CN1052721C - Jinghong goniothalamicin A and its preparation method and use - Google Patents
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- CN1052721C CN1052721C CN95115708A CN95115708A CN1052721C CN 1052721 C CN1052721 C CN 1052721C CN 95115708 A CN95115708 A CN 95115708A CN 95115708 A CN95115708 A CN 95115708A CN 1052721 C CN1052721 C CN 1052721C
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- goniothalamicin
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- sherwood oil
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- NBVJDUCRUAUMAA-CGWDHHCXSA-N (2s)-2-methyl-4-[(2r,8r,11r)-2,8,11-trihydroxy-11-[(2r,5r)-5-[(1r)-1-hydroxypentadecyl]oxolan-2-yl]undecyl]-2h-furan-5-one Chemical compound O1[C@@H]([C@H](O)CCCCCCCCCCCCCC)CC[C@@H]1[C@H](O)CC[C@H](O)CCCCC[C@@H](O)CC1=C[C@H](C)OC1=O NBVJDUCRUAUMAA-CGWDHHCXSA-N 0.000 title claims abstract description 22
- NBVJDUCRUAUMAA-VFCVDYGLSA-N goniothalamicin Natural products O=C1C(C[C@H](O)CCCCC[C@@H](O)CC[C@@H](O)[C@@H]2O[C@H]([C@H](O)CCCCCCCCCCCCCC)CC2)=C[C@@H](C)O1 NBVJDUCRUAUMAA-VFCVDYGLSA-N 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003814 drug Substances 0.000 claims abstract description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 14
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- 241000629067 Goniothalamus cheliensis Species 0.000 claims description 12
- 241000196324 Embryophyta Species 0.000 claims description 7
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- 230000001093 anti-cancer Effects 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- 241000039384 Goniothalamus Species 0.000 abstract 2
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- 241001081440 Annonaceae Species 0.000 description 10
- 230000002401 inhibitory effect Effects 0.000 description 4
- 229930012538 Paclitaxel Natural products 0.000 description 3
- 241001529246 Platymiscium Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- AHZVYVPVHRHEHF-MYPMTAMASA-N [(2r,3s)-6-oxo-2-[(2s,3r)-3-phenyloxiran-2-yl]-2,3-dihydropyran-3-yl] acetate Chemical compound CC(=O)O[C@H]1C=CC(=O)O[C@H]1[C@@H]1[C@@H](C=2C=CC=CC=2)O1 AHZVYVPVHRHEHF-MYPMTAMASA-N 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- AHZVYVPVHRHEHF-UHFFFAOYSA-N cheliensisin A Natural products CC(=O)OC1C=CC(=O)OC1C1C(C=2C=CC=CC=2)O1 AHZVYVPVHRHEHF-UHFFFAOYSA-N 0.000 description 3
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- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 3
- 241000722951 Annona Species 0.000 description 2
- 235000007755 Annona Nutrition 0.000 description 2
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- 206010003445 Ascites Diseases 0.000 description 2
- MBABCNBNDNGODA-LTGLSHGVSA-N Bullatacin Natural products O=C1C(C[C@H](O)CCCCCCCCCC[C@@H](O)[C@@H]2O[C@@H]([C@@H]3O[C@H]([C@@H](O)CCCCCCCCCC)CC3)CC2)=C[C@H](C)O1 MBABCNBNDNGODA-LTGLSHGVSA-N 0.000 description 2
- WSTYNZDAOAEEKG-UHFFFAOYSA-N Mayol Natural products CC1=C(O)C(=O)C=C2C(CCC3(C4CC(C(CC4(CCC33C)C)=O)C)C)(C)C3=CC=C21 WSTYNZDAOAEEKG-UHFFFAOYSA-N 0.000 description 2
- WSTYNZDAOAEEKG-QSPBTJQRSA-N Maytenin Natural products CC1=C(O)C(=O)C=C2[C@@](CC[C@@]3([C@@H]4C[C@H](C(C[C@@]4(CC[C@]33C)C)=O)C)C)(C)C3=CC=C21 WSTYNZDAOAEEKG-QSPBTJQRSA-N 0.000 description 2
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- MBABCNBNDNGODA-LUVUIASKSA-N bullatacin Chemical compound O1[C@@H]([C@@H](O)CCCCCCCCCC)CC[C@@H]1[C@@H]1O[C@@H]([C@H](O)CCCCCCCCCC[C@@H](O)CC=2C(O[C@@H](C)C=2)=O)CC1 MBABCNBNDNGODA-LUVUIASKSA-N 0.000 description 2
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- VGEREEWJJVICBM-UHFFFAOYSA-N phloretin Chemical compound C1=CC(O)=CC=C1CCC(=O)C1=C(O)C=C(O)C=C1O VGEREEWJJVICBM-UHFFFAOYSA-N 0.000 description 2
- MBABCNBNDNGODA-WPZDJQSSSA-N rolliniastatin 1 Natural products O1[C@@H]([C@@H](O)CCCCCCCCCC)CC[C@H]1[C@H]1O[C@@H]([C@H](O)CCCCCCCCCC[C@@H](O)CC=2C(O[C@@H](C)C=2)=O)CC1 MBABCNBNDNGODA-WPZDJQSSSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- WSTYNZDAOAEEKG-GWJSGULQSA-N tingenone Chemical compound CC1=C(O)C(=O)C=C2[C@@](CC[C@]3([C@@H]4C[C@H](C(C[C@@]4(CC[C@@]33C)C)=O)C)C)(C)C3=CC=C21 WSTYNZDAOAEEKG-GWJSGULQSA-N 0.000 description 2
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- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a Jinghong goniothalamicin A compound, a preparation method thereof and application thereof in preparing medicaments for treating cancer diseases. The preparation method comprises the steps of adopting air-dried and crushed Goniothalamus japonica plants, performing cold-leaching extraction by using ethanol, performing silica gel column chromatography on the extract, performing gradient elution by using petroleum ether and ethyl acetate-petroleum ether in sequence, and collecting fractions to obtain a new compound with strong anticancer activity, namely the Goniothalamus japonica A, namely 6(7, 8-epoxy-styryl) -5-acetoxyl-5 and 6-dihydro-2-pyrone, wherein the molecular formula is C15H14O5Molecular weight of 274, white columnar crystal, melting point of 152-153 ℃. The raw materials of the invention belong to renewable resources, the yield is high, harvest is fast; the obtained new compound has strong activity in antitumor activity screening.
Description
The present invention relates to Jinghong goniothalamicin A, promptly 6 (7,8-epoxy-styryl)-5-acetoxyl group-5,6-dihydro-2-pyrone compound, and preparation method thereof and the especially application in preparation treatment Cancerous disease medicine in medicine.
In the annonaceae plant, find (to have seen 1982 since first annonaceous acetogenins from nineteen eighty-two Shivanan D.Jolad etc., J.Org.Chem, 47:3151-3153), because Annonaceousacetogenicompounds compounds is to the 9PS leukemic lymphoblastoid, the 9kB nasopharyngeal carcinoma, A549 lung cancer, MCF-7 mammary cancer, the HF29 colorectal carcinoma, L-1210 leukemia etc. has very strong inhibition activity, several Annona lactone Acetogenin compounds are arranged, the strong 40-300 of in vivo test specific activity taxol doubly, as bullatacin (Bullatacin) to the active ED of 9KB nasopharyngeal carcinoma
50/ 10
-15μ g/ml is strong far beyond maytenin and taxol.Therefore, the research to activeconstituents in the annonaceae plant has become a focus of fitochemical studies in the world.Reports such as T.W.Sam (are seen document 1987, Tetrahedron Letters 28 (22): 2541-2544), from receiving fragrant platymiscium, the annonaceae brother obtains the anticancer component Annona lactone, and the vinylbenzene pyrone compound of having an abortion and acting on is arranged, but the report of the vinylbenzene pyrone compound of antitumous effect is not arranged all.
The object of the present invention is to provide a kind of new compound that from the Goniothalamus cheliensis Hu. platymiscium, obtains, its extraction and separation method and the particularly application in preparation treatment Cancerous disease medicine in medicine thereof with antitumour activity.
Obtain the strong compound of antitumour activity in order to receive the fragrant platymiscium from the brother, it is material that the present invention selects Goniothalamus cheliensis Hu. (Goniothalamus Cheliensis hu), extract, system works such as separation, structure evaluation, screening active ingredients, therefrom obtain the strong compound Jinghong goniothalamicin A of new antitumour activity promptly 6 (7,8-epoxy-styryl)-5-acetoxyl group-5,6-dihydro-2-pyrone, structural formula is as (I):
The method of preparation formula provided by the present invention (I) compound may further comprise the steps: adopt the Goniothalamus cheliensis Hu. plant sample through air-dry pulverizing, extract with the ethanol cold soaking, decompression recycling ethanol, get ethanol extraction, extract is carried out silica gel column chromatography, use sherwood oil, ethyl acetate-sherwood oil gradient elution more successively, collect stream part, obtain compound 6 (7,8-epoxy-styryl)-5-acetoxyl group-5,6-dihydro-2-pyrone from ethyl acetate-sherwood oil 1: 1 or 4: 6 stream parts.
Among the preparation method of the present invention, after preferably getting ethanol extraction, earlier concentrated solution being added water mixes well, use chloroform extraction, reclaim chloroform, get chloroform extract, this extract is carried out silica gel column chromatography, use sherwood oil, ethyl acetate-sherwood oil gradient elution more successively, collect stream part, obtain compound 6 (7,8-epoxy-styryl)-5-acetoxyl group-5,6-dihydro-2-pyrone from ethyl acetate-sherwood oil 1: 1 or 4: 6 stream parts.
Jinghong goniothalamicin A of the present invention can be used for preparing the purposes of the medicine for the treatment of cancer.
Compound Jinghong goniothalamicin A of the present invention (Cheliensisin A) molecular formula is C15H14O5, and molecular weight is 274, is white column crystallization, and fusing point is 152-153 ℃.
Compound Jinghong goniothalamicin A antitumor activity screening result of the present invention is as follows:
1. external HL-60 (human promyelocytic leukemia) cell screening result:
Drug level 100/ μ g/ml 10 μ g/ml 1 μ g/ml
The compounds of this invention inhibiting rate 100% 100% 95%
2. external K562 (erythrocyte leucocythemia) cell screening result:
Drug level 100 μ g/ml 10 μ g/ml 1 μ g/ml
The compounds of this invention inhibiting rate 100% 90% 65%
3. external SGC-7901 (people's adenocarcinoma of stomach Nude Mice solid-type and ascitic type) cell screening result:
Drug level 100 μ g/ml 10 μ g/ml 1 μ g/ml
The compounds of this invention inhibiting rate 94% 75% 30%
It is active strong that above result proves that the The compounds of this invention antitumor activity screening shows, is the highest active compound in 80 annonaceae plant antitumor activity components that filtered out so far.
In addition, The compounds of this invention is 15mg/kg to mouse EC (liver ascites solid tumor) growth inhibition ratio, and inhibiting rate reaches 33%, will be higher if improve the water-soluble curative effect of this compound.
The The compounds of this invention Jinghong goniothalamicin A at plant materials intensive amount height, all contains this activeconstituents in axis, the leaf, and it is the highest with the yield of leaf, also can send young leaves after leaf is suitably gathered every year, the starting material that preparation method therefore of the present invention adopts belong to renewable resource, and yield height, results are fast.The Jinghong goniothalamicin A yield is 0.0042% from plant stem, and yield is 0.163% in the leaf, than extract maytenin from Caulis Mayteni, to extract the taxol yield from Chinese yew all high.
New compound Jinghong goniothalamicin A antitumor activity screening of the present invention shows active strong, shows foreseeable valuable pharmacological activity, and human white blood disease, adenocarcinoma of stomach and small white mouse liver ascites solid tumor are had effect, therefore can be used for preparing antitumor drug.And use suitable vehicle or solvent on inertia, nontoxic, the medicine, new compound of the present invention can be converted into conventional formulation, make the medicine that contains the Jinghong goniothalamicin A compound, be used for the treatment of Cancerous disease.
Contain the currently known methods that the medicine production of Jinghong goniothalamicin A can be used in this technology and carry out, as the dosage of clinical medicine preferably within the scope of 0.0001 to 5 milligram/kg body weight, preferably in 0.01-5 milligram/kg body weight scope.
Use Jinghong goniothalamicin A of the present invention as medicine, the formulation that can adopt is the lid human relations form of administration of habitually practising, for example: ointment, tablet, pill, capsule, suppository emulsion, input liquid and injection liquid.These preparations use traditional additive and excipient to make by well-known method.The medicine that makes thus as required can be by part, non-enteron aisle, administration such as oral.
Advantage of the present invention and positively effect are: starting material belong to renewable resource, and yield height, results are soon; The new compound antitumor activity screening that obtains shows active strong.
Compound of the present invention and preparation method thereof, provide by following examples, but technical scheme of the present invention is not limited thereto, anyly take similar vegetable material, adopt similar technical scheme of the present invention, the scheme that does not need those of ordinary skills' creative work to make all should be thought and belongs to the technical solution of the present invention category.
Embodiment 1: adopt annonaceae (Annonaceae) Goniothalamus cheliensis Hu. (GoniothalamusCheliensis Hu) plant, through 4.5 kilograms of cane samples of air-dry pulverizing, extract with 95% ethanol cold soaking, decompression recycling ethanol, concentrated solution adds water and mixes well, use chloroform extraction, reclaim chloroform, get chloroform extract, this extract carries out column chromatography through 100 order silica gel, use sherwood oil successively, ethyl acetate-sherwood oil gradient elution, collection stream part gets 190 milligrams of Jinghong goniothalamicin As (CheliensisinA) from 1: 1 stream part of acetate-sherwood oil.
Embodiment 2: adopt through 4.5 kilograms in annonaceae (Annonaceae) Goniothalamus cheliensis Hu. (Goniothalamus Cheliensis Hu) the plant leaf sample of air-dry pulverizing, extract with the industrial spirit cold soaking, decompression recycling ethanol, get ethanol extraction, water and chloroform (volume 1: 1) distribute, get chloroform layer, the reclaim under reduced pressure chloroform, get chloroform extract, chloroform extract is carried out silica gel column chromatography (silica gel for chromatography 200-300 order), use sherwood oil successively, ethyl acetate-sherwood oil gradient elution, collection stream part gets 7335 milligrams of Jinghong goniothalamicin As (CheliensisinA) from 1: 1 stream part of ethyl acetate-sherwood oil.
Embodiment 3: adopt through 5 kilograms in annonaceae (Annonaceae) Goniothalamus cheliensis Hu. (Goniothalamus Cheliensis Hu) the plant leaf sample of air-dry pulverizing, extract with 95% ethanol cold soaking, decompression recycling ethanol gets ethanol extraction, ethanol extraction is carried out silica gel column chromatography (silica gel for chromatography 100 orders), use sherwood oil more successively, ethyl acetate-sherwood oil gradient elution, collection stream part gets 6010 milligrams of Jinghong goniothalamicin As (Cheliensisin A) from 4: 6 stream parts of ethyl acetate-sherwood oil.
Embodiment 1-3 products obtained therefrom Jinghong goniothalamicin A (Cheliensisin A) structural formula is shown in (I), and physico-chemical property is white column crystallization, C15H14O5[M
-] 274, MP152-153 ℃, [α]
D 24-3=+293.45 ° (C, 1.31, CHCI3), and MSm/e:, 274 (M
+) (36), 257 (5), 233 (41), 232 (31), 216 (61), 197 (85), 169 (52), 168 (41), 157 (44), 154 (42), 148 (93), 131 (48), 129 (70), 128 (67), 108 (100), 105 (56), 96 (88), 85 (64).
Claims (4)
1, a kind of name is called the compound of Jinghong goniothalamicin A, promptly 6 (7,8-epoxy-styryl)-5-acetoxyl group-5,6-dihydro-2-pyrone, and its structural formula is shown in (I):
2, the preparation method of the Jinghong goniothalamicin A of claim 1, it is characterized in that adopting vegetable chemistry method separation and Extraction from the plant Goniothalamus cheliensis Hu., said vegetable chemistry method adopts the Goniothalamus cheliensis Hu. plant through air-dry pulverizing, extract with the ethanol cold soaking, decompression recycling ethanol, get ethanol extraction, extract is carried out silica gel column chromatography, use sherwood oil more successively, ethyl acetate-sherwood oil gradient elution, collect stream part, obtain compound 6 (7 from ethyl acetate-sherwood oil 1: 1 or 4: 6 stream parts, 8-epoxy-styryl)-5-acetoxyl group-5,6-dihydro-2-pyrone.
3, as the preparation method of the said Jinghong goniothalamicin A of claim 2, it is characterized in that behind the ethanol extraction, concentrated solution is added water to be mixed well, use chloroform extraction, reclaim chloroform, get chloroform extract, this extract is carried out silica gel column chromatography, use sherwood oil, ethyl acetate-sherwood oil gradient elution more successively, collect stream part, obtain compound 6 (7,8-epoxy-styryl)-5-acetoxyl group-5,6-dihydro-2-pyrone from ethyl acetate-sherwood oil 1: 1 or 4: 6 stream parts.
4, Jinghong goniothalamicin A is used to prepare the purposes of the medicine for the treatment of cancer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN95115708A CN1052721C (en) | 1995-09-01 | 1995-09-01 | Jinghong goniothalamicin A and its preparation method and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN95115708A CN1052721C (en) | 1995-09-01 | 1995-09-01 | Jinghong goniothalamicin A and its preparation method and use |
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| Publication Number | Publication Date |
|---|---|
| CN1144221A CN1144221A (en) | 1997-03-05 |
| CN1052721C true CN1052721C (en) | 2000-05-24 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95115708A Expired - Fee Related CN1052721C (en) | 1995-09-01 | 1995-09-01 | Jinghong goniothalamicin A and its preparation method and use |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100391968C (en) * | 2005-02-18 | 2008-06-04 | 复旦大学 | Goniothalamicim cyclopeptide B of anti-tumor compound and isomer and its preparing method |
| CN102329311A (en) * | 2011-07-26 | 2012-01-25 | 苏州宝泽堂医药科技有限公司 | Method for purifying cheliensisin A |
| CN102329310A (en) * | 2011-07-26 | 2012-01-25 | 苏州宝泽堂医药科技有限公司 | Method for preparing cheliensisin A |
| CN103130759B (en) * | 2013-01-30 | 2015-10-07 | 中国科学院昆明植物研究所 | Jinghong goniothalamicin A derivative and the application in pharmacy thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4721727A (en) * | 1986-05-06 | 1988-01-26 | The United States Of America As Represented By The Secretary Of Agriculture | Control of pests with annonaceous acetogenins |
| US4855319A (en) * | 1986-05-06 | 1989-08-08 | The United States Of America As Represented By The Secretary Of Agriculture | Control of pests with annonaceous acetogenins |
-
1995
- 1995-09-01 CN CN95115708A patent/CN1052721C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4721727A (en) * | 1986-05-06 | 1988-01-26 | The United States Of America As Represented By The Secretary Of Agriculture | Control of pests with annonaceous acetogenins |
| US4855319A (en) * | 1986-05-06 | 1989-08-08 | The United States Of America As Represented By The Secretary Of Agriculture | Control of pests with annonaceous acetogenins |
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| Publication number | Publication date |
|---|---|
| CN1144221A (en) | 1997-03-05 |
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