CN106317155B - A kind of reproducibility cucurbit alkane type triterpenoid and its preparation method and purposes - Google Patents
A kind of reproducibility 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 10
- 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 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 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 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000010828 elution Methods 0.000 claims description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 9
- 235000019441 ethanol Nutrition 0.000 claims description 7
- 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
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 229940041181 antineoplastic drug Drugs 0.000 claims description 2
- 238000002845 discoloration Methods 0.000 claims description 2
- 239000012467 final product Substances 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 terpenes Chemical class 0.000 abstract description 8
- 239000003814 drug Substances 0.000 abstract description 5
- 238000004458 analytical method Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 206010028980 Neoplasm Diseases 0.000 abstract description 3
- 230000002265 prevention Effects 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 2
- 210000004881 tumor cell Anatomy 0.000 abstract description 2
- 150000003505 terpenes Chemical class 0.000 description 9
- 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
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 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
- 150000003648 triterpenes Chemical class 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229960004679 doxorubicin Drugs 0.000 description 2
- 229940079593 drug 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
- 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
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010023126 Jaundice Diseases 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
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 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
- 230000007812 deficiency Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 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
- 238000004043 dyeing Methods 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
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum 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
- 230000001629 suppression Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses the reproducibility cucurbit alkane type triterpenoid isolated and purified in a kind of hymsleya amabilis rhizome from Jinfo Shan Mountain and its preparation methods and purposes, and its chemical constitution and physicochemical property is determined using modern analysis means, and 3 are named as according to there is the naming rule of related compoundsβ,11α,20β, 26- tetrahydroxy cucurbitane terpenes -5,24 (E)-diene, be colourless powder, be soluble in chloroform, methanol, the compound be a noval chemical compound.It is proved through functional trial：3β,11α,20β, 26- tetrahydroxy cucurbitane terpenes -5,24 (E)-diene has stronger inhibiting effect to the tumour cells such as HeLa cells and KB cells, can have stronger application value and market prospects as the raw material for preparing prevention tumour medicine.
Description
Technical field
The present invention relates to a kind of reproducibility cucurbit alkane type triterpenoid and its preparation methods and purposes, refer specifically to 3β, 11α, 20β,
- 5,24 (E)-diene of 26- tetrahydroxy cucurbitanes terpene 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 4-5 centimetres oval, long, diameter 2.5-3.5
Centimetre, there is tiny verruca on pericarp surface and is 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 have clearing heat and detoxicating, the multiple efficacies such as antibacterial anti-inflammatory, clinical
On be mainly used for 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 characterize, and are of great significance for developing and using Jinfo Shan Mountain hymsleya amabilis resource.
Invention content
The present invention is exactly to overcome the deficiencies of the prior art and provide isolated in a kind of hymsleya amabilis rhizome from Jinfo Shan Mountain to have
The reproducibility cucurbit alkyl-type triterpenoids of important biomolecule activity and industrialization utility value.The monomeric compound is from Jinfo Shan Mountain
It is isolated for the first time in hymsleya amabilis, after characterizing its structure using modern analysis means and confirm its bioactivity, according to related chemical combination
The naming rule of object is named as 3β, 11α, 20β, 26- tetrahydroxy cucurbitane terpenes -5,24 (E)-diene, which is one
Noval chemical compound.
Isolated 3 in a kind of hymsleya amabilis rhizome from Jinfo Shan Mountainβ, 11α, 20β, 26- tetrahydroxy cucurbitanes terpene -5,24
(E)-diene has the structure that is shown below：
Isolated 3 in above-mentioned hymsleya amabilis rhizome from Jinfo Shan Mountainβ, 11α, 20β, 26- tetrahydroxy cucurbitanes terpene -5,
24 (E)-dienes obtain as follows：
Jinfo Shan Mountain hymsleya amabilis rhizome crushed after being dried is sieved, and adds 95% ethyl alcohol heating and refluxing extraction 3 times, 1-3 hours each, is closed
And extracting solution, solvent is recovered under reduced pressure, total medicinal extract is obtained after concentration, after total medicinal extract is water-dispersible, uses petroleum ether, chloroform, acetic acid successively
Ethyl ester, extracting n-butyl alcohol, extract liquor are concentrated to dryness；Ethyl acetate extract medicinal extract is taken to be detached with silica gel column chromatography, chloroform-methanol
(1:0-0:1) gradient elution obtains 12 parts fraction Fr A-L, Fr.F and is 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 obtains four part Fr. F1-4, and wherein Fr. F4 are detached through high-efficient liquid phase chromatogram purification, using first
Alcohol-water elution, the eluent collected 13.4 minutes crystallize to obtain the final product.
The mass volume ratio of Jinfo Shan Mountain hymsleya amabilis rhizome and ethyl alcohol 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 85 in the methanol-water eluent:15.
3β, 11α, 20β, 26- tetrahydroxy cucurbitane terpenes -5,24 (E)-diene is colourless powder, is soluble in chloroform, first
Alcohol, by 3β, 11α, 20β, 26- tetrahydroxy cucurbitane terpenes -5,24 (E)-diene progress extracorporeal anti-tumor pharmacodynamic experiment, body
Outer antitumor pharmacodynamic experiment utilizes MTT colorimetric methods.
With 3β, 11α, 20β, 26- tetrahydroxy cucurbitane terpenes -5,24 (E)-diene is experimental group, with Doxorubicin
（Doxorubicin, antitumor drug）For control group, while blank group is set up, experimental group, control group and blank group choose HeLa（People
Cervical carcinoma）Cell and KB（Human mouth epidermoid carcinoma）It is inoculated with the density of 6 × 104/ml after culture medium dilution for experimental subjects
In 96 orifice plates, per 100 μ l of hole, after normally cultivating 24 hours in incubator, corresponding drug is added in each group, makes each group drug
Ultimate density 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), and 40
μ g/ml (5 groups) set 5 concentration, 3 multiple holes of each concentration altogether；After culture 48 hours, add 10 μ l dyeing of MTT in every hole；After
After continuous culture four hours, original fluid is abandoned in suction, and 100 μ l of DMSO are added per hole, sets 10 min of low-speed oscillation on shaking table, makes crystallization
Object fully dissolves, and OD value is detected at 570 nm wavelength of enzyme-linked immunosorbent assay instrument, and 50% suppression is calculated according to OD value
Concentration processed（IC50, μ g/mL), OD value calculates IC50Computational methods be existing known technology.Experimental group, control group pair
The IC of HeLa cells and KB cells50As shown in table 1.
Table 1
| Group | HeLa cells | KB cells |
| Experimental group | 10.4 ± 3.2 | 44.1± 2.7 |
| 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, 11α, 20β, 26- tetrahydroxy cucurbitanes terpene -5,
24 (E)-dienes all have certain inhibiting effect to HeLa cells and KB cells, can be as the original for preparing prevention tumour medicine
Material has stronger commercial application value.
Compared with prior art, the beneficial effects of the present invention are：
For the first time from Jinfo Shan Mountain hymsleya amabilis rhizome it is isolated with important antitumor activity 3β, 11α, 20β, 26-
Tetrahydroxy cucurbitane terpene -5,24 (E)-diene, and its chemical constitution and physicochemical property is determined using modern analysis means.Through
Functional trial proves：3β, 11α, 20β, -5,24 (E)-diene of 26- tetrahydroxy cucurbitanes terpene to tumour cell have compared with
Strong inhibiting effect can have stronger application value and market prospects as the raw material for preparing prevention tumour medicine.
Description of the drawings
Fig. 1 is 3β, 11α, 20β, the schematic arrangement of -5,24 (E)-diene of 26- tetrahydroxy cucurbitanes terpene.
Fig. 2 is 3β, 11α, 20β, the nuclear magnetic resonance spectroscopy of -5,24 (E)-diene of 26- tetrahydroxy cucurbitanes terpene（1H-
NMR）.
Fig. 3 is 3β, 11α, 20β, the carbon-13 nmr spectra of -5,24 (E)-diene of 26- tetrahydroxy cucurbitanes terpene（13C-
APT）.
Specific implementation mode
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 sieve.Second step：Medicinal powder adds 10 times
It measures ethyl alcohol heating and refluxing extraction 3 times, 2 hours every time, merges extracting solution, solvent is recovered under reduced pressure, 1033 g of total medicinal extract is obtained after concentration.
Third walks：The total medicinal extract of Jinfo Shan Mountain hymsleya amabilis rhizome add suitable quantity of water carry out decentralized processing after, respectively use petroleum ether, chloroform, ethyl acetate,
N-butanol is extracted, and is extracted to colourless, and extract liquor is concentrated to dryness, the total medicinal extract 56g of petroleum ether part, chloroform are weighed to obtain
The total medicinal extract 302g in position, the total medicinal extract 151g of ethyl acetate extract, total 409 g of medicinal extract of n-butanol portion.4th step：Take ethyl acetate
Layer 151 g of medicinal extract is detached through silica gel column chromatography (100~200 mesh), chloroform-methanol (1:0-0:1) gradient elution obtains 12 and evaporates
Divide Fr A-L.5th step：The parts Fr.F are eluted 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 obtains
To four the 6th steps of part Fr. F1-4.：Wherein Fr. F4 are detached through high-efficient liquid phase chromatogram purification, using methanol-water (85:
15) it elutes, the eluent crystallization collected 13.4 minutes obtains colourless powder, is 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 nuclear magnetic resonance spectroscopy（1H-NMR）And carbon-13 nmr spectra（13C-APT）Analysis
,1H-NMR spectrum as shown in Fig. 2,13C-APT spectrograms are as shown in Figure 3.
Spectrum analysis is carried out to Fig. 2 and Fig. 3, each peaks Fig. 2 and Fig. 3 are belonged to, the peak of Fig. 2 and Fig. 3 belong to such as 2 institute of table
Show, by the data of Fig. 2, Fig. 3 and table 1 it is found that 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, 11α, 20β, -5,24 (E)-diene of 26- tetrahydroxy cucurbitanes terpene.
English entitled 3β, 11α, 20β, 26-tetrahydroxycucurbita-5, 24(E)-diene。
2 compound 1 of table1H-NMR and13C-NMR (150MHz, C5D5N) modal data
Above-mentioned only presently preferred embodiments of the present invention, is not intended to limit the present invention in any form.It is any to be familiar with sheet
The technical staff in field, without deviating from the scope of the technical scheme of the present invention, 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, all
It is the content without departing from technical solution of the present invention, technical spirit is made to the above embodiment according to the present invention any simply repaiies
Change, equivalent variations and modification, all shall fall within the protection scope of the technical scheme of the invention.
Claims (6)
1. a kind of compound, it is characterised in that：The compound is colourless powder, chloroform, methanol is soluble in, to HeLa cells and KB
Cell all has stronger inhibiting effect, and with the structure that is shown below
。
2. compound application in preparation of anti-tumor drugs described in claim 1.
3. the preparation method of compound described in a kind of claim 1, it is characterised in that：Jinfo Shan Mountain hymsleya amabilis rhizome crushed after being dried mistake
Sieve, adds 95% ethyl alcohol heating and refluxing extraction 3 times, 1-3 hours each, merges extracting solution, solvent is recovered under reduced pressure, and obtains after concentration and always soaks
Cream after total medicinal extract is water-dispersible, uses petroleum ether, chloroform, ethyl acetate, extracting n-butyl alcohol, extract liquor to be concentrated to dryness successively；Take second
Acetoacetic ester position medicinal extract is detached with silica gel column chromatography, and the volume ratio of chloroform-methanol is by 1:0 is transitioned into 0:1 carries out gradient elution, obtains
Chloroform-methanol is used to remove discoloration as elution again after gel chromatography elutes to 12 parts fraction Fr A-L, Fr.F
Element, then inverted middle pressure volume ratio of the chromatographic column through methanol-water of sample is respectively 60:40,70:30,80:20 and 90:10 ladders
Degree elution, obtains four part Fr. F1-4, and wherein Fr. F4 are detached through high-efficient liquid phase chromatogram purification, eluted using methanol-water,
The eluent collected 13.4 minutes crystallizes to obtain the final product.
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 ethyl alcohol 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 85 in methanol-water eluent:15.
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| CN115141245B (en) * | 2022-08-03 | 2024-02-23 | 河南中医药大学 | Cucurbitane-type tetracyclic triterpene compound with anti-mastitis activity extracted from Chinese hemsleya root, and preparation method and application thereof |
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| CN105832748A (en) * | 2016-05-06 | 2016-08-10 | 深圳以诺生物制药有限公司 | Method for preparing novel mogrol derivatives from momordica grosvenori total saponins |
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| CN105832748A (en) * | 2016-05-06 | 2016-08-10 | 深圳以诺生物制药有限公司 | Method for preparing novel mogrol derivatives from momordica grosvenori total saponins |
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| Title |
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| Potential AMPK activators of cucurbitane triterpenoids fromSiraitia grosvenorii Swingle;Xu-bing Chen et al.;《Bioorganic & Medicinal Chemistry》;20110822;第19卷;第5776–5781页 * |
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Application publication date: 20170111 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 Reducing Cucurbitane Triterpene and Its Preparation and Application Granted publication date: 20181102 License type: Common License Record date: 20231122 |
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