CN102260307A - Method for preparing specnuezhenide - Google Patents
Method for preparing specnuezhenide Download PDFInfo
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- CN102260307A CN102260307A CN2010101868672A CN201010186867A CN102260307A CN 102260307 A CN102260307 A CN 102260307A CN 2010101868672 A CN2010101868672 A CN 2010101868672A CN 201010186867 A CN201010186867 A CN 201010186867A CN 102260307 A CN102260307 A CN 102260307A
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- ligustrum lucidum
- lucidum ait
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Abstract
The invention discloses a method for extracting and separating specnuezhenide from Chinese medicine of glossy privet fruit. The method comprises the following steps of: performing extraction on the Chinese medicine of glossy privet fruit by using 80 percent ethanol water, concentrating an extracting solution, extracting by using ethyl acetate, extracting by using water saturated n-butyl alcohol, concentrating a n-butyl alcohol extracting solution, dissolving in water, loading on macroporous resin, eluting by using 10 to 30 percent and 50 to 70 percent methanol water, collecting eluant of the 50 to 70 percent methanol water, concentrating until dryness, dissolving in a small amount of methanol, loading on a gel column, eluting by using 30 to 50 percent methanol water, collecting specnuezhenide-containing eluant, volatilizing the solvent completely, and recrystallizing to obtain the high-purity target compound of specnuezhenide, wherein the purity of the specnuezhenide is over 98 percent. The specnuezhenide successfully prepared by the method meets the requirement of market for Chinese reference substance specnuezhenide, and the method is simple.
Description
One, technical field
The present invention relates to a kind of method that from the Chinese medicinal materials Glossy Privet Fruit, prepares special Ligustrum lucidum Ait (nuezhenoside), belong to the extracts active ingredients separation field of crude drug.
Two, background technology
Glossy Privet Fruit is the dry mature fruit of Oleaceae plant glossy privet Ligustrum lucidum Ait., is the conventional Chinese medicine material.Special Ligustrum lucidum Ait (nuezhenoside) is an activeconstituents main in the Glossy Privet Fruit, belongs to secoiridoid glycoside composition, and its structure is as scheming:
According to bibliographical information, the iridoid glycoside in the Glossy Privet Fruit has preferably multiple pharmacological effect such as hepatic cholagogic, anti-hepatic fibrosis, antisepsis and anti-inflammation, antitumor, reducing blood-fat, hypoglycemic, blood viscosity lowering, enhancing body immunomodulatory.We through a series of separation and purification, obtain the pure product of special Ligustrum lucidum Ait from Glossy Privet Fruit, content is more than 98%.
Three, summary of the invention
1, goal of the invention: the purpose of this invention is to provide a kind of practicable preparation method who obtains special Ligustrum lucidum Ait.
2, technical scheme: the preparation method of special Ligustrum lucidum Ait of the present invention is characterized in that this method may further comprise the steps:
(1) Glossy Privet Fruit is heated to 85 ℃ of refluxing extraction with the solvent of 80% ethanol water.
(2) extracting solution with (1) ethanol-water extraction concentrates steaming to nothing alcohol flavor, behind ethyl acetate extraction,
The water saturated n-butanol extraction of the aqueous solution.
(3) after being concentrated, (2) water saturated butanol extraction liquid uses water dissolution.
(4) aqueous solution of (3) is crossed macroporous resin column, use 10-30%, 50%-70% methanol-water with this wash-out.
(5) (4) 50%-70% methanol-water elutriant is concentrated into dried, crosses gel column with small amount of methanol dissolving back, with 30%-50% methanol-water wash-out.
(6) collect the cut that contains special Ligustrum lucidum Ait in (5) 30%-50% methanol-water elutriant, after concentrating, recrystallization can obtain the special Ligustrum lucidum Ait of highly purified target compound.
In step (1), 80% used aqueous ethanolic solution, its consumption are 10-15 times of medicinal material weight, and the time that the medicinal material thermal backflow is extracted is 6-8 hour, and the thermal backflow number of times is 3-5 time.
In step (2), used ethyl acetate consumption is to be extracted the long-pending 1-3 of liquid doubly, and used water saturated propyl carbinol consumption is to be extracted the long-pending 1-4 of liquid doubly.Extract 2-4 time.
In step (3), butanol extraction liquid is concentrated into solid state, and the consumption of water is 0.5-1.0 a times of medicinal material weight.
In step (4), used polymeric adsorbent is D101 and AB-8 macroporous resin, 50%-70% methanol-water during solutions employed.
In step (5), used is gel column, 30%-50% weight methanol-water during solutions employed, and used solvent is water and organic solvent, organic solvent can be methyl alcohol or alcohol solvent; The number of times of recrystallization can be 1-3 time.
3, beneficial effect: adopt special Ligustrum lucidum Ait extracting and purifying method of the present invention, (1) separates the special Ligustrum lucidum Ait yield that obtains more than 1% from Glossy Privet Fruit, and purity is more than 95%.(2) according to the high performance liquid phase testing conditions of bibliographical information (" the HPLC method is measured the content of Ligustrum lucidum Ait in the Glossy Privet Fruit medicinal material " (pharmaceutical analysis magazine, 2009,29:824-826)) measure, the result shows, the special Ligustrum lucidum Ait content of gained shows this feasible process more than 98%.
Four, description of drawings
Accompanying drawing is to utilize the HPLC of the special Ligustrum lucidum Ait that this method prepares to detect collection of illustrative plates.
Five, embodiment
Be embodiments of the invention below, but the present invention is not limited only to described embodiment.
Embodiment 1: Glossy Privet Fruit was heated to 85 ℃ of refluxing extraction 8 hours with the solvent of 80% ethanol water of 10 times of medicinal material weight, extracting solution is concentrated steaming to nothing alcohol flavor, with the ethyl acetate extraction of 1 times of medicinal material weight 3 times, the aqueous solution is used the n-butanol extraction 3 times of 1 times of medicinal material weight again, butanol extraction liquid concentrates the back with crossing macroporous resin column after the water dissolution with 50% weight methanol-water wash-out, 50% weight methanol-water elutriant is concentrated the back with crossing gel column after the water dissolution, with 30% weight methanol-water wash-out, after 30% weight methanol-water elutriant concentrates, can obtain the special Ligustrum lucidum Ait of highly purified target compound with 60% methanol-water recrystallization, yield is 0.90%, and purity is 98.1%.
Embodiment 2: Glossy Privet Fruit was heated to 85 ℃ of refluxing extraction 7 hours with the solvent of 80% ethanol water of 15 times of medicinal material weight, extracting solution is concentrated steaming to nothing alcohol flavor, with the ethyl acetate extraction of 2 times of medicinal material weight 2 times, the aqueous solution is used the n-butanol extraction 3 times of 3 times of medicinal material weight again, butanol extraction liquid concentrates the back with crossing macroporous resin column after the water dissolution with 60% weight methanol-water wash-out, 60% weight methanol-water elutriant is concentrated the back with crossing gel column after the water dissolution, with 40% weight methanol-water wash-out, after 40% weight methanol-water elutriant concentrates, can obtain the special Ligustrum lucidum Ait of highly purified target compound with 80% ethanol water recrystallization, yield is 0.95%, and purity is 99.0%.
Embodiment 3: Glossy Privet Fruit was heated to 85 ℃ of refluxing extraction 7 hours with the solvent of 80% ethanol water of 13 times of medicinal material weight, extracting solution is concentrated steaming to nothing alcohol flavor, with the ethyl acetate extraction of 3 times of medicinal material weight 2 times, the aqueous solution is used the n-butanol extraction 3 times of 3 times of medicinal material weight again, butanol extraction liquid concentrates the back with crossing macroporous resin column after the water dissolution with 60% weight methanol-water wash-out, 60% weight methanol-water elutriant is concentrated the back with crossing gel column after the water dissolution, with 50% weight methanol-water wash-out, after 50% weight methanol-water elutriant concentrates, can obtain the special Ligustrum lucidum Ait of highly purified target compound with 90% methanol-water recrystallization, yield is 0.93%, and purity is 98.1%.
The purity detecting of special Ligustrum lucidum Ait
It is an amount of to get the special Ligustrum lucidum Ait monomer that method for preparing obtains, and methyl alcohol is dissolved in the volumetric flask, behind the filtering with microporous membrane, treats the sample introduction analysis.
Chromatographic condition: Agilent 1200 high performance liquid chromatograph devices, Agilent G1314A UV-detector; Chromatographic column: Welch Materials XB-C18,5 μ m, 250*4.6mm; Moving phase: methyl alcohol (A)-water (B), gradient elution [0～40min, 15%A → 40%A] detects wavelength: 240nm, flow velocity: 1ml/min; Sample size: 10 μ l; The concrete analysis spectrogram is asked for an interview Figure of description.
The special Ligustrum lucidum Ait self-control of reference substance, through mensuration such as 1H-NMR, 13C-NMR, MS, its data are consistent with document, are accredited as special Ligustrum lucidum Ait.The TLC collection of illustrative plates is a spot, and HPLC detects to unimodal, and normalization method content is more than 98%, and theoretical plate number is more than 8000.
More than described the extracting method of the special Ligustrum lucidum Ait among the present invention, wherein comprised variation understood by one of ordinary skill in the art and change but need to understand.These variations and change are also contained in the scope of the present invention that claim limits.
The spectral data of reference substance and parsing
1UV
max(MeOH/H2O?1∶1)：240，280nm。
2IR(KRr)Vmax：3421，1707，1630，1516，1442cm
-1。
3ESIMS：[M+1]＝625。
4?
1H-NMR(DMSO-d)：δ：7.49(1H，s，3-H)，7.01，7.00(2H，d，J＝8.4Hz)，6.64(2H，d，?J＝8.4Hz)，5.95(1H，q，8-H)，4.92(1H，d，J＝7.5Hz)，3.64(3H，s，-OCH
3-)，1.67(3H，d，10-CH
3)。
5?
13C-NMR(DMSO-d)：δ：92.9(C-1)，153.3(C-3)，107.71(C-4)，30.0(C-5)，39.5(C-6)，170.6(C-7)，123.0(C-8)，129.6(C-9)，13.0(C-10)，166.1(C-11)，70.0(α-CH2-)，34.8(β-CH2-)，51.1(-OCH3)，98.9(C-1`)，73.2(C-2`)，76.5(C-3`)，69.9(C-4`)，76.4(C-5`)，61.0(C-6`)，102.8(C-1``)，73.5(C-2``)，77.3(C-3``)，70.0(C-4``)，73.5(C-5``)，64.0(C-6``)，128.6(C-1```)，129.6(C-2```)，114.9(C-3```)，155.5(C-4```)，114.9(C-5```)，129.2(C-6```)。
Claims (7)
1. the preparation method of a special Ligustrum lucidum Ait is characterized in that this method may further comprise the steps:
(1) Glossy Privet Fruit is heated to 85 ℃ of refluxing extraction with the solvent of 80% ethanol water.
(2) extracting solution with (1) ethanol-water extraction concentrates steaming to nothing alcohol flavor, and behind ethyl acetate extraction, the aqueous solution extracts with water saturated butanol solution.
(3) after being concentrated, the extracting solution of (2) n-butanol extraction uses water dissolution.
(4) aqueous solution of (3) is crossed macroporous resin column 50%-70% methanol-water wash-out.
(5) (4) 50%-70% methanol-water elutriant is concentrated into dried, crosses gel column with small amount of methanol dissolving back, with 30%-50% methanol-water wash-out.
(6) will contain the cut of Saudi Arabia's Ligustrum lucidum Ait in (5) 30%-50% methanol-water elutriant, after concentrating, recrystallization can obtain the special Ligustrum lucidum Ait of highly purified target compound, and purity is more than 98%.
2. the preparation method of a kind of special Ligustrum lucidum Ait according to claim 1 is characterized in that in step (1), the ethanol ratio can be between 40%-95% in the used aqueous ethanolic solution, and its consumption is 6-15 a times of medicinal material; The time that the medicinal material thermal backflow is extracted is 6-12 hour, and the thermal backflow number of times is 3-5 time.
3. the preparation method of a kind of special Ligustrum lucidum Ait according to claim 1 is characterized in that in step (2), and used ethyl acetate consumption is to be extracted the long-pending 1-3 of liquid doubly, extracts 2-3 time; Used water saturated propyl carbinol consumption is to be extracted the long-pending 1-4 of liquid doubly, extracts 2-4 time.
4. the preparation method of a kind of special Ligustrum lucidum Ait according to claim 1 is characterized in that being concentrated into solid state in step (3); The consumption of water is 0.4-0.8 a times of medicinal material weight.
5. the preparation method of a kind of special Ligustrum lucidum Ait according to claim 1 is characterized in that in step (4), used polymeric adsorbent is the macroporous resin of D101 and AB-8; Solutions employed is the 50%-70% methanol-water.
6. the preparation method of a kind of special Ligustrum lucidum Ait according to claim 1 is characterized in that in step (5) used gel column; Solutions employed is the 30%-50% methanol-water; Used solvent is water and organic solvent.
7. the preparation method of a kind of special Ligustrum lucidum Ait according to claim 1 is characterized in that in step (6), organic solvent can be methyl alcohol or alcohol solvent; The number of times of recrystallization can be 1-3 time.
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| CN2010101868672A CN102260307A (en) | 2010-05-28 | 2010-05-28 | Method for preparing specnuezhenide |
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| CN2010101868672A CN102260307A (en) | 2010-05-28 | 2010-05-28 | Method for preparing specnuezhenide |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105330710A (en) * | 2015-10-23 | 2016-02-17 | 大连医科大学 | Method for simultaneously extracting three kinds of iridoid glycoside chemical reference substances from fructus ligustri lucidi |
| CN106466326A (en) * | 2016-09-30 | 2017-03-01 | 郑州大学第附属医院 | Specnuezhenside and combinations thereof and application in lipid-loweringing for the pharmaceutical preparation |
| CN106466325A (en) * | 2016-09-30 | 2017-03-01 | 郑州大学第附属医院 | The medicine of a kind of prevention or treatment diabetes, compositionss and its preparation |
| 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 |
| CN110041386A (en) * | 2019-04-24 | 2019-07-23 | 长沙学院 | Preparation method, Specnuezhenide and its application of Specnuezhenide |
-
2010
- 2010-05-28 CN CN2010101868672A patent/CN102260307A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105330710A (en) * | 2015-10-23 | 2016-02-17 | 大连医科大学 | Method for simultaneously extracting three kinds of iridoid glycoside chemical reference substances from fructus ligustri lucidi |
| CN105330710B (en) * | 2015-10-23 | 2018-03-16 | 大连医科大学 | A kind of method for extracting three kinds of iridoid glycosides chemical reference substances simultaneously from the fruit of glossy privet |
| CN106466326A (en) * | 2016-09-30 | 2017-03-01 | 郑州大学第附属医院 | Specnuezhenside and combinations thereof and application in lipid-loweringing for the pharmaceutical preparation |
| CN106466325A (en) * | 2016-09-30 | 2017-03-01 | 郑州大学第附属医院 | The medicine of a kind of prevention or treatment diabetes, compositionss and its preparation |
| CN106466325B (en) * | 2016-09-30 | 2019-02-22 | 郑州大学第一附属医院 | A kind of drug, composition and its preparation prevented or treat diabetes |
| 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 |
| CN110041386A (en) * | 2019-04-24 | 2019-07-23 | 长沙学院 | Preparation method, Specnuezhenide and its application of Specnuezhenide |
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