Xanthone compound as well as preparation method and application thereof

Abstract

The invention discloses a xanthone compound as well as a preparation method and application thereof, the xanthone compound is obtained by taking the thick-shell stem and leaf of a dry gambogic red thick-shell plant, namely, Yunnan red, as a raw material through extract extraction, organic solvent extraction, silica gel column chromatography and high-pressure liquid chromatography separation, and the molecular formula of the xanthone compound is C23H22O6. The xanthone compound provided by the invention can reduce generation of zebra fish neutrophils, has anti-inflammatory and repairing effects, can be used for preparing anti-inflammatory drugs, and has a good application prospect.

Description

Technical Field

[0001] The present invention relates to the technical field of plant active ingredient extraction, and particularly relates to an xanthone compound, a preparation method thereof, and an application thereof. Background Art

[0002] Calophyllum polyanthum Wall.ex Choisy. is a tall tree with a round trunk, mainly distributed in tropical regions of Asia. In China, it grows in the valley thick forests at an altitude of 1100 - 1800 m in Yunnan Province. This plant is used in Chinese folk medicine to treat traumatic bleeding and relieve pain. Its seed oil is often used to treat skin wounds and scabies. Phytochemical studies have shown that the main bioactive components of the Calophyllum genus are various types of compounds such as xanthones, chromanone derivatives, coumarins, flavonoids, triterpenoids, etc., which have various biological activities, such as antioxidant, anti-inflammatory, cytotoxic, anti-HIV, antibacterial, anti-tumor, anti-parasitic, and mitochondrial respiration activities.

[0003] How to more effectively utilize Calophyllum polyanthum Wall.ex Choisy. of the Calophyllum genus in Guttiferae and find active ingredients with development prospects therefrom is a technical problem that needs to be solved by those skilled in the art. Summary of the Invention

[0004] The first object of the present invention is to provide an xanthone compound; the second object is to provide a preparation method of the xanthone compound; the third object is to provide an application of the xanthone compound in the preparation of anti-inflammatory drugs.

[0005] The first object of the present invention is achieved as follows. An xanthone compound, which is obtained by taking the stems and leaves of the dried Calophyllum polyanthum Wall.ex Choisy. of the Calophyllum genus in Guttiferae as raw materials, through extract extraction, organic solvent extraction, silica gel column chromatography, and high-pressure liquid chromatography separation. The molecular formula of the xanthone compound is C 23 H 22 O6; in the present invention, this xanthone compound is named caledonixanthone N.

[0006] The structural formula of the xanthone compound is:

[0007]

[0008] The second object of the present invention is achieved as follows. A preparation method of an xanthone compound, comprising the following steps:

[0009] A. Extracting the extract: Coarsely crush the stems and leaves of Calophyllum polyanthum Wall. ex Choisy, a plant of the genus Calophyllum in the Clusiaceae family, to 20 - 40 mesh, and ultrasonically extract with an organic solvent 2 - 4 times, 30 - 60 minutes each time. Combine the extracts; filter the extract, and when the extract is concentrated under reduced pressure to 1 / 4 - 1 / 2 of its original volume, let it stand, filter out the precipitate, and concentrate it into extract a;

[0010] B. Organic solvent extraction: Add water in an amount 1 - 2 times the weight of extract a, and extract with an organic solvent of the same volume as water 3 - 5 times. Combine the organic solvent extraction phases and concentrate under reduced pressure to obtain extract b;

[0011] C. Silica gel column chromatography: Dissolve extract b in an organic solvent in an amount 1.5 - 3 times the weight of extract b, then mix it with silica gel of 100 - 200 mesh in an amount 0.8 - 1.2 times the weight of the extract, and then perform silica gel column chromatography. The silica gel for packing the column is 200 - 300 mesh, and the amount used is 6 - 8 times the weight of extract b; Gradient elute with a mixed organic solvent with a volume ratio of 1:0 - 0:1, collect the gradient eluate, concentrate it, and monitor by TLC, and combine the same parts;

[0012] D. Reverse - phase column chromatography: Load the eluate obtained by eluting with an organic solvent in a ratio of 4:1 onto a reverse - phase column chromatography. The reverse - phase column is packed with a reverse - phase material such as C - 18, C - 8, or ODS; Gradient elute with a methanol - aqueous solution with a volume content of 20 - 100%, collect each part of the eluate and concentrate it, and monitor by TLC, and combine the same parts;

[0013] E. Liquid chromatography separation: Purify the eluate obtained by eluting with a methanol - aqueous solution with a volume content of 60 - 100% through high - performance liquid chromatography to obtain the xanthone compounds.

[0014] Specifically, in step E, the high - performance liquid chromatography separation and purification uses methanol with a content of 60 - 100% as the mobile phase, a flow rate of 3 ml / min, a reverse - phase preparative column of 10×250 mm, 10 μm as the stationary phase, a detection wavelength of 254 nm for the ultraviolet detector, inject 20 - 100 μL each time, collect the chromatographic peaks from 10 - 40 minutes, evaporate to dryness after multiple accumulations to obtain the xanthone compounds.

[0015] Among them, in step A, the organic solvent is ethanol or methanol with a content of 70 - 100%.

[0016] Among them, in step B, the organic solvent is one of dichloromethane, petroleum ether, and chloroform.

[0017] Among them, in step C, the mixed organic solvent is dichloromethane - methanol, or dichloromethane - ethyl acetate, or chloroform - acetone, or petroleum ether - ethyl acetate.

[0018] Among them, in step C, the volume ratio of the mixed organic solvents is one of 1:0, 100:1, 20:1, 9:1, 8:2, 7:3, 3:2, 1:1, 1:2, 0:1.

[0019] The xanthone compounds of the present invention are isolated for the first time, determined to be xanthone compounds by nuclear magnetic resonance and other spectroscopic determination methods, and their specific structures are characterized as:

[0020]

[0021] Upon identification, compound caledonixanthone N is a yellow amorphous solid; ultraviolet spectrum (solvent is methanol), λ max : 196, 254, 306, 324 nm; infrared spectrum (KBr tablet) ν max 3436, 2934, 2834, 1709, 1601, 1512, 1463, 1432, 1349, 1268, 1237 cm -1 ; HRESIMS shows that the quasi-molecular ion peak of the compound of the present invention is m / z 395.1563 [M + H] + , (calculated value 395.1489), combined with 13 C and 1 HNMR spectra ( Figure 1 and Figure 2 , the data attribution of the carbon spectrum and hydrogen spectrum is shown in Table 1) gives its molecular formula as C 23 H 22 O6. 1 HNMR (CD3OD, 600 MHz) and 13 C NMR (CD3OD, 125 MHz) data are shown in Table 1.

[0022] HRESIMS shows that its quasi-molecular ion peak is the quasi-molecular ion peak m / z 395.1563 [M + H] + , (calculated value 395.1489), combined with 13 C NMR spectrum to determine the molecular formula as C 23 H 22 O6, and the degree of unsaturation is 13. The infrared spectrum shows that the compound contains hydroxyl groups (3436 cm -1 ), carbonyl groups (1709 cm -1 ) and phenyl groups (1601 cm -1 and 1512 cm -1 ) and other functional groups. According to its ultraviolet spectrum with maximum absorption at 196, 254, 306, 324 nm, the 1 H- and 13 C-NMR data attribution is shown in Table 1.1 1H-NMR spectrum (δ H 7.13, t, J = 7.7 Hz; δ H 7.18, dd, J = 1.7, 7.7 Hz; δ H 7.60, dd, J = 1.7, 7.7 Hz) shows the presence of a 1,2,3-trisubstituted benzene ring. In addition, the 1 1H and 13 13C NMR spectra show the presence of a 2,2-dimethylpyran group [δ H 7.03, d, J = 10.0 Hz; δ H 5.68, d, J = 10.0 Hz; δ H 1.47, s; δ C 116.5 (C-1′), 128.2 (C-2′), 79.7 (C-3′), 28.7 (C-4′, 5′) and a 3-hydroxy-2,2-dimethyldihydropyran group [δ H 2.89, dd, J = 17.0, 5.5 Hz; δ H 2.55, dd, J = 17.0, 7.0 Hz; δ H 3.78, t, J = 7.0 Hz; δ H 1.42, s; δ H 1.33, s; δ C 26.6 (C-1′), 69.2 (C-2′), 80.1 (C-3′), 25.6 (C-4′), 21.1 (C-5′)], similar to the known compound macluraisoflavone K, suggesting that this compound is an xanthone compound. Figure 3 In 1 1H- 1 1H COSY correlations (δ H 7.13, t, J = 7.7 Hz; δ H 7.18, dd, J = 1.7, 7.7 Hz; δ H 7.60, dd, J = 1.7, 7.7 Hz) and HMBC correlations δ H 7.60 to C-9 (δ C 177.8) indicate that the hydroxyl group is attached to C-4. The HMBC correlations between H-1″ / C-6, 5, 4b and H-2″ / C-5 determine the position of the dimethylpyran group at C-5 / 6. At the same time, the HMBC correlations between H-1′ / C-7, C-8 and H-2′ / C-7 indicate that the dimethyldihydropyran group is fused to C-7 and C-8. Based on these data, it is speculated that this compound is an xanthone with a 2,2-dimethylpyran group, and this compound is determined to be caledonixanthone N.

[0023] The third object of the present invention is achieved by using the xanthone compounds in the preparation of anti-inflammatory drugs. In vivo inflammation-clearing activity tests in zebrafish showed that the xanthone compounds significantly inhibited neutrophil aggregation in tail-decapitated zebrafish, with an effect comparable to that of the positive control, dexamethasone. These xanthone compounds can be used to prepare anti-inflammatory drugs and have good application prospects. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Figure 1 is the C NMR spectrum of compound caledonixanthone N ( 13 C NMR);

[0025] Figure 2 is the H NMR spectrum of compound caledonixanthone N ( 1 H NMR);

[0026] Figure 3 The main component of caledonixanthone N 1 H- 1 H COSY (—) and HMBC (→) correlation spectra;

[0027] Figure 4 The compound caledonixanthone N inhibits the accumulation of neutrophils in zebrafish tail amputation. DETAILED DESCRIPTION

[0028] To make the objects, features, and advantages of the present invention more readily apparent, the following detailed description of specific embodiments of the present invention is provided in conjunction with the accompanying drawings. The accompanying drawings illustrate several embodiments of the present invention. However, the present invention may be implemented in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided to provide a more thorough and comprehensive understanding of the present invention.

[0029] The present invention is described below in different embodiments. The plants of the Garcinia family in each embodiment are not limited by region or variety and can all be used to implement the present invention.

[0030] Example 1

[0031] Take 3.5 kg of the stems and leaves of **Calophyllum polyanthum** Wall., a plant of the genus **Calophyllum** in the family **Guttiferae**, and coarsely crush them to 20 mesh. Ultrasonically extract with 85% ethanol-water 4 times, 30 minutes each time, and combine the extracts; filter the extract, and concentrate it under reduced pressure to 1 / 4 of its original volume; let it stand, filter off the precipitate, and concentrate it into 76 g of extract a; add 76 g of water to extract a, and extract it 5 times with dichloromethane of the same volume as water, combine the extraction phases, and concentrate it under reduced pressure into 21 g of extract b; pack a column with 168 g of silica gel of 200 mesh, dissolve 42 g of methanol in extract b, then add 21 g of silica gel of 100 mesh for sample mixing, and load the sample onto the column after mixing; elute with a gradient of dichloromethane-methanol mixed organic solvents with volume ratios of 1:0, 20:1, 9:1, 8:2, 7:3, 3:2, 1:1, 1:2, 0:1 respectively, collect the gradient eluate, concentrate it, monitor by TLC, combine the same parts, and obtain 9 parts. The eluate c of the dichloromethane-methanol mixed organic solvent with a volume ratio of 20:1 is 5 g; pack a column with reverse-phase material C-18, load eluate c onto the reverse-phase column, and perform gradient elution with a methanol aqueous solution with a volume content of 20 - 100%, collect each part of the eluate and concentrate it, monitor by TLC, and combine the same parts; take the eluate eluted with a methanol aqueous solution with a volume content of 70 - 90%, then use 80% methanol as the mobile phase, with a flow rate of 3 ml / min, a 10×250 mm, 10 μm Agilent Zorbax SB-C18 reverse-phase preparative column as the stationary phase, the detection wavelength of the ultraviolet detector is 254 nm, inject 100 μL each time, collect the chromatographic peak at 29 minutes, evaporate to dryness after multiple accumulations, and obtain the xanthone compound called caledonixanthone N.

[0032] Example 2

[0033] Note: The scientific names in this translation are presented in italics for botanical nomenclature style. In a formal patent context, it's important to ensure the accuracy of such biological taxonomic information.Take 4.6 kg of the stems and leaves of Calophyllum polyanthum Wall. var. inophylloides Wall., which is a plant of the genus Calophyllum in the family Clusiaceae, and coarsely pulverize it to 20 mesh. Ultrasonically extract it 3 times with 75% ethanol for 30 minutes each time, and combine the extracts; filter the extract, and concentrate it under reduced pressure to 1 / 3 of its original volume; let it stand, filter off the precipitate, and concentrate it into 80 g of extract a; add 160 g of water to extract a, and extract it 3 times with dichloromethane in an equal volume to water, combine the extraction phases, and concentrate it under reduced pressure to 30 g of extract b; pack a column with 240 g of silica gel with a mesh size of 200 - 300, dissolve 48 g of dichloromethane in extract b, then add 30 g of silica gel with a mesh size of 100 for sample mixing, and load the sample onto the column after mixing; elute it with a gradient of dichloromethane - ethyl acetate mixed organic solvents with volume ratios of 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, 1:2, and 0:1 respectively, collect the gradient eluate, concentrate it, monitor it by TLC, and combine the same parts; the eluate c of the dichloromethane - ethyl acetate mixed organic solvent with a volume ratio of 6:4 is 6 g; pack a column with reverse-phase material C-18, load eluate c onto the reverse-phase column, and perform gradient elution with a methanol aqueous solution with a volume content of 20 - 100%, collect each part of the eluate and concentrate it, monitor it by TLC, and combine the same parts; take the eluate eluted with a methanol aqueous solution with a volume content of 65 - 85%, then use 75% methanol as the mobile phase, with a flow rate of 3 ml / min, a 10×250 mm, 10 μm Agilent Zorbax SB-C18 reverse-phase preparative column as the stationary phase, the detection wavelength of the ultraviolet detector is 254 nm, inject 50 μL each time, collect the chromatographic peak for 36 minutes, accumulate it multiple times and then evaporate to dryness to obtain the xanthone compound caledonixanthone N as described above.

[0034] Example 3

[0035] Take 8 kg of the stems and leaves of Calophyllum polyanthum Wall. var. inophylloides Wall., which are dried, coarsely pulverized to 30 mesh, and ultrasonically extracted 4 times with 80% methanol for 40 minutes each time. The extracts are combined, filtered, and concentrated under reduced pressure to 1 / 2 of the original volume. Let it stand, filter off the precipitate, and concentrate it into 159 g of extract a. Add 161 g of water to extract a, and extract it 4 times with chloroform of the same volume as water. Combine the extraction phases and concentrate them under reduced pressure to 53 g of extract b. Pack a column with 408 g of silica gel of 180 mesh. Dissolve 106 g of acetone in extract b, then add 66 g of silica gel of 120 mesh for sample mixing. After sample mixing, load the sample onto the column. Elute it with a gradient of chloroform-acetone mixed organic solvents with volume ratios of 1:0, 20:1, 9:1, 8:2, 7:3, 3:2, 1:1, 1:2, and 0:1 respectively. Collect the gradient eluate, concentrate it, monitor it by TLC, and combine the same parts. The eluate c with a volume ratio of 3:2 chloroform-acetone mixed organic solvent is 13 g. Pack a column with reverse-phase material ODS. Load eluate c onto the reverse-phase column and elute it with a gradient of methanol aqueous solution with a volume content of 20 - 100%. Collect each part of the eluate and concentrate it, monitor it by TLC, and combine the same parts. Take the eluate eluted with methanol aqueous solution with a volume content of 80 - 100%. Then, using 82% methanol as the mobile phase, a flow rate of 3 ml / min, a 10×250 mm, 10 μm Agilent Zorbax SB-C18 reverse-phase preparative column as the stationary phase, and a detection wavelength of 254 nm for the ultraviolet detector, inject 80 μL each time, collect the chromatographic peak at 23 minutes, and after multiple accumulations, evaporate to dryness to obtain the xanthone compound caledonixanthone N as described above.

[0036] Example 4

[0037] Take 5.9 kg of the stems and leaves of Garcinia cowa Roxb. var. oblongata Y. H. Li, a plant of the genus Garcinia in the family Clusiaceae, and coarsely pulverize it to 40 mesh. Extract it three times with 90% ethanol, and combine the extraction solutions. Filter the extraction solution and concentrate it under reduced pressure to 1 / 4 of its original volume. Let it stand, filter off the precipitate, and concentrate it into 89 g of extract a. Add 96 g of water to extract a, and extract it four times with petroleum ether of the same volume as the water. Combine the extraction phases and concentrate them under reduced pressure to 31 g of extract b. Pack a column with 1200 g of silica gel of 160 mesh. Dissolve 62 g of methanol in extract b, then add 37 g of silica gel of 200 mesh for sample mixing. After sample mixing, load it onto the column. Gradient elute with a mixed organic solvent of petroleum ether - ethyl acetate with volume ratios of 100:1, 20:1, 9:1, 8:2, 7:3, 3:2, 1:1, 1:2, and 0:1 respectively. Collect the gradient elution solution, concentrate it, and monitor it by TLC. Combine the same parts. The elution solution c of the mixed organic solvent of petroleum ether - ethyl acetate with a volume ratio of 9:1 is 6.6 g. Pack a column with reverse-phase material C-8, load elution solution c onto the reverse-phase column, and gradient elute with a methanol aqueous solution with a volume content of 20 - 100%. Collect each part of the elution solution and concentrate it. Monitor it by TLC and combine the same parts. Take the elution solution eluted with a methanol aqueous solution with a volume content of 60 - 80%, and then use 83% methanol as the mobile phase, with a flow rate of 3 ml / min, a 10×250 mm, 10 μm Agilent Zorbax SB-C18 reverse-phase preparative column as the stationary phase, and a detection wavelength of 254 nm for the ultraviolet detector. Collect the chromatographic peak at 26 min, evaporate to dryness after multiple accumulations, and obtain the xanthone compound caledonixanthone N as described above.

[0038] Example 5

[0039] Take the compound caledonixanthone N prepared in Example 1, which is a yellow amorphous solid; the determination method is: use nuclear magnetic resonance and combine other spectroscopic techniques to identify the structure.

[0040] (1) Ultraviolet spectrum (solvent is methanol), λ max : 196, 254, 306, 324 nm;

[0041] (2) Infrared spectrum (KBr tablet) ν max 3436, 2934, 2834, 1709, 1601, 1512, 1463, 1432, 1349, 1268, 1237 cm -1 ;

[0042] (3) HRESIMS shows that the quasi-molecular ion peak of the compound of the present invention is m / z 395.1563 [M + H] + , (calculated value 395.1489), combined with 13 C and 1 H NMR spectra (Figure 1 and Figure 2 , the carbon and hydrogen NMR data are summarized in Table 1), giving its molecular formula as C 23 H 22 O6. 1 H NMR (600 MHz, CD3OD) and 13 C NMR (125 MHz, CD3OD) data are shown in Table 1.

[0043] HRESIMS shows that its quasi-molecular ion peak is at m / z 395.1563 [M+H] + , (calculated value 395.1489), combined with 13 C NMR spectrum to determine the molecular formula as C 23 H 22 O6, with an unsaturation degree of 13. The infrared spectrum shows that the compound contains hydroxyl groups (3436 cm -1 ), carbonyl groups (1709 cm -1 ), and phenyl groups (1601 cm -1 and 1512 cm -1 ) and other functional groups. Based on its maximum absorption at 196, 254, 306, and 324 nm in the ultraviolet spectrum, it is speculated that the compound is an xanthone compound. The 1 H- and 13 C-NMR data assignments are shown in Table 1. 1 The H-NMR spectrum (δ H 7.13, t, J = 7.7 Hz; δ H 7.18, dd, J = 1.7, 7.7 Hz; δ H 7.60, dd, J = 1.7, 7.7 Hz) shows the presence of a 1,2,3-trisubstituted benzene ring. In addition, the 1 H and 13 C NMR spectra show the presence of a 2,2-dimethylpyran group [δ H 7.03, d, J = 10.0 Hz; δ H 5.68, d, J = 10.0 Hz; δ H 1.47, s; δ C 116.5 (C-1′), 128.2 (C-2′), 79.7 (C-3′), 28.7 (C-4′, 5′) and a 3-hydroxy-2,2-dimethyldihydropyran group [δ H 2.89, dd, J = 17.0, 5.5 Hz; δ H 2.55, dd, J = 17.0, 7.0 Hz; δ H 3.78, t, J = 7.0 Hz; δ H 1.42, s;H 1.33, s; δ C 26.6 (C-1′), 69.2 (C-2′), 80.1 (C-3′), 25.6 (C-4′), 21.1 (C-5′)], similar to the known macluraisoflavone K. In Figure 3 of 1 H- 1 HCOSY correlations (δ H 7.13, t, J = 7.7 Hz; δ H 7.18, dd, J = 1.7, 7.7 Hz; δ H 7.60, dd, J = 1.7, 7.7 Hz) and HMBC correlations δ H 7.60 to C-9 (δ C 177.8) indicate that the hydroxyl group is attached to C-4. The HMBC correlations between H-1″ / C-6, 5, 4b and H-2″ / C-5 determine the position of the dimethylpyran group at C-5 / 6. Meanwhile, the HMBC correlations between H-1′ / C-7, C-8 and H-2′ / C-7 indicate that the dimethyldihydropyran group is fused to C-7 and C-8. Based on the negative specific rotation value of the known compound macluraisoflavone K and its 1 same coupling constants in 1H-NMR, its absolute configuration is speculated to be the 2′R form. Based on these data, it is speculated that this compound is an xanthone with a 2,2-dimethylpyran group. In summary, the structure of the compound can be inferred, and this compound is determined to be caledonixanthone N.

[0044] Example 6

[0045] Take the compound prepared in Example 2, which is a yellow amorphous solid; perform structure determination according to the method in Example 5, and the result is: its structure is the same as that in Example 5, and the molecular formula is C 23 H 22 O6. It is confirmed that the compound prepared in Example 2 is the flavonoid compound caledonixanthone N.

[0046] Example 7

[0047] Take the compound prepared in Example 3, which is a yellow amorphous solid; perform structure determination according to the method in Example 5, and the result is: its structure is the same as that in Example 5, and the molecular formula is C 23 H 22 O6. It is confirmed that the compound prepared in Example 3 is the flavonoid compound caledonixanthone N.

[0048] Example 8

[0049] The compound prepared in Example 4 was a yellow amorphous solid. The structure was determined by the method in Example 5. The result was: the structure was the same as that in Example 5, and the molecular formula was C 23 H 22 O6. The compound prepared in Example 4 was confirmed to be the flavonoid compound caledonixanthone N.

[0050] Table 1 Compounds 1 H and 13 C NMR data (600 / 125 MHz, CD3OD)

[0051]

[0052] Example 9

[0053] The xanthone compound prepared in Example 1 was used to test its inflammation-clearing activity in zebrafish. The test results are as follows:

[0054] Neutrophils in zebrafish embryos are highly similar to human neutrophils in morphology, biochemistry, and physiological functions.

[0055] Neutrophils are the first white blood cells to appear at sites of injury or pathogen invasion, clearing out infections and harmful substances. A tail-cutting model was used to induce neutrophil accumulation in zebrafish embryos. Changes in neutrophil numbers in the tails of fish embryos were compared between the test substance-treated group and the control group.

[0056] Activity determination method:

[0057] (1) Construction of wound inflammation model: 3 dpf green fluorescent protein-labeled transgenic zebrafish Tg(mpx:EGFP) were anesthetized in 0.02% tricaine solution. The tail fin was transected using a sterile scalpel, and 5 ml of the test solution of the corresponding concentration group was immediately added. 15 zebrafish / group were placed in 3 parallel groups.

[0058] (2) After the test solution has been incubated for 96 h, the zebrafish are washed 2 to 3 times with culture water and added to a 96-well plate one by one, 1 fish per well.

[0059] (3) After anesthesia with 0.04% tricaine, the green fluorescent cells in the caudal fin wound at 96 hpf were observed under a fluorescence microscope and photographed.

[0060] (4) Count the number of green fluorescent cells (neutrophils and macrophages) within 200 μm of the incision.

[0061] The results are as follows Figure 4As shown, this xanthone compound can significantly inhibit the aggregation of neutrophils in tail-truncated zebrafish, and the effect is equivalent to that of the positive control dexamethasone.

[0062] In the description of this specification, the description with reference to terms such as "one embodiment", "some embodiments", "example", "specific example", or "some examples" means that the specific features, structures, materials, or characteristics described in connection with the embodiment or example are included in at least one embodiment or example of the present invention. In this specification, the schematic representations of the above terms do not necessarily refer to the same embodiment or example. Moreover, the specific features, structures, materials, or characteristics described can be combined in a suitable manner in any one or more embodiments or examples.

[0063] The above-described embodiments only represent several implementation manners of the present invention. The description is relatively specific and detailed, but it should not be construed as a limitation on the scope of the patent of the present invention. It should be noted that for those of ordinary skill in the art, without departing from the concept of the present invention, several modifications and improvements can still be made, and these all belong to the protection scope of the present invention. Therefore, the protection scope of the patent of the present invention shall be subject to the appended claims.

Claims

1. An xanthone compound, characterized in that, The xanthone compounds are obtained from the stems and leaves of **Calophyllum polyanthum** Wall. ex Choisy, a plant of the genus **Calophyllum** in the family **Clusiaceae**, through processes including extract preparation, organic solvent extraction, silica gel column chromatography, and high-pressure liquid chromatography separation. The molecular formula of the xanthone compounds is C 23 H 22 O6; The structural formula of the xanthone compound is as follows:

2. The preparation method of the xanthone compound according to claim 1, characterized in that, It includes the following steps: A. Extracting the extract: Coarsely crushing the stems and leaves of **Calophyllum polyanthum** Wall. ex Choisy in the family **Guttiferae** to 20 - 40 mesh, ultrasonically extracting with an organic solvent 2 - 4 times, each time for 30 - 60 min, and combining the extraction solutions; filtering the extraction solutions, concentrating the extraction solutions under reduced pressure to 1 / 4 - 1 / 2 of the original volume, standing, filtering off the precipitates, and concentrating into extract a; B. Extracting with an organic solvent: Adding 1 - 2 times the weight of water to extract a, extracting with an organic solvent of the same volume as water 3 - 5 times, combining the organic solvent extraction phases, and concentrating under reduced pressure into extract b; C. Silica gel column chromatography: Dissolving extract b with 1.5 - 3 times the weight of an organic solvent, then mixing with 100 - 200 mesh silica gel at 0.8 - 1.2 times the weight of the extract, and then performing silica gel column chromatography. The silica gel for packing the column is 200 - 300 mesh, and the amount used is 6 - 8 times the weight of extract b; Gradient eluting with a mixed organic solvent with a volume ratio of 1:0 - 0:1, collecting the gradient elution solutions, concentrating, monitoring by TLC, and combining the same parts; D. Reverse - phase column chromatography: Subjecting the elution solution obtained by eluting with an organic solvent in a ratio of 4:1 to reverse - phase column chromatography. The reverse - phase column is packed with a reverse - phase material such as C - 18, C - 8, or ODS; Gradient eluting with a methanol - aqueous solution with a volume content of 20 - 100%, collecting each part of the elution solution and concentrating, monitoring by TLC, and combining the same parts; E. Liquid chromatography separation: Subjecting the elution solution obtained by eluting with a methanol - aqueous solution with a volume content of 60 - 100% to high - performance liquid chromatography separation and purification to obtain the xanthone compound.

3. The preparation method of the xanthone compound according to claim 2, characterized in that, In step E, the high - performance liquid chromatography separation and purification uses methanol with a content of 60 - 100% as the mobile phase, a flow rate of 3 ml / min, a 10×250 mm, 10 μm reverse - phase preparation column as the stationary phase, a detection wavelength of 254 nm for the ultraviolet detector, injecting 20 - 100 μL each time, collecting the chromatographic peaks within 10 - 40 min, evaporating to dryness after multiple accumulations to obtain the xanthone compound.

4. The preparation method of the xanthone compound according to claim 2, characterized in that, In step A, the organic solvent is ethanol or methanol with a content of 70 - 100%.

5. The method for preparing the xanthone compound according to claim 2, characterized in that, In step B, the organic solvent is one of dichloromethane, petroleum ether, and chloroform.

6. The preparation method of the xanthone compound according to claim 2, characterized in that, In step C, the mixed organic solvent is dichloromethane - methanol, or dichloromethane - ethyl acetate, or chloroform - acetone, or petroleum ether - ethyl acetate.

7. The method for preparing the xanthone compound according to claim 2, characterized in that, In step C, the volume ratio of the mixed organic solvent is one of 1:0, 100:1, 20:1, 9:1, 8:2, 7:3, 3:2, 1:1, 1:2, 0:

1.

8. Use of the xanthone compound according to claim 1 in the preparation of anti - inflammatory drugs.

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