10×250mm), using a semi-preparative high performance liquid chromatograph [Shimadzu, Japan, pump: LC-6AD (SHIMADZU, LIQUID CHROMATOGRAPH); detector: SPD-20A (prominence UV / VIS DETECTOR); workstation: LCsolution]. The mobile phase for the compounds of the present invention was acetonitrile-water-formic acid in a volume ratio of 15:85:0.05, respectively. The detection wavelength was 240 nm, and the flow rate was 3 mL / min.

[0047] Example 2 Preparation of the compound of the present invention

[0048] (1) Take the dried leaves of Carthamus tinctorius and extract them with 50% ethanol under reflux twice for 2 hours each time. Combine the extracts and remove the solvent under reduced pressure to obtain the total extract. The total extract is dissolved in water and separated by HP-20 macroporous adsorption resin column chromatography. The extracts are eluted with water, 30% ethanol, 50% ethanol, and 95% ethanol in sequence. The eluates are collected and concentrated under reduced pressure until there is no alcohol smell. The water elution fraction, 30% ethanol elution fraction, 50% ethanol elution fraction, and 95% ethanol elution fraction are obtained.

[0049] (2) The 50% ethanol elution portion of step (1) was separated by silica gel column chromatography and eluted with dichloromethane-methanol gradient (100:0; 95:5; 90:10; 85:15; 80:20; 70:30 to 60:40, 0:100, v / v) to obtain 15 fractions (3A-3O). Fraction 3G was subjected to ODS column chromatography with methanol-water (30:70; 40:60; 50:50; 70:30 to 100:0, v / v) gradient elution to obtain 9 fractions, 3G1-3G9. Fraction 3G9 was subjected to semi-preparative liquid chromatography to obtain the compound of the present invention.

[0050] Wherein, the semi-preparative liquid chromatography conditions in step (2) are as follows: semi-preparative chromatography column: Phenomenex Gemini (C 18 , 5μm, 10×250mm) using a semi-preparative high performance liquid chromatograph (Shimadzu, Japan, pump: LC-6AD (SHIMADZU, LIQUID CHROMATOGRAPH); detector: SPD-20A (prominence UV / VIS DETECTOR); workstation: LCsolution). The mobile phase for the compounds of the present invention was acetonitrile-water-formic acid in a volume ratio of 20:80:0.1, respectively. The detection wavelength was 254 nm, and the flow rate was 3 mL / min.

[0051] Example 3 Preparation of the compound of the present invention

[0052] (1) Take dried leaves of Carthamus tinctorius, extract them twice with 60% ethanol under reflux, each time for 2 hours, combine the extracts, and remove the solvent under reduced pressure to obtain a total extract. The total extract is dissolved in water and separated by HP-20 macroporous adsorption resin column chromatography, eluting with water, 35% ethanol, 55% ethanol, and 100% ethanol in sequence. The eluates are collected and concentrated under reduced pressure until there is no alcohol smell, thereby obtaining a water elution fraction, a 35% ethanol elution fraction, a 55% ethanol elution fraction, and a 100% ethanol elution fraction;

[0053] (2) The 55% ethanol elution portion of step (1) was separated by silica gel column chromatography and eluted with a dichloromethane-methanol gradient (90:10; 80:20; 75:25; 70:30 to 60:40, v / v) to obtain 15 fractions (3A-3O). Fraction 3G was subjected to ODS column chromatography with a methanol-water gradient elution (20:80; 50:50; 55:45 to 100:0, v / v) to obtain 9 fractions, 3G1-3G9. Fraction 3G9 was subjected to semi-preparative liquid chromatography to obtain the compound of the present invention.

[0054] Wherein, the semi-preparative liquid chromatography conditions in step (2) are as follows: semi-preparative chromatography column: Phenomenex Gemini (C 18, 5μm, 10×250mm), using a semi-preparative high performance liquid chromatograph [Shimadzu, Japan, pump: LC-6AD (SHIMADZU, LIQUID CHROMATOGRAPH); detector: SPD-20A (prominence UV / VIS DETECTOR); workstation: LCsolution]. The mobile phase for the compounds of the present invention was acetonitrile-water-formic acid in a volume ratio of 25:75:0.5, respectively. The detection wavelength was 260 nm, and the flow rate was 3 mL / min.

[0055] Example 4 Structural Identification of the Compounds of the Invention

[0056] Yellow oily substance, HR-ESI-MS gave m / z 471.1870 [M+H] + (calculated value: 471.1866), the molecular formula was determined to be C 22 H 30 O 11 , the unsaturation is 8.

[0057] like Figure 1-12 As shown, the compound 1 The H-NMR (600 MHz, in CD3OD) spectrum showed a para-substituted benzene ring hydrogen signal [δ H 7.30 (2H, d, J = 8.7 Hz, H-2, 6), 6.91 (2H, d, J = 8.7 Hz, H-3, 5)], two oxymethylene hydrogen signals [δ H 4.15 (1H, d, J = 9.1 Hz, H-7), 3.86 (1H, dq, J = 12.5, 6.4 Hz, H-8)] and one methyl hydrogen signal [δ H 0.98 (3H, d, J = 6.3 Hz, H3-9)] and a methoxy hydrogen signal [δ H 3.79 (3H, s, 4-OCH3)]. Combined carbon signal (δ C 161.0,131.1,130.2×2,114.8×2,85.0,78.1,17.1) and H-2 / C-4;H-7 / C-6;H-9 / C-7;H-8 / C-1;4-OCH3 / C-4 HMBC correlation assigned the structure containing a C6-C3 structure fragment. 5 oxymethyl groups [δ H4.57 (1H, d, J = 7.8 Hz, H-1′), 3.14 (1H, dd, J = 9.5, 7.9 Hz, H-2′), 3.58 (1H, t, J = 9.2 Hz, H-3′), 3.43 (1H, t, J = 9.3 Hz, H-4′), 3.68 (1H, ddd, J = 9.5, 5.6, 1.8 Hz, H-5′)] and one oxymethylene [δ H 4.49 (1H, dd, J = 11.9, 1.9 Hz, H-6′a), 4.26 (1H, dd, J = 11.9, 5.7 Hz, H-6′b)], further 1 H- 1 The H-COSY spectrum of H-1′ / H-2′ / H-3′ / H-4′ / H-5′ / H-6′ and the HMBC correlation of H-1′ / C-3′,5′; H-2′ / C-4′; H-3′ / C-5′; H-4′ / C-6′ attributed the structure to contain a glucose group. In addition, the NMR data [δ H 2.74(2H,dd,J=14.5,10.3Hz,H-2″) / δ C 46.4(C-2″),2.66(2H,brs,H-4″) / δ C 46.1(C-4″),1.40(3H,s,H-6″) / δ C 27.7(C-6″),δ C 175.3(C-5″), 172.4(C-1″), 70.8(C-3″)] and HMBC correlations of H-2″ / C-1″, 3″, 4″, 6″; H-4″ / C-2″, 3″, 5″, 6″ indicated that the structure also contained a 3-hydroxy-3-methylglutaric acid fragment. The absolute configuration of the C-3″ position was determined to be S based on its biogenic and optical rotation values. Finally, the C6-C3 structural fragment was connected to the 3-hydroxy-3-methylglutaric acid fragment through the glucose group through the HMBC long-range correlations of H-8 / C-1′; H-2′ / C-7 and H-6′ / C-1″, forming a planar structure of the compound.

[0058] The coupling constants and NOSY correlations between H-2′ / H-4′ / H-7 and H-1′ / H-3′ / H-5′ / H-8 confirmed that the relative configurations of H-7, H-8, H-1′, H-2′, H-3′, H-4′, and H-5′ were all trans. ECD combined with CD results indicated the absolute configuration of the compound was (7S, 8S, 1'R, 2'R, 3'S, 4'S, 5'R). Combined with the one- and two-dimensional NMR information (Table 1), it was identified as a new phenolic glycoside compound and named illiciumside A. The structure is as follows:

[0059]

[0060] Table 1. Compounds 1 H and 13 C NMR data

[0061]

[0062] measured at 600MHz for 1 H and 150MHz for 13 C in CD3OD

[0063] Multiplets and or overlapped signals are reported without designatingmultiplicity

[0064] Example 5 In vitro anti-PGE2 experiment of the compounds of the present invention

[0065] 1. Materials

[0066] 1.1 Drugs Compounds of the present invention;

[0067] 1.2 Cell model The mouse macrophage cell line RAW 264.7 was obtained from the Chinese Academy of Traditional Chinese Medicine; culture conditions: DMEM + 10% fetal bovine serum (FBS), 37°C, 5% CO2.

[0068] 2. Principles and methods

[0069] 2.1 Experimental Principle

[0070] Lipopolysaccharide (LPS) (Sigma, USA, Lot No. 114M4009), expressed in the outer membrane of Gram-negative bacteria, is one of the most important pathogenic molecules mediating infectious inflammatory damage. Many diseases are closely associated with persistent subclinical inflammation induced by LPS. LPS is widely used to induce inflammation in animal and cell-based experiments.

[0071] Macrophages play a crucial role in inflammatory responses. Upon stimulation, they produce a large number of inflammatory factors and mediators, such as TNF-α, IL-1β, IL-6, NO, and PGE2. The activation of these inflammatory factors and mediators is a key process in inflammation, and their inhibition is often used as an important indicator for evaluating the anti-inflammatory activity of drugs.

[0072] 2.2 Drug inhibition test on PGE2 secretion

[0073] Method steps:

[0074] (1) Preparation of drug solution: The compound of the present invention was dissolved in DMEM medium containing 10% FBS to prepare a 2 mg / ml stock solution.

[0075] (2) Experimental method: The cells were digested with 0.25% trypsin (containing 0.02% EDTA) and the cell density was adjusted to 1×10 5 The cells were evenly inoculated into 24-well plates, 400 μl per well, and placed in an incubator for 24 hours.

[0076] Blank control group (N group): 495 μl serum-free DMEM medium was added to each well;

[0077] Vehicle group / solvent control group (RM group): 495 μl of serum-free DMEM medium containing 1 / 1000 DMSO was added to each well;

[0078] Model group (M group): 495 μl of 100 μg / ml LPS was added to each well;

[0079] Drug-dosing sample group: 495 μl of culture medium containing drugs at different concentrations was added to each well;

[0080] Six replicate wells were set up simultaneously. After drug addition, the 24-well plate was placed in a CO2 cell culture incubator and cultured for 1 hour. After 1 hour, 5 μl of 100 μg / ml LPS (final concentration 1 μg / ml) was added to each well except for the blank control and solvent control groups. 5 μl of serum-free DMEM medium was added to each well of the solvent control and blank control groups. After drug addition, the 24-well plate was placed in a CO2 cell culture incubator and cultured for another 18 hours.

[0081] After 18 hours, the cell culture fluid was collected and the PGE2 content in the cell supernatant was detected by ELISA according to the kit instructions.

[0082] PGE2 inhibition rate (%) = (average PGE2 content in the model group - average PGE2 content in the sample group) / (average PGE2 content in the model group - average PGE2 content in the solvent group) × 100%.

[0083] 3. Experimental Results

[0084] 3.1 Effects of drug samples on PGE2 in the supernatant of mouse macrophage cell line RAW 264.7

[0085] The results showed that the drug sample could significantly inhibit the secretion of PGE2 in mouse macrophage RAW 264.7 cells induced by LPS, showing a strong anti-inflammatory effect. The data results are shown in Table 2.

[0086] Table 2 Effects of various concentrations of compounds on PGE2 in the supernatant of mouse macrophage cell line RAW264.7 ( n=6)

[0087]

[0088] The present invention uses Graphad prism 7.00 analysis software to measure the average IC of the compounds of the present invention in vitro for inhibiting LPS-induced secretion of inflammatory mediator PGE2 by mouse macrophage RAW 264.7 by linear regression analysis. 50 It is 8.86μM.

[0089] 4. Conclusion

[0090] The compound of the present invention has a significant inhibitory effect on the secretion of inflammatory mediator PGE2 by LPS-induced mouse macrophage RAW 264.7, showing a strong anti-inflammatory effect. As the drug concentration increases, the inhibitory effect on PGE2 secretion also increases. IC 50 It is 8.86μM.

[0091] The above is only a preferred embodiment of the present invention. It should be pointed out that for ordinary technicians in this technical field, several improvements and modifications can be made without departing from the principles of the present invention. These improvements and modifications should also be regarded as within the scope of protection of the present invention.

Claims

1. Use of a phenolic glycoside compound or a pharmaceutically acceptable salt, tautomer, or stereoisomer thereof in the preparation of an anti-inflammatory drug, wherein the compound structure is shown in Formula I: 。 2. A use according to claim 1, characterized in that The preparation method of the phenolic glycoside compound comprises: A) Extract the leaves of Carthamus tinctorius with 40-60% ethanol under reflux, and remove the solvent to obtain a total extract; B) the total extract is dissolved in water, separated by macroporous adsorption resin column chromatography, and eluted with water, 25-35% ethanol, 45-55% ethanol, and 90-100% ethanol in sequence, and the eluates are collected and concentrated under reduced pressure to obtain a water elution fraction, a 25-35% ethanol elution fraction, a 45-55% ethanol elution fraction, and a 90-100% ethanol elution fraction; C) The 45-55% ethanol elution fraction was separated by silica gel column chromatography and gradient elution with dichloromethane-methanol to obtain 15 fractions, 3A-3O. Fraction 3G was separated by ODS column chromatography with a methanol-water gradient elution to obtain 9 fractions, 3G1-3G9. Fraction 3G9 was separated by semi-preparative liquid phase separation.

3. The use according to claim 2, characterized in that The step A) comprises: The dried safflower star anise leaves are extracted with 3-5 times the amount of 40-60% ethanol through reflux for 1-3 times, each time for 1-3 hours, the extracts are combined, and the solvent is removed under reduced pressure to obtain the total extract.

4. The use according to claim 2, characterized in that The step B) comprises: eluting with water, 30% ethanol, 50% ethanol, and 95% ethanol in sequence, collecting the eluates respectively, and concentrating under reduced pressure until there is no alcohol smell, thereby obtaining a water elution fraction, a 30% ethanol elution fraction, a 50% ethanol elution fraction, and a 95% ethanol elution fraction.

5. The use according to claim 2, characterized in that The dichloromethane-methanol gradient elution in step C) is performed at a volume ratio of 100:0 to 0:100; the methanol-water gradient elution is performed at a volume ratio of 15:85 to 100:

0.

6. The use according to claim 2, characterized in that The macroporous adsorption resin includes one or more of D101 macroporous adsorption resin, HP-20 macroporous adsorption resin, HPD-100 macroporous adsorption resin, HPD-100A macroporous adsorption resin or HPD-300 macroporous adsorption resin.

7. The use according to claim 2, characterized in that The conditions of the semi-preparative liquid chromatography include: Specification is C 18 ,5μm,10×250mm Phenomenex Gemini column; the mobile phase volume ratio for preparing the phenolic glycoside compound is: acetonitrile-water-formic acid 15~25:85~75:0.05-0.5, the detection wavelength is 240-260nm, and the flow rate is 2-4mL / min.

8. The use according to claim 7, characterized in that The step A) is to extract with 50% ethanol under reflux twice, each time for 2 hours; The mobile phase volume ratio for preparing the compound was 20:80: 0.1 acetonitrile-water-formic acid, detection wavelength at 254 nm, flow rate at 3 mL / min.

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