CN117185915A - Monoterpene compound in ailanthus altissima, and preparation method and application thereof - Google Patents
Monoterpene compound in ailanthus altissima, and preparation method and application thereof Download PDFInfo
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- 241001093951 Ailanthus altissima Species 0.000 title claims abstract description 33
- -1 Monoterpene compound Chemical class 0.000 title claims abstract description 22
- 229930003658 monoterpene Natural products 0.000 title claims abstract description 22
- 235000002577 monoterpenes Nutrition 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
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- 238000004440 column chromatography Methods 0.000 claims description 13
- 238000004007 reversed phase HPLC Methods 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 102000003425 Tyrosinase Human genes 0.000 claims description 10
- 108060008724 Tyrosinase Proteins 0.000 claims description 10
- 238000010828 elution Methods 0.000 claims description 8
- 102100033639 Acetylcholinesterase Human genes 0.000 claims description 7
- 108010022752 Acetylcholinesterase Proteins 0.000 claims description 7
- 108010053652 Butyrylcholinesterase Proteins 0.000 claims description 7
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- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 claims description 7
- 229940022698 acetylcholinesterase Drugs 0.000 claims description 7
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 claims description 7
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 7
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- 229910002027 silica gel Inorganic materials 0.000 claims description 7
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 6
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- GJYVZUKSNFSLCL-UHFFFAOYSA-N dichloromethanol Chemical compound OC(Cl)Cl GJYVZUKSNFSLCL-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 4
- 150000002773 monoterpene derivatives Chemical class 0.000 claims 2
- 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 claims 1
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- 241001093962 Simaroubaceae Species 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000000990 heteronuclear single quantum coherence spectrum Methods 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
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- 238000001052 heteronuclear multiple bond coherence spectrum Methods 0.000 description 9
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 7
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 229940088598 enzyme Drugs 0.000 description 4
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- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
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- KIUMMUBSPKGMOY-UHFFFAOYSA-N 3,3'-Dithiobis(6-nitrobenzoic acid) Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(SSC=2C=C(C(=CC=2)[N+]([O-])=O)C(O)=O)=C1 KIUMMUBSPKGMOY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
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- WEQAAFZDJROSBF-UHFFFAOYSA-M 2-butanoylsulfanylethyl(trimethyl)azanium;iodide Chemical compound [I-].CCCC(=O)SCC[N+](C)(C)C WEQAAFZDJROSBF-UHFFFAOYSA-M 0.000 description 1
- 238000005084 2D-nuclear magnetic resonance Methods 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical class C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- VTNULXUEOJMRKZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2H-tetrazol-5-ylmethyl)benzamide Chemical compound N=1NN=NC=1CNC(C1=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)=O VTNULXUEOJMRKZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 101100391174 Dictyostelium discoideum forC gene Proteins 0.000 description 1
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- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
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- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
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- BJRNKVDFDLYUGJ-UHFFFAOYSA-N p-hydroxyphenyl beta-D-alloside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-UHFFFAOYSA-N 0.000 description 1
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- 150000003648 triterpenes Chemical class 0.000 description 1
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Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a monoterpene compound in Ailanthus and a preparation method and application thereof, belongs to the technical field of medicines, and particularly relates to a compound prepared from Ailanthus altissima [ Ailanplus Desf ] of Ailanthus of Simaroubaceae.]The extracted and separated 5 monoterpene compounds have good anti-tyrosinase activity. The preparation method is simple and easy to implement, and has better reproducibility and higher purity.
Description
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to 5 monoterpene compounds prepared from ailanthus altissima and application of the compounds in preparation of tyrosinase, acetylcholinesterase and/or butyrylcholinesterase inhibitors.
Background
Ailanthus (Ailanthus altissima (mill.) swing) is a plant of the genus ailanthus (ailanthus desf.) of the family quassiaceae (Simaroubaceae). Widely distributed in Shaanxi province, gansu province, sichuan province, yunnan province and other places in China. The cortex Ailanthi is dry root bark or dry bark of Ailanthus altissima, also called cortex Ailanthi, cortex Toonae sinensis, and is a common Chinese herbal medicine in China. Since ailanthus leaves are not generally used as medicinal sites, the chemical composition of the ailanthus leaf portions is less studied. The bitter element, triterpene, coumarin, alkaloid and lignan compound are main chemical components in the ailanthus altissima; the chemical components in the ailanthus have pharmacological activities of resisting tumor, malaria, virus, inflammation and the like.
Based on previous researches, the invention systematically researches the chemical components and pharmacological activities of ailanthus altissima leaves and root barks.
Disclosure of Invention
The invention aims to solve the defects of the prior art, and provides 5 monoterpene compounds with novel structures in ailanthus altissima, a preparation method thereof and application thereof in preparing tyrosinase, acetylcholinesterase and/or butyrylcholinesterase inhibitors.
In order to achieve the purpose of the invention, the invention adopts the following technical scheme:
the invention also provides application of the monoterpene compound in the aspect of anti-tumor activity.
In a first aspect, the present invention provides 5 monoterpene compounds isolated from Ailanthus altissima [ Ailanthus Desf ] of the genus Ailanthus of the family Simaroubaceae, having the following structure:
in a second aspect, the invention provides a preparation method of the monoterpene compound in the ailanthus altissima, which comprises the following steps:
reflux extracting dried Ailanthus altissima leaves with 70% industrial ethanol, mixing the extractive solutions, concentrating to obtain extract, extracting the extract with dichloromethane-n-butanol, subjecting the obtained components to silica gel column chromatography, and gradient eluting with dichloro-methanol system 100:0-1:1 to obtain 4 components Fr.A-D;
performing gradient elution on the component Fr.D and the component Fr.D by using an ethanol-water system 20:80-100:0 by using HP20 and ODS column chromatography to obtain 2 components Fr.D1-Fr.D2;
column chromatography on silica gel with dichloromethane-methanol system 10: eluting with 0-10:1 to obtain Fr.D1.3.1-Fr.D1.3.8, and gradient eluting the Fr.D component with ethanol-water system 20:80-90:10 to obtain 4 components Fr.D1-Fr.D2;
performing gradient elution on the component Fr.D1 by using an ODS column chromatography in an ethanol-water system of 10:90-90:10 to obtain 4 components Fr.D1.1-Fr.D1.4; column chromatography on silica gel with dichloromethane-methanol system 10: eluting with 0-10:1 to obtain Fr.D1.3.1-Fr.D1.3.8, fr.D1.3.1, separating with methanol-water mobile phase on preparative reverse phase high performance liquid chromatography to obtain 6 components Fr.D1.3.1.1-Fr.D1.3.1.6, fr.D1.3.1.1, and separating with acetonitrile-water mobile phase on semi-preparative reverse phase high performance liquid chromatography to obtain compounds 1-2.
Fr. d1.4 was purified by column chromatography on silica gel with dichloromethane-methanol system 10: elution was performed at 0-10:1 to yield Fr.D1.4.1-Fr.D1.4.6.Fr.D1.4.5 was separated on preparative reverse phase HPLC using a methanol-water mobile phase to give 6 components Fr.D1.4.1-Fr.D1.4.5.6, fr.D1.4.5.5 and Fr.D1.4.5.6 was separated on semi-preparative reverse phase HPLC using an acetonitrile-water mobile phase to give compounds 3-5.
Alternatively, in the above preparation method, the ailanthus is a plant ailanthus altissima [ ailanthus desf. ].
Alternatively, in the above preparation method, the dried ailanthus altissima leaves are extracted with 70% industrial ethanol under reflux for 3 times, each for 2-3 hours.
Alternatively, in the above preparation method, the ratio of the components is 30:70-20: 80. Acetonitrile-water mobile phase separation fr.d1.3.1.1.
The results of the system structure identification of the obtained compound are as follows:
the structure of compounds 1-5 was identified by high resolution mass spectrometry, one-dimensional NMR and two-dimensional NMR, the corresponding spectra being shown in FIGS. 1-20 and tables 1-2.
Chouchunoinone a (1): colorless oil.HRESIMS(m/z):[M+Na] + (m/z):291.1567(calcd for C 15 H 24 NaO 4 291.1567) by analysis of Chouchunoinene A 1 H NMR、 13 C NMR, HSQC spectrum, HMBC spectrum, the structure of Chouchunonone A was determined as a new compound.
Chouchunoinone B (2): colorless oil.UV (methanol) λmax (log epsilon) 240nm (2.30); HRESIMS: [ M+Na ]] + (m/z):263.1608(calcd for C 14 H 24 NaO 3 263.1618) by analysis of Chouchunoinone B 1 H NMR、 13 C NMR, HSQC spectrum and HMBC spectrum, and the structure of Chouchunone B is determined as a novel compound.
Chouchunoinone C (3): pale yellow amorphous powder.UV (methanol) λmax (log ε) 230nm (2.34), 205nm (2.34); HRESIMS: [ M+H ]] + (m/z):371.2063,(calcd for C 19 H 31 O 7 371.2064,) by analysis of Chouchunone C 1 HNMR、 13 C NMR, HSQC spectrum and HMBC spectrum, and the structure of Chouchunone C is determined, and the Chouchunone C is a novel compound.
Chouchunoinone D (4): colorless oil.UV (methanol) λmax (log epsilon) 264 (2.29); HRESIMS: [ M+Na ]] + (m/z):393.1884(calcd forC 19 H 30 O 7 Na, 393.1883) by analysis of Chouchunonone D 1 HNMR、 13 C NMR, HSQC spectrum, HMBC spectrum, the structure of Chouchunone D was determined as a new compound.
Chouchunoinone E (5): an amorphous powder of yellowish white color.UV (methanol) λmax (log epsilon) 219 (1.63); HRESIMS: [ M+H ]] + (m/z):447.2227(calcd for C 21 H 35 O 10 447.2225) by analysis of chouchunone E 1 H NMR、 13 C NMR, HSQC spectrum, HMBC spectrum, the structure of Chouchunone E was determined as a new compound.
In a third aspect, the invention provides a pharmaceutical composition comprising a monoterpene compound or a pharmaceutically acceptable salt thereof prepared from ailanthus altissima and a pharmaceutically acceptable carrier or excipient.
In a fourth aspect, the invention provides the use of a monoterpene compound prepared from ailanthus altissima or a pharmaceutical composition comprising the same in the preparation of tyrosinase, acetylcholinesterase and/or butyrylcholinesterase inhibitors.
The activity of the tyrosinase, acetylcholinesterase and/or butyrylcholinesterase of the 5 novel compounds is examined, and the compound 3 shows good activity of tyrosinase resistance, so that the monoterpene compound has the prospect of further developing tyrosinase resistance medicines.
Compared with the prior art, the invention has the following beneficial effects:
the invention has the advantages that the compounds are novel compounds, the monoterpene compounds with novel structures, and the compound 3 has good anti-tyrosinase activity and further development value.
Table 1 Hydrogen spectral data (600 MHz) for Compounds 1-5 (Compounds 2,3,5 were dissolved in deuterated dimethyl sulfoxide solution and Compounds 1,4 were dissolved in deuterated chloroform solution)
Table 2 carbon spectrum data (150 MHz) for Compounds 1-5 (Compounds 2,3,5 were dissolved in deuterated dimethyl sulfoxide solution and Compounds 1,4 were dissolved in deuterated chloroform solution)
Drawings
Hresis spectrum of compound 1 of fig. 1;
FIG. 2 Compound 1 1 H-NMR spectrum;
FIG. 3 Compound 1 13 C-NMR spectrum;
FIG. 4 HSQC spectrum of Compound 1;
FIG. 5 HMBC spectra of Compound 1;
FIG. 6 HRESIMS spectrum of Compound 2;
FIG. 7 Compound 2 1 H-NMR spectrum;
FIG. 8 Compound 2 13 C-NMR spectrum;
FIG. 9 HSQC spectrum of Compound 2;
FIG. 10 HMBC spectra of Compound 2;
FIG. 11 HRESIMS spectrum of Compound 3;
FIG. 12 HSQC spectrum of Compound 3;
FIG. 13 HMBC spectra of Compound 3;
hresis spectrum of compound 4 of fig. 14;
FIG. 15 Compound 4 1 H-NMR spectrum;
FIG. 16 HSQC spectrum of Compound 4;
HMBC profile of compound 4 of fig. 17;
hresis spectrum of compound 5 of fig. 18;
FIG. 19 HSQC spectrum of Compound 5;
FIG. 20 HMBC spectra of Compound 5.
Detailed Description
The examples set forth below are presented to aid one skilled in the art in a better understanding of the present invention and are not intended to limit the invention in any way.
Example 1: preparation of Compounds 1-5
Reflux-extracting dried Ailanthus altissima leaves with 70% industrial ethanol for 3 times, each for 2 hr. Mixing the extractive solutions, concentrating to obtain extract, extracting with dichloromethane-n-butanol, subjecting the obtained components to silica gel column chromatography, and gradient eluting with dichloro-methanol system 100:0-1:1 to obtain 4 components Fr.A-D;
performing gradient elution on the component Fr.D by using an HP20 column chromatography in an ethanol-water system of 20:80-90:10 to obtain 4 components Fr.D1-Fr.D2;
performing gradient elution on the component Fr.D1 by using an ODS column chromatography in an ethanol-water system of 10:90-90:10 to obtain 4 components Fr.D1.1-Fr.D1.4;
fr. d1.3 column chromatography on silica gel with dichloromethane-methanol system 10: eluting with 0-10:1 to obtain Fr.D1.3.1-Fr.D1.3.8, fr.D1.3.1, separating with methanol-water mobile phase on preparative reverse phase high performance liquid chromatography to obtain 6 components Fr.D1.3.1.1-Fr.D1.3.1.6, fr.D1.3.1.1, and separating with acetonitrile-water mobile phase on semi-preparative reverse phase high performance liquid chromatography to obtain compounds 1-2.
Fr. d1.4 was purified by column chromatography on silica gel with dichloromethane-methanol system 10: elution was performed at 0-10:1 to obtain Fr.D1.4.1-Fr.D1.4.6, fr.D1.4.5, which was separated on preparative reverse phase HPLC using a methanol-water mobile phase to obtain 6 components Fr.D1.4.5.1-Fr.D1.4.5.6, fr.D1.4.5.5 and Fr.D1.4.5.6, which was separated on semi-preparative reverse phase HPLC using an acetonitrile-water mobile phase to obtain compounds 3-5.
Example 2: investigation of anti-tyrosinase Activity of Compounds 1-5
Compounds 1 to 5 were dissolved in DMSO and buffered with potassium phosphate buffer (KH 2 PO 4 /K 2 HPO 4 0.1m, ph 7.4) to 5 series of concentrations. The reaction system contains 40 mu L of tyrosine, 40 mu L of compound to be tested or positive drug arbutin and 80 mu LPBS buffer solution, and after 40 mu L of tyrosinase is added, the reaction is started. The absorbance was measured 3 times at 492nm for 10min after enzyme addition. Nonlinear regression analysis of response concentration (log) curves was performed using Graph-Pad Prism program to calculate IC 50 Values. The results of the experiment are shown in Table 3, wherein Compound 3 has a remarkable anti-tyrosinase effect.
Table 3: inhibitory Activity of compounds from Ailanthus altissima against tyrosinase
a Results are expressed as mean ± SD (n=3).
Example 3: investigation of anti-acetylcholinesterase and butyrylcholinesterase Activity of Compounds 1-5
Compounds 1 to 5 were dissolved in DMSO and buffered with potassium phosphate buffer (KH 2 PO 4 /K 2 HPO 4 0.1m, ph 7.4) to 5 series of concentrations. The reaction system contained 25. Mu.L of the test compound, 12.5. Mu.L of the enzyme, 125. Mu.L of DTNB (dithiobis-p-nitrobenzoic acid), and 50. Mu.L of ATCI (acetylcholine iodide). Adding enzymesAfter that, the reaction was started. After overnight incubation in a refrigerator, 50 μlatci was added to each well to terminate the reaction. The absorbance was measured 3 times with a microplate reader at 412nm for 10 min. Nonlinear regression analysis of response concentration (log) curves was performed using Graph-Pad Prism program to calculate IC 50 Values. The experimental results are shown in table 4.
Table 4: inhibitory Activity of Ailanthus altissima derived Compounds against acetylcholinesterase
a Results are expressed as mean ± SD (n=3).
Compounds 1 to 5 were dissolved in DMSO and buffered with potassium phosphate buffer (KH 2 PO 4 /K 2 HPO 4 0.1m, ph 7.4) to 5 series of concentrations. The reaction system contained 25. Mu.L of the test compound, 12.5. Mu.L of the enzyme, 125. Mu.L of DTNB, and 50. Mu.L of BTCI (S-butyrylthiocholine iodide). After the enzyme is added, the reaction starts. After overnight incubation in a refrigerator, 50 μl BTCI was added to each well to stop the reaction and absorbance was measured 3 times at 412nm for 10 min. Nonlinear regression analysis of response concentration (log) curves was performed using Graph-Pad Prism program to calculate IC 50 Values. The experimental results are shown in table 5.
Table 5: inhibitory Activity of Ailanthus altissima derived Compounds against butyrylcholinesterase
a Results are expressed as mean ± SD (n=3).
It will be apparent to those skilled in the art that various modifications and variations can be made to the present invention without departing from the spirit or scope of the invention. Thus, it is intended that the present invention also include such modifications and alterations insofar as they come within the scope of the appended claims or the equivalents thereof.
Claims (9)
1. A monoterpene compound in ailanthus altissima, which is characterized by comprising two isopentenyl groups, wherein the monoterpene compound is any one of the following structures:
2. the monoterpene compound in Ailanthus altissima according to claim 1, wherein the Ailanthus altissima is a plant Ailanthus altissima [ Ailanthus Desf.
3. A method for preparing a monoterpene compound in ailanthus altissima according to claim 1 or claim 2, which comprises the following steps:
reflux extracting dried Ailanthus altissima leaves with 70% industrial ethanol, mixing the extractive solutions, concentrating to obtain extract, extracting the extract with dichloromethane-n-butanol, subjecting the obtained components to silica gel column chromatography, and gradient eluting with dichloro-methanol system 100:0-1:1 to obtain 4 components Fr.A-D;
performing gradient elution on the component Fr.D by using an HP20 column chromatography in an ethanol-water system of 20:80-90:10 to obtain 4 components Fr.D1-Fr.D2;
performing gradient elution on the component Fr.D1 by using an ODS column chromatography in an ethanol-water system of 10:90-90:10 to obtain 4 components Fr.D1.1-Fr.D1.4;
column chromatography on silica gel with dichloromethane-methanol system 10: eluting with 0-10:1 to obtain Fr.D1.3.1-Fr.D1.3.8, fr.D1.3.1, separating with methanol-water mobile phase on preparative reverse phase high performance liquid chromatography to obtain 6 components Fr.D1.3.1.1-Fr.D1.3.1.6, fr.D1.3.1.1, and separating with acetonitrile-water mobile phase on semi-preparative reverse phase high performance liquid chromatography to obtain compounds 1-2;
fr. d1.4 was purified by column chromatography on silica gel with dichloromethane-methanol system 10: eluting with 0-10:1 to obtain Fr.D1.4.1-Fr.D1.4.6, fr.D1.4.5, separating with methanol-water mobile phase on preparative reversed phase high performance liquid chromatography to obtain 6 components Fr.D1.4.5.1-Fr.D1.4.5.6, fr.D1.4.5.5 and Fr.D1.4.5.6, and separating with acetonitrile-water mobile phase on semi-preparative reversed phase high performance liquid chromatography to obtain compounds 3-5.
4. A method for the preparation of monoterpenes in Ailanthus altissima according to claim 3, wherein the Ailanthus altissima is a plant of the genus quassia of the family quassiaceae [ Ailanthus Desf ].
5. A process for the preparation of monoterpenes from ailanthus altissima as claimed in claim 3, characterised in that dried ailanthus altissima leaves are extracted 3 times, each for 2-3 hours, with 70% industrial ethanol under reflux.
6. A method for preparing monoterpene compounds in ailanthus altissima according to claim 3, which is characterized by comprising the following steps of: 80, fr.d1.3.1.1, fr.d1.4.5.5 and fr.d1.4.5.6.
7. A pharmaceutical composition comprising a monoterpene compound or a pharmaceutically acceptable salt thereof in ailanthus altissima of claim 1 or claim 2 and a pharmaceutically acceptable carrier or excipient.
8. Use of a monoterpene compound or a pharmaceutically acceptable salt thereof in ailanthus altissima as claimed in claim 1 or claim 2 in the preparation of a tyrosinase, acetylcholinesterase and/or butyrylcholinesterase inhibitor.
9. Use of a pharmaceutical composition according to claim 7 for the preparation of tyrosinase, acetylcholinesterase and/or butyrylcholinesterase inhibitors.
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