CN1252082C - Process for preparing protopanoxadiol and protopanaxatriol - Google Patents
Process for preparing protopanoxadiol and protopanaxatriol Download PDFInfo
- Publication number
- CN1252082C CN1252082C CN 200410018038 CN200410018038A CN1252082C CN 1252082 C CN1252082 C CN 1252082C CN 200410018038 CN200410018038 CN 200410018038 CN 200410018038 A CN200410018038 A CN 200410018038A CN 1252082 C CN1252082 C CN 1252082C
- Authority
- CN
- China
- Prior art keywords
- protopanoxadiol
- protopanaxatriol
- reaction
- extract
- organic solvent
- 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.)
- Expired - Lifetime
Links
- SHCBCKBYTHZQGZ-DLHMIPLTSA-N protopanaxatriol Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2[C@@H](O)C[C@@]3(C)[C@]4(C)CC[C@H]([C@](C)(O)CCC=C(C)C)[C@H]4[C@H](O)C[C@@H]3[C@]21C SHCBCKBYTHZQGZ-DLHMIPLTSA-N 0.000 title claims abstract description 43
- BBEUDPAEKGPXDG-UHFFFAOYSA-N protopanaxatriol Natural products CC(CCC=C(C)C)C1CCC2(C)C1C(O)CC3C4(C)CCC(O)C(C)(C)C4C(O)CC23C BBEUDPAEKGPXDG-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 229930182490 saponin Natural products 0.000 claims abstract description 50
- 150000007949 saponins Chemical class 0.000 claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- 239000000284 extract Substances 0.000 claims abstract description 22
- 241000208343 Panax Species 0.000 claims abstract description 11
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 238000000746 purification Methods 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 241001065361 Gynostemma Species 0.000 claims abstract description 6
- 238000004440 column chromatography Methods 0.000 claims abstract description 6
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 6
- 239000001397 quillaja saponaria molina bark Substances 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 229930182494 ginsenoside Natural products 0.000 claims description 15
- 229940089161 ginsenoside Drugs 0.000 claims description 15
- -1 sodium alkoxide Chemical class 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 229940058015 1,3-butylene glycol Drugs 0.000 claims description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 229910001882 dioxygen Inorganic materials 0.000 claims 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims 1
- 235000017709 saponins Nutrition 0.000 abstract description 48
- 238000000034 method Methods 0.000 abstract description 17
- 241000196324 Embryophyta Species 0.000 abstract description 15
- 235000002956 Gynostemma pentaphyllum Nutrition 0.000 abstract description 7
- 230000000259 anti-tumor effect Effects 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 28
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 244000131316 Panax pseudoginseng Species 0.000 description 11
- 238000003810 ethyl acetate extraction Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 238000005406 washing Methods 0.000 description 11
- 238000010898 silica gel chromatography Methods 0.000 description 10
- 238000010828 elution Methods 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 240000006509 Gynostemma pentaphyllum Species 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 241000168720 Panax japonicus Species 0.000 description 6
- 235000003140 Panax quinquefolius Nutrition 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- JKLISIRFYWXLQG-UHFFFAOYSA-N Epioleonolsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4CCC3C21C JKLISIRFYWXLQG-UHFFFAOYSA-N 0.000 description 5
- YBRJHZPWOMJYKQ-UHFFFAOYSA-N Oleanolic acid Natural products CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C1)C(=O)O YBRJHZPWOMJYKQ-UHFFFAOYSA-N 0.000 description 5
- MIJYXULNPSFWEK-UHFFFAOYSA-N Oleanolinsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MIJYXULNPSFWEK-UHFFFAOYSA-N 0.000 description 5
- 235000003181 Panax pseudoginseng Nutrition 0.000 description 5
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 5
- 235000008434 ginseng Nutrition 0.000 description 5
- 229940100243 oleanolic acid Drugs 0.000 description 5
- HZLWUYJLOIAQFC-UHFFFAOYSA-N prosapogenin PS-A Natural products C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC1OCC(O)C(O)C1O HZLWUYJLOIAQFC-UHFFFAOYSA-N 0.000 description 5
- 241000180649 Panax notoginseng Species 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- 241000208340 Araliaceae Species 0.000 description 3
- 235000003143 Panax notoginseng Nutrition 0.000 description 3
- 244000138620 Talinum patens Species 0.000 description 3
- 235000004083 Talinum patens Nutrition 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 235000005769 Japanese ginseng Nutrition 0.000 description 2
- 235000002791 Panax Nutrition 0.000 description 2
- 235000002789 Panax ginseng Nutrition 0.000 description 2
- 235000003174 Panax japonicus Nutrition 0.000 description 2
- 241000620166 Panax pseudoginseng subsp. himalaicus Species 0.000 description 2
- 241000168719 Panax zingiberensis Species 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000002481 ethanol extraction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- TXEWRVNOAJOINC-UHFFFAOYSA-N ginsenoside Rb2 Natural products CC(=CCCC(OC1OC(COC2OCC(O)C(O)C2O)C(O)C(O)C1O)C3CCC4(C)C3C(O)CC5C6(C)CCC(OC7OC(CO)C(O)C(O)C7OC8OC(CO)C(O)C(O)C8O)C(C)(C)C6CCC45C)C TXEWRVNOAJOINC-UHFFFAOYSA-N 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 240000008027 Akebia quinata Species 0.000 description 1
- 235000007756 Akebia quinata Nutrition 0.000 description 1
- 241000219104 Cucurbitaceae Species 0.000 description 1
- UFNDONGOJKNAES-UHFFFAOYSA-N Ginsenoside Rb1 Natural products CC(=CCCC(C)(OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)C3CCC4(C)C3C(O)CC5C6(C)CCC(OC7OC(CO)C(O)C(O)C7OC8OC(CO)C(O)C(O)C8O)C(C)(C)C6CC(O)C45C)C UFNDONGOJKNAES-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 240000005373 Panax quinquefolius Species 0.000 description 1
- 241000168721 Panax stipuleanatus Species 0.000 description 1
- 241001527087 Panax vietnamensis Species 0.000 description 1
- 235000003176 Panax zingiberensis Nutrition 0.000 description 1
- YQKCHRBAJSATCG-UHFFFAOYSA-N UNPD30744 Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC(C)(CCC=C(C)C)C2C3C(C4(CCC5C(C)(C)C(OC6C(C(O)C(O)C(CO)O6)OC6C(C(O)C(O)C(CO)O6)O)CCC5(C)C4CC3O)C)(C)CC2)O1 YQKCHRBAJSATCG-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- BDFJWKALVSRGSR-UHFFFAOYSA-N butan-1-ol;sodium Chemical compound [Na].CCCCO BDFJWKALVSRGSR-UHFFFAOYSA-N 0.000 description 1
- 239000002021 butanolic extract Substances 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- GZYPWOGIYAIIPV-JBDTYSNRSA-N ginsenoside Rb1 Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)O[C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(CC[C@H]4C(C)(C)[C@@H](O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O)CC[C@]4(C)[C@H]3C[C@H]2O)C)(C)CC1)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GZYPWOGIYAIIPV-JBDTYSNRSA-N 0.000 description 1
- NODILNFGTFIURN-USYOXQFSSA-N ginsenoside Rb3 Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)O[C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(CC[C@H]4C(C)(C)[C@@H](O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O)CC[C@]4(C)[C@H]3C[C@H]2O)C)(C)CC1)O[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O NODILNFGTFIURN-USYOXQFSSA-N 0.000 description 1
- PFSIGTQOILYIIU-UHFFFAOYSA-N ginsenoside Rb3 Natural products CC(=CCCC(C)(O)C1CCC2(C)C3CCC4C(C)(C)C(CCC4(C)C3CC(OC5OC(COC6OCC(O)C(O)C6O)C(O)C(O)C5O)C12C)OC7OC(CO)C(O)C(O)C7OC8OC(CO)C(O)C(O)C8O)C PFSIGTQOILYIIU-UHFFFAOYSA-N 0.000 description 1
- UVBLDLGZDSGCSN-UHFFFAOYSA-N ginsenoside-Rb3 Natural products C1=CC2C3(C)CCC(O)C(C)(C)C3CCC2(C)C2(C)CCC34CCC(C)C(C)C4C21OC3=O UVBLDLGZDSGCSN-UHFFFAOYSA-N 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- IUCHKMAZAWJNBJ-RCYXVVTDSA-N oleanolic acid 3-O-beta-D-glucosiduronic acid Chemical compound O([C@H]1CC[C@]2(C)[C@H]3CC=C4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@]1(CCC(C[C@H]14)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O IUCHKMAZAWJNBJ-RCYXVVTDSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical group N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 1
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- Steroid Compounds (AREA)
Abstract
Description
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200410018038 CN1252082C (en) | 2004-04-29 | 2004-04-29 | Process for preparing protopanoxadiol and protopanaxatriol |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200410018038 CN1252082C (en) | 2004-04-29 | 2004-04-29 | Process for preparing protopanoxadiol and protopanaxatriol |
Publications (2)
Publication Number | Publication Date |
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CN1569882A CN1569882A (en) | 2005-01-26 |
CN1252082C true CN1252082C (en) | 2006-04-19 |
Family
ID=34479315
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN 200410018038 Expired - Lifetime CN1252082C (en) | 2004-04-29 | 2004-04-29 | Process for preparing protopanoxadiol and protopanaxatriol |
Country Status (1)
Country | Link |
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CN (1) | CN1252082C (en) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100438876C (en) | 2006-06-09 | 2008-12-03 | 上海中药创新研究中心 | Use of 20(S)-protopanoxadiol in preparation of antidepressant medicine |
CN101508965B (en) * | 2008-10-27 | 2011-08-03 | 昆明诺唯金参生物工程有限责任公司 | Process of preparing 20(S)-ginsenoside Rh1 with streptomycete fermentation of pseudo-ginseng saponin |
CN102311474B (en) * | 2010-07-07 | 2016-02-24 | 北京师范大学 | Application solventless method prepares protopanoxadiol and Protopanaxatriol |
CN102558271A (en) * | 2012-01-16 | 2012-07-11 | 沈阳药科大学 | Industrial preparation method of pseudoginsenoside |
CN103961358B (en) * | 2013-01-31 | 2016-07-06 | 上海中药创新研究中心 | Protopanoxadiol derivative, the application in pharmacy of Protopanaxatriol's derivant |
CN106957351A (en) * | 2016-01-08 | 2017-07-18 | 杨丽娟 | The preparation method of 20 (S)-protopanoxadiols |
CN108558976B (en) * | 2018-04-13 | 2019-09-06 | 深圳以诺生物制药有限公司 | The preparation method of low polarity rare ginsenoside Δ PPD and Δ PPT |
CN113637044B (en) * | 2021-05-08 | 2023-11-03 | 中国人民解放军海军军医大学 | Method for preparing protopanoxadiol and protopanaxatriol |
CN113214338A (en) * | 2021-05-21 | 2021-08-06 | 吉林大学 | Crystal and single crystal of protopanaxatriol and preparation method thereof |
CN114702541B (en) * | 2022-01-23 | 2022-12-02 | 吉林农业大学 | Large-scale preparation method of compound 20 (S) -protopanaxatriol PPT |
-
2004
- 2004-04-29 CN CN 200410018038 patent/CN1252082C/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
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CN1569882A (en) | 2005-01-26 |
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Effective date of registration: 20200729 Address after: Room 310, 3rd floor, town living room, No. 999, Gaoxin East Road, Xinxiang City, Henan Province Patentee after: Xinxiang yiruida Pharmaceutical Technology Co.,Ltd. Address before: 214101 No. three, No. 99, Furong Road, Xishan Economic Development Zone, Jiangsu, Wuxi Patentee before: Wuxi Zhonghui Medicine Co.,Ltd. |
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Effective date of registration: 20221017 Address after: 214192 99 Xishan road three, Xishan Economic Development Zone, Wuxi, Jiangsu Patentee after: Wuxi Zhonghui Medicine Co.,Ltd. Address before: Room 310, 3rd floor, small town living room, 999 Gaoxin East Road, Xinxiang City, Henan Province Patentee before: Xinxiang yiruida Pharmaceutical Technology Co.,Ltd. |
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Effective date of registration: 20221219 Address after: Room 118, building 20, no.1-42, Lane 83, Hongxiang North Road, Lingang New District, China (Shanghai) pilot Free Trade Zone, Pudong New Area, Shanghai, 2013 13 Patentee after: Yiruida (Shanghai) Pharmaceutical Technology Co.,Ltd. Address before: 214192 99 Xishan road three, Xishan Economic Development Zone, Wuxi, Jiangsu Patentee before: Wuxi Zhonghui Medicine Co.,Ltd. |
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Granted publication date: 20060419 |