CN110240585B - Preparation method of agilawood tetraol - Google Patents
Preparation method of agilawood tetraol Download PDFInfo
- Publication number
- CN110240585B CN110240585B CN201910495963.6A CN201910495963A CN110240585B CN 110240585 B CN110240585 B CN 110240585B CN 201910495963 A CN201910495963 A CN 201910495963A CN 110240585 B CN110240585 B CN 110240585B
- Authority
- CN
- China
- Prior art keywords
- organic solvent
- agalloch eaglewood
- agilawood
- tetraol
- tetrol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/74—Benzo[b]pyrans, hydrogenated in the carbocyclic ring
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a preparation method of agilawood tetraol, which comprises the following steps: (i) extracting to obtain an extract of linalool; (ii) Coarse separation by macroporous adsorption resin column to obtain crude linalool; (iii) separating by normal phase column chromatography to obtain a semi-finished product of the agilawood tetrol; (iv) Separating by a medium-pressure preparation column to obtain a high-purity agalloch eaglewood tetrol sample; (v) And (5) post-treating, concentrating and drying to obtain the agalloch eaglewood tetrol. The method provided by the invention has the advantages of high purity, high yield, stable process, convenient operation, high separation efficiency, high flux, low cost, economy and environmental protection, is suitable for industrial production, and has higher economic value.
Description
Technical Field
The invention relates to the technical field of chemical preparation of traditional Chinese medicines, in particular to a separation preparation method of agilawood tetrol and high-purity agilawood tetrol prepared by the separation preparation method.
Background
The eaglewood is woods containing resin and made of aquilaria sinensis (Lour.) of the daphnaceae, is pungent and bitter in taste and slightly warm in nature, has the effects of promoting qi circulation, relieving pain, warming middle-jiao, relieving vomiting, absorbing qi and relieving asthma, and is used for treating chest and abdominal distention, pain, vomiting and hiccup due to stomach cold, and dyspnea due to kidney deficiency. Modern pharmaceutical researches have shown that agilawood has laxative, spasmolytic, analgesic, antiallergic and antitumor activities.
The lignum Aquilariae Resinatum mainly contains 2- (2-phenethyl) chromone, sesquiterpenes, and aromatic components. The main component of the agalloch eaglewood alcohol extract is 2- (2-phenethyl) chromone derivative, wherein the agalloch eaglewood tetraol content is higher, has close relation with the quality grade of agalloch eaglewood, and can be used as an index component in agalloch eaglewood. Agalloch eaglewood tetrol is recorded as a reference in the part of the Chinese pharmacopoeia of 2015 edition.
Agalloch eaglewood tetrol (agarotetrol) is a white powder, chemical name: (5 s,6r,7r,8 s) -5,6,7, 8-tetra-hydroxy-2-phen-ethyl-5, 6,7, 8-tetra-hydro-chrome-4-one; the molecular formula: c (C) 17 H 18 O 6 The method comprises the steps of carrying out a first treatment on the surface of the Molecular weight: 318.32; CAS 69809-22-9. The structural formula is as follows:
there are many patents and documents for researching chemical components of agilawood at present, but there are few patents and documents for researching a preparation method of high-purity agilawood tetraol.
Chinese patent No. 102070594A discloses a method for preparing high purity agalloch tetraol and 4' -methoxy agalloch tetraol. The method adopts a High-Speed Counter-current chromatography (HSCCC) technology to separate agalloch eaglewood from agalloch eaglewood to obtain agalloch eaglewood tetraol and 4' -methoxy agalloch eaglewood tetraol with the purity of 97 percent, and mainly comprises the following steps: 1. preparing crude agilawood extract; 2. preparing a two-phase solvent system for forming a stationary phase and a mobile phase; 3. filling the high-speed countercurrent chromatograph separation column with fixity; 4. rotating the host, and then pumping the mobile phase into the column; 5. sampling, detecting and receiving a sample; 6. and (5) evaporating the received sample to dryness, and recrystallizing with methanol to obtain the agalloch eaglewood tetrol product. The defects of the technology are that: 1) The treatment capacity is small. The method is limited by a high-speed countercurrent chromatograph, only 100g of medicinal materials can be processed each time, and the method is only suitable for research and development in laboratories, but is not suitable for industrial production, and the preparation efficiency of products is low; 2) The product can not be directly obtained through chromatographic separation, and the agilawood tetraol product can be obtained through one-step methanol recrystallization, so that the solvent consumption is high, and the operation is complex and time-consuming; 3) The purity of the prepared agalloch eaglewood tetrol product is low, the process is unstable, the purity can only reach more than 97%, and the purity of the agalloch eaglewood tetrol product can not be ensured to be more than 99%.
In order to meet the requirement of industrial production, but the literature materials reported by the prior publications have a plurality of defects, the separation preparation method of the invention is developed.
Disclosure of Invention
The invention aims to solve the technical problems of providing a preparation method of agilawood tetraol, which has the advantages of simple operation, less solvent consumption, high product purity and large preparation flux, and is suitable for industrial production. The obtained high purity agalloch eaglewood tetrol can be used as reference substance.
In order to solve the technical problems, the invention adopts the following technical scheme:
a preparation method of agilawood tetraol comprises the following steps:
(i) Extracting: pulverizing the agilawood medicinal materials, and adding 5-20L of extraction solvent into each 1kg of agilawood medicinal materials; the extraction solvent is a first organic solvent-water solution with the volume fraction of 50-80%; the first organic solvent is selected from one or more of methanol and ethanol; the extraction time is 24-72 h, and the extraction temperature is 20-70 ℃; filtering, concentrating to obtain agalloch eaglewood tetra-alcohol extract;
(ii) The method comprises the following steps Coarse separation of macroporous adsorption resin column: diluting the agilawood tetraol extract obtained in the step (i) with water, adding the diluted agilawood tetraol extract into macroporous adsorption resin, carrying out static adsorption for 12-36h, and filtering; loading the column, eluting sequentially by water, a second organic solvent-water solution with the volume fraction of 5-15%, a second organic solvent-water solution with the volume fraction of 25-35% and a second organic solvent-water solution with the volume fraction of 55-65%, collecting eluent of a second organic solvent-water solution part with the volume fraction of 55-65%, and concentrating to obtain a crude product of the agilawood tetrol; the second organic solvent is selected from one or more of methanol, ethanol and acetonitrile;
(iii) Separating by normal phase column chromatography: separating the crude product of the agalloch eaglewood tetrol obtained in the step (ii) by normal phase column chromatography, and performing gradient elution by a solvent system consisting of a third organic solvent and a fourth organic solvent to obtain a semi-finished product of the agalloch eaglewood tetrol; the gradient elution is carried out by a volume ratio of the third organic solvent: fourth organic solvent= (8-15): 1 is the initial solvent ratio, gradually decreasing to a third organic solvent: fourth organic solvent= (1-6): 1, a step of; the normal phase column filler is normal phase silica gel or polyamide; the third organic solvent is selected from one or more of ethyl acetate or chloroform; the fourth organic solvent is selected from one or more of methanol, ethanol and acetone;
(iv) Medium pressure preparative column separation: separating the agilawood tetraol semi-finished product obtained in the step (iii) through a medium-pressure preparation column, eluting with a fifth organic solvent-water solution with the volume fraction of 30-50%, and collecting to obtain an agilawood tetraol sample; the filler of the medium-pressure preparation column is octadecylsilane chemically bonded silica, tetraalkyl silane chemically bonded silica or octaalkyl silane chemically bonded silica; the fifth organic solvent is selected from one or more of methanol, ethanol or acetonitrile;
(v) Post-treatment: concentrating and drying the components of the agalloch eaglewood tetrol sample obtained in the step (iv) to obtain the agalloch eaglewood tetrol pure product.
Specifically, in the step (ii), the filler of the macroporous adsorption resin is selected from D101 resin, AB-8 resin or XDA-8 resin.
Specifically, in the step (ii), the extract is diluted with water and then added to the macroporous adsorption resin; wherein the water is 2-5 times of the volume of the extract, and the macroporous adsorption resin is 2-6 times of the volume of the extract.
Preferably, in the step (ii), the static adsorption time is 18 to 30 hours; more preferably 24h.
Preferably, in the step (ii), the eluting mode is to sequentially perform eluting with water, a second organic solvent-water solution with a volume fraction of 5-15%, a second organic solvent-water solution with a volume fraction of 25-35%, and a second organic solvent-water solution with a volume fraction of 55-65%, and collect the eluent of the second organic solvent-water solution part with a volume fraction of 55-65%.
More preferably, in the step (ii), the eluting manner is to sequentially perform eluting with water, a volume fraction of 10% of the second organic solvent-water solution, a volume fraction of 30% of the second organic solvent-water solution, and a mass fraction of 60% of the second organic solvent-water solution, and collect the eluent of the volume fraction of 60% of the second organic solvent-water solution.
Preferably, in the step (iii), the gradient elution is performed by using a volume ratio of the third organic solvent: fourth organic solvent= (8-10): 1 is the initial solvent ratio, gradually decreasing to a third organic solvent: fourth organic solvent= (1-4): 1.
specifically, in the step (iii), the elution flow rate is 50-70 ml/min, HPLC detection is adopted, and the parts with the agalloch eaglewood tetrol content of more than 40% are combined. Preferably, the fraction having greater than 50% of agalloch eaglewood tetrol is combined.
The invention also provides the agalloch eaglewood tetrol prepared by the method.
The purity of the agalloch eaglewood tetrol provided by the invention reaches more than 99%.
The preparation method of the agalloch eaglewood tetrol improves the product quality of the agalloch eaglewood tetrol, and the purity of the prepared agalloch eaglewood tetrol reaches more than 99 percent, meets the reference substance requirements of Chinese food and drug verification institute, and can be used as a reference substance. In a more preferred embodiment, the purity of the agilawood tetrol is as high as 99.5% or more.
According to the preparation method of the agalloch eaglewood tetrol, the yield of the prepared agalloch eaglewood tetrol is high, 9-13.0 g of agalloch eaglewood tetrol can be prepared from 1kg of agalloch eaglewood raw material, the purity is as high as more than 99%, and the method is remarkably improved compared with the prior art.
The preparation method of the agilawood tetraol provided by the invention adopts the solid packed column for purification, does not depend on special equipment, is easy to put into production, is convenient to use and operate, and can recycle and reuse the solvent in the process.
The preparation method of the agalloch eaglewood tetrol provided by the invention has the advantages that the single batch of samples is large in quantity, more than 100kg of raw materials can be processed, the process is stable and reliable, the reproducibility is good, and the method is suitable for high-throughput production of high-purity agalloch eaglewood tetrol; the separation scale of the solid packed column can be further amplified according to the production requirement, technical difficulties or equipment limitations do not exist, the amplification technology is pure, the cost is low, and the large-scale industrial production is facilitated.
The invention is the first report of separating the agalloch eaglewood tetrol with the high purity reference grade of more than 99 percent in China, and has higher academic value and application value.
Drawings
FIG. 1 is an HPLC chart of the agalloch eaglewood tetrol product obtained in example 1 of the present invention.
Detailed Description
The following description of the present invention will be made clearly and fully, and it is apparent that the embodiments described are some, but not all, of the embodiments of the present invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
Pulverizing 3KG lignum Aquilariae Resinatum, adding 50% ethanol 25L, extracting at 30deg.C for 72 hr, and concentrating to obtain lignum Aquilariae Resinatum tetraol extract. The agalloch eaglewood tetrol extract is statically adsorbed for 12 hours by using D101 macroporous adsorption resin, loaded on a column, eluted by water, 10 percent acetonitrile, 25 percent acetonitrile and 55 percent acetonitrile in sequence, and the eluent of the water part of 55 percent acetonitrile is collected and concentrated to obtain the agalloch eaglewood tetrol crude product. Mixing the crude linalool with silica gel, oven drying, separating by silica gel column chromatography, and separating with ethyl acetate: gradually reducing methanol from 8:1 (v/v) to 1:1 (v/v), performing gradient elution, performing HPLC tracking detection, and combining the parts with the content of the agalloch eaglewood tetraol of more than 50% to obtain the agalloch eaglewood tetraol semi-finished product. Separating the agalloch eaglewood tetrol semi-finished product by adopting octadecylsilane chemically bonded silica gel, detecting by using 40% ethanol water solution as an eluent by HPLC, and collecting the part with the agalloch eaglewood tetrol content of more than 98.5%; concentrating and drying to give 30g of agalloch tetraol with an HPLC purity of 99.0%.
Example 2
Pulverizing 5KG lignum Aquilariae Resinatum, adding 70% methanol 40L, extracting at 40deg.C for 24 hr, and concentrating to obtain lignum Aquilariae Resinatum tetraol extract. The agalloch eaglewood tetraol extract is statically adsorbed for 24 hours by using D101 macroporous adsorption resin, is packed into a column, is eluted by water, 15 percent ethanol, 30 percent ethanol and 55 percent ethanol in sequence, and the eluent of the water part of the 55 percent ethanol is collected and concentrated to obtain the agalloch eaglewood tetraol crude product. Mixing the crude linalool with silica gel, oven drying, separating by silica gel column chromatography, and separating with ethyl acetate: gradually reducing acetone from 12:1 (v/v) to 3:1 (v/v), performing gradient elution, performing HPLC tracking detection, and combining the parts with the content of the agalloch eaglewood tetraol of more than 50% to obtain the agalloch eaglewood tetraol semi-finished product. Repeatedly separating the agalloch eaglewood tetrol semi-finished product by adopting octaalkylsilane bonded silica gel for a plurality of times, detecting by using an HPLC (high performance liquid chromatography) with a 35% ethanol water solution as an eluent, and collecting a part with the agalloch eaglewood tetrol content of more than 98.5%; concentration and drying gave 55g of agalloch eaglewood tetrol with an HPLC purity of 99.0%.
Example 3
Pulverizing 2KG lignum Aquilariae Resinatum, adding 80% ethanol 20L, extracting at 70deg.C for 24 hr, and concentrating to obtain lignum Aquilariae Resinatum tetraol extract. The agalloch eaglewood tetrol extract is statically adsorbed for 36 hours by AB-8 macroporous adsorption resin, is filled into a column, is eluted by water, 10 percent methanol, 30 percent methanol and 60 percent methanol in sequence, and is concentrated to obtain the agalloch eaglewood tetrol crude product by collecting eluent of 60 percent methanol water part. Mixing crude agalloch eaglewood tetraol with silica gel, oven drying, separating by silica gel column chromatography, gradient eluting with chloroform to methanol from 10:1 (v/v) to 1:1 (v/v), tracking by HPLC, and mixing the parts with agalloch eaglewood tetraol content of more than 60% to obtain agalloch eaglewood tetraol semi-product. Separating the agalloch eaglewood tetrol semi-finished product by adopting tetraalkylsilane bonded silica gel, detecting by using an HPLC (high performance liquid chromatography) with a 32% acetonitrile water solution as an eluent, and collecting a part with the agalloch eaglewood tetrol content of more than 98.5%; concentration and drying gave 18g of linalool with an HPLC purity of 99.2%.
Example 4
Pulverizing 8KG lignum Aquilariae Resinatum, adding 60% methanol 100L, extracting at 40deg.C for 48 hr, and concentrating to obtain lignum Aquilariae Resinatum tetraol extract. The agalloch eaglewood tetraol extract is statically adsorbed for 18 hours by using XDA-8 macroporous adsorption resin, is packed into a column, is eluted by water, 10 percent ethanol, 25 percent ethanol and 60 percent ethanol in sequence, and is collected and concentrated to obtain the agalloch eaglewood tetraol crude product. Mixing the crude product of the agalloch eaglewood tetrol with polyamide, drying, separating by adopting polyamide column chromatography, and using ethyl acetate: gradually reducing methanol from 15:1 (v/v) to 6:1 (v/v), performing gradient elution, performing HPLC tracking detection, and combining the parts with the content of the agalloch eaglewood tetraol of more than 50% to obtain an agalloch eaglewood tetraol semi-finished product. Separating the agalloch eaglewood tetrol semi-finished product by adopting octadecylsilane chemically bonded silica gel, detecting by using 30% acetonitrile water solution as an eluent by HPLC, and collecting the part with the agalloch eaglewood tetrol content of more than 98.5%; concentration and drying gave 92g of linalool with an HPLC purity of 99.5%.
Example 5
Pulverizing 1kg of lignum Aquilariae Resinatum, adding 60% ethanol 10L, extracting at 40deg.C for 40 hr, and concentrating to obtain lignum Aquilariae Resinatum tetraol extract. The agalloch eaglewood tetraol extract is statically adsorbed for 24 hours by using D101 macroporous adsorption resin, is packed into a column, is eluted by water, 10 percent ethanol, 30 percent ethanol and 60 percent ethanol in sequence, and is collected and concentrated to obtain the agalloch eaglewood tetraol crude product.
The crude product is screened by adopting different fillers and different mobile phases as normal phase column chromatography, and specific experimental data are shown in table 1:
TABLE 1 normal phase column chromatography screening test
The agalloch eaglewood tetrol semi-finished product obtained by separating the normal phase column chromatography is screened by adopting different reversed phase fillers, different eluents and proportions according to the reversed phase column chromatography method conditions, and specific experimental data are shown in table 2:
TABLE 2 reverse phase column chromatography screening test
Experiment number | Sample loading amount | Type of filler | Eluting solvent and ratio | Pure product quantity and purity | Feasibility of the process |
1 | 0.5g | C18 | Methanol-water (v/v) 50:50 | 0.25g/98.9% | Feasible |
2 | 0.5g | C18 | ethanol-Water (v/v) 40:60 | 0.23g/98.7% | Feasible |
3 | 0.5g | C18 | Acetonitrile-water (v/v) 35:65 | 0.27g/99.1% | Feasible |
4 | 0.5g | C8 | Methanol-water (v/v) 47:53 | 0.28g/99.0% | Feasible |
5 | 0.5g | C8 | ethanol-Water (v/v) 38:62 | 0.23g/99.5% | Feasible |
6 | 0.5g | C8 | Acetonitrile-water (v/v) 32:68 | 0.26g/98.9% | Feasible |
7 | 0.5g | C4 | Methanol-water (v/v) 44:56 | 0.29g/99.2% | Feasible |
8 | 0.5g | C4 | ethanol-Water (v/v) 35:65 | 0.21g/99.8% | Feasible |
9 | 0.5g | C4 | Acetonitrile-water (v/v) 30:70 | 0.28g/99.5% | Feasible |
In summary, the above embodiments are only preferred embodiments of the present invention, and are not intended to limit the scope of the present invention, but any modifications, equivalent substitutions, improvements, etc. within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (4)
1. The preparation method of the agalloch eaglewood tetrol is characterized by comprising the following steps of:
(i) Extracting: pulverizing the agilawood medicinal materials, and adding 5-20L of extraction solvent into each 1kg of agilawood medicinal materials; the extraction solvent is a first organic solvent-water solution with the volume fraction of 50-80%; the first organic solvent is selected from one or more of methanol and ethanol; the extraction time is 24-72 h, and the extraction temperature is 20-70 ℃; filtering, concentrating to obtain agalloch eaglewood tetra-alcohol extract;
(ii) The method comprises the following steps Coarse separation of macroporous adsorption resin column: diluting the agilawood tetraol extract obtained in the step (i) with water, adding the diluted agilawood tetraol extract into macroporous adsorption resin, carrying out static adsorption for 12-36h, and filtering; loading the column, eluting sequentially with water, a second organic solvent-water solution with the volume fraction of 10%, a second organic solvent-water solution with the volume fraction of 30% and a second organic solvent-water solution with the volume fraction of 60%, collecting the eluent of the second organic solvent-water solution part with the volume fraction of 60%, and concentrating to obtain a crude product of the agilawood tetrol; the second organic solvent is selected from one or more of methanol, ethanol and acetonitrile, and the filler of the macroporous adsorption resin is selected from D101 resin, AB-8 resin or XDA-8 resin;
(iii) Separating by normal phase column chromatography: separating the crude product of the agalloch eaglewood tetrol obtained in the step (ii) through normal phase column chromatography, and performing gradient elution by a solvent system consisting of a third organic solvent and a fourth organic solvent to obtain a semi-finished product of the agalloch eaglewood tetrol; the gradient elution is carried out by a volume ratio of the third organic solvent: fourth organic solvent= (8-10): 1 is the initial solvent ratio, gradually decreasing to a third organic solvent: fourth organic solvent= (1-4): 1, the normal phase column filler is normal phase silica gel or polyamide; the third organic solvent is selected from one or more of ethyl acetate or chloroform; the fourth organic solvent is selected from one or more of methanol, ethanol and acetone;
(iv) Medium pressure preparative column separation: separating the agilawood tetraol semi-finished product obtained in the step (iii) through a medium-pressure preparation column, eluting with a fifth organic solvent-water solution with the volume fraction of 30-50%, and collecting to obtain an agilawood tetraol sample; the filler of the medium-pressure preparation column is tetraalkyl silane bonded silica gel or octaalkyl silane bonded silica gel; the fifth organic solvent is selected from one or more of methanol, ethanol or acetonitrile;
(v) Post-treatment: concentrating and drying the components of the agalloch eaglewood tetrol sample obtained in the step (iv) to obtain the agalloch eaglewood tetrol with the purity of more than 99%.
2. The method of claim 1, wherein in step (ii), the extract is diluted with water and then added to the macroporous adsorbent resin; wherein the water is 3-5 times of the volume of the extract, and the macroporous adsorption resin is 2-3 times of the volume of the extract.
3. The method of claim 1, wherein in step (ii), the static adsorption time is 18 to 30 hours.
4. The method of claim 1, wherein in step (iii), the elution flow rate is 50-70 ml/min, and the fraction having greater than 40% of agilawood tetraol is combined by HPLC.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910495963.6A CN110240585B (en) | 2019-06-10 | 2019-06-10 | Preparation method of agilawood tetraol |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910495963.6A CN110240585B (en) | 2019-06-10 | 2019-06-10 | Preparation method of agilawood tetraol |
Publications (2)
Publication Number | Publication Date |
---|---|
CN110240585A CN110240585A (en) | 2019-09-17 |
CN110240585B true CN110240585B (en) | 2023-08-22 |
Family
ID=67886302
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910495963.6A Active CN110240585B (en) | 2019-06-10 | 2019-06-10 | Preparation method of agilawood tetraol |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110240585B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113694055B (en) * | 2021-09-02 | 2023-05-02 | 中国科学院昆明植物研究所 | Application of agalloch eaglewood tetrol in preparing medicine for treating vascular dementia |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB882537A (en) * | 1958-09-12 | 1961-11-15 | Recordati Lab Farmacologico S | Chromones and processes for the preparation thereof |
JP2006241112A (en) * | 2005-03-07 | 2006-09-14 | Shiono Koryo Kk | Mildewproofing agent antifungal agent |
CN102070594A (en) * | 2009-11-24 | 2011-05-25 | 上海中药制药技术有限公司 | Separation preparation method for high-purity agarotetrol and 4'-methoxy agarotetrol |
CN105801546A (en) * | 2016-04-15 | 2016-07-27 | 中国医学科学院药用植物研究所海南分所 | Chromone compounds separated from Chinese eaglewood and method and application of chromone compounds |
-
2019
- 2019-06-10 CN CN201910495963.6A patent/CN110240585B/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB882537A (en) * | 1958-09-12 | 1961-11-15 | Recordati Lab Farmacologico S | Chromones and processes for the preparation thereof |
JP2006241112A (en) * | 2005-03-07 | 2006-09-14 | Shiono Koryo Kk | Mildewproofing agent antifungal agent |
CN102070594A (en) * | 2009-11-24 | 2011-05-25 | 上海中药制药技术有限公司 | Separation preparation method for high-purity agarotetrol and 4'-methoxy agarotetrol |
CN105801546A (en) * | 2016-04-15 | 2016-07-27 | 中国医学科学院药用植物研究所海南分所 | Chromone compounds separated from Chinese eaglewood and method and application of chromone compounds |
Non-Patent Citations (1)
Title |
---|
高速逆流色谱法分离制备沉香中的沉香四醇和4′-甲氧基沉香四醇;郑克敏 等;《中成药》;20110131;第33卷(第01期);第96-99页 * |
Also Published As
Publication number | Publication date |
---|---|
CN110240585A (en) | 2019-09-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102976909B (en) | Method for extracting and purifying 6-gingerol from ginger | |
CN103145677B (en) | Method for separating active ingredients from aquilaria sinensis lamina by utilizing high-speed countercurrent chromatography | |
CN103408602A (en) | Separation and preparation method for four glycoside chemical reference substances in Tibetan capillary artemisia | |
CN105566414B (en) | The method that four kinds of flavone glycosides are isolated and purified from waxberry flesh | |
Huang et al. | Purification of lignans from Schisandra chinensis fruit by using column fractionation and supercritical antisolvent precipitation | |
CN101863935B (en) | Preparation method of 1,4-di-[4-(glucosyloxy) benzyl]-2-isobutyl malate comparison product | |
CN104892687A (en) | Method for separating and purifying monomeric compound from Chinese mahonia leaves through high-speed counter-current chromatography | |
CN110590882B (en) | Method for simultaneously separating and purifying 6 flavone compounds from sunflower seeds | |
CN106632542B (en) | Preparation method of cimicidin glycoside and 5-O-methylvisammioside reference substance | |
Wang et al. | An Efficient Strategy Based on Liquid–Liquid Extraction With Acid Condition and HSCCC for Rapid Enrichment and Preparative Separation of Three Caffeoylquinic Acid Isomers From Mulberry Leaves | |
CN110240585B (en) | Preparation method of agilawood tetraol | |
CN104997840A (en) | Dracocephalum heterophyllum Benth pentacyclic triterpene component sample pretreatment method and use of Dracocephalum heterophyllum Benth pentacyclic triterpene component | |
CN104370895B (en) | A kind of preparation method of orientin and Lutonaretin | |
CN101322693B (en) | Carthamus tinctorius yellow colour injection and preparation technique thereof | |
CN109081858A (en) | The directional separation and purification method of flavone compound in Tang Gute kiss-me | |
CN104892620B (en) | A kind of preparation method of high-purity karanjin | |
CN111675741A (en) | Separation method for simultaneously obtaining four kinds of epimedium rare flavone by using preparative liquid phase method | |
CN108341845B (en) | Method for preparing morroniside from dogwood extract | |
CN106831892B (en) | Preparation method of flavone monomer in hawthorn leaves | |
CN107721857A (en) | A kind of method that high-purity chlorogenic acid is prepared from Gynura procumbens (Lour.) Merr | |
CN111718318B (en) | Method for separating flavone monomer in spina gleditsiae based on countercurrent chromatography | |
CN102389456A (en) | Method for extracting isodon japonica var.galaucocalyx total diterpenoids or Glaucocalyxin A | |
CN102133258A (en) | Extracting and purifying process of pongamia pinnata flavonoids | |
CN109320572B (en) | Method for extracting flavonoid compounds from camellia reticulata | |
CN112457282A (en) | Method for preparing 2' -hydroxy-7- (3-hydroxypropyl) -6-methoxy-flavone |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |