CN102372754A - Method for preparing specnuezhenide - Google Patents
Method for preparing specnuezhenide Download PDFInfo
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- CN102372754A CN102372754A CN2011103371086A CN201110337108A CN102372754A CN 102372754 A CN102372754 A CN 102372754A CN 2011103371086 A CN2011103371086 A CN 2011103371086A CN 201110337108 A CN201110337108 A CN 201110337108A CN 102372754 A CN102372754 A CN 102372754A
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- ligustrum lucidum
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- lucidum ait
- specnuezhenide
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract
The invention relates to a method for extracting specnuezhenide crude products (higher than 80 percent) and high-purity specnuezhenide (higher than 98 percent) from fructus ligustri lucidi, which belongs to the field of natural medicine chemistry. The fructus ligustri lucidi is used as a raw material, medicine materials are firstly crushed, a water decoction extraction method is selected, extracting solution is rarefied by macroporous resin columns after being slightly concentrated, then, the alcohol deposition treatment is carried out, and finally, the positive silica gel column purification and the opposite silica gel column purification are selected for preparing the specnuezhenide with different content requirements. The method can be used for preparing the specnuezhenide with lower content in a scale way, the yield is high, the operation is simple, and the cost is low; and the specnuezhenide with higher content can also be prepared, the yield is lower, the cost is higher, the selection can be carried out according to the content requirement, raw material parts and reagent parts during the preparation by the two method can be repeatedly utilized, and the preparation cost is lower than that of the existing preparation method.
Description
Technical field
The invention belongs to the Natural Medicine Chemistry field, relate to a kind of method of from Glossy Privet Fruit, extracting special Ligustrum lucidum Ait bullion (＞80%) and the special Ligustrum lucidum Ait of high purity (＞98%).
Background technology
Glossy Privet Fruit is the dry mature fruit of Oleaceae plant glossy privet Ligustrum lucidum Ait..Glossy Privet Fruit mainly contains chemical ingredientss such as triterpenes, ether terpene, phenylethanol, flavonoid.Special Ligustrum lucidum Ait, English Specnuezhenide by name is a kind of secoiridoid glycosides in the Glossy Privet Fruit, and special Ligustrum lucidum Ait is as a stronger composition of specificity, and recording first is the index components of 2010 editions Chinese Pharmacopoeia Glossy Privet Fruit medicinal material assays, and its molecular formula is C
31H
42O
17, molecular weight is 686.5, and it is a composition that content is higher in Glossy Privet Fruit, and its pharmacological research is less, discovers that it has pharmacological actions such as immunomodulatory, mutation.
Bibliographical information is less about the separation purification method of special Ligustrum lucidum Ait at present; See an invention disclosed patent CN101704857A is arranged; This patent relates to the method that from Glossy Privet Fruit separation and purification obtains the special Ligustrum lucidum Ait of high purity, and this method is mainly uses extraction using alcohol, uses sherwood oil, chloroform, propyl carbinol, organic solvent extraction then; Through macroporous resin purification, get with the reverse phase silica gel purifying again.This method can separation and purification obtain highly purified special Ligustrum lucidum Ait, but flow process is comparatively complicated with operation, is not suitable for preparing in a large number the higher special Ligustrum lucidum Ait of purity simultaneously.
Summary of the invention
The present invention provides a kind of mass-producing, the special Ligustrum lucidum Ait of flow process easy manufacture to give birth to the operational path and the method for bullion and the special Ligustrum lucidum Ait of high purity.
The technical solution adopted for the present invention to solve the technical problems is:
1) pulverize: get the Glossy Privet Fruit medicinal material, put drying in the loft drier, taking-up is put cold, and kibbler is pulverized, and crosses sieve No. three, gets the Glossy Privet Fruit medicinal powder.
2) extract: get the Glossy Privet Fruit powder, add water 5-10 at every turn and doubly decoct 2h, extract 3 times, filter, merge filtrating three times.
3) macroporous resin purification: get the Glossy Privet Fruit extracting solution, be concentrated into sample solution concentration and be about 0.5g medicinal material/ml, last appearance, first water is the elutriant wash-out, discards water elution liquid, uses the 20%-40% ethanol elution again, collects elutriant.
4) ethanol sedimentation: the macroporous resin elutriant is concentrated into flowing soaking paste, and getting industrial spirit (95% ethanol), to adjust alcohol concn in right amount be 80%-95%, and shake well mixes, and places deposition, filters, and gets the filtrating evaporate to dryness.
5) silicagel column purifying: use earlier the purification on normal-phase silica gel column purification, wet method dress post, appearance on the dry method, elutriant is trichloromethane-methyl alcohol 5: 1.Make the more special Ligustrum lucidum Ait of high purity and then need use reverse silicagel column purifying, moving phase is methanol-water 30: 70.
Description of drawings
Accompanying drawing is the process route chart of the special Ligustrum lucidum Ait of preparation.
Embodiment
Followingly with reference to embodiment the present invention is described, present embodiment only is used for better explaining the present invention, the invention scope that it does not limit the present invention in any way.
The concrete grammar of the performance liquid content assaying method among the following embodiment with reference to " content assaying method of regulation in 2010 editions one one of the Chinese pharmacopoeia, combining method is learned and is investigated, the final feasible HPLC assay condition of confirming is:
Chromatographic column: ZorbaxC18 post (5 μ m, 4.6 * 150mm)
Moving phase: methanol-water (30: 70, v/v)
Flow velocity: 1.0mlmin-1
Detect wavelength: 224nm
Column temperature: 35 ℃.
Used Glossy Privet Fruit medicinal material is according to " content that the content assaying method under 2010 editions glossy privet subitems of Chinese pharmacopoeia records special Ligustrum lucidum Ait is 2.13%, and the content that records special Ligustrum lucidum Ait in the Glossy Privet Fruit medicinal material according to process for extracting of the present invention is 3.23%.
Embodiment one
Get Glossy Privet Fruit medicinal material 10kg, pulverize, successively add 10 times, 8 times, 8 times medicinal material water gagings and decoct 3 times, decoct 2h at every turn, each respectively the filtration and merging filtrate, filtrating suitably concentrates; Liquid concentrator is splined on the D-101 macroporous resin column, earlier with water elution, discards water lotion, uses 20% ethanol elution again, collects elutriant, is concentrated into flowing soaking paste; Add methyl alcohol and fully stir, place deposition, filter, the filtrating evaporate to dryness; Obtain a purity with normal phase silicagel column with reverse silicagel column separation and purification at last and reach 98% the about 28g of compound, syncaryon Magnetic Resonance Spectrum qualification result and existing literature research spectral data confirm that this compound is special Ligustrum lucidum Ait.
Embodiment two
Get the Glossy Privet Fruit medicinal material, pulverize; Claim 203g, add water 400ml and soak 30min, add water 1200ml again and extract 2h, filter, add water 1600ml more respectively and extract twice, filter, merges filtrating three times, filtrating is concentrated into about 400ml; Be splined on the D-101 macroporous resin column, use water elution earlier, discard water elution liquid, use 40% ethanol elution again, elutriant is concentrated into flowing soaking paste (about 40ml); Add industrial spirit (95% ethanol) 200ml, fully stirring shakes up, and places the 2h deposition, filters the filtrating evaporate to dryness; Use the normal phase silica gel chromatography column purification again, the special Ligustrum lucidum Ait bullion 3.375g that obtains, purity is 81.18%; The yield of this moment is 63.61%, uses reverse silica gel chromatography column purification again, the pure article 1.440g of the special Ligustrum lucidum Ait that obtains; Purity is 98.13%, and the yield of this moment is 21.55%.
Embodiment three
Prepare the method for special Ligustrum lucidum Ait according to patent CN101704857A, get and pulverize Glossy Privet Fruit medicinal material 227g, purifying obtains the pure article 1.853g of special Ligustrum lucidum Ait, and it is 98.40% that the HPLC assay gets its content, and this moment, the yield of special Ligustrum lucidum Ait was 20.03%.The yield that contrast discovery patent of invention CN101704857A prepares special Ligustrum lucidum Ait is a little less than this patent method.Embodiment two makes the pure article 1.440g of special Ligustrum lucidum Ait, and purity is 98.13%, and its cost of calculation of price that reference laboratories is bought each reagent and material is 799.3 yuan/g; Patent CN101704857A preparation method makes the pure article 1.853g of special Ligustrum lucidum Ait, and content is 98.40%, and assessing the cost with the method for cost accounting of embodiment two is 925.0 yuan/g.When strengthening dosage to 100kg; Cost further reduces; Further reasonably calculate and calculate the cost that this patent prepares special Ligustrum lucidum Ait in conjunction with the market value of each reagent and material and can reduce to about 608 yuan/g, patent CN101704857A can be reduced to about 766 yuan/g.But not only can prepare highly purified special Ligustrum lucidum Ait by last knowledge capital patent, and yield is high, its cost also has tangible reduction.Respectively to above three embodiment samples
1The HNMR spectrogram with
13The data of C NMR spectrogram are analyzed, and its spectral data is consistent:
1H-NMR (600MHz, CD30D): δ 7.58 (1H, s, H-3), 7.12 (2H, dd, J=8.5,1.9Hz, H-4 " ' and H-8 " '), 6.76 (2H, dd, J=8.5; 1.9Hz, H-5 " ' and H-7 " '), 6.15 (1H, q, J=6.8Hz, H-8), 5.98 (1H, br.s, H-1), 4.87 (1H, d, J=7.4Hz; H-1 '), 4.37 (1H, d, J=7.4Hz, H-1 "), 4.28 (1H, dd, J=11.9,5.8Hz, H-1 " '), 4.27 (1H; M, H-5), 3.94 (1H, dd, J=12.2,5.8Hz, H-1 " '), 4.42-3.39 (10H, m, sugars), 3.75 (3H; s ,-OCH3), 3.61 (1H, m, H-5), 2.91 (2H, m, H-2 " '), 2.82 (1H, dd, J=14.3; 4.9Hz, H-6), 2.55 (1H, dd, J=14.3,4.9Hz, H-6), 1.66 (3H, d, J=7.2Hz, H-10); 13C-NMR (150MHz, CD3OD): δ 173.2 (C-7), 168.9 (C-11), 156.9 (C-6 " '), 153.6 (C-3), 131.1 (C-4 " ', C-8 " '); 130.7 (C-8), 125.1 (C-9), 116.3 (C-5 " ', C-7 " '), 109.6 (C-4), 104.5 (C-1 "); (101.0 C-1 '), 95.3 (C-1), 78.5 (C-5 '), 78.1 (C-3 '), 78.0 (C-3 "), 75.3 (C-5 "); (75.1 C-2 '), 74.9 (C-2 "), 71.7 (C-4 '), 72.3 (C-4 "), 71.6 (C-1 " '), 65.2 (C-6 "); (62.8 C-6 '), 52.1 (OMe), 41.5 (C-6), 36.5 (C-2 " '), 31.9 (C-5), 13.9 (C-10).Its NMR data are consistent with the spectral data of the special Ligustrum lucidum Ait of existing document [1] (Nuezhenide), confirm that this compound is special Ligustrum lucidum Ait.
Claims (8)
1. the preparation method of a special Ligustrum lucidum Ait is characterized in that: may further comprise the steps:
1) pulverize: get Glossy Privet Fruit, put in the loft drier dryly, put coldly, kibbler is pulverized, and crosses sieve No. three;
2) extract: get the Glossy Privet Fruit powder in the step 1), boiling is filtered, and concentrates;
3) liquid concentrator macroporous resin purification: get step 2), last macroporous resin column, wash-out concentrates;
4) ethanol sedimentation: macroporous resin wash-out liquid concentrator in the step 3) is carried out ethanol sedimentation, and post precipitation filters, and filtrating is concentrated into dried cream;
5) silicagel column purifying: get dried cream in the step 4),, obtain special Ligustrum lucidum Ait bullion with normal phase silica gel column chromatography method purifying; Carry out purifying with reverse silica gel column chromatography and obtain highly purified special Ligustrum lucidum Ait.
2. the preparation method of special Ligustrum lucidum Ait as claimed in claim 1 is characterized in that: step 2) process for extracting be: boiling 3 times, decoct 2h at every turn, each water consumption is a 5-10 times of medicinal material amount.
3. the preparation method of special Ligustrum lucidum Ait as claimed in claim 1, it is characterized in that: macroporous resin sample solution concentration is 0.3-0.7g medicinal material/ml in the step 3).
4. the preparation method of special Ligustrum lucidum Ait as claimed in claim 1, it is characterized in that: the elution order of step 3) is: first water is the elutriant wash-out, discards water elution liquid, uses the 20%-40% ethanol elution again, collects elutriant.
5. the preparation method of special Ligustrum lucidum Ait as claimed in claim 1, it is characterized in that: the elutriant concentrating degree of step 3) is for being concentrated into flowing soaking paste.
6. the preparation method of special Ligustrum lucidum Ait as claimed in claim 1, it is characterized in that: the solution alcohol concn is 70%-95% in the step 4) alcohol precipitation process.
7. the preparation method of special Ligustrum lucidum Ait as claimed in claim 1 is characterized in that: moving phase is trichloromethane-methyl alcohol 5: 1～3: 1 in the normal phase silica gel chromatography purifying that step 5) is used.
8. the preparation method of special Ligustrum lucidum Ait as claimed in claim 1, it is characterized in that: moving phase is methanol-water solution in the reverse phase silica gel chromatogram purification that step 5) is used, methanol concentration is 20%～40%.
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| CN2011103371086A CN102372754A (en) | 2011-10-31 | 2011-10-31 | Method for preparing specnuezhenide |
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| CN2011103371086A CN102372754A (en) | 2011-10-31 | 2011-10-31 | Method for preparing specnuezhenide |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103592391A (en) * | 2013-11-21 | 2014-02-19 | 贵州信邦制药股份有限公司 | Method for determining specnuezhenide content in Zhenqifuzheng preparation |
| CN103868943A (en) * | 2013-01-30 | 2014-06-18 | 河南省科高植物天然产物开发工程技术有限公司 | Method for identifying glossy privet fruit medicinal material or derivative |
| CN106632544A (en) * | 2016-12-21 | 2017-05-10 | 上海诗丹德标准技术服务有限公司 | Method for preparing specnuezhenide reference substance |
| KR20170076449A (en) * | 2015-12-24 | 2017-07-04 | 주식회사 엘지생활건강 | Composition for improving skin conditions comprising Specnuezhenide |
| CN108329367A (en) * | 2018-04-23 | 2018-07-27 | 福建中医药大学 | A method of preparing Specnuezhenide from the fruit of glossy privet |
| CN110041386A (en) * | 2019-04-24 | 2019-07-23 | 长沙学院 | Preparation method, Specnuezhenide and its application of Specnuezhenide |
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| CN101347470A (en) * | 2008-08-01 | 2009-01-21 | 石任兵 | Glossy privet fruit total triterpenes extract and total phenols extract as well as preparation method thereof |
| CN101704857A (en) * | 2009-09-25 | 2010-05-12 | 中国中医科学院中药研究所 | Process for separating and purifying special component specnuezhenide of glossy privet fruit |
| CN101817864A (en) * | 2010-04-08 | 2010-09-01 | 苏州宝泽堂医药科技有限公司 | Method for extracting and purifying oleanolic acid and Ligustrum lucidum Ait |
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| CN101704857A (en) * | 2009-09-25 | 2010-05-12 | 中国中医科学院中药研究所 | Process for separating and purifying special component specnuezhenide of glossy privet fruit |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103868943A (en) * | 2013-01-30 | 2014-06-18 | 河南省科高植物天然产物开发工程技术有限公司 | Method for identifying glossy privet fruit medicinal material or derivative |
| CN103592391A (en) * | 2013-11-21 | 2014-02-19 | 贵州信邦制药股份有限公司 | Method for determining specnuezhenide content in Zhenqifuzheng preparation |
| KR20170076449A (en) * | 2015-12-24 | 2017-07-04 | 주식회사 엘지생활건강 | Composition for improving skin conditions comprising Specnuezhenide |
| KR102503109B1 (en) | 2015-12-24 | 2023-02-22 | 주식회사 엘지생활건강 | Composition for improving skin conditions comprising Specnuezhenide |
| CN106632544A (en) * | 2016-12-21 | 2017-05-10 | 上海诗丹德标准技术服务有限公司 | Method for preparing specnuezhenide reference substance |
| CN106632544B (en) * | 2016-12-21 | 2019-12-20 | 上海诗丹德标准技术服务有限公司 | Method for preparing specnuezhenide reference substance |
| CN108329367A (en) * | 2018-04-23 | 2018-07-27 | 福建中医药大学 | A method of preparing Specnuezhenide from the fruit of glossy privet |
| CN110041386A (en) * | 2019-04-24 | 2019-07-23 | 长沙学院 | Preparation method, Specnuezhenide and its application of Specnuezhenide |
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Application publication date: 20120314 |