CN102020682A - Preparation method of neuchebulagicacid - Google Patents
Preparation method of neuchebulagicacid Download PDFInfo
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- CN102020682A CN102020682A CN2010105353675A CN201010535367A CN102020682A CN 102020682 A CN102020682 A CN 102020682A CN 2010105353675 A CN2010105353675 A CN 2010105353675A CN 201010535367 A CN201010535367 A CN 201010535367A CN 102020682 A CN102020682 A CN 102020682A
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- China
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- preparation
- chebulagic acid
- macroporous adsorbent
- acid
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- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000011347 resin Substances 0.000 claims abstract description 23
- 229920005989 resin Polymers 0.000 claims abstract description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 18
- 239000007788 liquid Substances 0.000 claims abstract description 13
- 238000000605 extraction Methods 0.000 claims abstract description 12
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000010828 elution Methods 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 6
- 238000004064 recycling Methods 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 28
- 229920002052 Chebulagic acid Polymers 0.000 claims description 24
- HGJXAVROWQLCTP-YABCKIEDSA-N Chebulagic acid Chemical compound O([C@H]1[C@H]2[C@H]3OC(=O)C4=CC(O)=C(O)C(O)=C4C4=C(O)C(O)=C(O)C=C4C(=O)OC[C@@H](O1)[C@H]3OC(=O)[C@@H](CC(O)=O)[C@@H]1[C@@H](C(OC=3C(O)=C(O)C=C(C1=3)C(=O)O2)=O)O)C(=O)C1=CC(O)=C(O)C(O)=C1 HGJXAVROWQLCTP-YABCKIEDSA-N 0.000 claims description 22
- UGIVASYMZSZAMP-UHFFFAOYSA-N chebulagic acid Natural products OC1C2c3c(OC1=O)c(O)c(O)cc3C(=O)OC4C(OC(=O)c5cc(O)c(O)c(O)c5)OC6COC(=O)c7cc(O)c(O)c(O)c7c8c(O)c(O)c(O)cc8C(=O)OC4C6OC(=O)C2(O)C(=O)O UGIVASYMZSZAMP-UHFFFAOYSA-N 0.000 claims description 21
- 239000003463 adsorbent Substances 0.000 claims description 13
- 239000012141 concentrate Substances 0.000 claims description 10
- 239000000284 extract Substances 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 241001534869 Terminalia Species 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 230000006837 decompression Effects 0.000 claims description 5
- -1 filter Substances 0.000 claims description 5
- 235000012054 meals Nutrition 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 abstract description 2
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 238000001914 filtration Methods 0.000 abstract 3
- 235000015489 Emblica officinalis Nutrition 0.000 abstract 2
- 244000277583 Terminalia catappa Species 0.000 abstract 2
- 235000011517 Terminalia chebula Nutrition 0.000 abstract 2
- 238000000874 microwave-assisted extraction Methods 0.000 abstract 2
- 239000000843 powder Substances 0.000 abstract 2
- 230000003321 amplification Effects 0.000 abstract 1
- 239000003957 anion exchange resin Substances 0.000 abstract 1
- 239000003729 cation exchange resin Substances 0.000 abstract 1
- 229940023913 cation exchange resins Drugs 0.000 abstract 1
- 239000003480 eluent Substances 0.000 abstract 1
- 238000003199 nucleic acid amplification method Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 235000009330 Terminalia Nutrition 0.000 description 5
- 241000407877 Combretum Species 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 241000001522 Terminalia chebula Species 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 241000132536 Cirsium Species 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- 241001093760 Sapindaceae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000001142 anti-diarrhea Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a preparation method of neuchebulagicacid, which is simple and convenient in operation, and has small pollution and less energy consumption. The method comprises the following process steps: taking coarse powder of myrobalan leaves; putting the coarse powder of myrobalan leaves into a microwave extraction device for microwave extraction; collecting an extraction liquid; filtering; absorbing through strongly basic styrene-type anion exchange resins; eluting by a NaOH solution with the concentration of 0.5mol/L; collecting eluent; filtering; collecting an effluent liquid after strongly acid styrene-type cation exchange resins; filtering; condensing; adding the condensed substance on a macroporous absorption resin for absorbing; eluting with ethanol; collecting an elution liquid; reducing pressure and recycling ethanol and condensing; adding methanol for crystallizing; washing; and drying to obtain the neuchebulagicacid. The neuchebulagicacid prepared by using the invention has high product purity and is easy to realize industrialized amplification.
Description
Technical field
The present invention relates to a kind of preparation method of chebulagic acid, especially a kind of preparation method who from plant, extracts chebulagic acid.
Background technology
Chebulagic acid (Chebulagic acid), molecular formula: C
41H
30O
27, molecular weight: 954.672, CAS accession number: 23094-71-5 mainly is present in Caesalpiniaceae, Combretum Racemosum, setose thistle section, the Sapindaceae various plants.Wherein content is abundant in the leaf of Combretum Racemosum plant myrobalan Terminalia chebula Retz..Its molecular formula is as follows:
Modern study shows that chebulagic acid has stronger antiviral activity, and it is also as the raw material that synthesizes other reactive derivative simultaneously.
The Chinese medicine Medicine Terminalia Leaf beginning is stated from Compendium of Material Medica, is the dry leave of Combretum Racemosum plant myrobalan Terminalia chebula Retz..Effect with lowering the adverse-rising QI to resolve phlegm, antidiarrheal dysentery.Wherein contain a large amount of chebulagic acids.
In the prior art, still be not applicable to preparation technology's report of high purity chebulagic acid industrialized production.
Summary of the invention
Technical problem to be solved by this invention provides a kind of preparation method who is beneficial to big production operation, chebulagic acid that product purity is high.
For solving the problems of the technologies described above, the present invention adopts following technical proposal:
Get the Medicine Terminalia Leaf meal, add water that its quality 3-6 doubly measures volume and drop in the microwave extracting apparatus and carry out microwave extracting, extraction power 300-600W, extract 1-3 time, each 3-10 minute, united extraction liquid, filter, by the absorption of strong-basicity styrene type anionite-exchange resin,, collect elutriant with the NaOH eluant solution of 0.5mol/L, filter, by strongly acidic styrene's type Zeo-karb, collect effluent liquid, filter, concentrate, be added on the macroporous adsorbent resin and adsorb, the 20-40% ethanol elution is collected 3-8 and is doubly measured the column volume elutriant, decompression recycling ethanol also concentrates, add methanol crystallization, washing, drying, promptly.
The water consumption of microwave extracting is preferably 4 times of amount volumes of raw materials quality.
The condition optimization of microwave extracting extracts each 7 minutes 2 times for extraction power 400W.
Strong-basicity styrene type anionite-exchange resin is selected from a kind of in 201 * 7 types, 201 * 4 types, the D201 type anionite-exchange resin.
Strongly acidic styrene's type Zeo-karb is selected from a kind of in 001 * 7 type, 001 * 4 type, the D001 type Zeo-karb.
Macroporous adsorbent resin is selected from a kind of in D101 type, D102 type, the AB8 type macroporous adsorbent resin.
The macroporous adsorbent resin wash-out is preferably 30% with concentration of ethanol.
The macroporous adsorbent resin wash-out is preferably 6 times of amount column volumes with the alcoholic acid collecting amount.
Preparation gained chebulagic acid can adopt following method to detect:
Test routine 1HPLC method and measure chebulagic acid purity
Chromatographic condition
Chromatographic column: octadecylsilane bonding glue silica gel is weighting agent; Moving phase: CH
3OH-EtOAc-KH
2PO
4/ H
3PO
4(0.05mol/L) (volume ratio 34: 2: 64); Flow velocity: 1.0ml/min; Detect wavelength: 254nm; Column temperature: 30 ℃.
Measuring method
Precision takes by weighing chebulagic acid 2mg, places the 50mL measuring bottle, adds people's methyl alcohol 20mL, and sonic oscillation makes dissolving, and methanol constant volume is drawn 10 μ L to scale, injects high performance liquid chromatograph, adopts normalization method working sample purity.
Adopt the present invention to prepare chebulagic acid, be beneficial to big production operation, energy consumption is little, pollutes little.
The present invention is further elaborated below in conjunction with embodiment, but the scope of protection of present invention is not limited to following embodiment.
Embodiment
Embodiment 1
Get Medicine Terminalia Leaf meal 10Kg, add in the 30L water input microwave extracting apparatus and carry out microwave extracting, extraction power 300W, extract 1 time, 3 minutes, collect extracting solution, filter, adsorb by 201 * 7 type strong-basicity styrene type anionite-exchange resin, with the NaOH eluant solution of 0.5mol/L, collect elutriant, filter, by 001 * 7 type strongly acidic styrene type Zeo-karb, collect effluent liquid, filter, concentrate, be added on the D101 type macroporous adsorbent resin and adsorb, 20% ethanol elution is collected 3 times of amount column volume elutriants, and decompression recycling ethanol also concentrates, add methanol crystallization, washing, drying promptly gets prism-chebulagic acid 32.4g, detects through HPLC, purity is 95.7%, UV, IR, MS;
2HNMR,
13The data of its physical behavior of sign such as CNMR are consistent with prior art.
Embodiment 2
Get Medicine Terminalia Leaf meal 10Kg, add in the 60L water input microwave extracting apparatus and carry out microwave extracting, extraction power 600W, extract 3 times, each 10 minutes, united extraction liquid filtered, adsorb by 201 * 4 type strong-basicity styrene type anionite-exchange resin, with the NaOH eluant solution of 0.5mol/L, collect elutriant, filter, by 001 * 4 type strongly acidic styrene type Zeo-karb, collect effluent liquid, filter, concentrate, be added on the D102 type macroporous adsorbent resin and adsorb, 40% ethanol elution is collected 8 times of amount column volume elutriants, and decompression recycling ethanol also concentrates, add methanol crystallization, washing, drying promptly gets prism-chebulagic acid 37.6g, detects through HPLC, purity is 94.2%, UV, IR, MS;
2HNMR,
13The data of its physical behavior of sign such as CNMR are consistent with prior art.
Embodiment 3
Get Medicine Terminalia Leaf meal 10Kg, add in the 40L water input microwave extracting apparatus and carry out microwave extracting, extraction power 400W, extract 2 times, each 7 minutes, united extraction liquid filtered, adsorb by D201 type strong-basicity styrene type anionite-exchange resin, with the NaOH eluant solution of 0.5mol/L, collect elutriant, filter, by D001 type strongly acidic styrene type Zeo-karb, collect effluent liquid, filter, concentrate, be added on the AB8 type macroporous adsorbent resin and adsorb, 30% ethanol elution is collected 6 times of amount column volume elutriants, and decompression recycling ethanol also concentrates, add methanol crystallization, washing, drying promptly gets prism one chebulagic acid 34.9g, detects through HPLC, purity is 98.2%, UV, IR, MS;
2HNMR,
13The data of its physical behavior of sign such as CNMR are consistent with prior art.
Claims (8)
1. the preparation method of a chebulagic acid, it is characterized in that described method is made up of the following step: get the Medicine Terminalia Leaf meal, add water that its quality 3-6 doubly measures volume and drop in the microwave extracting apparatus and carry out microwave extracting, extraction power 300-600W extracts 1-3 time, each 3-10 minute, united extraction liquid filters, and adsorbs by strong-basicity styrene type anionite-exchange resin, NaOH eluant solution with 0.5mol/L, collect elutriant, filter, by strongly acidic styrene's type Zeo-karb, collect effluent liquid, filter, concentrate, be added on the macroporous adsorbent resin and adsorb, the 20-40% ethanol elution, collect 3-8 and doubly measure the column volume elutriant, decompression recycling ethanol also concentrates, and adds methanol crystallization, washing, drying, promptly.
2. according to the preparation method of the described a kind of chebulagic acid of claim 1, the water consumption that it is characterized in that described microwave extracting is 4 times of amount volumes of raw materials quality.
3. according to the preparation method of the described a kind of chebulagic acid of claim 1, the condition that it is characterized in that described microwave extracting extracts each 7 minutes 2 times for extraction power 400W.
4. according to the preparation method of the described a kind of chebulagic acid of claim 1, it is characterized in that described strong-basicity styrene type anionite-exchange resin is selected from a kind of in 201 * 7 types, 201 * 4 types, the D201 type anionite-exchange resin.
5. according to the preparation method of the described a kind of chebulagic acid of claim 1, it is characterized in that described strongly acidic styrene's type Zeo-karb is selected from a kind of in 001 * 7 type, 001 * 4 type, the D001 type Zeo-karb.
6. according to the preparation method of the described a kind of chebulagic acid of claim 1, it is characterized in that described macroporous adsorbent resin is selected from a kind of in D101 type, D102 type, the AB8 type macroporous adsorbent resin.
7. according to the preparation method of the described a kind of chebulagic acid of claim 1, it is characterized in that described macroporous adsorbent resin wash-out concentration of ethanol is 30%.
8. according to the preparation method of the described a kind of chebulagic acid of claim 1, it is characterized in that described macroporous adsorbent resin wash-out is 6 times of amount column volumes with the alcoholic acid collecting amount.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010535367 CN102020682B (en) | 2010-11-09 | 2010-11-09 | Preparation method of neuchebulagicacid |
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|---|---|---|---|
| CN 201010535367 CN102020682B (en) | 2010-11-09 | 2010-11-09 | Preparation method of neuchebulagicacid |
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| CN102020682B CN102020682B (en) | 2013-06-05 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102329342A (en) * | 2011-05-31 | 2012-01-25 | 苏州派腾生物医药科技有限公司 | Preparation method of elaeocarpusin |
| CN104817567A (en) * | 2015-04-03 | 2015-08-05 | 宝鸡市虹源生物科技有限公司 | Method for preparing high-purity ellagic acid by using macroporous resin method to purify tannin |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1398871A (en) * | 2002-09-10 | 2003-02-26 | 北京富邦博尔生物科技有限公司 | Tannic acid purifying process |
| CN101134766A (en) * | 2006-08-30 | 2008-03-05 | 上海康文医药中间体有限公司 | Method for preparing high-purity maple tannin by acer ginnala leaf |
| CN101265279A (en) * | 2008-04-29 | 2008-09-17 | 云南省化工研究院 | Method for extracting tannin from tarra bean-pod by micro-wave method |
-
2010
- 2010-11-09 CN CN 201010535367 patent/CN102020682B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1398871A (en) * | 2002-09-10 | 2003-02-26 | 北京富邦博尔生物科技有限公司 | Tannic acid purifying process |
| CN101134766A (en) * | 2006-08-30 | 2008-03-05 | 上海康文医药中间体有限公司 | Method for preparing high-purity maple tannin by acer ginnala leaf |
| CN101265279A (en) * | 2008-04-29 | 2008-09-17 | 云南省化工研究院 | Method for extracting tannin from tarra bean-pod by micro-wave method |
Non-Patent Citations (4)
| Title |
|---|
| BRUNO FOGLIANI，等: "Bioactive ellagitannins from Cunonia macrophylla, an endemic Cunoniaceae from New Caledonia", 《PHYTOCHEMISTRY》 * |
| K.B.契莫托夫: "《离子交换剂的理论与实际应用》", 30 November 1958, 科学出版社 * |
| QUANBIN HAN，等: "Preparative isolation of hydrolysable tannins chebulagic acid and chebulinic acid from Terminalia chebula by high-speed counter-current chromatography", 《JOURNAL OF SEPARATION SCIENCE》 * |
| 丁岗，等: "诃子中主要可水解丹宁的结构鉴定", 《中国药科大学学报》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102329342A (en) * | 2011-05-31 | 2012-01-25 | 苏州派腾生物医药科技有限公司 | Preparation method of elaeocarpusin |
| CN104817567A (en) * | 2015-04-03 | 2015-08-05 | 宝鸡市虹源生物科技有限公司 | Method for preparing high-purity ellagic acid by using macroporous resin method to purify tannin |
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| CN102020682B (en) | 2013-06-05 |
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