CN104045553A - Method for extracting 1'-acetoxychavicol acetate from Actinostemma tenerum Griff - Google Patents
Method for extracting 1'-acetoxychavicol acetate from Actinostemma tenerum Griff Download PDFInfo
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- CN104045553A CN104045553A CN201410297953.9A CN201410297953A CN104045553A CN 104045553 A CN104045553 A CN 104045553A CN 201410297953 A CN201410297953 A CN 201410297953A CN 104045553 A CN104045553 A CN 104045553A
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- Prior art keywords
- ethanol
- acetate
- extracting
- herb
- chavicol
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Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- NKRBAUXTIWONOV-UHFFFAOYSA-N 1'-Acetoxyeugenol acetate Natural products COC1=CC(C(OC(C)=O)C=C)=CC=C1OC(C)=O NKRBAUXTIWONOV-UHFFFAOYSA-N 0.000 title abstract description 4
- JAMQIUWGGBSIKZ-ZDUSSCGKSA-N 1'-acetoxychavicol acetate Chemical compound CC(=O)O[C@@H](C=C)C1=CC=C(OC(C)=O)C=C1 JAMQIUWGGBSIKZ-ZDUSSCGKSA-N 0.000 title abstract description 4
- JAMQIUWGGBSIKZ-UHFFFAOYSA-N rac-galangal acetate Natural products CC(=O)OC(C=C)C1=CC=C(OC(C)=O)C=C1 JAMQIUWGGBSIKZ-UHFFFAOYSA-N 0.000 title abstract description 4
- 241000481593 Actinostemma tenerum Species 0.000 title abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 56
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000011347 resin Substances 0.000 claims abstract description 10
- 229920005989 resin Polymers 0.000 claims abstract description 10
- 238000010992 reflux Methods 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 241000481592 Actinostemma Species 0.000 claims description 23
- 230000006837 decompression Effects 0.000 claims description 15
- AXHHVVBUOKYKJO-UHFFFAOYSA-N chavicol acetate Natural products CC(=O)OC1=CC=C(CC=C)C=C1 AXHHVVBUOKYKJO-UHFFFAOYSA-N 0.000 claims description 14
- 238000004064 recycling Methods 0.000 claims description 10
- 238000000605 extraction Methods 0.000 claims description 7
- 235000012054 meals Nutrition 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 230000000274 adsorptive effect Effects 0.000 claims description 5
- 239000003480 eluent Substances 0.000 claims description 5
- 238000010828 elution Methods 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- 238000010898 silica gel chromatography Methods 0.000 claims description 5
- 238000007796 conventional method Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003463 adsorbent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000010298 pulverizing process Methods 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 238000001179 sorption measurement Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 5
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- -1 acetoxyl group Chemical group 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 206010003445 Ascites Diseases 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000015817 Infant Nutrition disease Diseases 0.000 description 1
- 241001520921 Leersia virginica Species 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 208000004078 Snake Bites Diseases 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 244000000053 intestinal parasite Species 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 231100000611 venom Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a method for extracting 1'-acetoxychavicol acetate from Actinostemma tenerum Griff. The method comprises the following steps: taking dry complete Actinostemma tenerum Griff, pulverizing, extracting by heating under reflux twice (1.5 hours each time), merging the reflux liquids, filtering, recovering ethanol under reduced pressure, concentrating, adding into a D101 macroporous adsorbent resin column for adsorption, eluting with ethanol, collecting the eluate, recovering ethanol under reduced pressure, concentrating, adding into a silica gel chromatographic column, eluting by using methanol and dichloromethane in a volume ratio of 8:3 as eluting agents, recovering the solvent, concentrating, and recovering the solvent under reduced pressure. The method for preparing 1'-acetoxychavicol acetate is simple to operate, and the product purity is high.
Description
Technical field
The present invention relates to natural product field, especially from plant, extract compound technical.
Background technology
Chinese medicine Lobed Actinostemma Herb, has another name called Lobed Actinostemma Herb, celestial sphere grass, without white grass etc., for cucurbitaceous plant Lobed Actinostemma Herb (
actinostemma tenerumgriff) herb, seed and leaf, be distributed in various places, China north and south, and Korea, Japan, the Soviet Union, India, South East Asia Mainland also have distribution.Lobed Actinostemma Herb is cold in nature, bitter, slightly poisonous, there is inducing diuresis to remove edema, clearing heat and detoxicating, the effect of drying, cure mainly nephritic edema, ascites swelling, venomous snake bite and infantile malnutrition due to digestive disturbances or intestinalparasites from the beginning of etc. illness.
Modern study finds that Lobed Actinostemma Herb contains the very significant saponin component of a lot of novel structures, anti-tumor activity and flavonoid, amino acid and trace element.
Pharmaceutical research discovery, Lobed Actinostemma Herb has significant anti-tumor activity, and energy strengthening immunity, antithrombotic, anti-inflammatory are anti-oxidant etc.
1 '-ethanoyl chavicol-acetate (1 '-acetoxychavicol acetate), CAS accession number: 108147-21-3, molecular formula C
13h
l40
4, structural formula is as follows:
Research shows, the multiple pharmacologically active such as that 1 '-ethanoyl chavicol-acetate has is antitumor, antiulcer agent.
In prior art, do not have about containing the relevant report of 1 '-ethanoyl chavicol-acetate in Lobed Actinostemma Herb.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of method of extracting 1 '-ethanoyl chavicol-acetate from Lobed Actinostemma Herb, makes that the method is easy and simple to handle, product purity is high.。
In order to solve the problems of the technologies described above, the present invention proposes following technical proposal:
From Lobed Actinostemma Herb, extract a method for 1 '-ethanoyl chavicol-acetate, it is characterized in that described method comprises the following steps: get dry Lobed Actinostemma Herb herb, pulverize, extract according to a conventional method separation, obtain.
Preferably, described method is: get dry Lobed Actinostemma Herb herb, pulverize, by every 1g meal, add the ethanol that the concentration of volume percent of 8-12mL is 75-90%, heating and refluxing extraction 2 times, each 1.5 hours, merge phegma, filter, decompression recycling ethanol is also concentrated into thick paste, join on D101 type macroporous adsorptive resins and adsorb, the ethanol elution that is 50-60% with concentration of volume percent, collect the elutriant that 3-8 doubly measures column volume, decompression recycling ethanol is also concentrated, be added on silica gel column chromatography, methyl alcohol-the methylene dichloride that is 8:3 by volume ratio is eluent wash-out, the column volume of take is collected elutriant by part as unit, the stream part that merges 8-12 part, decompression and solvent recovery, obtain.
Preferably, the condition of described heating and refluxing extraction is: by every 1g meal, add the ethanol that the volume percent of 10mL is 80%.
Preferably, described macroporous resin wash-out is 55% by the concentration of ethanol.
Preferably, the collecting amount of described macroporous resin elutriant is 5 times of column volumes.
Adopt method of the present invention to prepare 1 '-ethanoyl chavicol-acetate, easy and simple to handle, product purity is high.
In order better to set forth technical scheme, below in conjunction with embodiment, the present invention is further illustrated, but protection domain of the presently claimed invention is not limited to the following example.
Embodiment
embodiment 1
Get dry Lobed Actinostemma Herb herb 100Kg, pulverize, by every 1g meal, add the ethanol that the concentration of volume percent of 8mL is 75%, heating and refluxing extraction 2 times, each 1.5 hours, merge phegma, filter, decompression recycling ethanol is also concentrated into thick paste, join on D101 type macroporous adsorptive resins and adsorb, the ethanol elution that is 50% with concentration of volume percent, collect the elutriant of 3 times of amount column volumes, decompression recycling ethanol is also concentrated, be added on silica gel column chromatography, methyl alcohol-the methylene dichloride that is 8:3 by volume ratio is eluent wash-out, the column volume of take is collected elutriant by part as unit, the stream part that merges 8-12 part, decompression and solvent recovery, obtain and obtain oily matter 11.2g.
Through HPLC, detect, the purity of compound is 99.1%.
Its spectrum, mass spectrum, spectral data are as follows:
UV λ max ((EtOH) nm (ε): 220; IRv
maxcm
-1: 1753,1509,1374; EIS-MSm/z:257 (Na
+, C
13h
l40
4), EI-MSm/z:234 (M+, C
13h
140
4);
1h-NMR δ: 2.10 (3 H, s, acetyl-H), 2.29 (3H, s, acetyl-H), 5.23 (1H, ddd, H-3 ' b, J 3'b, 2'=10.2 Hz; J 3'b, 1'=1.5Hz; J 3'b, 3'a=1.5Hz), 5.31 (1H, ddd, H-3'a, J3'a, 2 '=16.8 Hz; J 3'a, 1'=1.5Hz; J 3'b, 3'a=1.5 Hz), 6.02 (1H, ddd, H-2', J2', 3'a=16.8Hz; J2'3'b=10.2Hz; J2', 1'=5.9 Hz), 6.25 (1H, brd, 1', 2'=5.9Hz), 7.26 (2H, d, fragrance-H, J=8.8 Hz), 7.42 (2H, d, fragrance-H, J=8.8Hz);
13cNMR δ: 21.1 (2s connects acetoxyl group group on the carbon of 2x methyl), 77.3 (s, C-l'); 117.0 (s, C-3'), 121.6 (s, C-2 and C-6); 128.3 (s, C-3 and C-5), 136.0 (s; C-2 '), 136.4 (s, C-l); (150.4 s, C-4), 169.7 (2s; 2x acetoxyl group group), basically identical with document, therefore determine that this compound is 1 '-ethanoyl chavicol-acetate.
embodiment 2
Get dry Lobed Actinostemma Herb herb 100Kg, pulverize, by every 1g meal, add the ethanol that the concentration of volume percent of 12mL is 90%, heating and refluxing extraction 2 times, each 1.5 hours, merge phegma, filter, decompression recycling ethanol is also concentrated into thick paste, join on D101 type macroporous adsorptive resins and adsorb, the ethanol elution that is 60% with concentration of volume percent, collect the elutriant of 8 times of amount column volumes, decompression recycling ethanol is also concentrated, be added on silica gel column chromatography, methyl alcohol-the methylene dichloride that is 8:3 by volume ratio is eluent wash-out, the column volume of take is collected elutriant by part as unit, the stream part that merges 8-12 part, decompression and solvent recovery, obtain 11.2g.
Through HPLC, detect, the purity of compound is 98.9%.
Its spectrum, mass spectrum, spectral data are with embodiment 1.
embodiment 3
Get dry Lobed Actinostemma Herb herb 100Kg, pulverize, by every 1g meal, add the ethanol that the concentration of volume percent of 10mL is 80%, heating and refluxing extraction 2 times, each 1.5 hours, merge phegma, filter, decompression recycling ethanol is also concentrated into thick paste, join on D101 type macroporous adsorptive resins and adsorb, the ethanol elution that is 55% with concentration of volume percent, collect the elutriant of 5 times of amount column volumes, decompression recycling ethanol is also concentrated, be added on silica gel column chromatography, methyl alcohol-the methylene dichloride that is 8:3 by volume ratio is eluent wash-out, the column volume of take is collected elutriant by part as unit, the stream part that merges 8-12 part, decompression and solvent recovery, obtain 1 '-ethanoyl chavicol-acetate 11.3g.
Through HPLC, detect, the purity of compound is 99.4%.
Its spectrum, mass spectrum, spectral data are with embodiment 1.
Claims (5)
1. from Lobed Actinostemma Herb, extract a method for 1 '-ethanoyl chavicol-acetate, it is characterized in that described method comprises the following steps: get dry Lobed Actinostemma Herb herb, pulverize, extract according to a conventional method separation, obtain.
2. a kind of method of extracting 1 '-ethanoyl chavicol-acetate from Lobed Actinostemma Herb according to claim 1, it is characterized in that described method comprises the following steps: get dry Lobed Actinostemma Herb herb, pulverize, by every 1g meal, add the ethanol that the concentration of volume percent of 8-12mL is 75-90%, heating and refluxing extraction 2 times, each 1.5 hours, merge phegma, filter, decompression recycling ethanol is also concentrated into thick paste, join on D101 type macroporous adsorptive resins and adsorb, the ethanol elution that is 50-60% with concentration of volume percent, collect the elutriant that 3-8 doubly measures column volume, decompression recycling ethanol is also concentrated, be added on silica gel column chromatography, methyl alcohol-the methylene dichloride that is 8:3 by volume ratio is eluent wash-out, the column volume of take is collected elutriant by part as unit, the stream part that merges 8-12 part, decompression and solvent recovery, obtain.
3. a kind of method of extracting 1 '-ethanoyl chavicol-acetate from Lobed Actinostemma Herb according to claim 2, is characterized in that, the condition of described heating and refluxing extraction is: by every 1g meal, add the ethanol that the volume percent of 10mL is 80%.
4. a kind of method of extracting 1 '-ethanoyl chavicol-acetate from Lobed Actinostemma Herb according to claim 2, is characterized in that, described macroporous resin wash-out is 55% by the concentration of ethanol.
5. a kind of method of extracting 1 '-ethanoyl chavicol-acetate from Lobed Actinostemma Herb according to claim 2, is characterized in that, the collecting amount of described macroporous resin elutriant is 5 times of column volumes.
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| CN201410297953.9A CN104045553B (en) | 2014-06-30 | 2014-06-30 | A kind of method of extracting ACA from Lobed Actinostemma Herb |
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| CN201410297953.9A CN104045553B (en) | 2014-06-30 | 2014-06-30 | A kind of method of extracting ACA from Lobed Actinostemma Herb |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6487418A (en) * | 1987-09-30 | 1989-03-31 | Nec Corp | Feeding device for printed circuit board |
| JPH1087418A (en) * | 1996-09-13 | 1998-04-07 | Res Inst For Prod Dev | Acaricide |
| WO2007088408A1 (en) * | 2006-02-03 | 2007-08-09 | Council Of Scientific And Industrial Research | A method of curing antibiotic resistant plasmids |
| CN101020638A (en) * | 2007-03-18 | 2007-08-22 | 南昌弘益科技有限公司 | 1'-acetoxy chavicol acetic ester |
| CN102643196A (en) * | 2012-04-24 | 2012-08-22 | 南京泽朗医药科技有限公司 | Method for preparing 1'-acetoxy chavicol acetate |
| CN102826997A (en) * | 2012-09-20 | 2012-12-19 | 南京泽朗农业发展有限公司 | Method for extracting 1'-acetoxychavicol acetate from fructus galangae |
-
2014
- 2014-06-30 CN CN201410297953.9A patent/CN104045553B/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6487418A (en) * | 1987-09-30 | 1989-03-31 | Nec Corp | Feeding device for printed circuit board |
| JPH1087418A (en) * | 1996-09-13 | 1998-04-07 | Res Inst For Prod Dev | Acaricide |
| WO2007088408A1 (en) * | 2006-02-03 | 2007-08-09 | Council Of Scientific And Industrial Research | A method of curing antibiotic resistant plasmids |
| CN101020638A (en) * | 2007-03-18 | 2007-08-22 | 南昌弘益科技有限公司 | 1'-acetoxy chavicol acetic ester |
| CN102643196A (en) * | 2012-04-24 | 2012-08-22 | 南京泽朗医药科技有限公司 | Method for preparing 1'-acetoxy chavicol acetate |
| CN102826997A (en) * | 2012-09-20 | 2012-12-19 | 南京泽朗农业发展有限公司 | Method for extracting 1'-acetoxychavicol acetate from fructus galangae |
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|---|---|
| CN104045553B (en) | 2016-05-11 |
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Effective date of registration: 20170417 Address after: 314200 Zhejiang City, Pinghu Province Economic Development Zone, the new road No. 988, building 413-2, room Patentee after: Pinghu blue ocean Biotechnology Co.,Ltd. Address before: Tianhe District Tong East Road Guangzhou city Guangdong province 510665 B-101 No. 5, room B-118 Patentee before: GUANGDONG GAOHANG INTELLECTUAL PROPERTY OPERATION Co.,Ltd. Effective date of registration: 20170417 Address after: Tianhe District Tong East Road Guangzhou city Guangdong province 510665 B-101 No. 5, room B-118 Patentee after: GUANGDONG GAOHANG INTELLECTUAL PROPERTY OPERATION Co.,Ltd. Address before: No. 2 Taishan Road, Jiangsu science and Technology Park, 215000 Canton City of Suzhou province high tech Zone 2-104 Patentee before: Suzhou Paiteng Biological Medical Technology Co.,Ltd. |
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Denomination of invention: Method for extracting 1'-acetoxychavicol acetate from Actinostemma tenerum Griff Effective date of registration: 20180223 Granted publication date: 20160511 Pledgee: Zhejiang Pinghu rural commercial bank Limited by Share Ltd. science and Technology Branch Pledgor: Pinghu blue ocean Biotechnology Co.,Ltd. Registration number: 2018330000046 |
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