Phenolic compound as well as preparation method and application thereof

Abstract

The invention belongs to the technical field of traditional Chinese medicine biology, and particularly relates to a phenolic compound and a preparation method and application thereof.The phenolic compound is a pair of diastereoisomers, the formula I of the phenolic compound is dextroisomer and is named as (+)-fresh bamboo juice phenol B, and the formula II of the phenolic compound is levoisomer and is named as (-)-fresh bamboo juice phenol B. A pair of diastereoisomer phenolic compounds (+)-fresh bamboo juice phenol B and (-)-fresh bamboo juice phenol B are successfully obtained from fresh bamboo juice, and the diastereoisomer phenolic compounds (+)-fresh bamboo juice phenol B and (-)-fresh bamboo juice phenol B have remarkable inhibition effects on gastric cancer cells, liver cancer cells, colorectal cancer cells, bladder cancer cells and lung cancer cells of a human body through in-vitro cell tests; the compound can be used for preparing medicines for preventing or treating tumors, and has a wide application prospect.

Description

Technical Field

[0001] The present invention belongs to the field of traditional Chinese medicine biotechnology, and particularly relates to a phenolic compound, a preparation method thereof and an application thereof. Background Art

[0002] Fresh bamboo juice is a liquid flowing out from fresh stems after high-temperature heating, with a color ranging from yellow to reddish-brown, slightly sweet in taste, and is used for treating symptoms such as excessive phlegm and cough due to lung heat, asthma and chest tightness, stiffness of the tongue due to stroke, profuse phlegm, and infantile convulsions due to phlegm-heat.

[0003] Currently, the research on fresh bamboo juice mainly focuses on its pharmacological research, and the material basis of its efficacy is not clear. The chemical components of fresh bamboo juice are complex and diverse. Relevant research shows that fresh bamboo juice mainly contains chemical components such as amino acids, sugars, phenols, alcohols, aldehydes, organic acids, phenylpropanoids and lignans, and inorganic elements, but most of them have not been confirmed as what compounds. In order to further improve the quality control standard of fresh bamboo juice and ensure the safety and effectiveness of its clinical application, it is necessary to conduct in-depth analysis of its components. Summary of the Invention

[0004] Aiming at the problems existing in the prior art, the present invention provides a phenolic compound, a preparation method thereof and an application thereof. The phenolic compound is extracted from fresh bamboo juice, has a novel structure and pharmacological activity, and can provide a basis for the pharmacological research and safety of fresh bamboo juice.

[0005] The present invention provides a phenolic compound, which is a pair of diastereoisomers and has chemical structural formulas shown in Formula I and Formula II, wherein Formula I is the dextrorotatory form, named (+)-fresh bamboo juice phenol B, and Formula II is the levorotatory form, named (-)-fresh bamboo juice phenol B.

[0006] 。

[0007] The present invention also provides a preparation method of the above phenolic compound, comprising the following steps: (1) Cutting bamboo culms, carbonizing them by dry distillation, and concentrating under reduced pressure to obtain an extract, which is reserved for later use; (2) Taking an appropriate amount of the extract, extracting it 3 - 4 times with ethyl acetate and n-butanol respectively, and concentrating to obtain an ethyl acetate part and an n-butanol part; (3) Passing the n-butanol part through a D101 macroporous resin column, flushing it with 10%, 30%, 60%, and 90% ethanol aqueous solutions respectively, collecting each component and concentrating under reduced pressure to obtain a 60% ethanol part of the macroporous resin; (4) Subjecting the 60% ethanol part to silica gel column chromatography, eluting it with dichloromethane - methanol as an eluent by gradient, checking it by thin layer chromatography, and combining the similar components to finally obtain six components A, B, C, D, E, and F; (5) Subject the components in Group B to silica gel column chromatography, and perform gradient elution using petroleum ether - ethyl acetate as the eluent. After inspection by thin - layer chromatography, combine the similar components to obtain 4 components B1 - B4; (6) Subject the component B4 to gel permeation chromatography and elute with methanol to obtain 3 components B4.1 - B4.3; (7) Subject B4.2 to preparative reverse - phase high - performance liquid chromatography to obtain phenolic compounds; (8) Take the phenolic compounds and perform chiral resolution by reverse - phase high - performance liquid chromatography to obtain phenolic compounds of Formula I and Formula II.

[0008] Further, in step (1) of the above technical solution, the temperature of dry distillation is 120 °C, the pressure of vacuum concentration is 0.7 MPa, and the temperature is 60 °C.

[0009] Further, in step (2) of the above technical solution, the mass - to - volume ratio of the extract to ethyl acetate or n - butanol is 1:1.2 - 1.5, preferably 1:1.32.

[0010] Further, in step (4) of the above technical solution, the pore size of the silica gel column chromatography is 100 - 200 mesh; during gradient elution, the volume ratios of dichloromethane - methanol are 40:1, 30:1, 20:1, 10:1, 5:1 in sequence.

[0011] Further, in step (5) of the above technical solution, during gradient elution, the volume ratios of petroleum ether - ethyl acetate are 5:1, 4:1, 3:1, 2:1, 1:1, 0:1 in sequence.

[0012] Further, in step (7) of the above technical solution, for preparative reverse - phase high - performance liquid chromatography, the mobile phase is acetonitrile - water with a volume ratio of 26:74, and the flow rate is 7 mL / min.

[0013] Further, in step (8) of the above technical solution, for reverse - phase high - performance liquid chromatography, Phenomenex LuxCellulose - 4 is used as the chiral semi - preparative chromatographic column, and the mobile phase is acetonitrile - water with a volume ratio of 38:62.

[0014] The present invention also provides a pharmaceutical composition comprising the above - mentioned phenolic compounds and a pharmaceutically acceptable carrier.

[0015] The present invention also provides the use of the above - mentioned phenolic compounds or pharmaceutical composition in the preparation of drugs for preventing or treating tumor diseases, wherein the tumors include human gastric cancer cells, human liver cancer cells, human colorectal cancer cells, human bladder cancer cells, and human lung cancer cells.

[0016] Beneficial effects compared with the prior art: 1. The phenolic compounds successfully obtained in the present invention are prepared from fresh bamboo juice through processes such as dry distillation, vacuum concentration, extraction, macroporous resin column separation, two silica gel column chromatography separations, one gel filtration, reversed-phase preparative high-performance liquid chromatography, and finally chiral resolution by reversed-phase high-performance liquid chromatography. The phenolic compounds are a pair of diastereoisomer compounds, namely (+)-fresh bamboo juice phenol B and (-)-fresh bamboo juice phenol B. The preparation method is simple, rapid, and efficient.

[0017] 2. In vitro cell experiments show that both (+)-fresh bamboo juice phenol B and (-)-fresh bamboo juice phenol B have significant inhibitory effects on human gastric cancer cells, liver cancer cells, colorectal cancer cells, bladder cancer cells, and lung cancer cells, indicating that both have certain anti-tumor activities and can be used in the preparation of drugs for preventing or treating tumors. Comparatively, the inhibitory effect of (-)-fresh bamboo juice phenol B on the proliferation of the above cells is stronger than that of (+)-fresh bamboo juice phenol B, indicating that the anti-tumor activity of (-)-fresh bamboo juice phenol B is stronger than that of (+)-fresh bamboo juice phenol B. Description of the Drawings

[0018] Figure 1 This is the chromatogram of the diastereoisomers of the phenolic compounds of the present invention, where the left peak is (+)-fresh bamboo juice phenol B and the right peak is (-)-fresh bamboo juice phenol B; Figure 2 This is the high-resolution mass spectrum of the diastereoisomers of the phenolic compounds of the present invention; Figure 3 This is the UV spectrum of the diastereoisomers of the phenolic compounds of the present invention; Figure 4 This is for the diastereoisomers of the phenolic compounds of the present invention 1 1H NMR spectrum; Figure 5 This is for the diastereoisomers of the phenolic compounds of the present invention 13 13C NMR spectrum; Figure 6 This is the TOCSY spectrum of the diastereoisomers of the phenolic compounds of the present invention; Figure 7 This is the HMBC spectrum of the diastereoisomers of the phenolic compounds of the present invention; Figure 8 This is the HSQC spectrum of the diastereoisomers of the phenolic compounds of the present invention; Figure 9 This is the NOESY spectrum of the diastereoisomers of the phenolic compounds of the present invention; Figure 10 This is the ECD spectrum of (+)-fresh bamboo juice phenol B of the phenolic compounds of the present invention; Figure 11 This is the ECD spectrum of (-)-fresh bamboo juice phenol B of the phenolic compounds of the present invention. Detailed Embodiments

[0019] All the above technical features of the present invention can be combined with the technical features specifically described below (such as in the embodiments) to form new or preferred technical solutions. However, the present invention is not limited to these embodiments, and these embodiments do not limit the present invention in any way.

[0020] Unless otherwise specified, the experimental methods in the following examples are all conventional methods. Unless otherwise specified, the preparations involved in the following examples are all ordinary commercially available products and can be obtained through market purchase.

[0021] The Phyllostachys edulis used in the present invention is collected from Tonggu County, Yichun City, Jiangxi Province, and it is a plant of Phyllostachys edulis in the genus Phyllostachys of the Poaceae family. Phyllostachys edulis (Carr.) The fresh rhizome of H. de Lehaie.

[0022] The present invention will be further described in detail below in conjunction with the drawings and embodiments: Example 1: Preparation of phenolic compounds The preparation method of phenolic compounds includes the following steps: (1) Cut 10 t of Phyllostachys edulis, carry out dry distillation at 120 °C, and carry out reduced pressure concentration at 60 °C and 0.7 MPa to obtain an extract (96 kg) for standby; (2) Take 37.8 kg of the extract, extract it 3 times (50 L each time) with ethyl acetate and n-butanol in sequence, and concentrate to obtain an ethyl acetate part (310 g) and an n-butanol part (857 g); (3) Pass the 857 g of the n-butanol part through a D101 macroporous resin column, wash it with 10%, 30%, 60%, and 90% ethanol aqueous solutions respectively, collect each component and carry out reduced pressure concentration to obtain a 60% ethanol part of the macroporous resin (55 g); (4) Pass the 55 g of the 60% ethanol part through silica gel column chromatography (100 mesh - 200 mesh, 1000 g, inner diameter 80 mm, wet packing), and carry out gradient elution with dichloromethane - methanol as the eluent, where the volume ratio of dichloromethane - methanol is 40:1, 30:1, 20:1, 10:1, 5:1 in sequence. After inspection by thin layer chromatography, combine the similar components to finally obtain six components A, B, C, D, E, and F; (5) Pass the B component (1.3 g) through silica gel column chromatography (100 mesh - 200 mesh, 40 g, inner diameter 20 mm, wet packing), and carry out gradient elution with petroleum ether - ethyl acetate as the eluent, where the volume ratio of petroleum ether - ethyl acetate is 5:1, 4:1, 3:1, 2:1, 1:1, 0:1 in sequence. After inspection by thin layer chromatography, combine the similar components to obtain 4 components B1 - B4; (6) Pass the B4 component through Sephadex LH-20 gel and elute it with methanol to obtain 3 components B4.1, B4.2, and B4.3; (7) B4.2 (100 mg) was subjected to reversed-phase preparative high performance liquid chromatography using an XTerra prep MSC 18 column (300 mm × 19 mm, 10 μm), with acetonitrile-water (26:74) as the mobile phase and a flow rate of 7 mL / min to obtain a phenolic compound (19 mg).

[0023] Example 2: Resolution and Structure Identification of Diastereoisomers of Phenolic Compounds 1. Resolution The phenolic compound obtained in Example 1 was dissolved in 1 mL of methanol and subjected to reversed-phase high performance liquid chromatography using a Phenomenex Lux Cellulose-4 (250 mm × 4.6 mm, 5 μm) chiral semi-preparative chromatographic column, with acetonitrile-water (38:62) as the mobile phase to obtain Compounds I and II, which were named (+)-fresh bamboo juice phenol B and (-)-fresh bamboo juice phenol B respectively. Their chromatograms are as Figure 1 shown. The left peak is (+)-fresh bamboo juice phenol B and the right peak is (-)-fresh bamboo juice phenol B.

[0024]

[0025] 2. Structure Analysis (±)-Fresh bamboo juice phenol B is a yellow powder and is soluble in methanol; HRESIMS was measured by Waters ACQUITY UPLC / Xevo G2 QTOF (HR-Q-TOF-MS: Waters Co., Ltd., USA) m / z 405.1925 [M–H] – (calcd. for C 22 H 29 O7, 405.1913), and its molecular formula was determined to be C 22 H 30 O7. Among them, the high-resolution mass spectrum is as Figure 2 shown, and other confirmation spectra are as Figures 3 to 11 shown. The 1 1H-NMR, 13 13C-NMR nuclear magnetic data of (±)-fresh bamboo juice phenol B are shown in Table 1.

[0026] Table 1 1H-NMR, 1 13C-NMR Nuclear Magnetic Data of (±)-Fresh Bamboo Juice Phenol B 13 C-NMR nuclear magnetic data

[0027] a Recorded in CD3OD (1H NMR 600 MHz, 13C NMR 150 MHz). 1 In the 1H NMR spectrum, the hydrogen signals of the benzene ring at positions 1, 3, 4, and 5 are given: 6.26 (2H, s, H-2′, 6′), and a set of proton signals of an ABX system: 6.63 (1H, d, J J = 8.0 Hz, H-5′′), 6.55 (1H, dd, J J = 8.0, 1.9 Hz, H-6′′), 6.53 (1H, d, J J = 1.9 Hz, H-2′′); 4.38 (1H, d, J J = 8.3 Hz, H-3), 2.98 (1H, ddd, J J = 8.3, 7.3, 5.7 Hz, H-2) is the hydrogen signal of the methylene group adjacent to oxygen; 4.10 (1H, dd, J J = 10.9, 5.7 Hz, H-1) and 3.91 (1H, dd, J J = 10.9, 7.3 Hz, H-1) are the hydrogen signals of the methylene group adjacent to oxygen; 3.71 (6H, s, 3′, 5′-OCH3) and 3.68 (3H, s, 3′′-OCH3) are the hydrogen signals of 3 methoxy groups; 3.34 (1H, m, H-1′′′), 3.29 (1H,m, H-1′′′), 1.55 (2H, m, H-2′′′), 1.42 (2H, m, H-3′′′) and 0.91 (3H, t, J J = 7.4 Hz,H-4′′′) are the hydrogen signals of the n-butyl group. 13 In the 13C NMR spectrum, 10 aromatic ring carbon signals are shown: 131.8 (C-1′), 107.7 (C-2′, 6′), 148.7 (C-3′, 5′), 135.1 (C-4′), 133.4 (C-1′′), 112.2 (C-2′′), 148.4 (C-3′′), 146.7 (C-4′′), 115.4 (C-5′′), 121.3 (C-6′′); 4 n-butyl carbon signals: 69.4 (C-1′′′), 33.2 (C-2′′′), 20.6 (C-3′′′), 14.3 (C-4′′′); 2 methoxy carbon signals: 56.7 (3′, 5′-OCH3) and 56.6 (3′′-OCH3); the remaining 3 carbon signals: 64.8 (C-1), 56.3 (C-2 ), 85.7 (C-3). Analyze the above 1 1HNMR, 13Based on the 13C NMR and HR-Q-TOF-MS data, it can be known that this compound is a phenolic compound.

[0028] In the HMBC spectrum, J 2,3 J = 8.3 Hz, it can be inferred that the relative configuration of the compound is threo, and in the NOESY spectrum, 4.38 (1H, d, J J = 8.3 Hz, H-3) has no correlation with 2.98 (1H, ddd, J J = 8.3, 7.3, 5.7 Hz, H-2), which further proves this inference. In the HMBC spectrum, δ H 4.38 (1H, d, J J = 8.3 Hz, H-3) is correlated with δ C 69.4 (C-1′′′), 133.4 (C-1′′), indicating that C-3 is connected to the oxygenated butyl group and the benzene ring C-1′′ position; δ H 2.98 (1H, ddd, J J = 8.3, 7.3, 5.7 Hz, H-2) is correlated with δ C 131.8 (C-1′), indicating that C-2 is connected to the benzene ring C-1′ position. Therefore, the compound was identified as threo-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-3-butoxypropanol, and its main HMBC (H→C) correlation signals are shown as follows: .

[0029] The CD spectrum of the compound was measured by a circular dichroism spectrometer, and the result did not show an obvious trend, suggesting that it might be a mixture. Analysis by a chiral column confirmed that it was indeed a mixture.

[0030] (+)-Fresh Bamboo Shoots Phenol B is a yellow powder, soluble in methanol, and measured with a Perkin-Elmer 341 polarimeter (PerkinElmer, Inc., USA) +12° ( c 0.04, MeOH); measured with a JASCO J-815 circular dichroism spectrometer (JASCO Corporation, Japan) for ECD (MeOH) λ max (Δε) 242 (24.99), 282 (15.42) nm. The positive Cotton effects shown by its ECD at 242 nm and 282 nm are similar to those of eucophenolic D. Combining its relative configuration as threo, its absolute configuration was determined to be 2R, 3R.

[0031] (-)-Sinocalamusphenol B is a yellow powder, soluble in methanol, and determined by a Perkin-Elmer 341 polarimeter (PerkinElmer, Inc., USA). -16° ( c 0.04, MeOH); ECD (MeOH) λ was determined by a JASCO J-815 circular dichroism spectrometer (JASCO Corporation, Japan). max (Δε) 242 (-23.65), 282 (-12.91) nm. The negative Cotton effects shown by its ECD at 242 nm and 282 nm are similar to those of eucophenolic C. Considering its relative configuration is threo, its absolute configuration is thus determined to be 2S, 3S.

[0032] Example 3: Screening for anti-tumor cell activity Principle of MTT assay: There is a dehydrogenase related to NAPP (nicotinamide adenine dinucleotide phosphate, coenzyme II) in the mitochondria of living cells. Succinate dehydrogenase can reduce exogenous yellow thiazolyl blue MTT (3-(4,5)-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) to water-insoluble blue-violet crystalline formazan, which deposits in the cells. This enzyme disappears in dead cells and MTT is not reduced. After dissolving formazan with dimethyl sulfoxide (DMSO), the absorbance can be detected by an enzyme-linked immunosorbent assay (ELISA) reader at 570 nm and 630 nm. The optical density value is proportional to the number of living cells.

[0033] The cell lines used were: SGC7901 (human gastric cancer cells), SMMC-7721 (human liver cancer cells), HCT116 (human colorectal cancer cells), BIU87 (human bladder cancer cells), and SPCA-1 (human lung cancer cells).

[0034] Experimental method of MTT assay: Take logarithmically growing cells, digest them, and thoroughly pipette them into a single-cell suspension. After counting, dilute them to 1×10 5Cells were inoculated at a density of cells / mL into a 96-well culture plate, with 100 μL of cell suspension added to each well. After culturing in an incubator at 37 °C and 5% CO₂ for 24 hours, the original culture medium was discarded. Four concentration gradients were designed for each sample, and then 100 μL of medium containing each concentration gradient of the sample and paclitaxel (positive control) was added to the test wells, with 6 parallel wells for each concentration; the control group was added with an equal volume of solvent. After culturing the 96-well culture plate in an incubator at 37 °C and 5% CO₂ with saturated humidity for 72 hours, 20 μL of freshly prepared serum-free medium containing 5 mg / mL MTT was added to each well and continued to be cultured at 37 °C for 4 hours, and then the supernatant was removed. 150 μL of DMSO was added to each well to dissolve the Formazan precipitate, and shaken for 5 minutes. The absorbance at 570 nm and 630 nm was measured on an enzyme-linked immunosorbent assay (ELISA) reader, which can reflect the number of viable cells. The calculation formula is as follows: Tumor cell growth inhibition rate (%) = (measured value of control well - measured value of test well) / measured value of control well × 100%. The test results are shown in Tables 1 to 5.

[0035] Table 1 Detection results of the growth inhibition rate of phenolic compounds on gastric cancer cells (SGC7901) at different concentrations

[0036] Table 2 Detection results of the growth inhibition rate of phenolic compounds on liver cancer cells (SMMC-7721) at different concentrations

[0037] Table 3 Detection results of the growth inhibition rate of phenolic compounds on colorectal cancer cells (HCT116) at different concentrations

[0038] Table 4 Detection results of the growth inhibition rate of phenolic compounds on bladder cancer cells (BIU87) at different concentrations

[0039] Table 5 Detection results of the growth inhibition rate of phenolic compounds on lung cancer cells (SPCA-1) at different concentrations

[0040] From the above test results, it can be seen that both (+)-phyllostachysin B and (-)-phyllostachysin B have significant inhibitory effects on human gastric cancer cells, liver cancer cells, colorectal cancer cells, bladder cancer cells and lung cancer cells. Moreover, the inhibition rate shows a certain dose-effect relationship with the drug concentration. As the drug concentration increases, the inhibitory effect becomes stronger, indicating that both of them have certain potential anti-tumor activities. In comparison, the inhibitory effect of (-)-phyllostachysin B on the proliferation of the above cells is stronger than that of (+)-phyllostachysin B, indicating that the anti-tumor activity of (-)-phyllostachysin B is stronger than that of (+)-phyllostachysin B.

[0041] In summary, the phenolic compounds obtained in the present invention are a pair of diastereoisomers, and both have significant inhibitory effects on human gastric cancer cells, liver cancer cells, colorectal cancer cells, bladder cancer cells and lung cancer cells, and have anti-tumor activities. They can be used in the preparation of drugs for preventing or treating tumors and have broad application prospects.

[0042] Finally, it should be emphasized that the above are only the preferred embodiments of the present invention and are not used to limit the present invention. For those skilled in the art, the present invention can have various changes and modifications. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principle of the present invention shall be included within the protection scope of the present invention.

Claims

1. A phenolic compound, characterized in that The phenolic compound is a pair of diastereoisomers having chemical structural formulas as shown in Formula I and Formula II: 。 2. A method for preparing a phenolic compound as claimed in claim 1, characterized in that: The following steps are involved: (1) Cutting the bamboo, dry distilling, and concentrating under reduced pressure to obtain an extract for later use; (2) Take an appropriate amount of extract, extract it with ethyl acetate and n-butanol for 3 to 4 times respectively, and concentrate it to obtain the ethyl acetate part and the n-butanol part; (3) The n-butanol fraction was passed through a D101 macroporous resin column and washed with 10%, 30%, 60%, and 90% ethanol aqueous solutions, respectively. Each component was collected and concentrated under reduced pressure to obtain a 60% ethanol fraction of the macroporous resin; (4) The 60% ethanol fraction was subjected to silica gel column chromatography with a gradient elution of dichloromethane-methanol as the eluent. After thin layer chromatography inspection, similar components were combined to finally obtain six components A, B, C, D, E, and F; (5) Pass group B through a silica gel column and use petroleum ether-ethyl acetate as the eluent for gradient elution. After thin layer chromatography, combine similar components to obtain four components B1 to B4; (6) Component B4 was passed through gel and eluted with methanol to obtain three components B4.1 to B4.3; (7) subjecting B4.2 to reverse phase preparative high performance liquid chromatography to obtain phenolic compounds; (8) The phenolic compounds are subjected to chiral separation by reverse phase high performance liquid chromatography to obtain phenolic compounds of formula I and formula II.

3. The method for preparing a phenolic compound according to claim 2, characterized in that: In step (1), the temperature of carbonization is 120°C, the pressure of reduced pressure concentration is 0.7 MPa, and the temperature is 60°C.

4. The method for preparing a phenolic compound according to claim 2, characterized in that: In step (2), the mass volume ratio of the extract to ethyl acetate or n-butanol is 1:1.2-1.

5.

5. The method for preparing a phenolic compound according to claim 2, characterized in that: In step (4), the pore size of the silica gel column chromatography is 100-200 mesh; during gradient elution, the volume ratio of dichloromethane to methanol is 40:1, 30:1, 20:1, 10:1, and 5:1, respectively.

6. The method for preparing a phenolic compound according to claim 2, characterized in that: In step (5), during gradient elution, the volume ratios of petroleum ether to ethyl acetate are 5:1, 4:1, 3:1, 2:1, 1:1, and 0:1, respectively.

7. The method for preparing a phenolic compound according to claim 2, characterized in that: In step (7), the reverse phase preparative HPLC uses acetonitrile-water in a volume ratio of 26:74 as the mobile phase at a flow rate of 7 mL / min.

8. The method for preparing a phenolic compound according to claim 2, wherein In step (8), the reverse phase high performance liquid chromatography uses Phenomenex Lux Cellulose-4 as a chiral semi-preparative column and acetonitrile-water with a volume ratio of 38:62 as the mobile phase.

9. A pharmaceutical composition, characterized in that It comprises the phenolic compound as claimed in claim 1 and a pharmaceutically acceptable carrier.

10. Use of the phenolic compound according to claim 1 or the pharmaceutical composition according to claim 9 in preparing a drug for preventing or treating tumor diseases, characterized in that: The tumors include human gastric cancer cells, human liver cancer cells, human colorectal cancer cells, human bladder cancer cells and human lung cancer cells.

Images