CN106397523B - A kind of methylhydroxy cucurbit alkane type triterpenoid and its preparation method and purposes - Google Patents
A kind of methylhydroxy cucurbit alkane type triterpenoid and its preparation method and purposes Download PDFInfo
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- CN106397523B CN106397523B CN201610701139.8A CN201610701139A CN106397523B CN 106397523 B CN106397523 B CN 106397523B CN 201610701139 A CN201610701139 A CN 201610701139A CN 106397523 B CN106397523 B CN 106397523B
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- methanol
- chloroform
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- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- -1 methylhydroxy Chemical group 0.000 title abstract description 16
- XBZYWSMVVKYHQN-MYPRUECHSA-N (4as,6as,6br,8ar,9r,10s,12ar,12br,14bs)-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-9-[(sulfooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid Chemical compound C1C[C@H](O)[C@@](C)(COS(O)(=O)=O)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C XBZYWSMVVKYHQN-MYPRUECHSA-N 0.000 title abstract description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 title abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 239000000843 powder Substances 0.000 claims abstract description 8
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 4
- 239000000284 extract Substances 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 11
- 238000010828 elution Methods 0.000 claims description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 9
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 6
- 239000003480 eluent Substances 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 238000005227 gel permeation chromatography Methods 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000010898 silica gel chromatography Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 230000000118 anti-neoplastic effect Effects 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical group CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 235000007586 terpenes Nutrition 0.000 abstract description 14
- 210000004027 cell Anatomy 0.000 abstract description 8
- 239000003814 drug Substances 0.000 abstract description 5
- 238000004458 analytical method Methods 0.000 abstract description 4
- 206010028980 Neoplasm Diseases 0.000 abstract description 3
- 150000002576 ketones Chemical class 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 210000004881 tumor cell Anatomy 0.000 abstract description 2
- 150000001993 dienes Chemical class 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 6
- 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 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
- 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
- 238000002474 experimental method Methods 0.000 description 3
- 150000003648 triterpenes Chemical class 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 2
- 229960004679 doxorubicin Drugs 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000005311 nuclear magnetism Effects 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 208000019065 cervical carcinoma Diseases 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000000205 computational method Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 1
- 201000005113 shigellosis Diseases 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 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
Description
Group | HeLa cells | KB cells |
Experimental group | 18.4 ± 3.1 | 37.6 ± 1.5 |
Control group | 1.3 ± 0.11 | 0.89 ± 0.03 |
Claims (6)
- A kind of 1. compound, it is characterised in that:The compound is colourless powder, is soluble in chloroform, methanol, to HeLa cells and KB Cell is respectively provided with stronger inhibitory action, and with the structure that is shown below。
- 2. application of the compound described in claim 1 in antineoplastic is prepared.
- A kind of 3. preparation method of compound described in claim 1, it is characterised in that:Jinfo Shan Mountain hymsleya amabilis rhizome crushed after being dried mistake Sieve, adds 95% ethanol heating and refluxing extraction 3 times, each 1-3 hours, merges extract solution, solvent is recovered under reduced pressure, and obtains after concentration and always soaks Cream, after total medicinal extract is water-dispersible, it is concentrated to dryness successively with petroleum ether, chloroform, ethyl acetate, extracting n-butyl alcohol, extract;Take second Acetoacetic ester position medicinal extract is separated with silica gel column chromatography, and the volume ratio of chloroform-methanol is by 1:0 is transitioned into 0:1 carries out 12 gradient elutions, Obtain 12 cut Fr A-L, Fr.G parts to elute through gel chromatography, chloroform-methanol removes depigmentaton as elution, so Inverted middle pressure volume ratio of the chromatographic column through methanol-water of sample is respectively 60 afterwards:40、70:30、80:20 and 90:10 4 gradients are washed It is de-, four part Fr. G1-4 are obtained, wherein Fr. G2 are separated through high-efficient liquid phase chromatogram purification, eluted using methanol-water, collected The eluent of 26.8 minutes, which crystallizes, to be produced.
- 4. the preparation method of compound according to claim 3:It is characterized in that:Jinfo Shan Mountain is avenged in the heating and refluxing extraction The mass volume ratio of courage rhizome and ethanol is 1:8-1:12.
- 5. the preparation method of compound according to claim 3:It is characterized in that:In the gel chromatography elution, chloroform-first The volume ratio of chloroform and methanol is 45 in alcohol eluen:55-60:40.
- 6. the preparation method of compound according to claim 3:It is characterized in that:The high-efficient liquid phase chromatogram purification separation In, the volume ratio of methanol and water is 68 in methanol-water eluent:32.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201610701139.8A CN106397523B (en) | 2016-08-23 | 2016-08-23 | A kind of methylhydroxy cucurbit alkane type triterpenoid and its preparation method and purposes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610701139.8A CN106397523B (en) | 2016-08-23 | 2016-08-23 | A kind of methylhydroxy cucurbit alkane type triterpenoid and its preparation method and purposes |
Publications (2)
Publication Number | Publication Date |
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CN106397523A CN106397523A (en) | 2017-02-15 |
CN106397523B true CN106397523B (en) | 2018-03-02 |
Family
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Family Applications (1)
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CN201610701139.8A Active CN106397523B (en) | 2016-08-23 | 2016-08-23 | A kind of methylhydroxy cucurbit alkane type triterpenoid and its preparation method and purposes |
Country Status (1)
Country | Link |
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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 CN201610701139.8A patent/CN106397523B/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 |
---|
Cucurbitane-Type Triterpenoids from the Stems of Cucumis melo;Chuan Chen 等;《J. Nat. Prod.》;20090406;第72卷(第5期);第824-829页 * |
Cytotoxic cucurbitane triterpenoids isolated from the rhizomes of Hemsleya amabilis;Xu-Bing Chen 等;《Fitoterapia》;20140124;第94卷;第88-93页 * |
Five new cucurbitane triterpenoids with cytotoxic activity from Hemsleya jinfushanensis;Ying Li 等;《Phytochemistry Letters》;20151110;第14卷;第239-244页 * |
Three new cucurbitane triterpenoids from Hemsleya penxianensis and their cytotoxic activities;Xiaoting Xu 等;《Bioorganic & Medicinal Chemistry Letters》;20140320;第24卷(第9期);第2159-2162页 * |
雪胆属植物的化学成分及生物活性研究进展;李莹 等;《中草药》;20150930;第46卷(第18期);第2800-2808页 * |
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CN106397523A (en) | 2017-02-15 |
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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 |
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EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20170215 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 methylhydroxylated cucurbitane type triterpenoid and its preparation and application Granted publication date: 20180302 License type: Common License Record date: 20231122 |
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EE01 | Entry into force of recordation of patent licensing contract |