Phenylpropanoid compound as well as preparation method and application thereof

Abstract

According to the present invention, a plurality of chromatographic separation methods such as silica gel column chromatography, HP20 chromatographic column, polyamide chromatographic column, reversed-phase C18 column chromatography, preparative high performance liquid chromatography and the like are adopted to systematically separate and purify the chemical components of the roxburgh rose root, and the structure of the compound is identified through the physicochemical properties and the spectroscopy means (1D-NMR, 2D-NMR, UV, MS and CD) so as to separate and prepare the four compounds, the invention also finds that the compounds have anti-inflammatory activity.

Description

Technical Field

[0001] The present invention relates to the field of natural drug chemistry, and more specifically to phenylpropanoid compounds in goldenrod and their medicinal activities. Background Art

[0002] Berberis polyantha Hemsl. is a medicinal material of the berberidaceae family. It is used as a substitute for Coptis chinensis by the people in western Sichuan. The roots are boiled in water to reduce internal heat, or used for washing eyes to treat eye diseases.

[0003] Berberis has abundant wild resources. Its medicinal parts are diverse, including roots, stems, leaves, root bark, stem bark, flowers or fruits, etc., which have the effects of clearing away heat and dampness, purging fire and detoxifying. It is mainly used to treat red and swollen eyes, sore throat, hot dysentery with blood in the stool, jaundice due to dryness and dampness, eczema, yellow and swollen sores and other diseases. Pharmacological activities include anti-inflammatory, anti-tumor, antioxidant, analgesic and antibacterial effects.

[0004] However, basic research on the active substances of R. spinulosa is relatively rare. Summary of the invention

[0005] The present invention adopts a variety of chromatographic separation methods such as silica gel column chromatography, HP20 column chromatography, polyamide column chromatography, reverse phase C18 column chromatography, preparative high performance liquid chromatography, etc. to systematically separate and purify the chemical components of the root of Tripterygium wilfordii, and identifies the structure of the compound through physicochemical properties and spectroscopy means (1D-NMR, 2D-NMR, UV, MS and CD), and separates and prepares 4 compounds. The present invention also finds that these compounds have anti-inflammatory activity.

[0006] Based on the research of the present invention, a phenylpropanoid compound shown in the following structure, or a pharmaceutically acceptable salt thereof is specifically provided:

[0007]

[0008] The present invention also provides a method for preparing the phenylpropanoid compound shown in Formula 1, comprising the following steps:

[0009] (1) Extract the flower of Goldenrod with 80-95% methanol, extract the extract with dichloromethane and n-butanol in sequence, and take the n-butanol extracted part for later use;

[0010] (2) The n-butanol extraction part was passed through a silica gel column and gradient eluted with the mobile phase gradient of dichloromethane:methanol 100:1, 50:1, 40:1, 20:1, 10:1, 2:1, 0:1 to obtain 14 fractions in sequence;

[0011] (3) taking the 11th fraction and performing gradient elution through a macroporous adsorption resin column, wherein the gradient is water, 30% methanol, 60% methanol, and 100% methanol, to obtain four fractions in sequence;

[0012] (4) taking the second fraction, separating it through a polyamide column, and separating it with a mobile phase gradient of ethyl acetate:methanol 100:1, 50:1, 30:1, 20:1, 10:1, and 0:1, to obtain 9 fractions in sequence;

[0013] (5) The first fraction was taken and subjected to isocratic elution by preparative high performance liquid chromatography with a mobile phase of 26% methanol to obtain compound 1.

[0014] Further, in step (2), each gradient elution is 10 column volumes;

[0015] In step (3), the macroporous adsorption resin is selected from SP825;

[0016] In step (4), each gradient elution was 7 column volumes.

[0017] The present invention also provides use of the phenylpropanoid compound of formula 1 or a pharmaceutically acceptable salt thereof in the preparation of a drug having anti-inflammatory activity.

[0018] Furthermore, the drug is a drug for treating inflammation caused by Gram-negative bacteria or lipopolysaccharide.

[0019] The present invention also provides a method for extracting and separating multiple anti-inflammatory components from Goldenrod, comprising the following steps:

[0020] (1) Extract the flower of Goldenrod with 80-95% methanol, extract the extract with dichloromethane and n-butanol in sequence, and take the dichloromethane extraction part and the n-butanol extraction part for later use;

[0021] (2) taking the dichloromethane extraction part, passing it through a silica gel column, and gradient eluting it. The mobile phase gradient was dichloromethane:methanol 100:1, 50:1, 40:1, 20:1, 10:1, 2:1, and 0:1, and 7 fractions were obtained in sequence. The second, third, and fifth fractions were respectively taken for use;

[0022] (3) The second fraction of step (2) was taken and subjected to isocratic elution by preparative high performance liquid chromatography with a mobile phase of 40% methanol to obtain compound 3, the structural formula of which is as follows:

[0023]

[0024] (4) The third fraction of step (2) was taken and gradient eluted through an HP20 column, the gradient being water, 30% methanol, 60% methanol, and 100% methanol, to obtain 4 fractions. The third fraction was taken and separated through a polyamide column, the mobile phase being EtOAc:MeOH=100:1, 50:1, 30:1, 20:1, 10:1, and 0:1, to obtain 6 fractions in sequence. The first fraction was taken and isocratically eluted through preparative high performance liquid chromatography, the mobile phase being 32% methanol, to obtain compound 2, the structural formula of which is as follows:

[0025]

[0026] (5) The fifth fraction of step (2) was gradient eluted through an SP825 column, the mobile phases were water, 30% methanol, 60% methanol, 100% methanol, and four fractions were obtained in sequence. The third fraction was separated through a polyamide column, the mobile phase was ethyl acetate: methanol = 100:1, 50:1, 40:1, 30:1, 20:1, 10:1, 0:1, the 50:1, 40:1 elution positions were taken, and gradient eluted through an octadecyl bonded silica column, methanol was the organic phase, water was the aqueous phase, the organic phase gradient was 20%, 60%, 80%, 100%, each gradient elution was 7 BV, and 12 fractions were obtained in sequence. The sixth fraction was isocratically eluted through preparative high performance liquid chromatography, the mobile phase was 31% methanol, and compound 4 was obtained, the structural formula of which is as follows:

[0027]

[0028] The present invention also provides a method for simultaneously extracting four anti-inflammatory active ingredients, which comprises the following steps:

[0029] (1) Extract the flower of Goldenrod with 80-95% methanol, extract the extract with dichloromethane and n-butanol in sequence, and take the dichloromethane extraction part and the n-butanol extraction part for later use;

[0030] (2) taking the dichloromethane extraction part, passing it through a silica gel column, and gradient eluting it. The mobile phase gradient was dichloromethane:methanol 100:1, 50:1, 40:1, 20:1, 10:1, 2:1, and 0:1, and 7 fractions were obtained in sequence. The second, third, and fifth fractions were respectively taken for use;

[0031] (3) The second fraction of step (2) was subjected to isocratic elution by preparative high performance liquid chromatography with a mobile phase of 40% methanol to obtain compound 3;

[0032] (4) The third fraction of step (2) was taken and gradient eluted through an HP20 column, the gradient being water, 30% methanol, 60% methanol, and 100% methanol, to obtain 4 fractions. The third fraction was taken and separated through a polyamide column, the mobile phase being EtOAc:MeOH=100:1, 50:1, 30:1, 20:1, 10:1, and 0:1, to obtain 6 fractions in sequence. The first fraction was taken and isocratically eluted through preparative high performance liquid chromatography, the mobile phase being 32% methanol, to obtain compound 2;

[0033] (5) Take the fifth fraction of step (2) and perform gradient elution through an SP825 column. The mobile phase is water, 30% methanol, 60% methanol, and 100% methanol, respectively. Four fractions are obtained in sequence. The third fraction is separated by a polyamide column. The mobile phase is ethyl acetate: methanol = 100:1, 50:1, 40:1, 30:1, 20:1, 10:1, and 0:1. The elution positions of 50:1 and 40:1 are taken and gradient eluted through an octadecyl bonded silica column. Methanol is the organic phase and water is the aqueous phase. The organic phase gradient is 20%, 60%, 80%, and 100%. Each gradient elution is 7 BV. Twelve fractions are obtained in sequence. The sixth fraction is isocratically eluted by preparative high performance liquid chromatography. The mobile phase is 31% methanol to obtain compound 4.

[0034] (6) Take the n-butanol extraction portion of step (1), pass it through a silica gel column, and perform gradient elution. The mobile phase gradient is as follows: dichloromethane: methanol 100:1, 50:1, 40:1, 20:1, 10:1, 2:1, 0:1, and 14 fractions are obtained in sequence; take the 11th fraction, and perform gradient elution through a macroporous adsorption resin column. The gradient is water, 30% methanol, 60% methanol, and 100% methanol in sequence, and 4 fractions are obtained in sequence; take the second fraction, and separate it through a polyamide chromatography column. The mobile phase gradient is ethyl acetate: methanol 100:1, 50:1, 30:1, 20:1, 10:1, and 0:1, and 9 fractions are obtained in sequence; take the first fraction, and perform isocratic elution through preparative high performance liquid chromatography. The mobile phase is 26% methanol to obtain compound 1.

[0035] In the elution process of the present invention, thin layer chromatography can be used to track the elution situation and merge the elution parts with the same spots.

[0036] The present invention also provides the use of the Goldenrod extract in preparing a drug with anti-inflammatory activity. The preparation method of the Goldenrod extract comprises: taking the Goldenrod, extracting with 80-95% methanol, extracting the extract with dichloromethane and n-butanol in sequence, and taking the dichloromethane extraction part or the n-butanol extraction part, that is, the Goldenrod extract.

[0037] The present invention also provides use of compound 2 or compound 4, or a pharmaceutically acceptable salt thereof, in preparing a drug having anti-inflammatory activity.

[0038] Furthermore, the drug is a drug for treating inflammation caused by Gram-negative bacteria or lipopolysaccharide.

[0039] Beneficial effects of the present invention:

[0040] (1) In the present invention, compound 1 is a new compound that has not been reported in the literature, and the other compounds are isolated from this plant for the first time.

[0041] (2) By measuring the release of NO in the culture medium of mouse RAW264.7 macrophages induced by lipopolysaccharide (LPS), the three compounds can inhibit the release of NO in LPS-induced RAW264.7 cells and exert anti-inflammatory effects. BRIEF DESCRIPTION OF THE DRAWINGS

[0042] Figure 1 The key HMBC and 1 H- 1 H COSY signal

[0043] Figure 2 CD and ECD spectra of compound 1

[0044] Figure 3 Anti-inflammatory activity of compounds 1, 2, and 4 (###P<0.001, compared with the control group; *P<0.05, ***P<0.001, compared with the LPS group, One-way ANOVA test) DETAILED DESCRIPTION

[0045] Materials and Equipment

[0046] Waters 2487 high performance liquid chromatograph (Waters, USA); Bruker avance 600M AVIII nuclear magnetic resonance spectrometer (Bruker, USA); 6540UHD accurate mass Q-TOF MS mass spectrometer (Agilent, USA); preparative liquid chromatograph LC-16P (Shimadzu, Japan); semi-preparative liquid phase (Jiangsu Hanbang Technology Co., Ltd.); automatic polarimeter (SGW-533, Shanghai Yidian Physical Optical Instrument Co., Ltd.); YMC-Pack ODS-A reversed phase chromatographic column (250×10mm, 5μm); HP-20 adsorption resin (Mitsubishi Chemical Co., Ltd., Japan); MCI GEL SP825 (Mitsubishi Chemical Co., Ltd., Japan); silica gel (100-200 mesh and 300-400 mesh, Qingdao Ocean Chemical Co., Ltd.); polyamide (100-200 mesh, Roen Reagent Co., Ltd.); dichloromethane, ethyl acetate, methanol (analytical grade, Chengdu Kelong Chemical Co., Ltd.); methanol (chromatographic grade, Fisher Chemical).

[0047] The roots of B. polyantha Hemsl. were collected from Yadu Village, Chibusu Town, Maoxian County, Aba Tibetan and Qiang Autonomous Prefecture, Sichuan Province (E103°19′25.41″N31°52′42.64″, 2613 meters above sea level), and were identified as B. polyantha Hemsl. of the Berberidaceae family by Professor Liu Yuan from the College of Grassland Resources of Southwest University for Nationalities. The voucher sample (CHH-202112) is stored in the specimen room of the Key Laboratory of the State Ethnic Affairs Commission for the Protection and Utilization of Ethnic Medicinal Resources on the Qinghai-Tibet Plateau, Southwest University for Nationalities.

[0048] EtOAc: ethyl acetate

[0049] MeOH: Methanol

[0050] Water: water

[0051] BV: Column Volume

[0052] pHPLC: preparative high performance liquid chromatography

[0053] Example 1

[0054] Dried medicinal materials of 20 kg of thorny yellow flower were crushed, added with 90% methanol (solid-liquid ratio 1:12), and heated under reflux for extraction 3 times, each time for 1 hour. The extracts were combined, redissolved with water, and extracted with dichloromethane and n-butanol in a ratio of 1:1, respectively, for 3 times, and the extracts were combined and dried under reduced pressure to obtain 786 g of dichloromethane layer and 645 g of n-butanol layer.

[0055] Dissolve 786g of extract obtained from the dichloromethane layer with methanol, weigh out the same amount of 100-200 mesh silica gel as the dichloromethane layer, add the dissolved extract to the silica gel in small amounts and multiple times for mixing (1:1), and set aside after mixing and evaporating the organic solvent. Weigh out 200-300 mesh silica gel twice the weight of the dichloromethane layer extract, load it into a vacuum chromatography column, and perform gradient elution with a gradient dichloromethane: methanol (100:1, 50:1, 40:1, 20:1, 10:1, 2:1, MeOH) system, 10 BV for each gradient elution, and obtain 7 fractions (D-1 to D-7).

[0056] D-2 was subjected to isocratic elution using pHPLC with a mobile phase of 40% methanol-water to obtain compound 3 (DPD-2, t R =48min, 20mg). The D-3 fraction was gradient eluted through an HP20 column, and the mobile phases were methanol-water = Water, 30%, 60%, and MeOH, respectively, to obtain 4 fractions, namely D-3-1 to D-3-4. Fr.D-3-3 was separated through a polyamide column, and the mobile phases were EtOAc:MeOH = 100:1, 50:1, 30:1, 20:1, 10:1, and MeOH, to obtain 6 fractions, namely D-3-3-1 to D-3-3-6. Fr.D-3-3-1 was isocratically eluted by pHPLC, and the mobile phase was 32% methanol-water to obtain compound 2 (CH-5, t R =80min, 8mg). The D-5 fraction was gradient eluted through an SP825 column, and the mobile phases were methanol-water = Water, 30%, 60%, and MeOH, respectively, to obtain 4 fractions (D-5-1, D-5-2, D-5-3, and D-5-4). Fr.D-5-3 was separated through a polyamide column, and the mobile phases were EtOAc:MeOH = 100:1, 50:1, 30:1, 20:1, 10:1, and MeOH. After thin layer chromatography identification, 5 fractions were obtained, namely D-5-3-1 (100:1), D-5-3-2 (50:1, 40:1), D-5-3-3 (30:1), D-5-3-4 (20:1, 10:1), D-5-3-5 (MeOH), Fr.D-5-3-2 was subjected to gradient elution by open ODS reverse phase column chromatography, the mobile phase was methanol-water = 20% to 60%, 80%, MeOH, 7 BV for each gradient elution, and 12 fractions (Fr.1 to Fr.12) were obtained by spot thin layer merging, Fr.D-5-3-2-6 was subjected to isocratic elution by pHPLC, the mobile phase was 31% methanol-water, compound 4 (D-5-3-2-6, t R =57min, 8mg).

[0057] The n-butanol layer was gradient eluted through a silica gel column, with a gradient of dichloromethane:methanol (100:1, 50:1, 40:1, 20:1, 10:1, 2:1, MeOH) for 10 BV each gradient elution to obtain 14 fractions (Z-1 to Z-14). Z-11 was gradient eluted through an SP825 column, with the mobile phases of methanol-water = Water, 30%, 60%, MeOH in sequence, to obtain 4 fractions, namely Z-11-1 to Z-11-4, of which Z-11-2 was separated through a polyamide column, with the mobile phases of EtOAc:MeOH = 100:1, 50:1, 30:1, 20:1, 10:1, MeOH, with 7 BV each gradient elution, and 9 fractions (Fr.1 to Fr.9) were obtained after identification and merging by thin layer chromatography. Fr.1 was eluted isocratically by pHPLC with a mobile phase of 26% methanol-water to obtain compound 1 (Z-11-2-7-2-1, t R =25min, 5mg), structural formula see Fig.1.

[0058]

[0059] Structure identification:

[0060] Compound 1: light yellow oil. UV(MeOH)λ max : 215.4 and 307.9 nm indicate the presence of π-π conjugated benzene rings and n-π transition carbonyl groups in the structure. High resolution mass spectrometry data gives [M+Na] at m / z 411.127 4 + Ion peak (calculated value 411.126 7, C 17 H 24 O 10 Na), and its molecular formula is estimated to be C 17 H 24 O 10 , the unsaturation is 6.

[0061] 1 H-NMR (600MHz, MeOD-d4) spectrum: δ H 7.37 (2H, brs) is the meta hydrogen signal of the symmetrical tetrasubstituted benzene ring; 5.53 (1H, d, J = 6.9 Hz) indicates a proton signal of an oxygen-linked methine. H 3.89 (6H, s) indicates two methoxy signals, 1.49 (3H, d, J = 6.9 Hz) is a methyl proton signal, H 4.28 (1H, d, J = 7.6 Hz) is the terminal proton signal of β-configuration glucose.

[0062] 13In the C-NMR (150 MHz, MeOD-d4) spectrum: 14 carbon signals can be observed, combined with the 135° DEPT spectrum, δ C 199.6 is the signal of the benzylic keto carbon, δ C 147.8, 147.8, 142.4, 125.2, 106.6 and 106.6 are carbon signals on the benzene ring, δ C 74.9 indicates a signal of 1 oxygen-linked methine. C 55.6×2 are two methoxy carbon signals. In addition, there is a group of glucose signals: δ C 101.9, 76.5, 76.8, 74.0, 70.2 and 61.5. The NMR spectrum data of compound 1 were assigned in detail by HSQC and HMBC spectra, as shown in Table 1.

[0063] Table 1 Compound 1 1 H-NMR (600MHz) and 13 C-NMR (150MHz) nuclear magnetic data

[0064]

[0065] Measured in CD3OD-d4; chemical shift values ​​are in ppm.

[0066] In HMBC (Fig. 2), δ H 7.37(H-2',6') and δ C 199.6 (C-1) has relevant hints that the carbonyl group at position 1 is connected to the benzene ring, δ H 4.28(H-1") and δ C 74.9 (C-2) has a correlation suggesting that glucose is linked to C-2, δ H 1.49(H-3) and δ C 19.1(C-3), combined 1 H- 1 δ in H COSY spectrum H 5.53 (H-2) is correlated with 1.49 (H-3), suggesting that the 3-methyl group is attached to the 2-position.

[0067] After acid hydrolysis of compound 1, the derivative (t R =26.7min) and standard D-glc (t R =26.4min) and L-glc(t R =23.8min) was determined to be glucose in D configuration. maxThe ECD spectra of R-1 and S-1 were compared with the theoretically calculated ECD spectra (negative Cotton effect at 215 nm and positive Cotton effect at 307 nm). It was found that the ECD spectrum obtained from the theoretical calculation of R-1 was basically consistent with that obtained from the theoretical calculation (Fig. 3), indicating that the absolute configuration of C-2 of compound 1 is R configuration.

[0068] Based on the above results, the structure of compound 1 was determined to be (2R)-2-(β-D-glucopyranosyloxy)-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone. Through Scifinder literature search, it was found to be a new compound that had not been reported in the literature and was named (2R)-1-(4-hydroxy-3,5-dimethoxyphenyl)-propan-1-one-2-O-beta-D-glucoside ((2R)-2-(β-D-glucopyranosyloxy)-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone).

[0069] Compound 2: white amorphous powder. UV(MeOH)λ max :217.7and 275.8nm; 1 H-NMR (600 MHz, MeOD-d4), δ H 7.32(2H,s,H-2,H-6),3.88(6H,s,3,5-OCH3),3.86(3H,s,7-OCH3); 13 C-NMR (150 MHz, MeOD-d4), δ C 167.2(C-7),147.5(C-3,5),140.6(C-4),119.2(C-1),106.7(C-2,6),55.4(3,5-OCH3),51.1(7-OCH3).

[10] The compound was identified as methyl syringate (methyl-4-hydroxy-3,5-dimethoxybenzoate).

[0070] Compound 3: white amorphous powder. UV(MeOH)λ max :209.9 and 271.0nm; (c0.3, MeOH); 1 H-NMR (600MHz, DMSO-d6)δ H:6.60(4H,s,H-2,2′,6,6′),4.62(2H,d,J=3.6Hz,H-7,7′),4.16(2H,m,H-9,9′ ), 3.77(2H,m,H-9,9′), 3.75(12H,s,H-3,3′,5,5′-OCH3), 3.06(2H,m,H-8,8′). 13 C-NMR (150MHz, DMSO-d6) δ: 148.4 (C-3, 3′, 5, 5′), 135.3 (C-4, 4′), 131.9 (C-1, 1′), 104.0 (C-2, 2′, 6, 6′), 85.8 (C-7, 7′), 71.5 (C-9, 9′), 56.4 (3, 3′, 5, 5′-OCH3), 54.1 (C-8, 8′). The above data are basically consistent with those reported in the literature.

[11] Therefore, compound 3 was identified as (+)-syringaresinol.

[0071] Compound 4: white powder. UV(MeOH)λ max :209.9 and 271.0nm; 1 H-NMR (600MHz, MeOD-d4)δ H :6.70(2H,s,H-2',6'),6.64(2H,s,H-2,6),4.87(1H,overlap),4.75(1H,d,J=6.0Hz,H-1'),4.70(1H,d,J=6.0Hz,H-7'),4.69(1H, d,J=4.5Hz,H-7),4.27(2H,m,H-9,9'),3.85(6H,s,3,5-OCH3),3.84(6H,s,3',5'-OCH3),3.42(2H,m,H-9,9'),3.13(2H,m,H-8,8'); 13C-NMR(150MHz,MeOD-d4)δc: 131.68(C-1),147.94(C-3,5),134.8(C-4),103.4(C-2,6),85 .76(C-7),54.1(C-8),71.45(C-9),134.16(C-1'),153.0(C-3',5'),138.14(C-4'),103.93 (C-2',6'),86.16(C-7'),54.31(C-8'),71.52(C-9'),103.93(C-1″),74.31(C-2″),76.41(C-3″),69.92(C-4″),76.93(C-5″),61.17(C-6″),55.69(3,5-OCH3),55.43(3',5'-OCH3). The above data are basically consistent with those reported in the literature.

[12] , and the compound was identified as syringaresinol-4-O-β-D-glucopyranoside.

[0072] Experimental Example 1 Determination of anti-inflammatory activity

[0073] Dexamethasone (DEM) was used as a positive control drug, and LPS-induced RAW264.7 cells were used as an anti-inflammatory activity evaluation model to screen the anti-inflammatory activity of three monomer compounds isolated from the flower of goldenrod. The anti-inflammatory activity of each monomer compound was evaluated using the Griess reagent method, and the administration concentration of each compound was 10 μM. The results showed that all three compounds had the effect of inhibiting the release of NO from RAW264.7 cells induced by LPS, as shown in Figure 2. Figure 3 .

[0074] discuss

[0075] In this study, a variety of modern chromatographic separation methods were used to separate the chemical components of the roots of Berberis spicata and study their anti-inflammatory activity. Four propylamine monomer compounds were isolated and identified, of which compound 1 was a new compound and the remaining compounds were first fractions from plants. Lipopolysaccharide was used to induce RAW264.7 macrophages to construct an inflammatory model, and the NO production inhibition activity was determined using the Griess reagent method to evaluate the monomer anti-inflammatory activity. The results showed that at a drug concentration of 10 μM, the three compounds could inhibit the release of NO from RAW264.7 cells induced by LPS, and had good anti-inflammatory activity. This experimental study enriched the chemical composition of Berberis genus medicinal materials, provided a certain reference for the study of the anti-inflammatory effect of the plant, and provided a scientific basis for the in-depth development and utilization of the plant.

Claims

1. A phenylpropanoid compound as shown in the following structure, or a pharmaceutically acceptable salt thereof:

2. A method for preparing a phenylpropanoid compound as shown in formula 1, characterized in that: The steps include: (1) Extract the flower of Goldenrod with 80-95% methanol, extract the extract with dichloromethane and n-butanol in sequence, and take the n-butanol extracted part for later use; (2) The n-butanol extraction part was passed through a silica gel column and gradient eluted with the mobile phase gradient of dichloromethane:methanol 100:1, 50:1, 40:1, 20:1, 10:1, 2:1, 0:1 to obtain 14 fractions in sequence; (3) taking the 11th fraction and performing gradient elution through a macroporous adsorption resin column, wherein the gradient is water, 30% methanol, 60% methanol, and 100% methanol, to obtain four fractions in sequence; (4) taking the second fraction, separating it through a polyamide column, and separating it with a mobile phase gradient of ethyl acetate:methanol 100:1, 50:1, 30:1, 20:1, 10:1, and 0:1, to obtain 9 fractions in sequence; (5) The first fraction was taken and subjected to isocratic elution by preparative high performance liquid chromatography with a mobile phase of 26% methanol to obtain compound 1.

3. The preparation method according to claim 2, characterized in that: In step (1), the methanol concentration is selected from 90%; In step (2), each gradient elution was 10 column volumes; In step (3), the macroporous adsorption resin is selected from SP825; In step (4), each gradient elution was 7 column volumes.

4. Use of the phenylpropanoid compound or a pharmaceutically acceptable salt thereof according to claim 1 in the preparation of a drug having anti-inflammatory activity.

5. The use according to claim 4, characterized in that The medicine is a medicine for treating inflammation caused by Gram-negative bacteria or lipopolysaccharide.

6. A method for extracting and separating multiple anti-inflammatory components from Goldenrod, characterized in that: The steps include: (1) Extract the flower of Goldenrod with 80-95% methanol, extract the extract with dichloromethane and n-butanol in sequence, and take the dichloromethane extraction part and the n-butanol extraction part for later use; (2) taking the dichloromethane extraction part, passing it through a silica gel column, and gradient eluting it. The mobile phase gradient was dichloromethane:methanol 100:1, 50:1, 40:1, 20:1, 10:1, 2:1, and 0:1, and 7 fractions were obtained in sequence. The second, third, and fifth fractions were respectively taken for use; (3) The second fraction of step (2) was taken and subjected to isocratic elution by preparative high performance liquid chromatography with a mobile phase of 40% methanol to obtain compound 3, the structural formula of which is as follows: (4) The third fraction of step (2) was taken and gradient eluted through an HP20 column, the gradient being water, 30% methanol, 60% methanol, and 100% methanol, to obtain 4 fractions. The third fraction was taken and separated through a polyamide column, the mobile phase being EtOAc:MeOH=100:1, 50:1, 30:1, 20:1, 10:1, and 0:1, to obtain 6 fractions in sequence. The first fraction was taken and isocratically eluted through preparative high performance liquid chromatography, the mobile phase being 32% methanol, to obtain compound 2, the structural formula of which is as follows: (5) The fifth fraction of step (2) was gradient eluted through an SP825 column, the mobile phases were water, 30% methanol, 60% methanol, 100% methanol, and four fractions were obtained in sequence. The third fraction was separated through a polyamide column, the mobile phase was ethyl acetate: methanol = 100:1, 50:1, 40:1, 30:1, 20:1, 10:1, 0:1, the 50:1, 40:1 elution positions were taken, and gradient eluted through an octadecyl bonded silica column, methanol was the organic phase, water was the aqueous phase, the organic phase gradient was 20%, 60%, 80%, 100%, each gradient elution was 7 BV, and 12 fractions were obtained in sequence. The sixth fraction was isocratically eluted through preparative high performance liquid chromatography, the mobile phase was 31% methanol, and compound 4 was obtained, the structural formula of which is as follows:

7. Use of a thorny goldenrod extract in preparing a drug having anti-inflammatory activity, the preparation method of the thorny goldenrod extract comprising: Take the goldenrod flower, extract it with 80-95% methanol, extract the extract with dichloromethane and n-butanol in sequence, and take the dichloromethane extraction part or the n-butanol extraction part, which is the goldenrod flower extract.

8. Use of Compound 2 or Compound 4, or a pharmaceutically acceptable salt thereof, in the preparation of a medicament having anti-inflammatory activity.

9. The use according to claim 7 or 8, characterized in that The medicine is a medicine for treating inflammation caused by Gram-negative bacteria or lipopolysaccharide.

Images