CN104370929B - A kind of method preparing Fugu ocellatus toxin - Google Patents
A kind of method preparing Fugu ocellatus toxin Download PDFInfo
- Publication number
- CN104370929B CN104370929B CN201410573138.0A CN201410573138A CN104370929B CN 104370929 B CN104370929 B CN 104370929B CN 201410573138 A CN201410573138 A CN 201410573138A CN 104370929 B CN104370929 B CN 104370929B
- Authority
- CN
- China
- Prior art keywords
- fugu ocellatus
- ocellatus toxin
- gained
- concentrated solution
- feed liquid
- 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.)
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- 241000054452 Takifugu ocellatus Species 0.000 title claims abstract description 62
- 239000003053 toxin Substances 0.000 title claims abstract description 62
- 231100000765 toxin Toxicity 0.000 title claims abstract description 62
- 238000000034 method Methods 0.000 title claims abstract description 26
- 239000007788 liquid Substances 0.000 claims abstract description 80
- 238000005342 ion exchange Methods 0.000 claims abstract description 28
- 238000002425 crystallisation Methods 0.000 claims abstract description 22
- 230000008025 crystallization Effects 0.000 claims abstract description 22
- 238000004062 sedimentation Methods 0.000 claims abstract description 18
- 238000004440 column chromatography Methods 0.000 claims abstract description 12
- 238000005189 flocculation Methods 0.000 claims abstract description 9
- 230000016615 flocculation Effects 0.000 claims abstract description 9
- 239000000243 solution Substances 0.000 claims description 53
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 45
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 42
- 239000006228 supernatant Substances 0.000 claims description 28
- 229910021529 ammonia Inorganic materials 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 24
- 239000002244 precipitate Substances 0.000 claims description 17
- 239000008367 deionised water Substances 0.000 claims description 16
- 229910021641 deionized water Inorganic materials 0.000 claims description 16
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 15
- 238000002791 soaking Methods 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- 229910000831 Steel Inorganic materials 0.000 claims description 12
- 239000003480 eluent Substances 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 12
- 239000000741 silica gel Substances 0.000 claims description 12
- 229910002027 silica gel Inorganic materials 0.000 claims description 12
- 239000010959 steel Substances 0.000 claims description 12
- 239000008213 purified water Substances 0.000 claims description 10
- 239000003456 ion exchange resin Substances 0.000 claims description 9
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 238000004321 preservation Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000005352 clarification Methods 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- 238000004176 ammonification Methods 0.000 claims description 6
- 239000000872 buffer Substances 0.000 claims description 6
- 239000003729 cation exchange resin Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 210000004185 liver Anatomy 0.000 claims description 6
- 238000010898 silica gel chromatography Methods 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 4
- 238000007654 immersion Methods 0.000 claims description 4
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 claims description 4
- 229910000360 iron(III) sulfate Inorganic materials 0.000 claims description 4
- 239000012982 microporous membrane Substances 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 231100000331 toxic Toxicity 0.000 claims description 3
- 230000002588 toxic effect Effects 0.000 claims description 3
- 230000033228 biological regulation Effects 0.000 claims description 2
- 238000000703 high-speed centrifugation Methods 0.000 claims description 2
- 229920002401 polyacrylamide Polymers 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims description 2
- 229960001866 silicon dioxide Drugs 0.000 description 10
- CFMYXEVWODSLAX-QOZOJKKESA-N tetrodotoxin Chemical compound O([C@@]([C@H]1O)(O)O[C@H]2[C@@]3(O)CO)[C@H]3[C@@H](O)[C@]11[C@H]2[C@@H](O)N=C(N)N1 CFMYXEVWODSLAX-QOZOJKKESA-N 0.000 description 8
- 229950010357 tetrodotoxin Drugs 0.000 description 8
- CFMYXEVWODSLAX-UHFFFAOYSA-N tetrodotoxin Natural products C12C(O)NC(=N)NC2(C2O)C(O)C3C(CO)(O)C1OC2(O)O3 CFMYXEVWODSLAX-UHFFFAOYSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 6
- 238000011953 bioanalysis Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 3
- 229960000935 dehydrated alcohol Drugs 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 235000003891 ferrous sulphate Nutrition 0.000 description 3
- 239000011790 ferrous sulphate Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000004080 punching Methods 0.000 description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000005374 membrane filtration Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 238000010257 thawing Methods 0.000 description 2
- LFXVBFTVUBWIQT-UHFFFAOYSA-N 3,4,4a,5,6,7,8,8a-octahydro-2h-quinazolin-1-amine Chemical class C1CCCC2N(N)CNCC21 LFXVBFTVUBWIQT-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- 208000018526 Narcotic-Related disease Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000001949 anaesthesia Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 201000005040 opiate dependence Diseases 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002905 orthoesters Chemical group 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 230000005760 tumorsuppression Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
Description
Claims (9)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410573138.0A CN104370929B (en) | 2014-10-19 | 2014-10-19 | A kind of method preparing Fugu ocellatus toxin |
PCT/CN2014/092918 WO2016061874A1 (en) | 2014-10-19 | 2014-12-03 | Method for preparing tetrodotoxin |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410573138.0A CN104370929B (en) | 2014-10-19 | 2014-10-19 | A kind of method preparing Fugu ocellatus toxin |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104370929A CN104370929A (en) | 2015-02-25 |
CN104370929B true CN104370929B (en) | 2016-07-27 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410573138.0A Active CN104370929B (en) | 2014-10-19 | 2014-10-19 | A kind of method preparing Fugu ocellatus toxin |
Country Status (2)
Country | Link |
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CN (1) | CN104370929B (en) |
WO (1) | WO2016061874A1 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113321661B (en) | 2021-05-04 | 2022-04-12 | 中洋生物科技(上海)股份有限公司 | Method for efficiently extracting and separating high-purity tetrodotoxin from globefish viscera |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1385432A (en) * | 2001-05-15 | 2002-12-18 | 中国科学院水生生物研究所 | Method for purifying tetrodotoxin |
WO2008102253A2 (en) * | 2007-02-23 | 2008-08-28 | The Hong Kong Polytechnic University | Method of biosynthesizing tetrodotoxin |
CN101475575A (en) * | 2009-02-05 | 2009-07-08 | 王维国 | Extraction of tetraodontoxin, and preparation thereof used in drug dependence of dolantin |
CN102584843A (en) * | 2011-01-18 | 2012-07-18 | 王秀菊 | Extraction method for high-purity tetrodotoxin |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1187356C (en) * | 2000-11-22 | 2005-02-02 | 南宁枫叶药业有限公司 | System for extracting tetradoxin with high yield |
-
2014
- 2014-10-19 CN CN201410573138.0A patent/CN104370929B/en active Active
- 2014-12-03 WO PCT/CN2014/092918 patent/WO2016061874A1/en active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1385432A (en) * | 2001-05-15 | 2002-12-18 | 中国科学院水生生物研究所 | Method for purifying tetrodotoxin |
WO2008102253A2 (en) * | 2007-02-23 | 2008-08-28 | The Hong Kong Polytechnic University | Method of biosynthesizing tetrodotoxin |
CN101475575A (en) * | 2009-02-05 | 2009-07-08 | 王维国 | Extraction of tetraodontoxin, and preparation thereof used in drug dependence of dolantin |
CN102584843A (en) * | 2011-01-18 | 2012-07-18 | 王秀菊 | Extraction method for high-purity tetrodotoxin |
Non-Patent Citations (1)
Title |
---|
河豚毒素的提取及检测方法研究;阚丽丽,等;《中国药房》;20071010;第18卷(第28期);第2224-2226页 * |
Also Published As
Publication number | Publication date |
---|---|
CN104370929A (en) | 2015-02-25 |
WO2016061874A1 (en) | 2016-04-28 |
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Legal Events
Date | Code | Title | Description |
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C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C41 | Transfer of patent application or patent right or utility model | ||
CB03 | Change of inventor or designer information |
Inventor after: Zhong Xinjia Inventor before: Zhong Xinjia Inventor before: Liu Yandong |
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COR | Change of bibliographic data | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20160617 Address after: 518106 Winston Industrial Park, industrial zone, Gongming Town, Guangming New District, Guangdong, Shenzhen, China Applicant after: Zhong Xinjia Address before: 518106 Winston Industrial Park, industrial zone, Gongming Town, Guangming New District, Guangdong, Shenzhen, China Applicant before: Zhong Xinjia Applicant before: Liu Yandong |
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C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20161208 Address after: 518054 Guangdong city of Shenzhen province Qianhai Shenzhen Hong Kong cooperation zone before Bay Road No. 1 building 201 room A (in Shenzhen Qianhai City Secretary of Commerce Co., Ltd.) Patentee after: Ray Winston Battery Technology Co.,Ltd. Address before: 518106 Winston Industrial Park, industrial zone, Gongming Town, Guangming New District, Guangdong, Shenzhen, China Patentee before: Zhong Xinjia |
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TR01 | Transfer of patent right |
Effective date of registration: 20230619 Address after: No.10-96, Anheli, Linghe District, Jinzhou City, Liaoning Province, 121000 Patentee after: Liu Yandong Address before: 518054 Room 201, building a, No.1 Qianwan 1st Road, Qianhai Shenzhen Hong Kong cooperation zone, Shenzhen City, Guangdong Province Patentee before: Ray Winston Battery Technology Co.,Ltd. |
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Effective date of registration: 20240306 Address after: Room 409-392, 4th Floor, Building 1, No. 38 Yongda Road, Daxing Biomedical Industry Base, Zhongguancun Science and Technology Park, Daxing District, Beijing, 102600 (cluster registration) Patentee after: Beijing Tongzeda Pharmaceutical Co.,Ltd. Country or region after: China Address before: No.10-96, Anheli, Linghe District, Jinzhou City, Liaoning Province, 121000 Patentee before: Liu Yandong Country or region before: China |
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