CN106317157B - A kind of polyhydroxy diketone class cucurbit alkane type triterpenoid and its preparation method and purposes - Google Patents
A kind of polyhydroxy diketone 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 11
- 125000005594 diketone group Chemical group 0.000 title abstract description 5
- 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 3
- 150000001335 aliphatic alkanes Chemical class 0.000 title abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 24
- 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 15
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- 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
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 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
- 239000003480 eluent Substances 0.000 claims description 6
- 235000019441 ethanol Nutrition 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
- 229940079593 drug Drugs 0.000 claims description 3
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- 239000012467 final product Substances 0.000 claims description 2
- 206010041823 squamous cell carcinoma Diseases 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
- 210000000232 gallbladder Anatomy 0.000 claims 1
- 235000007586 terpenes Nutrition 0.000 abstract description 17
- -1 cucurbitane terpene Chemical class 0.000 abstract description 16
- 210000004027 cell Anatomy 0.000 abstract description 8
- 206010028980 Neoplasm Diseases 0.000 abstract description 3
- 238000004458 analytical method Methods 0.000 abstract description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
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- 239000002994 raw material Substances 0.000 abstract description 3
- 210000004881 tumor cell Anatomy 0.000 abstract description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 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
- 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 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 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
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- 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
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- 206010017915 Gastroenteritis shigella Diseases 0.000 description 1
- 241000466342 Hemsleya pengxianensis Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
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- 235000009797 Lagenaria vulgaris Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000014676 Phragmites communis Nutrition 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
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- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
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- 229940125904 compound 1 Drugs 0.000 description 1
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- 230000000857 drug effect Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 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
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 238000000034 method Methods 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
- 230000008439 repair process Effects 0.000 description 1
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- 201000005113 shigellosis Diseases 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 150000003535 tetraterpenes Chemical class 0.000 description 1
- 235000009657 tetraterpenes Nutrition 0.000 description 1
- 150000003648 triterpenes Chemical class 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a kind of polyhydroxy diketone class cucurbit alkane type triterpenoid isolated and purified from Jinfo Shan Mountain hymsleya amabilis rhizome and its preparation methods and purposes, and its chemical structure and physicochemical property has been determined using modern analysis means, according to there is the naming rule of related compounds to be named as 2β,3α,7β,16α,20β, -5 (E)-monoene -11,22- diketone of 25- hexahydroxy cucurbitane terpene, be colourless powder, be soluble in chloroform, methanol, the compound be a noval chemical compound.It is proved through functional trial: 2β,3α,7β,16α,20β, -5 (E)-monoene -11,22- diketone of 25- hexahydroxy cucurbitane terpene has stronger inhibiting effect to the tumour cells such as HeLa cell and KB cell, can have stronger application value and market prospects as the raw material of preparation prevention and treatment tumour medicine.
Description
Technical field
The present invention relates to a kind of polyhydroxy diketone class cucurbitane type tetraterpene derivatives and its preparation methods and purposes, refer specifically to 2β,
3α, 7β, 16α, 20β, -5 (E)-monoene -11,22- diketone of 25- hexahydroxy cucurbitane terpene and its preparation method and purposes.
Background technique
Jinfo Shan Mountain hymsleya amabilis (Hemsleya pengxianensis W. J. Chang var. jinfushanensis L.
D. Shen W. J. Chang) it is Curcurbitaceae (Fabaceae) hymsleya amabilis platymiscium, China region of Southeast is originated in, sea is born in
It pulls out in 2000 meters or so of border and mountain valley shrubbery.The fruit of Jinfo Shan Mountain hymsleya amabilis is in 4-5 centimetres oval, long, and 2.5-3.5 lis of diameter
There is tiny verruca on rice, pericarp surface and distinguishes with former mutation, and main active is respectively cucurbitane type Fourth Ring three
Terpene and its saponin(e and Triterpenoids sapogenins and its saponin(e have clearing heat and detoxicating, the multiple efficacies such as antibacterial anti-inflammatory, clinically
It is mainly used for treating a variety of diseases such as bacillary dysentery, various inflammation, ulcer, 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 development and utilization Jinfo Shan Mountain hymsleya amabilis resource.
Summary of the invention
The present invention is exactly to overcome the deficiencies of the prior art and provide a kind of isolated from Jinfo Shan Mountain hymsleya amabilis rhizome to have
The polyhydroxy diketone class Cucurbitanes of important biomolecule activity and industrialization utility value.The monomeric compound is from golden Buddhist
It is isolated for the first time in the hymsleya amabilis of mountain, after characterizing its structure using modern analysis means and confirm its bioactivity, according to relatedization
The naming rule for closing object is named as 2β, 3α, 7β, 16α, 20β, -5 (E)-monoene -11,22- of 25- hexahydroxy cucurbitane terpene
Diketone, the compound are a noval chemical compound.
A kind of isolated from Jinfo Shan Mountain hymsleya amabilis rhizome 2β, 3α, 7β, 16α, 20β, 25- hexahydroxy cucurbitane
Terpene -5 (E)-monoene -11,22- diketone has the structure that is shown below:
Above-mentioned isolated from Jinfo Shan Mountain hymsleya amabilis rhizome 2β, 3α, 7β, 16α, 20β, 25- hexahydroxy cucurbit
Alkane terpene -5 (E)-monoene -11,22- diketone obtains as follows:
The sieving of Jinfo Shan Mountain hymsleya amabilis rhizome crushed after being dried, adds 95% ethyl alcohol heating and refluxing extraction 3 times, 1-3 hours each, closes
And extracting solution, solvent is recovered under reduced pressure, total medicinal extract is obtained after concentration, after total medicinal extract is water-dispersible, successively uses petroleum ether, chloroform, acetic acid
Ethyl ester, extracting n-butyl alcohol, extract liquor 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 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. F3 is separated through high-efficient liquid phase chromatogram purification, using first
Alcohol-water elution, the eluent collected 16.7 minutes crystallize to obtain the final product.
The mass volume ratio of Jinfo Shan Mountain hymsleya amabilis rhizome and ethyl alcohol is 1:8-1:12 in the heating and refluxing extraction.
The volume ratio of chloroform and methanol is 45:55-60:40 in the chloroform-methanol eluent.
The volume ratio of methanol and water is 80:20 in the methanol-water eluent.
2β, 3α, 7β, 16α, 20β, -5 (E)-monoene -11,22- diketone of 25- hexahydroxy cucurbitane terpene is no toner
End is soluble in chloroform, methanol, by 2β, 3α, 7β, 16α, 20β, -5 (E)-monoene -11 of 25- hexahydroxy cucurbitane terpene,
22- diketone carries out extracorporeal anti-tumor pharmacodynamic experiment, and extracorporeal anti-tumor pharmacodynamic experiment utilizes MTT colorimetric method.
With 2β, 3α, 7β, 16α, 20β, -5 (E)-monoene -11,22- diketone of 25- hexahydroxy cucurbitane terpene is experiment
Group, with Doxorubicin(Doxorubicin, anti-tumor drug) be control group, while setting up blank group, experimental group, control group and
Blank group chooses HeLa(human cervical carcinoma) cell and KB(human mouth epidermoid carcinoma) it is experimental subjects, after culture medium dilution, with 6 ×
The density of 104/ml is inoculated in 96 orifice plates, every 100 μ l of hole, and after normally cultivating 24 hours in incubator, each group is added corresponding
Drug, making the ultimate density of each group drug 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) set 5 concentration, 3 multiple holes of each concentration altogether；After culture 48 hours, in every
Hole adds 10 μ l of MTT to dye；It after continuing culture four hours, inhales and abandons original fluid, every hole is added 100 μ l of DMSO, sets low on shaking table
Speed 10 min of oscillation, dissolve crystal sufficiently, and detect OD value, root at 570 nm wavelength of enzyme-linked immunosorbent assay instrument
50% inhibition concentration (IC is calculated according to OD value50, μ g/mL), OD value calculates IC50Calculation method be existing known skill
Art.Experimental group, control group are to the IC of HeLa cell and KB cell50As shown in table 1.
Table 1
| Group | HeLa cell | KB cell |
| Experimental group | 2.9 ± 0.8 | 14.7 ± 1.6 |
| Control group | 1.3 ± 0.11 | 0.89 ± 0.03 |
It can be seen that of the present invention 2 by the data of upper tableβ, 3α, 7β, 16α, 20β, 25- hexahydroxy calabash
- 5 (E)-monoene -11,22- diketone of reed alkane terpene all has certain inhibiting effect to HeLa cell and KB cell, can be as system
The raw material of standby prevention and treatment tumour medicine has stronger industrial application value.
Compared with prior art, the beneficial effects of the present invention are:
Isolated 2 with important anti-tumor activity from Jinfo Shan Mountain hymsleya amabilis rhizome for the first timeβ, 3α, 7β, 16α,
20β, -5 (E)-monoene -11,22- diketone of 25- hexahydroxy cucurbitane terpene, and it has been determined that its chemistry is tied using modern analysis means
Structure and physicochemical property.It is proved through functional trial: 2β, 3α, 7β, 16α, 20β, 25- hexahydroxy cucurbitane terpene -5 (E)-mono-
Alkene -11,22- diketone has stronger inhibiting effect to tumour cell, can be as the raw material of preparation prevention and treatment tumour medicine, tool
There are stronger application value and market prospects.
Detailed description of the invention
Fig. 1 is 2β, 3α, 7β, 16α, 20β, -5 (E)-monoene -11,22- diketone of 25- hexahydroxy cucurbitane terpene
Schematic arrangement.
Fig. 2 is 2β, 3α, 7β, 16α, 20β, -5 (E)-monoene -11,22- diketone of 25- hexahydroxy cucurbitane terpene
Nuclear magnetic resonance spectroscopy (1H-NMR).
Fig. 3 is 2β, 3α, 7β, 16α, 20β, -5 (E)-monoene -11,22- diketone of 25- hexahydroxy cucurbitane terpene
Carbon-13 nmr spectra (13C-APT).
Specific embodiment
Below in conjunction with specific embodiment, the present invention is further illustrated
Step 1: Jinfo Shan Mountain hymsleya amabilis rhizome (5.0 kg) crushed after being dried crosses 80 meshes.Step 2: medicinal powder adds 10 times
Amount ethyl alcohol heating and refluxing extraction 3 times, 2 hours every time, solvent was recovered under reduced pressure in combined extract, and total 1033 g of medicinal extract is obtained after concentration.
Step 3: 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, 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.Step 4: taking ethyl acetate
Layer 151 g of medicinal extract is separated through silica gel column chromatography (100~200 mesh), and chloroform-methanol (1:0-0:1) gradient elution obtains 12 and evaporates
Divide Fr A-L.Step 5: the part Fr.F is eluted through gel chromatography, chloroform-methanol (45:55) removes discoloration 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 part Fr. F1-4. step 6: wherein Fr. F3 is separated through high-efficient liquid phase chromatogram purification, using methanol-water (80:
20) it elutes, the eluent crystallization collected 16.7 minutes obtains colourless powder, is soluble in chloroform, methanol.
The structural characterization of above-mentioned colourless powder and confirmation are as follows:
By above-mentioned gained colourless powder carry out nuclear magnetic resonance spectroscopy (1H-NMR) and carbon-13 nmr spectra (13C-APT it) analyzes
,1H-NMR spectrum as shown in Fig. 2,13C-APT spectrogram is as shown in Figure 3.
Spectrum analysis is carried out to Fig. 2 and Fig. 3, each peak Fig. 2 and Fig. 3 is 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 2β, 3α, 7β, 16α, 20β, -5 (E)-monoene -11,22- two of 25- hexahydroxy cucurbitane terpene
Ketone.
English entitled 2β, 3α, 7β, 16α, 20β, 25-hexahydroxycucurbita-5(E)-ene-11,
22-dione。
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 or equivalent example modified to equivalent change are made to technical solution of the present invention.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 repairs
Change, equivalent variations and modification, all shall fall within the protection scope of the technical scheme of the invention.
Claims (5)
1. a kind of compound is preparing the application in anti-oral cavity epidermoid carcinoma KB cell drug, it is characterised in that: the compound is
Colourless powder is soluble in chloroform, methanol, and has structure as follows
。
2. a kind of 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% ethyl alcohol heating and refluxing extraction 3 times, and 1-3 hours each, solvent is recovered under reduced pressure in combined extract, obtains after concentration and always soaks
Cream after total medicinal extract is water-dispersible, successively uses petroleum ether, chloroform, ethyl acetate, extracting n-butyl alcohol, and extract liquor is concentrated to dryness；Take second
Acetoacetic ester position medicinal extract is separated with silica gel column chromatography, chloroform-methanol 1:0-0:1 gradient elution, obtains 12 fraction Fr A-L,
Fr.F after gel chromatography elutes uses chloroform-methanol to remove depigmentaton as elution in part again, then sample it is inverted in
Press chromatographic column through MeOH-H2O is with 60:40; 70:30; 80:20;90:10 carries out gradient elution, obtains four part Fr.
F1-4, wherein Fr. F3 is separated through high-efficient liquid phase chromatogram purification, is eluted using methanol-water, and 16.7 minutes eluent knots are collected
Crystalline substance to obtain the final product.
3. the preparation method of compound according to claim 2: it is characterized by: Jinfo Shan Mountain is avenged in the heating and refluxing extraction
The mass volume ratio of gallbladder rhizome and ethyl alcohol is 1:8-1:12.
4. the preparation method of compound according to claim 2: it is characterized by: in gel chromatography elution, chloroform-first
The volume ratio of chloroform and methanol is 45:55-60:40 in alcohol eluen.
5. the preparation method of compound according to claim 2: it is characterized by: the high-efficient liquid phase chromatogram purification separates
In, the volume ratio of methanol and water is 80:20 in methanol-water eluent.
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|---|---|---|---|---|
| CN103665082A (en) * | 2013-12-10 | 2014-03-26 | 山东省医学科学院药物研究所 | Hemsleya cucurbitane tetracyclic triterpenoid compound, pharmaceutical compositions containing same and application of compound and pharmaceutical composition |
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2016
- 2016-08-23 CN CN201610701251.1A patent/CN106317157B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103665082A (en) * | 2013-12-10 | 2014-03-26 | 山东省医学科学院药物研究所 | Hemsleya cucurbitane tetracyclic triterpenoid compound, pharmaceutical compositions containing same and application of compound and pharmaceutical composition |
Non-Patent Citations (1)
| Title |
|---|
| Cytotoxic cucurbitane triterpenoids isolated from the rhizomes of Hemsleya amabilis;Xu-Bing Chen et al.;《Fitoterapia》;20140124;第94卷;第91页图1，第92页表3，第89页 * |
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| CN106317157A (en) | 2017-01-11 |
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