CN106380503A - A trihydroxy monoketone cucurbitane type triterpene, a preparing method thereof and uses of the compound - Google Patents
A trihydroxy monoketone cucurbitane type triterpene, a preparing method thereof and uses of the compound Download PDFInfo
- Publication number
- CN106380503A CN106380503A CN201610701234.8A CN201610701234A CN106380503A CN 106380503 A CN106380503 A CN 106380503A CN 201610701234 A CN201610701234 A CN 201610701234A CN 106380503 A CN106380503 A CN 106380503A
- Authority
- CN
- China
- Prior art keywords
- compound
- methanol
- chloroform
- trihydroxy
- compound according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 21
- 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 title abstract description 5
- 150000003648 triterpenes Chemical class 0.000 title abstract description 4
- 238000000034 method Methods 0.000 title abstract description 3
- 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 18
- 239000000843 powder Substances 0.000 claims abstract description 8
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 4
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 238000010828 elution Methods 0.000 claims description 8
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 8
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 7
- 239000003480 eluent Substances 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 5
- 239000000284 extract Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 230000006837 decompression Effects 0.000 claims description 3
- 238000005227 gel permeation chromatography Methods 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 238000010898 silica gel chromatography Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 229940041181 antineoplastic drug Drugs 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 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
- 238000011321 prophylaxis Methods 0.000 claims 1
- 210000004027 cell Anatomy 0.000 abstract description 8
- 239000003814 drug Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 238000012360 testing method Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 2
- 210000004881 tumor cell Anatomy 0.000 abstract description 2
- 241000466342 Hemsleya pengxianensis Species 0.000 abstract 1
- -1 cucurbitane terpene Chemical class 0.000 description 16
- 235000007586 terpenes Nutrition 0.000 description 14
- 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
- 238000005516 engineering process Methods 0.000 description 4
- 240000009087 Crescentia cujete Species 0.000 description 3
- 235000005983 Crescentia cujete Nutrition 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 235000009797 Lagenaria vulgaris Nutrition 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 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 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 241000906682 Hemsleya Species 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 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
- 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
- 241000219104 Cucurbitaceae Species 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
- 206010023126 Jaundice Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 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
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 208000019065 cervical carcinoma Diseases 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000002026 chloroform extract Substances 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
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 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
- 239000000975 dye Substances 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
- 239000012467 final product Substances 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
- 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
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 231100000614 poison Toxicity 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
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
Classifications
-
- 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
Landscapes
- 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 a trihydroxy monoketone cucurbitane type triterpene prepared by separating from stems and roots of hemsleya pengxianensis var. jinfushanensis and purifying, a preparing method thereof and uses of the compound. The chemical structure and physical and chemical properties of the compound are determined by utilizing modern means. The compound is named as 3beta,20beta,24-trihydroxycucurbita-5,23(E)-diene-11-one according to naming rules of corresponding compounds, is colorless powder and can be easily dissolved into chloroform and methanol. Functionality tests prove that the 3beta,20beta,24-trihydroxycucurbita-5,23(E)-diene-11-one has high functions for inhibiting tumor cells such as HeLa cells and KB cells, can be adopted as a raw material for preparing a tumor preventing and treating medicine, and has high application value and a good market prospect.
Description
Technical field
The present invention relates to a kind of trihydroxy single ketones class calabash alkane type triterpenoid and its preparation method and purposes, refer specifically to 3β, 20β,
24- trihydroxy cucurbitane terpene -5,23 (E)-diene -11- ketone and its preparation method and purposes.
Background technology
Jinfo Shan Mountain Radix Hemsleyae Macrospermae (Hemsleya pengxianensisW. J. Chang var. jinfushanensis L.
D. Shen ＆ W. J. Chang) it is Cucurbitaceae (Fabaceae) Genus Hemsleya platymiscium, originate in China region of Southeast, be born in
In the border that 2000 meter about of height above sea level and mountain valley shrubbery.The fruit of Jinfo Shan Mountain Radix Hemsleyae Macrospermae is in avette, long 4-5 centimetre, diameter 2.5-3.5
Centimetre, peel surface has tiny verruca to distinguish with former mutation, and main active is respectively cucurbitane type Fourth Ring
Triterpene and its saponin and Triterpenoids sapogenins and its saponin, have heat-clearing and toxic substances removing, the multiple efficacies such as anti-inflammation, clinical
On be mainly used in treating bacillary dysentery, various inflammation, ulcer, multiple diseases such as jaundice.
The drug effect of Jinfo Shan Mountain Radix Hemsleyae Macrospermae is mainly derived from cucurbitane type triterpenoid compound therein, therefore, development and utilization
In Radix Hemsleyae Macrospermae cucurbitane type monomeric compound, excavate its potential medical value further, and the knot to monomer compound
Structure and physicochemical property are determined and characterize, and for developing, Jinfo Shan Mountain Radix Hemsleyae Macrospermae resource is significant.
Content of the invention
The present invention is exactly to overcome the deficiencies in the prior art, provides separately obtain a kind of Radix Hemsleyae Macrospermae rhizome from Jinfo Shan Mountain to have
Important biomolecule activity and the trihydroxy single ketones class Cucurbitanes of industrialization value.This monomeric compound is from golden Buddhist
Separately obtain first in the Radix Hemsleyae Macrospermae of mountain, characterize its structure using modern analysis means and confirm after its biological activity, according to relevantization
The naming rule of compound is named as 3β, 20β, 24- trihydroxy cucurbitane terpene -5,23 (E)-diene -11- ketone.
3 obtaining are separated a kind of Radix Hemsleyae Macrospermae rhizome from Jinfo Shan Mountainβ, 20β, 24- trihydroxy cucurbitane terpene -5,23 (E) -
Diene -11- ketone, is noval chemical compound, has the structure that is shown below：
Separate, the above-mentioned son from Jinfo Shan Mountain Radix Hemsleyae Macrospermae rhizome, 3 obtainingβ, 20β, 24- trihydroxy cucurbitane terpene -5,23 (E)-two
Alkene -11- ketone obtains as follows：
Jinfo Shan Mountain Radix Hemsleyae Macrospermae rhizome crushed after being dried is sieved, plus 95% alcohol heating reflux extracts 3 times, each 1-3 hour, and merging carries
Take liquid, decompression and solvent recovery, after concentration total extractum, after total extractum is water-dispersible, use successively petroleum ether, chloroform, ethyl acetate,
N-butanol extraction, extract is concentrated to dryness；Ethyl acetate extract extractum silica gel column chromatography is taken to separate, chloroform-methanol (1:0-0:
1) gradient elution, obtains 12 fraction Fr A-L, and Fr.F part uses chloroform-methanol as eluting after gel chromatography eluting again
Liquid eluting removes depigmentaton, and 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. F1 separates through high-efficient liquid phase chromatogram purification, using methanol-water
Eluting, the eluent crystallization collected 28.9 minutes obtains final product.
In described heating and refluxing extraction, Jinfo Shan Mountain Radix Hemsleyae Macrospermae rhizome and the mass volume ratio of ethanol are 1:8-1:12.
In described chloroform-methanol eluent, chloroform and the volume ratio of methanol are 45:55-60:40.
In described methanol-water eluent, methanol and the volume ratio of water are 60:40.
3β, 20β, 24- trihydroxy cucurbitane terpene -5,23 (E)-diene -11- ketone are colourless powder, are soluble in chloroform,
Methanol, by 3β, 20β, it is real that 24- trihydroxy cucurbitane terpene -5,23 (E)-diene -11- ketone carries out extracorporeal anti-tumor pharmacodynamicss
Test, extracorporeal anti-tumor pharmacodynamic experiment utilizes MTT colorimetry.
With 3β, 20β, 24- trihydroxy cucurbitane terpene -5,23 (E)-diene -11- ketone are experimental group, with
Doxorubicin（Doxorubicin, antitumor drug）For matched group, set up blank group, experimental group, matched group and blank group simultaneously
Choose HeLa（Human cervical carcinoma）Cell and KB（Human mouth epidermoid carcinoma）For experimental subject, after culture medium dilution, with 6 × 104/ml
Density be inoculated in 96 orifice plates, every hole 100 μ l, after normal culture 24 hours in incubator, 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), set 5 concentration altogether, 3 multiple holes of each concentration；After culture 48 hours, add MTT 10 in every hole
μ l dyes；After continuing culture four hours, inhale and abandon original fluid, every hole adds DMSO 100 μ l, puts low-speed oscillation 10 on shaking table
Min, makes crystal fully dissolve, and detects optical density value at enzyme-linked immunosorbent assay instrument 570 nm wavelength, according to optical density
Value calculates 50% inhibition concentration（IC50, μ g/mL), optical density value calculates IC50Computational methods be existing known technology.Experiment
Group, the matched group IC to HeLa cell and KB cell50As shown in table 1.
Table 1
| Group | HeLa cell | KB cell |
| Experimental group | 7.9 ± 2.4 | 32.1 ± 2.3 |
| Matched group | 1.3 ± 0.11 | 0.89 ± 0.03 |
Can be seen that of the present invention 3 by the data of upper tableβ, 20β, 24- trihydroxy cucurbitane terpene -5,23 (E)-two
Alkene -11- ketone is respectively provided with certain inhibitory action to HeLa cell and KB cell, can be former as preparation preventing and treating tumour medicine
Material, possesses stronger commercial application and is worth.
Compared with prior art, the beneficial effects of the present invention is：
Separate from Jinfo Shan Mountain Radix Hemsleyae Macrospermae rhizome first and obtained thering is the 3 of important anti-tumor activityβ, 20β, 24- trihydroxy calabash
Reed alkane terpene -5,23 (E)-diene -11- ketone, and determine its chemical constitution and physicochemical property using modern analysis means.Through work(
Can property test prove：3β, 20β, 24- trihydroxy cucurbitane terpene -5,23 (E)-diene -11- ketone has stronger to tumor cell
Inhibitory action, can as preparation preventing and treating tumour medicine raw material, have stronger using value and market prospect.
Brief description
Fig. 1 is 3β, 20β, the schematic arrangement of 24- trihydroxy cucurbitane terpene -5,23 (E)-diene -11- ketone.
Fig. 2 is 3β, 20β, the proton nmr spectra of 24- trihydroxy cucurbitane terpene -5,23 (E)-diene -11- ketone（1H-
NMR）.
Fig. 3 is 3β, 20β, the carbon-13 nmr spectra of 24- trihydroxy cucurbitane terpene -5,23 (E)-diene -11- ketone（13C-
APT）.
Specific embodiment
Below in conjunction with specific embodiment, the present invention is further illustrated
The first step：Jinfo Shan Mountain Radix Hemsleyae Macrospermae rhizome (5.0 kg) crushed after being dried crosses 80 mesh sieves.Second step：Medicinal powder adds 10 times amount second
Alcohol heating and refluxing extraction 3 times, 2 hours every time, united extraction liquid, decompression and solvent recovery, obtain total extractum 1033 g after concentration.3rd
Step：The total extractum of Jinfo Shan Mountain Radix Hemsleyae Macrospermae rhizome adds after suitable quantity of water carries out decentralized processing, uses petroleum ether, chloroform, ethyl acetate, positive fourth respectively
Alcohol is extracted, and is extracted to colourless, extract is evaporated to dry, weighs to obtain petroleum ether part total extractum 56g, chloroform extract
Total extractum 302g, ethyl acetate extract total extractum 151g, the total extractum of n-butanol portion 409 g.4th step：Ethyl acetate layer is taken to soak
Cream 151 g separates through silica gel column chromatography (100～200 mesh), chloroform-methanol (1:0-0:1) gradient elution, obtains 12 fractions
Fr A-L.5th step：Fr.F part is through gel chromatography eluting, chloroform-methanol（45:55）Remove depigmentaton as 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. the 6th steps：Wherein Fr. F1 separates through high-efficient liquid phase chromatogram purification, using methanol-water（60:40）
Eluting, the eluent crystallization collected 28.9 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 carried out proton nmr spectra（1H-NMR）And carbon-13 nmr spectra（13C-APT）Analysis,1H-
NMR spectra as shown in Fig. 213C-APT spectrogram is as shown in Figure 3.
Spectrum analysis are carried out to Fig. 2 and Fig. 3, each for Fig. 2 and Fig. 3 peak is belonged to, the peak of Fig. 2 and Fig. 3 belongs to as table 2 institute
Show, by the data of Fig. 2, Fig. 3 and table 1, the chemical structural formula of colourless powder is as shown in figure 1, according to there being related compounds
Naming rule be named as 3β, 20β, 24- trihydroxy cucurbitane terpene -5,23 (E)-diene -11- ketone.
English entitled 3β, 20β, 24-trihydroxycucurbita-5, 23(E)-diene-11-one.
Table 2 compound 11H-NMR and13C-NMR (150MHz, C5D5N) modal data
Above-mentioned simply presently preferred embodiments of the present invention, not makees any pro forma restriction to the present invention.Any it is familiar with this area
Technical staff, in the case of without departing from technical solution of the present invention scope, the technology contents of the disclosure above all can be utilized to this
Inventive technique scheme makes many possible variations and modification, or the Equivalent embodiments being revised as equivalent variations.Therefore, every not
Depart from technical solution of the present invention content, according to the technology of the present invention essence to any simple modification made for any of the above embodiments, etc.
With changing and modifying, all should fall in the range of technical solution of the present invention protection.
Claims (8)
1. a kind of compound it is characterised in that：There is the structure that is shown below.
2. compound according to claim 1 it is characterised in that：This compound is colourless powder, is soluble in chloroform, first
Alcohol.
3. compound according to claim 1 it is characterised in that：This compound is respectively provided with relatively to HeLa cell and KB cell
Strong inhibitory action.
4. claim 1 or compound described in 2 or 3 in prophylaxis of tumours and prepare the application in antitumor drug.
5. compound described in claim 1-3 preparation method it is characterised in that：Jinfo Shan Mountain Radix Hemsleyae Macrospermae rhizome crushed after being dried mistake
Sieve, plus 95% alcohol heating reflux extracts 3 times, each 1-3 hour, united extraction liquid, decompression and solvent recovery, obtain after concentration and always soak
Cream, after total extractum is water-dispersible, uses petroleum ether, chloroform, ethyl acetate, n-butanol extraction, extract is concentrated to dryness successively；Take second
Acetoacetic ester position extractum is separated with silica gel column chromatography, chloroform-methanol (1:0-0:1) gradient elution, obtains 12 fraction Fr A-
L, Fr.F part uses chloroform-methanol to remove depigmentaton as elution after gel chromatography eluting again, and then sample is inverted
Middle pressure chromatographic column is through MeOH-H2O (60:40; 70:30; 80:20; 90:10) gradient elution, obtains four part Fr. F1-
4, wherein Fr. F1 separate through high-efficient liquid phase chromatogram purification, and using methanol-water eluting, the eluent crystallization collected 28.9 minutes is
?.
6. the preparation method of compound according to claim 5：It is characterized in that：Jinfo Shan Mountain snow in described heating and refluxing extraction
Gallbladder rhizome is 1 with the mass volume ratio of ethanol:8-1:12.
7. the preparation method of compound according to claim 5：It is characterized in that：Chloroform in described chloroform-methanol eluent
Volume ratio with methanol is 45:55-60:40.
8. the preparation method of compound according to claim 5：It is characterized in that：In described methanol-water eluent methanol with
The volume ratio of water is 60:40.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610701234.8A CN106380503B (en) | 2016-08-23 | 2016-08-23 | A kind of trihydroxy single ketones class cucurbit alkane type triterpenoid and its preparation method and purposes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610701234.8A CN106380503B (en) | 2016-08-23 | 2016-08-23 | A kind of trihydroxy single ketones class cucurbit alkane type triterpenoid and its preparation method and purposes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106380503A true CN106380503A (en) | 2017-02-08 |
| CN106380503B CN106380503B (en) | 2018-03-02 |
Family
ID=57916874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610701234.8A Active CN106380503B (en) | 2016-08-23 | 2016-08-23 | A kind of trihydroxy single ketones class cucurbit alkane type triterpenoid and its preparation method and purposes |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106380503B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115160396A (en) * | 2022-08-03 | 2022-10-11 | 河南中医药大学 | Cucurbitane tetracyclic triterpenoid extracted from Hemsleya chinensis with anti-enteritis activity, and preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
2016
- 2016-08-23 CN CN201610701234.8A patent/CN106380503B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Non-Patent Citations (5)
| Title |
|---|
| CHUAN CHEN 等: "Cucurbitane-Type Triterpenoids from the Stems of Cucumis melo", 《J. NAT. PROD.》 * |
| XIAOTING XU 等: "Three new cucurbitane triterpenoids from Hemsleya penxianensis and their cytotoxic activities", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》 * |
| XU-BING CHEN等: "Cytotoxic cucurbitane triterpenoids isolated from the rhizomes of Hemsleya amabilis", 《FITOTERAPIA》 * |
| YING LI 等: "Five new cucurbitane triterpenoids with cytotoxic activity from Hemsleya jinfushanensis", 《PHYTOCHEMISTRY LETTERS》 * |
| 李莹 等: "雪胆属植物的化学成分及生物活性研究进展", 《中草药》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115160396A (en) * | 2022-08-03 | 2022-10-11 | 河南中医药大学 | Cucurbitane tetracyclic triterpenoid extracted from Hemsleya chinensis with anti-enteritis activity, and preparation method and application thereof |
| CN115160396B (en) * | 2022-08-03 | 2024-04-05 | 河南中医药大学 | Cucurbitane-type tetracyclic triterpene compound with anti-enteritis activity extracted from Chinese hemsleya root, and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106380503B (en) | 2018-03-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108003214B (en) | Saponin compound extracted from rhizoma bolbostemmae, and its preparation method and application | |
| CN101824067A (en) | Barrigenol-type triterpenoid saponins compound, preparation method and application thereof | |
| CN106317156B (en) | A kind of penta hydroxy group diones cucurbit alkane type triterpenoid and its preparation method and purposes | |
| CN104628531B (en) | A kind of compound S J-11 extracting Cong Shan Kashihara and preparation method thereof and application | |
| CN106045819B (en) | A kind of mysorethorn tricyclic diterpene and its preparation method and purposes | |
| CN106397530B (en) | A kind of condensed ring class cucurbit alkane type triterpenoid and its preparation method and purposes | |
| CN106317155B (en) | A kind of reproducibility cucurbit alkane type triterpenoid and its preparation method and purposes | |
| CN106317157A (en) | Polyhydroxy diketone cucuribitane triterpene as well as preparation method and application thereof | |
| CN106380503B (en) | A kind of trihydroxy single ketones class cucurbit alkane type triterpenoid and its preparation method and purposes | |
| CN103610762B (en) | Extract of corydalis impatiens total alkaloids and extraction method thereof | |
| CN103191143B (en) | New application of cardiac glycoside compound | |
| CN105418722B (en) | A kind of entitled Sasanguasaponin C4And C5Pentacyclic triterpenoid preparation method | |
| CN110183418A (en) | The sequiterpene and its separation method of a kind of lindera glauca plant root origin and application | |
| CN102772501A (en) | Rheum emodi Wall. extract and its preparing method | |
| CN109180471A (en) | Water cape jasmine monoterpenes compound crocusatinN and jasminosideB preparation method and application | |
| CN106397523B (en) | A kind of methylhydroxy cucurbit alkane type triterpenoid and its preparation method and purposes | |
| CN109456163B (en) | Cycloalkenone compound with symmetrical structure and preparation method and application thereof | |
| CN103479723A (en) | Diterpenoid tanshinone effective part and countercurrent chromatography preparation method and cancer treatment application thereof | |
| CN103623066B (en) | Corydalis impatiens total alkaloid extractive for preparing anti-cancer drugs and application thereof | |
| CN103183597A (en) | Diaryl neptanone compound having antineoplastic activity, preparing method and application | |
| CN106045951B (en) | A kind of mysorethorn lactone and its preparation method and purposes | |
| CN103833818B (en) | The antitumor drug of a kind of Sasanguasaponin compound, its preparation method, application and preparation thereof | |
| CN105330713B (en) | 3beta-acetoxyl ginsenoside F1 and extraction method and medicine application thereof | |
| CN109206392A (en) | A kind of coumarin kind compound and the preparation method and application thereof | |
| CN106967026A (en) | The preparation method and application of coumarin 1 in Radix Angelicae Sinensis |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right |
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 |
|
| TR01 | Transfer of patent right | ||
| EE01 | Entry into force of recordation of patent licensing contract |
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 |
|
| EE01 | Entry into force of recordation of patent licensing contract |