CN102093210A - Purified preparation method of six ginkgoic acid monomers - Google Patents
Purified preparation method of six ginkgoic acid monomers Download PDFInfo
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- CN102093210A CN102093210A CN2010106063044A CN201010606304A CN102093210A CN 102093210 A CN102093210 A CN 102093210A CN 2010106063044 A CN2010106063044 A CN 2010106063044A CN 201010606304 A CN201010606304 A CN 201010606304A CN 102093210 A CN102093210 A CN 102093210A
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Abstract
The invention belongs to the fields of food and traditional Chinese medicines and relates to a purified preparation method of six ginkgoic acid monomers. The method comprises the following steps of: purifying a petroleum ether extractive of ginkgo nut testae through a medium-and-low pressure silicagel column to obtain a methanol combination solution for a primary ginkgoic acid purified compound; carrying out gradient elution by adopting a preparation type high-efficiency liquid-phase chromatograph on a high-pressure preparation chromatographic column by using methanol and an aqueous solution containing acetic acid as a mobile phase, collecting eluents tube by tube according to the peak appearing time and the intensity, and purifying the samples; combining the eluents which contain the same ginkgoic acid and have purities larger than 99 percent, and rotating for concentrating to remove the methanol; and finally, freezing and drying the concentrated solution in vacuum to remove water to obtain solid powder of six ginkgoic acid monomers of which the purities all reach higher than 99 percent. The six ginkgoic acid monomers prepared by the method can be used for preparing standard ginkgoic acid substances as standard products for detecting ginkgoic acid extractives and ginkgoic acid in ginkgoic acid health-care food and ginkgoic acid medicines produced by using the ginkgoic acid extractives.
Description
Technical field
The invention belongs to food, the field of Chinese medicines, be specifically related to 6 kinds of monomeric method for preparing purified of ginkgoic acid.
Background technology
Ginkgo (Ginkgo biloal L.) is China's special product, and the resource owning amount accounts for 70% of world's total amount, ranks first in the world.Ginkgo is used for medicinal existing more than 600 year history in China, and it also is the maximum natural plant crude drugs of American-European clinical study.Modern pharmacological research has proved conclusively ginkgolic flavone glycoside and bilobalide is its main activeconstituents, have the cognitive function that improves the senile dementia patient, improve that astogeny causes be losing one's memory, treat effects such as peripheral vascular disease.(Ginkgo Biloba extract is one of the natural drug of at present domestic and international treatment cardiovascular and cerebrovascular diseases salable and senile dementia EGb) to Folium Ginkgo extract, is widely used in medicine, food supplement etc.
Except functional component ginkgolic flavone glycoside and bilobalide, in Ginkgo Leaf and exosper, also there is a class alkylphenol acid, its content accounts for 1%～2% of Ginkgo Leaf dry weight, 3%～4% of exosper dry weight.Mainly form by gingko phenolic acid (ginkgolic acids), bilobol (ginkgols) and bilobol (bilobols).Ginkgoic acid is 6-alkyl or the 6-thiazolinyl series derivates that longer side chain is arranged on the Whitfield's ointment molecule C6 position, and alkyl chain and alkenylene chain two big classes are arranged, and side chain lengths is that 13～17 carbon, double key number are 0～2.It is bilobol that the gingko phenolic acid removes carboxyl, belongs to 3-alkylphenol series matter.Bilobol is a 5-alkyl o-phenol series matter, and its alkyl length is 15 carbon, and double key number is 0～1, is called hydrogenation bilobol (hydrobilobol) again.The structure of 5 kinds of bilobol acids ginkgoic acid compounds having reported is as follows:
Contemporary toxicology studies show that ginkgoic acid has the bio-toxicity of sensitization, embryotoxicity, immunotoxicity and cytotoxin etc., is considered to toxic side effect composition main among the EGb.Germany Schwabe company in 1991 patent (DE3940095 (A1)) among the proposition EGb ginkgo acids substances content should be lower than 10ppm.1997, the German Ministry of Health required the content＜5ppm of ginkgoic acid in EGb and the preparation thereof, if preparation can not reach this standard, will force to cancel its number of registration and the selling right.At present universally acknowledged EGb quality index regulation ginkgoic acid content must be less than 5ppm.2005 editions new standards of issuing Semen Ginkgo extrac of Chinese Pharmacopoeia wherein require ginkgoic acid＜10ppm.
In order the ginkgoic acid among the EGb to be carried out accurately quantitatively, need to adopt highly purified ginkgoic acid compounds monomer as quantitatively using standard substance, to guarantee carrying out of EGb quality control standard.At present, Britain LGC provides Ginkgolic AcidI (C
20H
32O
3And C
22H
34O
3Mixture, purity 〉=95%) and Ginkgolic Acid II (C
24H
38O
3, purity 〉=95%), purity is not high, can only be used for qualitative.Germany Schwabe company provides ginkgoic acid hybrid standard product (C
13:0, 11.5%; C
15:1, 45%; C
17:2, 2%; C
15:0, 3%; C
17:1, 38.5%), total ginkgolic acids purity also can only be used for qualitative more than 99%.Tongtian Biochemical Technology Co., Ltd., Shanghai provides ginkgoic acid C
13:0, C
15:1And C
17:1Reference substance, it is inaccurate that purity indicates.
The extraction of relevant ginkgoic acid, the existing many pieces of bibliographical informations of preparation:
1.Teris?A.van?Beek，Martijn?S.Wintermans.Preparative?isolation?and?dual?column?high-performance?liquidchromatography?of?ginkgolic?acids?from?Ginkgo?biloba.Journal?of?Chromatography?A，2001，930：109-117.
2. Ni Lan sweet-smelling grass, Lin Yanfei opens a mirror .RP-HPLC and separates preparation separating Ginkgo phenolic acids monomer component. Chinese patent medicine, 2002,24 (1): 54-56.
3. Jiang Yong is red, Yu Peiwei, Li Wuzhou, Cao Liqun. the separation of ginkgoic acid and analysis in the Folium Ginkgo extract. and daily chemical industry, 2002,32 (3): 66-68.
4. face upward pomegranate green grass or young crops, Wu Xiangyang, Chen Jun. the preparation of ginkgoic acid monomeric compound, Chinese Pharmaceutical Journal, 2003,38 (12): 909-911.
More than these researchs all adopted octadecyl silane (C
18) the high pressure preparative chromatography post of filler, the particle diameter of filler is between 15 μ m～40 μ m, and the method for van Beek has also used the cationic exchange coloum that adds silver ions to be further purified.Because the ginkgoic acid series compound do not reach baseline separation, so after the ginkgoic acid purification process of bibliographical information behind a purifying, also needed collections liquid concentrated, the repetition sample introduction was with the increase degree of purity of production under identical preparation condition.Product purity is generally between 95%～98%.And former study only has been purified into 5 kinds in 6 kinds of ginkgoic acids, two cis-trans-isomers of ginkgoic acid C17:1 do not separated.
The method of this patent adopts octyl bonded silica gel (C
8) the high pressure preparative chromatography post of filler, the particle diameter 5 μ m of filler, separating effect obviously improves, and is purified into 6 kinds of ginkgoic acid compounds monomers, and purity all reaches more than 99%.C13:0, C15:1, C17:2, C15:0, cis C17:1, the yield of trans C17:1 is respectively: 85%-95%, 80%-90%, 90%-95%, 90%-95%, 50%-60%, 30%-40%.Can satisfy among the EGb ginkgoic acid detects the monomeric demand of highly purified ginkgoic acid compounds.
Summary of the invention
The object of the present invention is to provide a kind of 6 kinds of monomeric method for preparing purified of ginkgoic acid, be used for the development of ginkgoic acid reference material, as the standard substance of ginkgoic acid detection.
Ginkgoic acid involved in the present invention is the alkyl or alkenyl phenol compound, has the structure as figure below general formula.Wherein, the R chain is an alkyl or alkenyl, and carbonatoms is 13～17, double key number 0～2.
The concrete operations of 6 kinds of monomeric method for preparing purified of ginkgoic acid that the present invention sets up are as follows:
1, the elementary purifying thing of ginkgoic acid is redissolved with methyl alcohol, ultrasonic dissolution is mixed with the solution that concentration is 100～1000mg/mL, crosses the organic phase filter membrane of aperture 0.22 μ m, and is standby.
2, be moving phase with the methyl alcohol and the aqueous solution that contains acetic acid, gradient elution adopts the preparative high performance liquid chromatography instrument on high pressure preparative chromatography post sample to be carried out purifying, press the ginkgoic acid compounds in appearance time and the intensity collection elutriant.
3, the elutriant to collecting detects by pipe with the analysis mode high performance liquid chromatograph, will contain with a kind of ginkgoic acid and purity greater than 99% elutriant merging.
4, to the elutriant of the merging that contains different ginkgoic acid compound monomers, concentrate with the rotation concentrating instrument respectively, remove methyl alcohol wherein.
5, with the concentrated solution of 6 kinds of ginkgoic acid compounds-60 ℃～-80 ℃ freezing after, moisture is removed in lyophilize in the vacuum lyophilization instrument. obtain 6 kinds of monomeric pressed powders of ginkgoic acid compounds.
In the above-mentioned method for preparing purified, the upper prop sample is the elementary purifying thing of ginkgoic acid that the ligroin extraction of ginkgo nut exosper obtains through mesolow silicagel column purifying.
In the above-mentioned method for preparing purified, the concentration of upper prop sample is every milliliter and contains the elementary purifying thing of ginkgoic acid 100mg～1000mg, and last sample volume is 100～300 μ L, and applied sample amount is 30mg～150mg, but is not limited to this applied sample amount.
In the above-mentioned method for preparing purified, the filler of the high pressure preparative liquid chromatography post of employing is octyl bonded silica gel (C
8), particle diameter 5 μ m, column dimension are 19mm * 150mm (I.D. * L), but be not limited to this column dimension.
In the above-mentioned method for preparing purified, the moving phase that adopts is the methyl alcohol and the aqueous solution that contains 0.4%～1.5% acetic acid, gradient elution, methyl alcohol gradually becomes 80: 20～90: 10 (V/V) with the ratio that contains the aqueous solution of 0.4%～1.5% acetic acid from 60: 40～75: 25 (V/V), and the flow velocity of moving phase is 15～35mL/min.
In the above-mentioned method for preparing purified, the bath temperature that adopts when the rotation of the elutriant of 6 kinds of ginkgoic acid compounds concentrates is 40 ℃～60 ℃.
In the above-mentioned method for preparing purified, the concentrated solution of ginkgoic acid compounds adopts the mode of vacuum lyophilization to remove moisture, obtains the monomeric pressed powder of ginkgoic acid compounds.
In the above-mentioned method for preparing purified, can purifying obtain the monomer of 6 kinds of ginkgoic acid compounds.
Description of drawings
The UPLC analysis of spectra of the elementary purifying thing of Fig. 1 ginkgoic acid, the ginkgoic acid of six chromatographic peak correspondences is followed successively by C13:0, C15:1, C17:2, C15:0, cis C17:1, trans C17:1
The high pressure preparative liquid chromatography spectrogram of Fig. 2 ginkgoic acid
The UPLC analysis of spectra of Fig. 3 ginkgoic acid C13:0
The UPLC analysis of spectra of Fig. 4 ginkgoic acid C15:1
The UPLC analysis of spectra of Fig. 5 ginkgoic acid C17:2
The UPLC analysis of spectra of Fig. 6 ginkgoic acid C15:0
The UPLC analysis of spectra of Fig. 7 ginkgoic acid cis C17:1
The UPLC analysis of spectra of the trans C17:1 of Fig. 8 ginkgoic acid
Embodiment
Embodiment 1: the elementary purifying thing of ginkgoic acid is redissolved with methyl alcohol, and ultrasonic dissolution is mixed with the solution that concentration is 900mg/mL, crosses the organic phase filter membrane of aperture 0.22 μ m, and is standby.Adopt octyl bonded silica gel (C
8) high pressure preparative liquid chromatography post (19mm * 150mm (I.D. * L), particle diameter 5 μ m), moving phase is the methyl alcohol and the aqueous solution that contains 0.4% acetic acid, methyl alcohol gradually became 90: 10 (V/V) from 75: 25 (V/V) with the ratio that contains the aqueous solution of 0.4% acetic acid in 25 minutes, the flow velocity of moving phase is 15mL/min.Last sample volume is 150 μ L, and applied sample amount is 135mg.Press the ginkgoic acid compounds in appearance time and the intensity collection elutriant.To the elutriant of collecting, on the analysis mode high performance liquid chromatograph, adopt octyl bonded silica gel (C
8) analytical column (4.6mm * 150mm (I.D. * L), particle diameter 5 μ m), be moving phase with methyl alcohol with the aqueous solution that contains 0.4% acetic acid, detect by pipe.To contain with a kind of ginkgoic acid and purity and merge, concentrate at 45 ℃ with the rotation concentrating instrument respectively then, remove methyl alcohol wherein greater than 99% elutriant.With the concentrated solution of 6 kinds of ginkgoic acid compounds-80 ℃ freezing after, moisture is removed in lyophilize in the vacuum lyophilization instrument, obtains 6 kinds of monomeric pressed powders of ginkgoic acid compounds.
Embodiment 2: the elementary purifying thing of ginkgoic acid is redissolved with methyl alcohol, and ultrasonic dissolution is mixed with the solution that concentration is 500mg/mL, crosses the organic phase filter membrane of aperture 0.22 μ m, and is standby.Adopt octyl bonded silica gel (C
8) high pressure preparative liquid chromatography post (19mm * 150mm (I.D. * L), particle diameter 5 μ m), moving phase is the methyl alcohol and the aqueous solution that contains 0.8% acetic acid, methyl alcohol gradually became 80: 20 (V/V) from 75: 25 (V/V) with the ratio that contains the aqueous solution of 0.8% acetic acid in 15 minutes, keep in 5 minutes, becoming 75: 25 (V/V) again after 10 minutes.The flow velocity of moving phase is 18mL/min.Last sample volume is 150 μ L, and applied sample amount is 75mg.Press the ginkgoic acid compounds in appearance time and the intensity collection elutriant.To the elutriant of collecting, on the analysis mode high performance liquid chromatograph, adopt octyl bonded silica gel (C
8) analytical column (4.6mm * 150mm (I.D. * L), particle diameter 5 μ m), be moving phase with methyl alcohol with the aqueous solution that contains 0.8% acetic acid, detect by pipe.To contain with a kind of ginkgoic acid and purity and merge, concentrate at 50 ℃ with the rotation concentrating instrument respectively then, remove methyl alcohol wherein greater than 99% elutriant.With the concentrated solution of 6 kinds of ginkgoic acid compounds-80 ℃ freezing after, moisture is removed in lyophilize in the vacuum lyophilization instrument, obtains 6 kinds of monomeric pressed powders of ginkgoic acid compounds.
Embodiment 3: the elementary purifying thing of ginkgoic acid is redissolved with methyl alcohol, and ultrasonic dissolution is mixed with the solution that concentration is 500mg/mL, crosses the organic phase filter membrane of aperture 0.22 μ m, and is standby.Adopt octyl bonded silica gel (C
8) high pressure preparative liquid chromatography post (19mm * 150mm (I.D. * L), particle diameter 5 μ m), moving phase is the methyl alcohol and the aqueous solution that contains 0.8% acetic acid, and methyl alcohol gradually became 80: 20 (V/V) from 60: 40 (V/V) with the ratio that contains the aqueous solution of 0.8% acetic acid in 50 minutes, kept 10 minutes.The flow velocity of moving phase is 25mL/min.Last sample volume is 150 μ L, and applied sample amount is 75mg.Press the ginkgoic acid compounds in appearance time and the intensity collection elutriant.To the elutriant of collecting, on the analysis mode high performance liquid chromatograph, adopt octyl bonded silica gel (C
8) analytical column (4.6mm * 150mm (I.D. * L), particle diameter 5 μ m), be moving phase with methyl alcohol with the aqueous solution that contains 0.8% acetic acid, detect by pipe.To contain with a kind of ginkgoic acid and purity and merge, concentrate at 55 ℃ with the rotation concentrating instrument respectively then, remove methyl alcohol wherein greater than 99% elutriant.With the concentrated solution of 6 kinds of ginkgoic acid compounds-80 ℃ freezing after, moisture is removed in lyophilize in the vacuum lyophilization instrument, obtains 6 kinds of monomeric pressed powders of ginkgoic acid compounds.
Embodiment 4: the elementary purifying thing of ginkgoic acid is redissolved with methyl alcohol, and ultrasonic dissolution is mixed with the solution that concentration is 300mg/mL, crosses the organic phase filter membrane of aperture 0.22 μ m, and is standby.Adopt octyl bonded silica gel (C
8) high pressure preparative liquid chromatography post (19mm * 150mm (I.D. * L), particle diameter 5 μ m), moving phase is the methyl alcohol and the aqueous solution that contains 1.2% acetic acid, methyl alcohol gradually became 80: 20 (V/V) from 70: 30 (V/V) with the ratio that contains the aqueous solution of 1.2% acetic acid in 30 minutes, became 82: 28 (V/V) in 35 minutes again.The flow velocity of moving phase is 20mL/min.Last sample volume is 200 μ L, and applied sample amount is 60mg.Press the ginkgoic acid compounds in appearance time and the intensity collection elutriant.To the elutriant of collecting, on the analysis mode high performance liquid chromatograph, adopt octyl bonded silica gel (C
8) analytical column (4.6mm * 150mm (I.D. * L), particle diameter 5 μ m), be moving phase with methyl alcohol with the aqueous solution that contains 1.2% acetic acid, detect by pipe.To contain with a kind of ginkgoic acid and purity and merge, concentrate at 50 ℃ with the rotation concentrating instrument respectively then, remove methyl alcohol wherein greater than 99% elutriant.With the concentrated solution of 6 kinds of ginkgoic acid compounds-80 ℃ freezing after, moisture is removed in lyophilize in the vacuum lyophilization instrument, obtains 6 kinds of monomeric pressed powders of ginkgoic acid compounds.
Claims (9)
1.6 plant the monomeric method for preparing purified of ginkgoic acid, it is characterized in that: the elementary purifying thing with ginkgoic acid is the upper prop sample, adopts the preparative high performance liquid chromatography instrument, the monomer of 6 kinds of ginkgoic acid compounds of purifying.
2. 6 kinds of monomeric method for preparing purified of ginkgoic acid as claimed in claim 1, concrete grammar is:
(1) the elementary purifying thing with ginkgoic acid redissolves with methyl alcohol, and ultrasonic dissolution is mixed with the solution that concentration is 100mg/mL～1000mg/mL, crosses the organic phase filter membrane of aperture 0.22 μ m, and is standby.
(2) adopting the methyl alcohol and the aqueous solution that contains acetic acid is moving phase, gradient elution, adopt the preparative high performance liquid chromatography instrument on high pressure preparative chromatography post sample to be carried out purifying, last sample volume is 100 μ L～300 μ L, presses the ginkgoic acid compounds in appearance time and the intensity collection elutriant.
(3) elutriant to collecting detects by pipe with the analysis mode high performance liquid chromatograph, will contain with a kind of ginkgoic acid and purity greater than 99% elutriant merging.
(4) to the elutriant of the merging that contains different ginkgoic acid compound monomers, concentrate at 40 ℃～60 ℃ with the rotation concentrating instrument respectively, remove methyl alcohol wherein.
(5) with the concentrated solution of 6 kinds of ginkgoic acid compounds-60 ℃～-80 ℃ freezing after, moisture is removed in lyophilize in the vacuum lyophilization instrument, obtains 6 kinds of monomeric pressed powders of ginkgoic acid compounds.
3. 6 kinds of monomeric method for preparing purified of ginkgoic acid as claimed in claim 2 is characterized in that: the upper prop sample is the elementary purifying thing of ginkgoic acid that the ligroin extraction of ginkgo nut exosper obtains through mesolow silicagel column purifying.
4. 6 kinds of monomeric method for preparing purified of ginkgoic acid as claimed in claim 2 is characterized in that: the concentration of upper prop sample is every milliliter and contains the elementary purifying thing of ginkgoic acid 100mg～1000mg, and last sample volume is 100 μ L～300 μ L, and applied sample amount is 30mg～150mg.
5. 6 kinds of monomeric method for preparing purified of ginkgoic acid as claimed in claim 2 is characterized in that: the filler of the high pressure preparative liquid chromatography post of employing is octyl bonded silica gel (C
8), particle diameter 5 μ m, column dimension are 19mm * 150mm (I.D. * L).
6. 6 kinds of monomeric method for preparing purified of ginkgoic acid as claimed in claim 2, it is characterized in that: the moving phase of employing is the methyl alcohol and the aqueous solution that contains 0.4%～1.5% acetic acid, gradient elution, methyl alcohol gradually becomes 80: 20～90: 10 (V/V) with the ratio that contains the aqueous solution of 0.4%～1.5% acetic acid from 60: 40～75: 25 (V/V), and the flow velocity of moving phase is 15～35mL/min.
7. 6 kinds of monomeric method for preparing purified of ginkgoic acid as claimed in claim 2 is characterized in that: to the elutriant of 6 kinds of ginkgoic acid compounds, it is 40 ℃～60 ℃ that rotation concentrates the bath temperature that adopts.
8. 6 kinds of monomeric method for preparing purified of ginkgoic acid as claimed in claim 2 is characterized in that: the concentrated solution of ginkgoic acid compounds adopts the mode of vacuum lyophilization to remove moisture, obtains the monomeric pressed powder of ginkgoic acid compounds.
9. 6 kinds of monomeric method for preparing purified of ginkgoic acid as claimed in claim 2 is characterized in that: adopt present method, can purifying obtain the monomer of 6 kinds of ginkgoic acid compounds.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103175912A (en) * | 2013-02-06 | 2013-06-26 | 南京中医药大学 | Method for controlling quality of ginkgo leaves and extract thereof |
| CN109053417A (en) * | 2018-07-27 | 2018-12-21 | 山东省分析测试中心 | A kind of preparation method of high-purity ginkgoic acid |
| CN109369382A (en) * | 2018-07-27 | 2019-02-22 | 山东省分析测试中心 | A kind of preparation method of ginkgo acids ingredient |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1392167A (en) * | 2001-06-18 | 2003-01-22 | 中国林业科学研究院林产化学工业研究所 | Preparing process and use of ginkgo leaf polypentenol and ginkgo leaf extract |
| CN1871907A (en) * | 2006-06-23 | 2006-12-06 | 江苏大学 | Use of ginkgoic acid in use for killing Oncomelania snail distilled from outer seed coat of gingkgo |
| CN1899323A (en) * | 2005-07-18 | 2007-01-24 | 厦门国宇知识产权研究有限公司 | Ginkgo leaf extract, injection containing said extract and its preparing method |
-
2010
- 2010-12-15 CN CN2010106063044A patent/CN102093210A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1392167A (en) * | 2001-06-18 | 2003-01-22 | 中国林业科学研究院林产化学工业研究所 | Preparing process and use of ginkgo leaf polypentenol and ginkgo leaf extract |
| CN1899323A (en) * | 2005-07-18 | 2007-01-24 | 厦门国宇知识产权研究有限公司 | Ginkgo leaf extract, injection containing said extract and its preparing method |
| CN1871907A (en) * | 2006-06-23 | 2006-12-06 | 江苏大学 | Use of ginkgoic acid in use for killing Oncomelania snail distilled from outer seed coat of gingkgo |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103175912A (en) * | 2013-02-06 | 2013-06-26 | 南京中医药大学 | Method for controlling quality of ginkgo leaves and extract thereof |
| CN109053417A (en) * | 2018-07-27 | 2018-12-21 | 山东省分析测试中心 | A kind of preparation method of high-purity ginkgoic acid |
| CN109369382A (en) * | 2018-07-27 | 2019-02-22 | 山东省分析测试中心 | A kind of preparation method of ginkgo acids ingredient |
| CN109053417B (en) * | 2018-07-27 | 2021-03-05 | 山东省分析测试中心 | Preparation method of high-purity ginkgolic acid |
| CN109369382B (en) * | 2018-07-27 | 2021-10-26 | 山东省分析测试中心 | A method for preparing ginkgolic acids |
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Application publication date: 20110615 |