CN107397748B - 一种具有抗感染作用的蟾酥提取物及其制备方法 - Google Patents
一种具有抗感染作用的蟾酥提取物及其制备方法 Download PDFInfo
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- CN107397748B CN107397748B CN201710674561.3A CN201710674561A CN107397748B CN 107397748 B CN107397748 B CN 107397748B CN 201710674561 A CN201710674561 A CN 201710674561A CN 107397748 B CN107397748 B CN 107397748B
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- 239000000284 extract Substances 0.000 title claims abstract description 90
- 230000002924 anti-infective effect Effects 0.000 title claims abstract description 31
- 238000000605 extraction Methods 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- JGDCRWYOMWSTFC-AZGSIFHYSA-N 5-[(3s,5r,8r,9s,10s,11s,13r,14s,17r)-3,11,14-trihydroxy-10,13-dimethyl-12-oxo-2,3,4,5,6,7,8,9,11,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]pyran-2-one Chemical compound C=1([C@@H]2[C@@]3([C@@](CC2)(O)[C@H]2[C@@H]([C@@]4(C)CC[C@H](O)C[C@H]4CC2)[C@H](O)C3=O)C)C=CC(=O)OC=1 JGDCRWYOMWSTFC-AZGSIFHYSA-N 0.000 claims abstract description 59
- QEEBRPGZBVVINN-UHFFFAOYSA-N Desacetyl-bufotalin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C1(O)CCC2C=1C=CC(=O)OC=1 QEEBRPGZBVVINN-UHFFFAOYSA-N 0.000 claims abstract description 59
- JGDCRWYOMWSTFC-UHFFFAOYSA-N Arenobufagin Natural products C1CC(C2C(C3(C)CCC(O)CC3CC2)C(O)C2=O)(O)C2(C)C1C=1C=CC(=O)OC=1 JGDCRWYOMWSTFC-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000003814 drug Substances 0.000 claims abstract description 47
- 229940079593 drug Drugs 0.000 claims abstract description 43
- QEEBRPGZBVVINN-BMPKRDENSA-N bufalin Chemical compound C=1([C@H]2CC[C@]3(O)[C@H]4[C@@H]([C@]5(CC[C@H](O)C[C@H]5CC4)C)CC[C@@]32C)C=CC(=O)OC=1 QEEBRPGZBVVINN-BMPKRDENSA-N 0.000 claims abstract description 30
- ATLJNLYIJOCWJE-CWMZOUAVSA-N bufogenin Chemical compound C=1([C@H]2C[C@H]3O[C@@]43[C@H]3[C@@H]([C@]5(CC[C@H](O)C[C@H]5CC3)C)CC[C@@]42C)C=CC(=O)OC=1 ATLJNLYIJOCWJE-CWMZOUAVSA-N 0.000 claims abstract description 29
- 229950006858 bufogenin Drugs 0.000 claims abstract description 29
- ATLJNLYIJOCWJE-UHFFFAOYSA-N resibufogenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C11OC1CC2C=1C=CC(=O)OC=1 ATLJNLYIJOCWJE-UHFFFAOYSA-N 0.000 claims abstract description 29
- KBKUJJFDSHBPPA-UHFFFAOYSA-N 5beta-hydroxylcinobufagin Natural products CC(=O)OC1C2OC22C3CCC4(O)CC(O)CCC4(C)C3CCC2(C)C1C=1C=CC(=O)OC=1 KBKUJJFDSHBPPA-UHFFFAOYSA-N 0.000 claims abstract description 28
- KBKUJJFDSHBPPA-ZNCGZLKOSA-N cinobufotalin Chemical compound C=1([C@@H]2[C@@]3(C)CC[C@@H]4[C@@]5(C)CC[C@H](O)C[C@@]5(O)CC[C@H]4[C@@]43O[C@@H]4[C@@H]2OC(=O)C)C=CC(=O)OC=1 KBKUJJFDSHBPPA-ZNCGZLKOSA-N 0.000 claims abstract description 28
- TVKPTWJPKVSGJB-XHCIOXAKSA-N (3s,5s,8r,9s,10s,13r,14s,17r)-3,5,14-trihydroxy-13-methyl-17-(6-oxopyran-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene-10-carbaldehyde Chemical compound C=1([C@H]2CC[C@]3(O)[C@H]4[C@@H]([C@]5(CC[C@H](O)C[C@@]5(O)CC4)C=O)CC[C@@]32C)C=CC(=O)OC=1 TVKPTWJPKVSGJB-XHCIOXAKSA-N 0.000 claims abstract description 27
- AXUYMUBJXHVZEL-UHFFFAOYSA-N Hellebrigenin Natural products C1=CC(=O)OC=C1C1CCC2(O)C1(C)CCC(C1(CC3)C=O)C2CCC1(O)CC3OC1OC(CO)C(O)C(O)C1O AXUYMUBJXHVZEL-UHFFFAOYSA-N 0.000 claims abstract description 27
- PBSOJKPTQWWJJD-UHFFFAOYSA-N 5beta-hydroxy-bufalin Natural products CC12CCC(C3(CCC(O)CC3(O)CC3)C)C3C1(O)CCC2C=1C=CC(=O)OC=1 PBSOJKPTQWWJJD-UHFFFAOYSA-N 0.000 claims abstract description 26
- PBSOJKPTQWWJJD-ZBDZJSKLSA-N Telocinobufagin Chemical compound C=1([C@H]2CC[C@]3(O)[C@H]4[C@@H]([C@]5(CC[C@H](O)C[C@@]5(O)CC4)C)CC[C@@]32C)C=CC(=O)OC=1 PBSOJKPTQWWJJD-ZBDZJSKLSA-N 0.000 claims abstract description 26
- 239000000470 constituent Substances 0.000 claims abstract description 25
- SCULJPGYOQQXTK-OLRINKBESA-N Cinobufagin Chemical compound C=1([C@@H]2[C@@]3(C)CC[C@@H]4[C@@]5(C)CC[C@H](O)C[C@H]5CC[C@H]4[C@@]43O[C@@H]4[C@@H]2OC(=O)C)C=CC(=O)OC=1 SCULJPGYOQQXTK-OLRINKBESA-N 0.000 claims abstract description 24
- SCULJPGYOQQXTK-UHFFFAOYSA-N Cinobufagin Natural products CC(=O)OC1C2OC22C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C=1C=CC(=O)OC=1 SCULJPGYOQQXTK-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000004615 ingredient Substances 0.000 claims abstract description 15
- 230000000694 effects Effects 0.000 claims abstract description 14
- 239000004480 active ingredient Substances 0.000 claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- 239000011347 resin Substances 0.000 claims description 25
- 229920005989 resin Polymers 0.000 claims description 25
- 235000019441 ethanol Nutrition 0.000 claims description 22
- 241000269420 Bufonidae Species 0.000 claims description 18
- 239000000469 ethanolic extract Substances 0.000 claims description 18
- 239000002435 venom Substances 0.000 claims description 17
- 231100000611 venom Toxicity 0.000 claims description 17
- 210000001048 venom Anatomy 0.000 claims description 17
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 238000010828 elution Methods 0.000 claims description 11
- 239000012535 impurity Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 5
- 238000001802 infusion Methods 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 231100000135 cytotoxicity Toxicity 0.000 abstract description 8
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- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 5
- 230000000840 anti-viral effect Effects 0.000 description 5
- -1 bufotalien Chemical compound 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- 208000002606 Paramyxoviridae Infections Diseases 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- 239000012488 sample solution Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000588769 Proteus <enterobacteria> Species 0.000 description 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 3
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- 230000004083 survival effect Effects 0.000 description 3
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- 229940100050 virazole Drugs 0.000 description 3
- 208000035143 Bacterial infection Diseases 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- JMNQTHQLNRILMH-UHFFFAOYSA-N Marinobufagin Natural products CC12CCC(C3(CCC(O)CC3(O)CC3)C)C3C11OC1CC2C=1C=CC(=O)OC=1 JMNQTHQLNRILMH-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 208000036142 Viral infection Diseases 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
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- 231100000614 poison Toxicity 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 229960000329 ribavirin Drugs 0.000 description 2
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 231100000816 toxic dose Toxicity 0.000 description 2
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- 231100000419 toxicity Toxicity 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 102400000888 Cholecystokinin-8 Human genes 0.000 description 1
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- 241001478240 Coccus Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000003088 amphibian venom Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
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- 238000010936 aqueous wash Methods 0.000 description 1
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- 230000002458 infectious effect Effects 0.000 description 1
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- 231100000518 lethal Toxicity 0.000 description 1
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- 239000003973 paint Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
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- 150000003522 tetracyclines Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 241000712461 unidentified influenza virus Species 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
- A61K31/585—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin containing lactone rings, e.g. oxandrolone, bufalin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/56—Materials from animals other than mammals
- A61K35/65—Amphibians, e.g. toads, frogs, salamanders or newts
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
时间(min) | 流动相A(%) | 流动相B(%) |
0~5 | 10 | 90 |
5~10 | 10→23 | 90→77 |
10~27 | 23 | 77 |
27~32 | 23→30 | 77→70 |
32~44 | 30 | 70 |
44~49 | 30→40 | 70→60 |
49~64 | 40 | 60 |
64~69 | 40→60 | 60→40 |
69~90 | 60 | 40 |
组别 | CC50值(μM) |
测试组1 | 16.32 |
测试组2 | 18.23 |
测试组3 | 21.22 |
测试组4 | 17.32 |
测试组5 | 16.44 |
测试组6 | 25.44 |
测试组7 | 18.33 |
测试组8 | 19.21 |
测试组9 | 133.3 |
测试组10 | 135.4 |
测试组11 | 140.5 |
病毒唑 | 62.5 |
Claims (9)
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CN201710674561.3A CN107397748B (zh) | 2017-08-09 | 2017-08-09 | 一种具有抗感染作用的蟾酥提取物及其制备方法 |
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CN201710674561.3A CN107397748B (zh) | 2017-08-09 | 2017-08-09 | 一种具有抗感染作用的蟾酥提取物及其制备方法 |
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CN107397748A CN107397748A (zh) | 2017-11-28 |
CN107397748B true CN107397748B (zh) | 2018-10-02 |
Family
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Country Status (1)
Country | Link |
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CN (1) | CN107397748B (zh) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108096286A (zh) * | 2018-02-27 | 2018-06-01 | 张显英 | 一种蟾毒液提取工艺 |
CN109671467B (zh) * | 2018-12-12 | 2023-03-24 | 中国人民解放军军事科学院军事医学研究院 | 一种病原体感染损伤机理解析方法及装置 |
CN111437293B (zh) * | 2020-04-24 | 2023-07-25 | 江苏省中医药研究院 | 蟾酥提取物在制备治疗SARS-CoV-2病毒引起的感染性疾病的药物中的应用 |
CN113278044B (zh) * | 2021-06-18 | 2024-07-05 | 合肥华方医药科技有限公司 | 蟾皮甾烯内酯单体化合物在制备抗流感病毒药物中的用途 |
CN114903907A (zh) * | 2022-05-31 | 2022-08-16 | 合肥师范学院 | 一种沙蟾毒精及其衍生物的应用 |
Citations (5)
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CN1634577A (zh) * | 2004-10-15 | 2005-07-06 | 张平 | 一种华蟾素冻干粉针剂及其制备方法 |
CN101176739A (zh) * | 2006-11-08 | 2008-05-14 | 山东绿叶制药有限公司 | 一种蟾毒配基提取物及其制备方法与应用 |
CN102688248A (zh) * | 2012-03-28 | 2012-09-26 | 南京中医药大学 | 蟾蜍甾烯类化合物在制备治疗口腔黏膜恶性肿瘤药物中的应用 |
CN103705568A (zh) * | 2013-12-26 | 2014-04-09 | 南阳新先锋制药有限公司 | 治疗家禽呼吸系统疾病的复方盐酸左旋氧氟沙星可溶性粉 |
CN106138067A (zh) * | 2015-04-21 | 2016-11-23 | 中国科学院大连化学物理研究所 | 蟾蜍二烯内酯类化合物在制备抗胃癌药物中的应用 |
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2017
- 2017-08-09 CN CN201710674561.3A patent/CN107397748B/zh active Active
Patent Citations (5)
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CN1634577A (zh) * | 2004-10-15 | 2005-07-06 | 张平 | 一种华蟾素冻干粉针剂及其制备方法 |
CN101176739A (zh) * | 2006-11-08 | 2008-05-14 | 山东绿叶制药有限公司 | 一种蟾毒配基提取物及其制备方法与应用 |
CN102688248A (zh) * | 2012-03-28 | 2012-09-26 | 南京中医药大学 | 蟾蜍甾烯类化合物在制备治疗口腔黏膜恶性肿瘤药物中的应用 |
CN103705568A (zh) * | 2013-12-26 | 2014-04-09 | 南阳新先锋制药有限公司 | 治疗家禽呼吸系统疾病的复方盐酸左旋氧氟沙星可溶性粉 |
CN106138067A (zh) * | 2015-04-21 | 2016-11-23 | 中国科学院大连化学物理研究所 | 蟾蜍二烯内酯类化合物在制备抗胃癌药物中的应用 |
Non-Patent Citations (3)
Title |
---|
《蟾酥体外抑菌活性的实验研究》;吴盛海;《中华中医药学刊》;20100930;第28卷(第9期);第1883-1885页 * |
《蟾酥对痢疾杆菌抑菌作用的影响》;闫兵;《牡丹江师范学院学报(自然科学版)》;20100430(第4期);全文 * |
《蟾酥对金黄色葡萄球菌抑菌作用及机理的初步研究》;郭满;《中国优秀硕士学位论文全文数据库医药卫生科技辑》;20160215(第2期);全文 * |
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CN107397748A (zh) | 2017-11-28 |
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