CN106317155A - Reductive cucurbitane triterpene as well as preparation method and use thereof - Google Patents
Reductive cucurbitane triterpene as well as preparation method and use thereof Download PDFInfo
- Publication number
- CN106317155A CN106317155A CN201610701140.0A CN201610701140A CN106317155A CN 106317155 A CN106317155 A CN 106317155A CN 201610701140 A CN201610701140 A CN 201610701140A CN 106317155 A CN106317155 A CN 106317155A
- Authority
- CN
- China
- Prior art keywords
- compound
- methanol
- cucurbitane
- chloroform
- preparation
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- -1 cucurbitane triterpene Chemical class 0.000 title abstract description 7
- 230000002829 reductive effect Effects 0.000 title abstract 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 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 10
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 8
- 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
- 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
- 239000000284 extract Substances 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 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
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 239000000049 pigment 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
- 102000011759 adducin Human genes 0.000 claims 1
- 108010076723 adducin Proteins 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
- 238000011321 prophylaxis Methods 0.000 claims 1
- 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 abstract description 19
- 210000004027 cell Anatomy 0.000 abstract description 7
- 239000003814 drug Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 238000004458 analytical method Methods 0.000 abstract description 3
- 238000002474 experimental method Methods 0.000 abstract description 3
- 241000906682 Hemsleya Species 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 210000004881 tumor cell Anatomy 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 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
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 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
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 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
- 150000003648 triterpenes Chemical class 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
- 206010061218 Inflammation Diseases 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229960004679 doxorubicin Drugs 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- 238000000034 method Methods 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
- 206010008342 Cervix carcinoma 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
- 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
- 208000006105 Uterine Cervical Neoplasms 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
- 201000010881 cervical cancer 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
- 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
- 239000006185 dispersion Substances 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
- 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
- 238000002386 leaching Methods 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
- 231100000614 poison Toxicity 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
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses reductive cucurbitane triterpene separated and purified from rhizomes of Hemsleya jinfushanensis as well as a preparation method and use of reductive cucurbitane triterpene. The chemical structure and physicochemical properties of the reductive cucurbitane triterpene are determined by virtue of a modern analysis measure, the reductive cucurbitane triterpene is named as 3beta,11alpha,20beta,26-tetrahydroxy cucurbitane terpene-5,24(E)-diene according to a naming rule of relevant compounds, is colorless powder and can be easily dissolved in chloroform and methanol, and the compound is a novel compound. Functional experiments prove that 3beta,11alpha,20beta,26-tetrahydroxy cucurbitane terpene-5,24(E)-diene has relatively strong inhibition effects to tumor cells such as HeLa cells and KBcells, can be used as a raw material for preparing drugs for preventing and treating tumors and has relatively strong application values and market prospect.
Description
Technical field
The present invention relates to a kind of reproducibility calabash alkane type triterpenoid and preparation method thereof and purposes, refer specifically to 3β, 11α, 20β,
26-tetrahydroxy cucurbitane terpene-5,24 (E)-diene and preparation method thereof and purposes.
Background technology
Jinfo Shan Mountain Radix Hemsleyae Macrospermae (Hemsleya pengxianensis W. 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 border that height above sea level is about 2000 meters and mountain valley shrubbery.The fruit of Jinfo Shan Mountain Radix Hemsleyae Macrospermae is 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 saponin thereof and Triterpenoids sapogenins and saponin thereof, have the multiple efficacies such as heat-clearing and toxic substances removing, anti-inflammation, clinical
On be mainly used in treating the multiple disease such as bacillary dysentery, various inflammation, ulcer, 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 further its potential medical value, and the knot to monomer whose compound
Structure and physicochemical property are determined and characterize, significant for developing Jinfo Shan Mountain Radix Hemsleyae Macrospermae resource.
Summary of the invention
The present invention overcomes the deficiencies in the prior art exactly, it is provided that a kind of the having of isolated from Jinfo Shan Mountain Radix Hemsleyae Macrospermae rhizome
Important biomolecule activity and the reproducibility calabash alkyl-type triterpenoids of industrialization value.This monomeric compound is from Jinfo Shan Mountain
Isolated first in Radix Hemsleyae Macrospermae, after utilizing modern analysis means to characterize its structure and confirm its biological activity, according to relevant chemical combination
The naming rule named 3 of thingβ, 11α, 20β, 26-tetrahydroxy cucurbitane terpene-5,24 (E)-dienes, this compound is one
Noval chemical compound.
A kind of from Jinfo Shan Mountain Radix Hemsleyae Macrospermae rhizome the 3 of isolatedβ, 11α, 20β, 26-tetrahydroxy cucurbitane terpene-5,24
(E)-diene, has a structure that is shown below:
Above-mentioned from Jinfo Shan Mountain Radix Hemsleyae Macrospermae rhizome the 3 of isolatedβ, 11α, 20β, 26-tetrahydroxy cucurbitane terpene-5,24
(E)-diene obtains as follows:
Jinfo Shan Mountain Radix Hemsleyae Macrospermae rhizome crushed after being dried is sieved, and adds 95% alcohol heating reflux and extracts 3 times, and each 1-3 hour, merging carried
Take liquid, decompression and solvent recovery, after concentration total extractum, total extractum with after water-dispersible, use successively petroleum ether, chloroform, ethyl acetate,
N-butanol extraction, extract is concentrated to dryness；Take ethyl acetate extract extractum silica gel column chromatography to separate, chloroform-methanol (1:0-0:
1) gradient elution, obtains 12 fraction Fr A-L, Fr.F part and uses chloroform-methanol as eluting after gel chromatography eluting again
Liquid eluting removes pigment, 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. F4 separates through high-efficient liquid phase chromatogram purification, uses methanol-water
Eluting, the eluent collected 13.4 minutes crystallizes and get final product.
In described heating and refluxing extraction, Jinfo Shan Mountain Radix Hemsleyae Macrospermae rhizome is 1:8-1:12 with the mass volume ratio of ethanol.
In described chloroform-methanol eluent, chloroform is 45:55-60:40 with the volume ratio of methanol.
In described methanol-water eluent, methanol is 85:15 with the volume ratio of water.
3β, 11α, 20β, 26-tetrahydroxy cucurbitane terpene-5,24 (E)-dienes are colourless powder, are soluble in chloroform, first
Alcohol, by 3β, 11α, 20β, 26-tetrahydroxy cucurbitane terpene-5,24 (E)-dienes carry out extracorporeal anti-tumor pharmacodynamic experiment, body
Outer antitumor pharmacodynamic experiment utilizes MTT colorimetry.
With 3β, 11α, 20β, 26-tetrahydroxy cucurbitane terpene-5,24 (E)-dienes are experimental group, with Doxorubicin
(doxorubicin, antitumor drug) is matched group, sets up blank group, experimental group, matched group and blank group to choose HeLa(people simultaneously
Cervical cancer) cell and KB(human mouth epidermoid carcinoma) it is experimental subject, after culture medium dilution, inoculate with the density of 6 × 104/ml
In 96 orifice plates, every hole 100 μ l, after normally cultivating 24 hours in incubator, each group adds corresponding medicine, makes each group of medicine
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), 40
μ g/ml (5 groups), sets 5 concentration altogether, the multiple hole of each concentration 3；After cultivating 48 hours, add MTT 10 μ l dyeing in every hole；Continue
After continuous cultivation four hours, inhaling and abandon original fluid, every hole adds DMSO 100 μ l, puts low-speed oscillation 10 min on shaking table, makes crystallization
Thing fully dissolves, and detects optical density value at enzyme-linked immunosorbent assay instrument 570 nm wavelength, calculates 50% according to optical density value and presses down
Concentration (IC processed50, μ g/mL), optical density value calculates IC50Computational methods be existing known technology.Experimental group, matched group pair
HeLa cell and the IC of KB cell50As shown in table 1.
Table 1
| Group | HeLa cell | KB cell |
| Experimental group | 10.4 ± 3.2 | 44.1± 2.7 |
| Matched group | 1.3 ± 0.11 | 0.89 ± 0.03 |
By the data of upper table it can be seen that of the present invention 3β, 11α, 20β, 26-tetrahydroxy cucurbitane terpene-5,24
(E)-diene is respectively provided with certain inhibitory action to HeLa cell and KB cell, it is possible to prevent and treat the former of tumour medicine as preparation
Material, possesses stronger commercial application and is worth.
Compared with prior art, the beneficial effects of the present invention is:
Isolated has the 3 of important anti-tumor activity from the Jinfo Shan Mountain Radix Hemsleyae Macrospermae rhizome firstβ, 11α, 20β, 26-tetra-hydroxyl
Base cucurbitane terpene-5,24 (E)-dienes, and utilize modern analysis means to determine its chemical constitution and physicochemical property.Through function
Property test prove: 3β, 11α, 20β, tumor cell is had stronger by 26-tetrahydroxy cucurbitane terpene-5,24 (E)-diene
Inhibitory action, it is possible to as the raw material of preparation preventing and treating tumour medicine, there is stronger using value and market prospect.
Accompanying drawing explanation
Fig. 1 is 3β, 11α, 20β, the schematic arrangement of 26-tetrahydroxy cucurbitane terpene-5,24 (E)-diene.
Fig. 2 is 3β, 11α, 20β, the proton nmr spectra of 26-tetrahydroxy cucurbitane terpene-5,24 (E)-diene (1H-
NMR).
Fig. 3 is 3β, 11α, 20β, the carbon-13 nmr spectra of 26-tetrahydroxy cucurbitane terpene-5,24 (E)-diene (13C-
APT).
Detailed description of the invention
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, each 2 hours, 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 dispersion process, respectively by petroleum ether, chloroform, ethyl acetate, positive fourth
Alcohol extracts, and is extracted to colourless, is evaporated to do by extract, weighs to obtain petroleum ether part total extractum 56g, chloroform extract
Total extractum 302g, ethyl acetate extract total extractum 151g, n-butanol portion total extractum 409 g.4th step: take ethyl acetate layer leaching
Cream 151 g separates through silica gel column chromatography (100～200 mesh), and chloroform-methanol (1:0-0:1) gradient elution obtains 12 fractions
Fr A-L.5th step: Fr.F part removes pigment through gel chromatography eluting, chloroform-methanol (45:55) 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. F4 separates through high-efficient liquid phase chromatogram purification, uses methanol-water (85:15)
Eluting, the eluent crystallization collected 13.4 minutes i.e. 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) analyze,1H-
NMR spectra as in figure 2 it is shown,13C-APT spectrogram is as shown in Figure 3.
Fig. 2 and Fig. 3 being carried out spectrum analysis, is belonged at each for Fig. 2 and Fig. 3 peak, the peak of Fig. 2 and Fig. 3 belongs to such as table 2 institute
Showing, by Fig. 2, Fig. 3 and the data of table 1, the chemical structural formula of colourless powder is as it is shown in figure 1, according to there being related compounds
Naming rule named 3β, 11α, 20β, 26-tetrahydroxy cucurbitane terpene-5,24 (E)-diene.
English entitled 3β, 11α, 20β, 26-tetrahydroxycucurbita-5, 24(E)-diene。
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, all may utilize the technology contents of the disclosure above to this
Inventive technique scheme makes many possible variations and modification, or is revised as the Equivalent embodiments of 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 change and modification, all should fall in the range of technical solution of the present invention is protected.
Claims (8)
1. a compound, it is characterised in that: there is the structure that is shown below.
Compound the most according to claim 1, it is characterised in that: this compound is colourless powder, is soluble in chloroform, first
Alcohol.
Compound the most according to claim 1, it is characterised in that: HeLa cell and KB cell are respectively provided with relatively by this compound
Strong inhibitory action.
4. compound described in claim 1 or 2 or 3 in prophylaxis of tumours and prepares the application in antitumor drug.
5. the preparation method of compound described in claim 1-3, it is characterised in that: Jinfo Shan Mountain Radix Hemsleyae Macrospermae rhizome crushed after being dried mistake
Sieve, add 95% alcohol heating reflux extract 3 times, each 1-3 hour, united extraction liquid, decompression and solvent recovery, after concentration always soak
Cream, total extractum is with after water-dispersible, and successively with petroleum ether, chloroform, ethyl acetate, n-butanol extraction, extract is concentrated to dryness；Take second
Extractum silica gel column chromatography in acetoacetic ester position separates, and chloroform-methanol (1:0-0:1) gradient elution obtains 12 fraction Fr A-
L, Fr.F part removes pigment with chloroform-methanol 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. F4 separates through high-efficient liquid phase chromatogram purification, uses methanol-water eluting, collects the eluent crystallization of 13.4 minutes i.e.
?.
The preparation method of compound the most according to claim 5: it is characterized in that: Jinfo Shan Mountain snow in described heating and refluxing extraction
Gallbladder rhizome is 1:8-1:12 with the mass volume ratio of ethanol.
The preparation method of compound the most according to claim 5: it is characterized in that: chloroform in described chloroform-methanol eluent
It is 45:55-60:40 with the volume ratio of methanol.
The preparation method of compound the most according to claim 5: it is characterized in that: in described methanol-water eluent methanol with
The volume ratio of water is 85:15.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610701140.0A CN106317155B (en) | 2016-08-23 | 2016-08-23 | A kind of reproducibility cucurbit alkane type triterpenoid and its preparation method and purposes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610701140.0A CN106317155B (en) | 2016-08-23 | 2016-08-23 | A kind of reproducibility cucurbit alkane type triterpenoid and its preparation method and purposes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106317155A true CN106317155A (en) | 2017-01-11 |
| CN106317155B CN106317155B (en) | 2018-11-02 |
Family
ID=57742637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610701140.0A Active CN106317155B (en) | 2016-08-23 | 2016-08-23 | A kind of reproducibility cucurbit alkane type triterpenoid and its preparation method and purposes |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106317155B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114133422A (en) * | 2021-12-16 | 2022-03-04 | 中国医学科学院药用植物研究所 | Cucurbitane triterpenoid compound and preparation method and application thereof |
| CN115141245A (en) * | 2022-08-03 | 2022-10-04 | 河南中医药大学 | Cucurbitane tetracyclic triterpenoid extracted from Chinese hemsleya amabilis and having anti-mastitis activity, and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005040189A1 (en) * | 2003-10-27 | 2005-05-06 | Panagin Pharmaceuticals Inc. | Novel dammarane sapogenins and their use as anti-cancer agents |
| 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 |
-
2016
- 2016-08-23 CN CN201610701140.0A patent/CN106317155B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005040189A1 (en) * | 2003-10-27 | 2005-05-06 | Panagin Pharmaceuticals Inc. | Novel dammarane sapogenins and their use as anti-cancer agents |
| 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 |
Non-Patent Citations (1)
| Title |
|---|
| XU-BING CHEN ET AL.: "Potential AMPK activators of cucurbitane triterpenoids fromSiraitia grosvenorii Swingle", 《BIOORGANIC & MEDICINAL CHEMISTRY》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114133422A (en) * | 2021-12-16 | 2022-03-04 | 中国医学科学院药用植物研究所 | Cucurbitane triterpenoid compound and preparation method and application thereof |
| CN114133422B (en) * | 2021-12-16 | 2022-12-20 | 中国医学科学院药用植物研究所 | Cucurbitane triterpenoid compound and preparation method and application thereof |
| CN115141245A (en) * | 2022-08-03 | 2022-10-04 | 河南中医药大学 | Cucurbitane tetracyclic triterpenoid extracted from Chinese hemsleya amabilis and having anti-mastitis activity, and preparation method and application thereof |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106317155B (en) | 2018-11-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108003214B (en) | Saponin compound extracted from rhizoma bolbostemmae, and its preparation method and application | |
| CN104817432B (en) | A kind of anticancer usage of diterpene-kind compound | |
| CN101824067A (en) | Barrigenol-type triterpenoid saponins compound, preparation method and application thereof | |
| CN104622865A (en) | Application of ingenane diterpene compound in preparation of antitumor drug | |
| CN106317156A (en) | Pentahydroxy diketone cucurbitane type triterpene as well as preparation method and application thereof | |
| CN104873570B (en) | A kind of method for extraction and purification of Prunella vulgaris general flavone and its application | |
| CN106317155A (en) | Reductive cucurbitane triterpene as well as preparation method and use thereof | |
| CN106045819B (en) | A kind of mysorethorn tricyclic diterpene and its preparation method and purposes | |
| CN106317157A (en) | Polyhydroxy diketone cucuribitane triterpene as well as preparation method and application thereof | |
| CN106397530B (en) | A kind of condensed ring class cucurbit alkane type triterpenoid and its preparation method and purposes | |
| CN107286172B (en) | Aporphine alkaloid Illigerine B and its preparation method and application | |
| CN103191143B (en) | New application of cardiac glycoside compound | |
| CN102764320B (en) | Psychotria sp. extract, and preparation method and antineoplastic application thereof | |
| CN102772501A (en) | Rheum emodi Wall. extract and its preparing method | |
| CN106380503B (en) | A kind of trihydroxy single ketones class cucurbit alkane type triterpenoid and its preparation method and purposes | |
| CN101926921A (en) | Liriope muscari total saponin and preparation method thereof | |
| CN105418722B (en) | A kind of entitled Sasanguasaponin C4And C5Pentacyclic triterpenoid preparation method | |
| CN103833818B (en) | The antitumor drug of a kind of Sasanguasaponin compound, its preparation method, application and preparation thereof | |
| CN106397523B (en) | A kind of methylhydroxy cucurbit alkane type triterpenoid and its preparation method and purposes | |
| CN106045951B (en) | A kind of mysorethorn lactone and its preparation method and purposes | |
| CN105713005B (en) | A kind of extraction separation method of corymbose hedyotis herb middle ear humulone A | |
| CN109206392A (en) | A kind of coumarin kind compound and the preparation method and application thereof | |
| CN103739657B (en) | A kind of Sasanguasaponin compound, its preparation method, the antitumor drug applying and prepare | |
| CN102085293A (en) | Liriope muscari extract with anti-tumor action and preparation method thereof | |
| CN107987047A (en) | A kind of Mang ox base chromocor compound and its methods and applications extracted from the root bark of white mulberry |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | 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 | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20201105 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 |
|
| EE01 | Entry into force of recordation of patent licensing contract | ||
| EE01 | Entry into force of recordation of patent licensing contract |
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 |