CN1626067A - Preparation of honokiol, magnolol or their admixture and usage in preparing medication for treating cardiovascular and cerebrovascular diseases - Google Patents
Preparation of honokiol, magnolol or their admixture and usage in preparing medication for treating cardiovascular and cerebrovascular diseases Download PDFInfo
- Publication number
- CN1626067A CN1626067A CN 200310121303 CN200310121303A CN1626067A CN 1626067 A CN1626067 A CN 1626067A CN 200310121303 CN200310121303 CN 200310121303 CN 200310121303 A CN200310121303 A CN 200310121303A CN 1626067 A CN1626067 A CN 1626067A
- Authority
- CN
- China
- Prior art keywords
- magnolol
- honokiol
- mixture
- group
- cerebral
- 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
- VVOAZFWZEDHOOU-UHFFFAOYSA-N honokiol Natural products OC1=CC=C(CC=C)C=C1C1=CC(CC=C)=CC=C1O VVOAZFWZEDHOOU-UHFFFAOYSA-N 0.000 title claims abstract description 351
- 239000003814 drug Substances 0.000 title claims abstract description 49
- 208000026106 cerebrovascular disease Diseases 0.000 title claims abstract description 22
- 230000002526 effect on cardiovascular system Effects 0.000 title claims abstract description 14
- 208000024172 Cardiovascular disease Diseases 0.000 title claims abstract description 11
- FVYXIJYOAGAUQK-UHFFFAOYSA-N honokiol Chemical compound C1=C(CC=C)C(O)=CC=C1C1=CC(CC=C)=CC=C1O FVYXIJYOAGAUQK-UHFFFAOYSA-N 0.000 title claims description 111
- BYTORXDZJWWIKR-UHFFFAOYSA-N Hinokiol Natural products CC(C)c1cc2CCC3C(C)(CO)C(O)CCC3(C)c2cc1O BYTORXDZJWWIKR-UHFFFAOYSA-N 0.000 title claims description 108
- 238000002360 preparation method Methods 0.000 title claims description 41
- 229940079593 drug Drugs 0.000 title abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 98
- 238000002347 injection Methods 0.000 claims abstract description 41
- 239000007924 injection Substances 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 22
- 208000029078 coronary artery disease Diseases 0.000 claims abstract description 9
- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 8
- 201000001429 Intracranial Thrombosis Diseases 0.000 claims abstract description 8
- 206010003119 arrhythmia Diseases 0.000 claims abstract description 6
- 230000006793 arrhythmia Effects 0.000 claims abstract description 6
- 206010019280 Heart failures Diseases 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
- 239000000284 extract Substances 0.000 claims description 41
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 36
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 33
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 26
- 206010008118 cerebral infarction Diseases 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 20
- 230000002490 cerebral effect Effects 0.000 claims description 17
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- 235000010265 sodium sulphite Nutrition 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 13
- 238000009472 formulation Methods 0.000 claims description 12
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims description 11
- 235000010262 sodium metabisulphite Nutrition 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 claims description 10
- 229930003268 Vitamin C Natural products 0.000 claims description 10
- 230000000302 ischemic effect Effects 0.000 claims description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims description 10
- 235000019154 vitamin C Nutrition 0.000 claims description 10
- 239000011718 vitamin C Substances 0.000 claims description 10
- 238000000605 extraction Methods 0.000 claims description 9
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- 201000006474 Brain Ischemia Diseases 0.000 claims description 8
- 206010008088 Cerebral artery embolism Diseases 0.000 claims description 8
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 8
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 claims description 8
- 201000010849 intracranial embolism Diseases 0.000 claims description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 8
- 150000002989 phenols Chemical class 0.000 claims description 8
- 229920001993 poloxamer 188 Polymers 0.000 claims description 8
- 206010008132 Cerebral thrombosis Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- -1 polyoxyethylene Polymers 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 229920002685 Polyoxyl 35CastorOil Polymers 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 6
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 claims description 6
- 239000008389 polyethoxylated castor oil Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000012546 transfer Methods 0.000 claims description 6
- 239000001856 Ethyl cellulose Substances 0.000 claims description 5
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
- 229920001249 ethyl cellulose Polymers 0.000 claims description 5
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
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- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 235000019359 magnesium stearate Nutrition 0.000 claims description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 4
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- 239000008107 starch Substances 0.000 claims description 4
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- 239000004094 surface-active agent Substances 0.000 claims description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical group OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 3
- 241000218378 Magnolia Species 0.000 claims description 3
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- 239000003480 eluent Substances 0.000 claims description 3
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- 239000000796 flavoring agent Substances 0.000 claims description 3
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- 229960003511 macrogol Drugs 0.000 claims description 3
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- 229920002307 Dextran Polymers 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
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Images
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Group | Dosage (g/kg) | Cerebral infarct size (%) |
The blank group | 42.92±14.08 | |
Sham operated | 0 | |
Positive drug control group | 1.2 | 9.94±11.70 ** |
The heavy dose of group of honokiol | 5×10 -5 | 15.48±15.36 ** |
Dosage group in the honokiol | 5×10 -6 | 15.75±14.16 ** |
The honokiol small dose group | 5×10 -7 | 22.94±16.67 * |
Claims (16)
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Cited By (13)
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WO2006129898A1 (en) * | 2005-05-30 | 2006-12-07 | Korea Institute Of Oriental Medicine | A mass separation method of magnolol from magnoliae cortex ormagnoliae radix |
CN102178666A (en) * | 2011-03-21 | 2011-09-14 | 四川大学 | Application of Honokiol to preparing drugs for preventing or treating intracranial space occupying lesion and intracranial tissues and organs inflammation |
CN102267877A (en) * | 2011-09-05 | 2011-12-07 | 于华忠 | Method for extracting and separating magnolol and honokiol from leaf of magnolia officinalis |
CN104095817A (en) * | 2014-07-22 | 2014-10-15 | 武汉工程大学 | Nanoparticles containing magnolol or honokiol as well as preparation method and application of nanoparticles |
CN104739932A (en) * | 2013-12-31 | 2015-07-01 | 瑞普(天津)生物药业有限公司 | Preparation method of mangnolia officinalis perfusion fluid for dairy cow mastitis |
CN105012242A (en) * | 2015-07-21 | 2015-11-04 | 南京中医药大学 | Solid dispersion prepared from magnolol, honokiol or mixture of magnolol and honokiol and preparation method of solid dispersion by hot-melt extrusion |
CN105726521A (en) * | 2014-12-10 | 2016-07-06 | 瑞普(天津)生物药业有限公司 | Emulsion containing magnolol or honokiol, and preparation method of emulsion |
CN109771431A (en) * | 2018-02-10 | 2019-05-21 | 成都贝诺科成生物科技有限公司 | The new application of honokiol derivative |
CN109875983A (en) * | 2018-12-10 | 2019-06-14 | 广州医科大学附属第二医院 | A kind of agonist of aldehyde dehydrogenase 2 |
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CN112933302A (en) * | 2021-02-02 | 2021-06-11 | 四川大学华西医院 | Multifunctional biomedical coating material based on traditional Chinese medicine magnolia officinalis and preparation method thereof |
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Family Cites Families (2)
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CN1106391C (en) * | 1999-04-12 | 2003-04-23 | 李安荣 | Magnolol series of compounds, synthesizing process thereof, and medicinal composition using same as active component |
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2003
- 2003-12-11 CN CNB2003101213030A patent/CN100374107C/en not_active Expired - Fee Related
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WO2006129898A1 (en) * | 2005-05-30 | 2006-12-07 | Korea Institute Of Oriental Medicine | A mass separation method of magnolol from magnoliae cortex ormagnoliae radix |
US7608741B2 (en) * | 2005-05-30 | 2009-10-27 | Korea Institute Of Oriental Medicine | Mass separation method of magnolol from Magnoliae cortex radix |
CN102178666A (en) * | 2011-03-21 | 2011-09-14 | 四川大学 | Application of Honokiol to preparing drugs for preventing or treating intracranial space occupying lesion and intracranial tissues and organs inflammation |
CN102267877A (en) * | 2011-09-05 | 2011-12-07 | 于华忠 | Method for extracting and separating magnolol and honokiol from leaf of magnolia officinalis |
CN104739932A (en) * | 2013-12-31 | 2015-07-01 | 瑞普(天津)生物药业有限公司 | Preparation method of mangnolia officinalis perfusion fluid for dairy cow mastitis |
CN104095817A (en) * | 2014-07-22 | 2014-10-15 | 武汉工程大学 | Nanoparticles containing magnolol or honokiol as well as preparation method and application of nanoparticles |
CN105726521A (en) * | 2014-12-10 | 2016-07-06 | 瑞普(天津)生物药业有限公司 | Emulsion containing magnolol or honokiol, and preparation method of emulsion |
CN105012242A (en) * | 2015-07-21 | 2015-11-04 | 南京中医药大学 | Solid dispersion prepared from magnolol, honokiol or mixture of magnolol and honokiol and preparation method of solid dispersion by hot-melt extrusion |
CN109771431A (en) * | 2018-02-10 | 2019-05-21 | 成都贝诺科成生物科技有限公司 | The new application of honokiol derivative |
CN109875983A (en) * | 2018-12-10 | 2019-06-14 | 广州医科大学附属第二医院 | A kind of agonist of aldehyde dehydrogenase 2 |
CN111789811A (en) * | 2020-08-07 | 2020-10-20 | 火人科创(北京)药物研发有限公司 | Injection solution and freeze-dried powder of honokiol for injection and preparation method thereof |
CN112933302A (en) * | 2021-02-02 | 2021-06-11 | 四川大学华西医院 | Multifunctional biomedical coating material based on traditional Chinese medicine magnolia officinalis and preparation method thereof |
CN112933302B (en) * | 2021-02-02 | 2022-06-03 | 四川大学华西医院 | Multifunctional biomedical coating material based on traditional Chinese medicine magnolia officinalis and preparation method thereof |
CN115414339A (en) * | 2022-10-10 | 2022-12-02 | 深圳市中医院 | Application of honokiol in preparation of medicine for treating kidney diseases |
CN116270473A (en) * | 2023-05-25 | 2023-06-23 | 成都金瑞基业生物科技有限公司 | Co-carried liposome and preparation method thereof |
CN116270473B (en) * | 2023-05-25 | 2023-12-19 | 成都金瑞基业生物科技有限公司 | Co-carried liposome and preparation method thereof |
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