CN106380503B - A kind of trihydroxy single ketones class cucurbit alkane type triterpenoid and its preparation method and purposes - Google Patents
A kind of trihydroxy single ketones class cucurbit alkane type triterpenoid and its preparation method and purposes Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 150000002576 ketones Chemical class 0.000 title abstract description 7
- XBZYWSMVVKYHQN-MYPRUECHSA-N (4as,6as,6br,8ar,9r,10s,12ar,12br,14bs)-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-9-[(sulfooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid Chemical compound C1C[C@H](O)[C@@](C)(COS(O)(=O)=O)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C XBZYWSMVVKYHQN-MYPRUECHSA-N 0.000 title abstract description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 title abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000843 powder Substances 0.000 claims abstract description 8
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 4
- 239000000284 extract Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 11
- 238000010828 elution Methods 0.000 claims description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 9
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 6
- 239000003480 eluent Substances 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 238000005227 gel permeation chromatography Methods 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000010898 silica gel chromatography Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 230000000118 anti-neoplastic effect Effects 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical group CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 235000007586 terpenes Nutrition 0.000 abstract description 16
- 210000004027 cell Anatomy 0.000 abstract description 8
- -1 cucurbitane terpene Chemical class 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 5
- 238000004458 analytical method Methods 0.000 abstract description 4
- 206010028980 Neoplasm Diseases 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 210000004881 tumor cell Anatomy 0.000 abstract description 2
- 150000001993 dienes Chemical class 0.000 abstract 2
- 150000003505 terpenes Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 6
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- ZYZJWAJOTPNVPI-ZVBSCDOUSA-N cucurbitane Chemical compound C([C@H]1[C@]2(C)CC[C@@H]([C@]2(CC[C@]11C)C)[C@H](C)CCCC(C)C)CC2[C@H]1CCCC2(C)C ZYZJWAJOTPNVPI-ZVBSCDOUSA-N 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229960004679 doxorubicin Drugs 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 2
- 229930182490 saponin Natural products 0.000 description 2
- 150000007949 saponins Chemical class 0.000 description 2
- 150000003648 triterpenes Chemical class 0.000 description 2
- INLFWQCRAJUDCR-IQVMEADQSA-N (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane] Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 INLFWQCRAJUDCR-IQVMEADQSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 208000004429 Bacillary Dysentery Diseases 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 241000220485 Fabaceae Species 0.000 description 1
- 206010017915 Gastroenteritis shigella Diseases 0.000 description 1
- 241000906682 Hemsleya Species 0.000 description 1
- 241000466342 Hemsleya pengxianensis Species 0.000 description 1
- 206010023126 Jaundice Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241001529246 Platymiscium Species 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 241000934136 Verruca Species 0.000 description 1
- 208000000260 Warts Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 208000019065 cervical carcinoma Diseases 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000000205 computational method Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 1
- 201000005113 shigellosis Diseases 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses trihydroxy single ketones class cucurbit alkane type triterpenoid and its preparation method and the purposes for isolating and purifying in a kind of hymsleya amabilis rhizome from Jinfo Shan Mountain to obtain, and its chemical constitution and physicochemical property is determined using modern analysis means, it is named as 3 according to the naming rule for there are related compoundsβ,20β, the ketone of 24 trihydroxy cucurbitane terpene 5,23 (E) diene 11, it is colourless powder, is soluble in chloroform, methanol.Proved through functional trial：3β,20β, the ketone of 24 trihydroxy cucurbitane terpene 5,23 (E) diene 11 has stronger inhibitory action to the tumour cell such as HeLa cells and KB cells, can have stronger application value and market prospects as the raw material for preparing preventing and treating tumour medicine.
Description
Technical field
The present invention relates to a kind of trihydroxy single ketones class cucurbit alkane type triterpenoid and its preparation method and purposes, 3 are referred specifically toβ, 20β,
(E)-diene -11- ketone of 24- trihydroxy cucurbitanes terpene -5,23 and its preparation method and purposes.
Background technology
Jinfo Shan Mountain hymsleya amabilis (Hemsleya pengxianensis W. J. Chang var. jinfushanensis L.
D. Shen ＆ W. J. Chang) it is Curcurbitaceae (Fabaceae) Genus Hemsleya platymiscium, China region of Southeast is originated in, is born in
In the border that 2000 meter or so of height above sea level and mountain valley shrubbery.The fruit of Jinfo Shan Mountain hymsleya amabilis is in avette, long 4-5 centimetres, diameter 2.5-3.5
Centimetre, there is tiny verruca on pericarp surface and distinguished with former mutation, and main active is respectively cucurbitane type Fourth Ring
Triterpene and its saponin(e and Triterpenoids sapogenins and its saponin(e, there are clearing heat and detoxicating, the multiple efficacies such as anti-inflammation, it is clinical
On be mainly used in treating bacillary dysentery, various inflammation, ulcer, a variety of diseases such as jaundice.
The drug effect of Jinfo Shan Mountain hymsleya amabilis is mainly derived from cucurbitane type triterpene compound therein, therefore, develops and utilizes
Cucurbitane type monomeric compound in hymsleya amabilis, further excavates its potential medical value, and to the knot of monomer compound
Structure and physicochemical property are determined and characterized, significant for utilization Jinfo Shan Mountain hymsleya amabilis resource.
The content of the invention
The present invention is exactly overcome the deficiencies in the prior art, there is provided isolated in a kind of hymsleya amabilis rhizome from Jinfo Shan Mountain to have
The trihydroxy single ketones class Cucurbitanes of important biomolecule activity and industrialization value.The monomeric compound is from golden Buddhist
It is isolated first in the hymsleya amabilis of mountain, after characterizing its structure using modern analysis means and confirm its bioactivity, according to relevantization
The naming rule of compound is named as 3β, 20β, (E)-diene -11- ketone of 24- trihydroxy cucurbitanes terpene -5,23.
Isolated 3 in a kind of hymsleya amabilis rhizome from Jinfo Shan Mountainβ, 20β, 24- trihydroxy cucurbitanes terpene -5,23 (E) -
Diene -11- ketone, it is noval chemical compound, there is the structure that is shown below：
Isolated 3 in above-mentioned hymsleya amabilis rhizome from Jinfo Shan Mountainβ, 20β, 24- trihydroxy cucurbitanes terpene -5,23
(E)-diene -11- ketone obtains as follows：
Jinfo Shan Mountain hymsleya amabilis rhizome crushed after being dried is sieved, and adds 95% ethanol heating and refluxing extraction 3 times, each 1-3 hours, is closed
And extract solution, solvent is recovered under reduced pressure, total medicinal extract is obtained after concentration, after total medicinal extract is water-dispersible, successively with petroleum ether, chloroform, acetic acid
Ethyl ester, extracting n-butyl alcohol, extract are concentrated to dryness；Ethyl acetate extract medicinal extract is taken to be separated with silica gel column chromatography, chloroform-methanol
(1:0-0:1) gradient elution, 12 cut Fr A-L, Fr.F parts is obtained and are made again with chloroform-methanol after gel chromatography elutes
Depigmentaton is removed for elution, then the inverted middle pressure chromatographic column of sample is through MeOH-H2O (60:40; 70:30; 80:20;
90:10) gradient elution, four part Fr. F1-4 are obtained, wherein Fr. F1 separate through high-efficient liquid phase chromatogram purification, using first
Alcohol-water elution, the eluent collected 28.9 minutes, which crystallizes, to be produced.
The mass volume ratio of Jinfo Shan Mountain hymsleya amabilis rhizome and ethanol is 1 in the heating and refluxing extraction:8-1:12.
The volume ratio of chloroform and methanol is 45 in the chloroform-methanol eluent:55-60:40.
The volume ratio of methanol and water is 60 in the methanol-water eluent:40.
3β, 20β, 24- trihydroxy cucurbitane terpenes -5,23 (E)-diene -11- ketone is colourless powder, is soluble in chloroform,
Methanol, by 3β, 20β, it is real that (E)-diene -11- ketone of 24- trihydroxy cucurbitanes terpene -5,23 carries out extracorporeal anti-tumor pharmacodynamics
Test, extracorporeal anti-tumor pharmacodynamic experiment utilizes MTT colorimetric methods.
With 3β, 20β, 24- trihydroxy cucurbitane terpenes -5,23 (E)-diene -11- ketone is experimental group, with
Doxorubicin（Doxorubicin, antineoplastic）For control group, while blank group is set up, experimental group, control group and blank group
Choose HeLa（Human cervical carcinoma）Cell and KB（Human mouth epidermoid carcinoma）For experimental subjects, after culture medium dilution, with 6 × 104/ml
Density be inoculated in 96 orifice plates, per the μ l of hole 100, in incubator after normal culture 24 hours, each group adds corresponding medicine, makes
The ultimate density of each group medicine is respectively 2.5 μ g/ml (1 group), 5 μ g/ml (2 groups), 10 μ g/ml (3 groups), 20 μ g/ml
(four groups), 40 μ g/ml (5 groups), 5 concentration, each 3 multiple holes of concentration are set altogether；After culture 48 hours, add MTT 10 in every hole
μ l are dyed；After continuing culture four hours, original fluid is abandoned in suction, and the μ l of DMSO 100 are added per hole, put low-speed oscillation 10 on shaking table
Min, crystal is fully dissolved, and OD value is detected at the nm wavelength of enzyme-linked immunosorbent assay instrument 570, according to optical density
Value calculates 50% inhibition concentration（IC50, μ g/mL), OD value calculates IC50Computational methods be existing known technology.Experiment
Group, control group are to HeLa cells and the IC of KB cells50As shown in table 1.
Table 1
| Group | HeLa cells | KB cells |
| Experimental group | 7.9 ± 2.4 | 32.1 ± 2.3 |
| Control group | 1.3 ± 0.11 | 0.89 ± 0.03 |
Of the present invention 3 are can be seen that by the data of upper tableβ, 20β, 24- trihydroxy cucurbitanes terpene -5,23
(E)-diene -11- ketone is respectively provided with certain inhibitory action to HeLa cells and KB cells, can be used as and prepare preventing and treating tumour medicine
Raw material, possess stronger commercial application value.
Compared with prior art, the beneficial effects of the present invention are：
It is isolated from Jinfo Shan Mountain hymsleya amabilis rhizome first to have the 3 of important antitumor activityβ, 20β, the hydroxyls of 24- tri-
Base cucurbitane terpene -5,23 (E)-diene -11- ketone, and its chemical constitution and physicochemical property is determined using modern analysis means.
Proved through functional trial：3β, 20β, (E)-diene -11- ketone of 24- trihydroxy cucurbitanes terpene -5,23 has to tumour cell
Stronger inhibitory action, can have stronger application value and market prospects as the raw material for preparing preventing and treating tumour medicine.
Brief description of the drawings
Fig. 1 is 3β, 20β, the schematic arrangement of (E)-diene -11- ketone of 24- trihydroxy cucurbitanes terpene -5,23.
Fig. 2 is 3β, 20β, the proton nmr spectra of (E)-diene -11- ketone of 24- trihydroxy cucurbitanes terpene -5,23（1H-
NMR）.
Fig. 3 is 3β, 20β, the carbon-13 nmr spectra of (E)-diene -11- ketone of 24- trihydroxy cucurbitanes terpene -5,23（13C-
APT）.
Embodiment
Below in conjunction with specific embodiment, the present invention is further illustrated
The first step：Jinfo Shan Mountain hymsleya amabilis rhizome (5.0 kg) crushed after being dried crosses 80 mesh sieves.Second step：Medicinal powder adds 10 times
Measure ethanol heating and refluxing extraction 3 times, 2 hours every time, merge extract solution, solvent is recovered under reduced pressure, total g of medicinal extract 1033 is obtained after concentration.
3rd step：The total medicinal extract of Jinfo Shan Mountain hymsleya amabilis rhizome add suitable quantity of water carry out decentralized processing after, respectively with petroleum ether, chloroform, ethyl acetate,
N-butanol is extracted, and is extracted to colourless, extract is concentrated under reduced pressure into dry, is weighed to obtain the total medicinal extract 56g of petroleum ether part, chloroform
The total medicinal extract 302g in position, the total medicinal extract 151g of ethyl acetate extract, the total g of medicinal extract 409 of n-butanol portion.4th step：Take ethyl acetate
The layer g of medicinal extract 151 separates through silica gel column chromatography (100~200 mesh), chloroform-methanol (1:0-0:1) gradient elution, 12 is obtained and is evaporated
Divide Fr A-L.5th step：Fr.F parts elute through gel chromatography, chloroform-methanol（45:55）Discoloration is removed as elution
Element, then the inverted middle pressure chromatographic column of sample is through MeOH-H2O (60:40; 70:30; 80:20; 90:10) gradient elution, obtain
To four steps of part Fr. F1-4. the 6th：Wherein Fr. F1 separate through high-efficient liquid phase chromatogram purification, using methanol-water（60:
40）Elution, the eluent crystallization collected 28.9 minutes obtain colourless powder, are soluble in chloroform, methanol.
The structural characterization of above-mentioned colourless powder and confirmation are as follows：
Above-mentioned gained colourless powder is subjected to proton nmr spectra（1H-NMR）And carbon-13 nmr spectra（13C-APT）Analysis
,1H-NMR spectrum as shown in Fig. 213C-APT spectrograms are as shown in Figure 3.
Spectrum analysis are carried out to Fig. 2 and Fig. 3, each peaks of Fig. 2 and Fig. 3 are belonged to, Fig. 2 and Fig. 3 peak belong to such as the institute of table 2
Show, by Fig. 2, Fig. 3 and table 1 data, the chemical structural formula of colourless powder is as shown in figure 1, according to there are related compounds
Naming rule be named as 3β, 20β, (E)-diene -11- ketone of 24- trihydroxy cucurbitanes terpene -5,23.
English entitled 3β, 20β, 24-trihydroxycucurbita-5, 23(E)-diene-11-one。
The compound 1 of table 21H-NMR and13C-NMR (150MHz, C5D5N) modal data
Above-mentioned simply presently preferred embodiments of the present invention, not makees any formal limitation to the present invention.It is any to be familiar with sheet
The technical staff in field, in the case where not departing from technical solution of the present invention scope, all using the technology contents of the disclosure above
Many possible changes and modifications are made to technical solution of the present invention, or are revised as the equivalent embodiment of equivalent variations.Therefore, it is all
It is the content without departing from technical solution of the present invention, any is simply repaiied to made for any of the above embodiments according to the technology of the present invention essence
Change, equivalent variations and modification, all should fall in the range of technical solution of the present invention protection.
Claims (6)
- A kind of 1. compound, it is characterised in that：The compound is colourless powder, is soluble in chloroform, methanol, to HeLa cells and KB Cell is respectively provided with stronger inhibitory action, and with the structure that is shown below。
- 2. application of the compound described in claim 1 in antineoplastic is prepared.
- A kind of 3. preparation method of compound described in claim 1, it is characterised in that：Jinfo Shan Mountain hymsleya amabilis rhizome crushed after being dried mistake Sieve, adds 95% ethanol heating and refluxing extraction 3 times, each 1-3 hours, merges extract solution, solvent is recovered under reduced pressure, and obtains after concentration and always soaks Cream, after total medicinal extract is water-dispersible, it is concentrated to dryness successively with petroleum ether, chloroform, ethyl acetate, extracting n-butyl alcohol, extract；Take second Acetoacetic ester position medicinal extract is separated with silica gel column chromatography, and the volume ratio of chloroform-methanol is by 1:0 is transitioned into 0:1 carries out 12 gradient elutions, Obtain 12 cut Fr A-L, Fr.F parts to elute through gel chromatography, chloroform-methanol removes depigmentaton as elution, so Inverted middle pressure volume ratio of the chromatographic column through methanol-water of sample is respectively 60 afterwards:40、70:30、80:20 and 90:10 4 gradients are washed It is de-, four part Fr. F1-4 are obtained, wherein Fr. F1 are separated through high-efficient liquid phase chromatogram purification, eluted using methanol-water, collected The eluent of 28.9 minutes, which crystallizes, to be produced.
- 4. the preparation method of compound according to claim 3：It is characterized in that：Jinfo Shan Mountain is avenged in the heating and refluxing extraction The mass volume ratio of courage rhizome and ethanol is 1:8-1:12.
- 5. the preparation method of compound according to claim 3：It is characterized in that：In the gel chromatography elution, chloroform-first The volume ratio of chloroform and methanol is 45 in alcohol eluen:55-60:40.
- 6. the preparation method of compound according to claim 3：It is characterized in that：The high-efficient liquid phase chromatogram purification separation In, the volume ratio of methanol and water is 60 in methanol-water eluent:40.
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| CN103626824A (en) * | 2013-12-10 | 2014-03-12 | 山东省医学科学院药物研究所 | Hemsleya amabilis cucurbitane tetracyclic triterpene compound, pharmaceutical composition comprising compound and application of pharmaceutical composition and compound |
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| CN103626824A (en) * | 2013-12-10 | 2014-03-12 | 山东省医学科学院药物研究所 | Hemsleya amabilis cucurbitane tetracyclic triterpene compound, pharmaceutical composition comprising compound and application of pharmaceutical composition and compound |
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Effective date of registration: 20201104 Address after: No. 287, Minhe street, Anyang Town, Du'an Yao Autonomous County, Hechi City, Guangxi Zhuang Autonomous Region Patentee after: Du'an Yao Autonomous County metrological verification and Testing Institute Address before: 416000 Hunan, Xiangxi Tujia and Miao Autonomous Prefecture, Jishou City People's road, No. 120 Patentee before: JISHOU University |
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Application publication date: 20170208 Assignee: Hechi Food and Drug Inspection Institute Assignor: Du'an Yao Autonomous County metrological verification and Testing Institute Contract record no.: X2023980047639 Denomination of invention: A Trihydroxymonoketone Cucurbitane Triterpene and Its Preparation and Application Granted publication date: 20180302 License type: Common License Record date: 20231122 |