A phenylpropanoid compound and its preparation method and use

Abstract

The present invention adopts multiple chromatographic separation methods such as silica gel column chromatography, HP20 column chromatography, polyamide column chromatography, reversed-phase C18 column chromatography, and preparative high-performance liquid chromatography to systematically separate and purify the chemical components of the root of Tripterygium wilfordii. The compound structures are identified by physicochemical properties and spectroscopic methods (1D-NMR, 2D-NMR, UV, MS, and CD), and four compounds are separated and prepared. The present invention also finds that these compounds have anti-inflammatory activity.

Description

Technical Field

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

[0002] Berberis polyantha Hemsl. is a medicinal material of the genus Berberis in 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 to wash eyes and treat eye diseases.

[0003] Berberis is a rich wild resource. Its diverse medicinal parts, including roots, stems, leaves, root bark, stem bark, flowers, and fruits, are known to clear heat and dampness, purge fire, and detoxify. It is primarily used to treat conditions such as red and swollen eyes, sore throat, dysentery with blood in the stool, jaundice due to dampness, eczema, and ulcers with yellow, swollen, and toxic effects. Its pharmacological activities include anti-inflammatory, anti-tumor, antioxidant, analgesic, and antibacterial properties.

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

[0005] The present invention adopts multiple chromatographic separation methods such as silica gel column chromatography, HP20 column chromatography, polyamide column chromatography, reversed-phase C18 column chromatography, and preparative high-performance liquid chromatography to systematically separate and purify the chemical components of the root of Tripterygium wilfordii. The compound structures are identified by physicochemical properties and spectroscopic means (1D-NMR, 2D-NMR, UV, MS and CD), and four compounds are separated and prepared. 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 represented by 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 use the n-butanol-extracted portion for later use;

[0010] (2) The n-butanol extraction fraction 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, and 0:1, to obtain 14 fractions in sequence;

[0011] (3) The 11th fraction was taken and subjected to gradient elution through a macroporous adsorption resin column. The gradient was water, 30% methanol, 60% methanol, and 100% methanol, respectively, to obtain four fractions.

[0012] (4) The second fraction was separated by polyamide chromatography column 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 preparative high performance liquid chromatography with isocratic elution using 26% methanol as the mobile phase to obtain compound 1.

[0014] Furthermore, 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 performed for 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) The dichloromethane extraction fraction was passed through a silica gel column by gradient elution. The mobile phase gradient was dichloromethane:methanol 100:1, 50:1, 40:1, 20:1, 10:1, 2:1, and 0:1. Seven fractions were obtained in sequence, and the second, third, and fifth fractions were respectively taken for later use.

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

[0023]

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

[0025]

[0026] (5) The fifth fraction of step (2) was taken and gradient eluted through an SP825 column. The mobile phase was water, 30% methanol, 60% methanol, and 100% methanol in sequence. Four fractions were obtained in sequence. The third fraction was separated by a polyamide column. The mobile phase was 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 were taken and gradient eluted through an octadecyl bonded silica gel column. Methanol was the organic phase and water was the aqueous phase. The organic phase gradient was 20%, 60%, 80%, and 100%. Each gradient elution was 7 BV. Twelve fractions were obtained in sequence. The sixth fraction was taken and isocratically eluted by preparative high performance liquid chromatography. The mobile phase was 31% methanol to obtain compound 4. The structural formula 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) The dichloromethane extraction fraction was passed through a silica gel column by gradient elution. The mobile phase gradient was dichloromethane:methanol 100:1, 50:1, 40:1, 20:1, 10:1, 2:1, and 0:1. Seven fractions were obtained in sequence, and the second, third, and fifth fractions were respectively taken for later use.

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

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

[0033] (5) The fifth fraction of step (2) was subjected to gradient elution through an SP825 column, with the mobile phase being water, 30% methanol, 60% methanol, and 100% methanol, to obtain four fractions in sequence. The third fraction was separated by a polyamide column, with the mobile phase being 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 were taken and subjected to gradient elution through an octadecyl bonded silica column, with methanol as the organic phase and water as the aqueous phase, with an organic phase gradient of 20%, 60%, 80%, and 100%. Each gradient elution was performed for 7 BV, to obtain 12 fractions in sequence. The sixth fraction was subjected to isocratic elution by preparative high performance liquid chromatography, with the mobile phase being 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] During 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 a 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 portion or the n-butanol extraction portion as the Goldenrod extract.

[0037] The present invention also provides use of Compound 2 or Compound 4, or a pharmaceutically acceptable salt thereof, in the preparation of 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 amount of NO released 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 chromatography (Jiangsu Hanbang Technology Co., Ltd.); automatic polarimeter (SGW-533, Shanghai Yidian Physical Optical Instrument Co., Ltd.); YMC-Pack ODS-A reversed-phase chromatographic column (250×10 mm, 5 μm); 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 Hemsl. polyantha 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). They were identified as B. polyantha Hemsl., a species of the genus Berberis, in the Berberidaceae family, by Professor Liu Yuan of the College of Grassland Resources at Southwest University for Nationalities. The voucher sample (CHH-202112) is stored in the herbarium of the Key Laboratory for the Protection and Utilization of Ethnic Medicinal Resources on the Qinghai-Tibet Plateau, State Ethnic Affairs Commission, 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] 20 kg of dried Cordyceps sinensis was ground and extracted with 90% methanol (solid-to-liquid ratio 1:12) under heating and reflux for three 1-hour extractions. The combined extracts were reconstituted with water and then extracted three times with dichloromethane and n-butanol in a 1:1 ratio. The combined extracts were dried under reduced pressure to yield 786 g of the dichloromethane layer and 645 g of the n-butanol layer.

[0055] Dissolve 786g of extract from the dichloromethane layer in methanol. Weigh an equal amount of 100-200 mesh silica gel to the dichloromethane layer and add the dissolved extract dropwise to the silica gel in small amounts (1:1 ratio). Mix thoroughly and evaporate the organic solvent before use. Weigh twice the weight of 200-300 mesh silica gel as the dichloromethane layer extract and load it into a vacuum chromatography column. Elute with a gradient of dichloromethane:methanol (100:1, 50:1, 40:1, 20:1, 10:1, 2:1, MeOH) for 10 BV per gradient elution to 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). Fraction D-3 was subjected to gradient elution through an HP20 column with the mobile phase consisting of methanol-water = Water, 30%, 60%, and MeOH, to obtain four fractions, namely D-3-1 to D-3-4. Fraction D-3-3 was separated through a polyamide column with the mobile phase consisting of EtOAc:MeOH = 100:1, 50:1, 30:1, 20:1, 10:1, and MeOH, to obtain six fractions, namely D-3-3-1 to D-3-3-6. Fraction D-3-3-1 was subjected to isocratic elution through pHPLC with the mobile phase consisting of 32% methanol-water to obtain compound 2 (CH-5, t R =80min, 8mg). The D-5 fraction was gradient eluted through an SP825 column with the mobile phase consisting of methanol-water = Water, 30%, 60%, and MeOH, to obtain four fractions (D-5-1, D-5-2, D-5-3, and D-5-4). Fr. D-5-3 was separated through a polyamide column with the mobile phase consisting of EtOAc:MeOH = 100:1, 50:1, 30:1, 20:1, 10:1, and MeOH, and five fractions were obtained by thin layer chromatography, 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 open ODS reverse phase column chromatography for gradient elution, the mobile phase was methanol-water = 20% to 60%, 80%, MeOH, each gradient elution was 7 BV, and 12 fractions (Fr.1 to Fr.12) were obtained by spot thin layer elution. 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 eluted through a silica gel column using a gradient of dichloromethane:methanol (100:1, 50:1, 40:1, 20:1, 10:1, 2:1, MeOH) with a gradient of 10 BV each to obtain 14 fractions (Z-1 to Z-14). Z-11 was eluted through an SP825 column using a mobile phase of methanol-water (Water, 30%, 60%, MeOH) to obtain four fractions, Z-11-1 to Z-11-4. Z-11-2 was separated through a polyamide column using a mobile phase of EtOAc:MeOH (100:1, 50:1, 30:1, 20:1, 10:1, MeOH) with a gradient of 7 BV each. After thin-layer chromatography, the resulting products were combined to obtain nine fractions (Fr.1 to Fr.9). Fr.1 was eluted isocratically by pHPLC with a mobile phase of 26% methanol-water to give 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 suggest the presence of a π-π conjugated benzene ring and an n-π transition carbonyl group 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 the presence of a proton signal of the 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 benzyl ketone carbon signal, 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 oxymethylene, δ C 55.6×2 is two methoxy carbon signals. In addition, there is a group of glucose signals: δ C The NMR spectral 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 (600 MHz) and 13 C-NMR (150 MHz) 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 suggestions 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) suggests that glucose is connected to C-2, δ H 1.49(H-3) and δ C 19.1(C-3), combined 1 H- 1 δ in the 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 compound 1 was hydrolyzed by acid, 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 was basically consistent with the theoretically calculated ECD spectrum of R-1 (Fig. 3), suggesting 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. A Scifinder literature search revealed this compound to be a novel compound not previously reported in the literature and named (2R)-1-(4-hydroxy-3,5-dimethoxyphenyl)-propan-1-one-2-O-beta-D-glucoside.

[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 (600 MHz, 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 (600 MHz, 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] 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 monomeric compounds isolated from the flower of the Chinese goldenseal. The anti-inflammatory activity of each monomeric compound was evaluated using the Griess reagent method, and each compound was administered at a concentration of 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. 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 serrata and study their anti-inflammatory activity. Four propyl-containing monomeric compounds were isolated and identified, of which compound 1 is a new compound and the remaining compounds are first-generation plant fractions. An inflammatory model was constructed by inducing RAW264.7 macrophages with lipopolysaccharide. The NO production inhibitory activity was determined using the Griess reagent method to evaluate the monomeric anti-inflammatory activity. The results showed that at a concentration of 10 μM, the three compounds could inhibit the LPS-induced NO release from RAW264.7 cells 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 this plant, and provided a scientific basis for the in-depth development and utilization of this plant.

Claims

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

2. The method for preparing a phenylpropanoid compound according to claim 1, wherein: The steps include: (1) Take the flower of Goldenrod, extract it with 80-95% methanol, extract it with dichloromethane and n-butanol in sequence, and keep 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, and 0:1, to obtain 14 fractions in sequence; (3) The 11th fraction was taken and subjected to gradient elution through a macroporous adsorption resin column. The gradient was water, 30% methanol, 60% methanol, and 100% methanol, and four fractions were obtained in sequence. (4) The second fraction was separated by polyamide chromatography column 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 the phenylpropanoid compound.

3. The preparation method according to claim 2, wherein: 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 performed for 7 column volumes.

4. Use of the phenylpropanoid compound or a pharmaceutically acceptable salt thereof according to claim 1 in the preparation of a medicament 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.

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