CN101974063B - Method for preparing camellia saponin B2 - Google Patents
Method for preparing camellia saponin B2 Download PDFInfo
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- CN101974063B CN101974063B CN201010535344A CN201010535344A CN101974063B CN 101974063 B CN101974063 B CN 101974063B CN 201010535344 A CN201010535344 A CN 201010535344A CN 201010535344 A CN201010535344 A CN 201010535344A CN 101974063 B CN101974063 B CN 101974063B
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- Prior art keywords
- saponin
- tsubaki
- ethanol
- preparation
- reflux
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- 238000000034 method Methods 0.000 title claims abstract description 8
- YDGQDJXYFVWQDO-UHFFFAOYSA-N camelliasaponin B1 Natural products CC=C(/C)C(=O)OC1CC(C)(C)CC2C3=CCC4C5(C)CCC(OC6OC(CO)C(O)C(OC7OCC(O)C(O)C7OC8OC(CO)C(O)C(O)C8O)C6OC9OC(CO)C(O)C(O)C9O)C(C)(C=O)C5CCC4(C)C3(C)CC(O)C12CO YDGQDJXYFVWQDO-UHFFFAOYSA-N 0.000 title abstract description 5
- MGTOPLIWMNGFCQ-UHFFFAOYSA-N camelliasaponin B2 Natural products O=CC1(C)C2CCC3(C)C4(C)CC(O)C5(CO)C(OC(=O)C(C)=CC)CC(C)(C)CC5C4=CCC3C2(C)CCC1OC(C1OC2C(C(O)C(O)C(CO)O2)O)OC(C(O)=O)C(O)C1OC1OCC(O)C(O)C1OC1OC(CO)C(O)C(O)C1O MGTOPLIWMNGFCQ-UHFFFAOYSA-N 0.000 title abstract description 5
- MGTOPLIWMNGFCQ-PGGKNCGUSA-N camelliasaponin b2 Chemical compound O=CC1(C)C2CCC3(C)C4(C)CC(O)C5(CO)C(OC(=O)C(/C)=C/C)CC(C)(C)CC5C4=CCC3C2(C)CCC1OC(C1OC2C(C(O)C(O)C(CO)O2)O)OC(C(O)=O)C(O)C1OC1OCC(O)C(O)C1OC1OC(CO)C(O)C(O)C1O MGTOPLIWMNGFCQ-PGGKNCGUSA-N 0.000 title abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000011347 resin Substances 0.000 claims abstract description 14
- 229920005989 resin Polymers 0.000 claims abstract description 14
- 238000000605 extraction Methods 0.000 claims abstract description 13
- 239000012046 mixed solvent Substances 0.000 claims abstract description 13
- 238000010992 reflux Methods 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 238000004064 recycling Methods 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 7
- 235000018597 common camellia Nutrition 0.000 claims abstract description 6
- 238000002425 crystallisation Methods 0.000 claims abstract description 6
- 230000008025 crystallization Effects 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 239000001397 quillaja saponaria molina bark Substances 0.000 claims description 22
- 230000006837 decompression Effects 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 238000011084 recovery Methods 0.000 claims description 10
- 239000003463 adsorbent Substances 0.000 claims description 8
- 239000002699 waste material Substances 0.000 claims description 6
- 240000001548 Camellia japonica Species 0.000 claims description 5
- 230000000274 adsorptive effect Effects 0.000 claims description 5
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000012141 concentrate Substances 0.000 claims description 5
- 238000010828 elution Methods 0.000 claims description 5
- 238000001640 fractional crystallisation Methods 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 241000209507 Camellia Species 0.000 abstract description 3
- 239000013078 crystal Substances 0.000 abstract 1
- 239000003480 eluent Substances 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 238000001179 sorption measurement Methods 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 241000196324 Embryophyta 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
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 230000010355 oscillation Effects 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
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- Steroid Compounds (AREA)
Abstract
The invention relates to a method for preparing camellia saponin B2 which is convenient to operate, eco-friendly and energy-saving. The process comprises the following steps of: taking camellia seed residues after oil press, adding ethanol and heating and refluxing, merging reflux, filtering, taking filtrate, recycling the ethanol under reduced pressure until the ethanol is completely recycled, obtaining reflux, performing multistage countercurrent extraction by using an n-butyl alcohol-water mixed solvent with a ratio of 10:1, merging extractive, recycling the solvent under reduced pressure and concentrating, absorbing by using a macroporous adsorption resin column, eluting by using the ethanol, collecting eluent, recycling the solvent under reduced pressure and drying, adding methanol for crystallization, separating crystals, and washing and drying to prepare the camellia saponin B2. The camellia saponin B2 prepared by the method has high product purity and is easy to realize industrial production.
Description
Technical field
The present invention relates to the preparation method of a kind of Tsubaki-saponin B2, especially a kind of preparation method who from plant, extracts Tsubaki-saponin B2.
Background technology
Tsubaki-saponin B2 (Camelliasaponin B2), molecular formula: C
58H
90O
26, molecular weight: 1203.333, CAS accession number: 156317-50-9.Mainly be present in the seed of plant of theaceae camellia Camellia japonical L., and raw material sources are abundant.Its molecular formula is following:
Modern study shows that Tsubaki-saponin B2 has the stronger activity of relieving the effect of alcohol, and it is also as the raw material that synthesizes other reactive derivative simultaneously.
The seed of plant of theaceae camellia Camellia japonical L. is used to oil expression, contains a large amount of Tsubaki-saponin B2 in its waste residue.
In the prior art, still be not applicable to preparation technology's report of high purity Tsubaki-saponin B2 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, Tsubaki-saponin B2 that product purity is high.
For solving the problems of the technologies described above, the present invention adopts following technical proposal:
Get the camellia seeds waste residue after the oil expression, add 60-90% alcohol heating reflux 1-3 time that its quality 4-8 doubly measures volume, each 1-2 hour, merge phegma; Filter, get filtrating, decompression recycling ethanol gets phegma to the greatest extent; The use ratio is that 10: 1 n-butanol-water mixed solvent carries out the extraction of 6-8 stage countercurrent, and the volume ratio of liquid concentrator and the total consumption of mixed solvent is 1: 6-8, and combining extraction liquid, decompression and solvent recovery also concentrates; Be added on the macroporous adsorptive resins and adsorb, the 60-80% ethanol elution is collected 3-8 and is doubly measured the column volume elutriant, and decompression and solvent recovery is also dry; Add methanol crystallization, fractional crystallization washs, is drying to obtain.
It is 80% that reflux is used concentration of ethanol, and consumption is 6 times of amount volumes of raw materials quality.
The number of times of reflux is 2 times, each 1.5 hours.
The progression of counter-current extraction is 7 grades, and the volume ratio of liquid concentrator and the total consumption of mixed solvent is 1: 7.
Macroporous adsorbent resin is selected from a kind of in HPD-700 type, H-50 type, the CD-180 type macroporous adsorbent resin.
It is 70% that the macroporous adsorbent resin wash-out uses concentration of ethanol.
It is 5 times of amount column volumes that the macroporous adsorbent resin wash-out uses the alcoholic acid collecting amount.
Preparation gained Tsubaki-saponin B2 can adopt following method to detect:
Test Example 1HPLC method is measured Tsubaki-saponin B2 purity
Chromatographic condition
Chromatographic column: octadecylsilane bonding glue silica gel is weighting agent; Moving phase: methanol-water (80: 20); Flow velocity: 1.0mL/min; Detect wavelength: 224nm; Column temperature: 30 ℃.
Measuring method
Precision takes by weighing Tsubaki-saponin B22mg, 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 Tsubaki-saponin B2, be beneficial to big production operation, energy consumption is little, pollutes little.
To combine embodiment that the present invention is done further elaboration below, but the scope that the present invention requires to protect is not limited to following embodiment.
Embodiment
Embodiment 1
Get the camellia seeds waste residue 10Kg after the oil expression, add 60% alcohol heating reflux 1 time of 40L, 1 hour, collect phegma; Filter, get filtrating, decompression recycling ethanol gets phegma to the greatest extent; The use ratio is that 10: 1 n-butanol-water mixed solvent carries out the extraction of 6 stage countercurrents, and the volume ratio of liquid concentrator and the total consumption of mixed solvent is 1: 6, combining extraction liquid, and decompression and solvent recovery also concentrates; Be added on the HPD-700 type macroporous adsorptive resins and adsorb, 60% ethanol elution is collected 3 times of amount column volume elutriants, and decompression and solvent recovery is also dry; Add methanol crystallization, fractional crystallization washs, is drying to obtain Tsubaki-saponin B
252.3g, detecting through HPLC, purity is 95.5%, UV, IR, MS,
2HNMR,
13The data and the prior art of its physical behavior of sign such as CNMR are consistent.
Embodiment 2
Get the camellia seeds waste residue 10Kg after the oil expression, add 90% alcohol heating reflux 3 times of 80L, each 2 hours, merge phegma; Filter, get filtrating, decompression recycling ethanol gets phegma to the greatest extent; The use ratio is that 10: 1 n-butanol-water mixed solvent carries out the extraction of 8 stage countercurrents, and the volume ratio of liquid concentrator and the total consumption of mixed solvent is 1: 8, combining extraction liquid, and decompression and solvent recovery also concentrates; Be added on the H-50 type macroporous adsorptive resins and adsorb, 80% ethanol elution is collected 8 times of amount column volume elutriants, and decompression and solvent recovery is also dry; Add methanol crystallization, fractional crystallization washs, is drying to obtain Tsubaki-saponin B
277.5g, detecting through HPLC, purity is 94.2%, UV, IR, MS,
2HNMR,
13The data and the prior art of its physical behavior of sign such as CNMR are consistent.
Embodiment 3
Get the camellia seeds waste residue 10Kg after the oil expression, add 80% alcohol heating reflux 2 times of 60L, each 1.5 hours, merge phegma; Filter, get filtrating, decompression recycling ethanol gets phegma to the greatest extent; The use ratio is that 10: 1 n-butanol-water mixed solvent carries out the extraction of 7 stage countercurrents, and the volume ratio of liquid concentrator and the total consumption of mixed solvent is 1: 7, combining extraction liquid, and decompression and solvent recovery also concentrates; Be added on the CD-180 type macroporous adsorptive resins and adsorb, 70% ethanol elution is collected 5 times of amount column volume elutriants, and decompression and solvent recovery is also dry; Add methanol crystallization, fractional crystallization washs, is drying to obtain Tsubaki-saponin B
258.9g, detecting through HPLC, purity is 97.8%, UV, IR, MS,
2HNMR,
13The data and the prior art of its physical behavior of sign such as CNMR are consistent.
Claims (7)
1. the preparation method of a Tsubaki-saponin B2 is characterized in that described method is made up of the following step: get the camellia seeds waste residue after the oil expression, add 60-90% alcohol heating reflux 1-3 time that its quality 4-8 doubly measures volume, each 1-2 hour; Merge phegma, filter, get filtrating, decompression recycling ethanol is to most; Get phegma, the use ratio is that 10: 1 n-butanol-water mixed solvent carries out the extraction of 6-8 stage countercurrent, and the volume ratio of liquid concentrator and the total consumption of mixed solvent is 1: 6-8; Combining extraction liquid, decompression and solvent recovery also concentrates, and is added on the macroporous adsorptive resins and adsorbs; The 60-80% ethanol elution is collected 3-8 and is doubly measured the column volume elutriant, and decompression and solvent recovery is also dry; Add methanol crystallization, fractional crystallization washs, is drying to obtain.
2. according to the preparation method of the said a kind of Tsubaki-saponin B2 of claim 1, it is characterized in that it is 80% that said reflux is used concentration of ethanol, consumption is 6 times of amount volumes of raw materials quality.
3. according to the preparation method of the said a kind of Tsubaki-saponin B2 of claim 1, the number of times that it is characterized in that said reflux is 2 times, each 1.5 hours.
4. according to the preparation method of the said a kind of Tsubaki-saponin B2 of claim 1, the progression that it is characterized in that said counter-current extraction is 7 grades, and the volume ratio of liquid concentrator and the total consumption of mixed solvent is 1: 7.
5. according to the preparation method of the said a kind of Tsubaki-saponin B2 of claim 1, it is characterized in that said macroporous adsorbent resin is selected from a kind of in HPD-700 type, H-50 type, the CD-180 type macroporous adsorbent resin.
6. according to the preparation method of the said a kind of Tsubaki-saponin B2 of claim 1, it is characterized in that it is 70% that said macroporous adsorbent resin wash-out uses concentration of ethanol.
7. according to the preparation method of the said a kind of Tsubaki-saponin B2 of claim 1, it is characterized in that it is 5 times of amount column volumes that said macroporous adsorbent resin wash-out uses the alcoholic acid collecting amount.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010535344A CN101974063B (en) | 2010-11-09 | 2010-11-09 | Method for preparing camellia saponin B2 |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010535344A CN101974063B (en) | 2010-11-09 | 2010-11-09 | Method for preparing camellia saponin B2 |
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| Publication Number | Publication Date |
|---|---|
| CN101974063A CN101974063A (en) | 2011-02-16 |
| CN101974063B true CN101974063B (en) | 2012-10-03 |
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|---|---|---|---|
| CN201010535344A Expired - Fee Related CN101974063B (en) | 2010-11-09 | 2010-11-09 | Method for preparing camellia saponin B2 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101301401A (en) * | 2008-06-18 | 2008-11-12 | 沈阳药科大学 | Camellia effective ingredients and extracting method and use thereof |
| CN101392015A (en) * | 2008-07-22 | 2009-03-25 | 沈阳药科大学 | Triterpene saponin in camellia seeds, preparation method and medical use thereof |
-
2010
- 2010-11-09 CN CN201010535344A patent/CN101974063B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101301401A (en) * | 2008-06-18 | 2008-11-12 | 沈阳药科大学 | Camellia effective ingredients and extracting method and use thereof |
| CN101392015A (en) * | 2008-07-22 | 2009-03-25 | 沈阳药科大学 | Triterpene saponin in camellia seeds, preparation method and medical use thereof |
Non-Patent Citations (1)
| Title |
|---|
| Massyuki Yoshikawa et.al.Bioactive saponins and glycosides.V. acylated polyhydroxyolean-12-ene triterpene oligoglycosides, camelliasaponins A1, A2, B1, B2, C1, and C2, from the seeds of Camellia japonica L.: structures and inhibitory activity on alcohol absorption.《Chem.Pharm.Bull》.1996,第44卷(第10期),1899-1907. * |
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| CN101974063A (en) | 2011-02-16 |
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Owner name: NANTONG WEIHE MARINE PARTS CO., LTD. Free format text: FORMER OWNER: SUZHOU PAITENG BIOPHARMACEUTICAL TECHNOLOGY CO., LTD. Effective date: 20131121 |
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Effective date of registration: 20180917 Address after: 226000 639 north outer ring road, Nantong, Jiangsu Patentee after: NANTONG BEICHENG SCIENCE & TECHNOLOGY ENTREPRENEURIAL MANAGEMENT CO., LTD. Address before: 226000 Nantong road Gangzha District, Jiangsu Province Tang Gate Town Street Industrial Park, Changtai road 687 Patentee before: Nantong Weihe shipboard Fittings Co. Ltd. |
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