CN105585600A - Preparation method of secoxyloganin - Google Patents
Preparation method of secoxyloganin Download PDFInfo
- Publication number
- CN105585600A CN105585600A CN201510864523.5A CN201510864523A CN105585600A CN 105585600 A CN105585600 A CN 105585600A CN 201510864523 A CN201510864523 A CN 201510864523A CN 105585600 A CN105585600 A CN 105585600A
- Authority
- CN
- China
- Prior art keywords
- preparation
- loganin
- oxidation loganin
- disconnected
- disconnected oxidation
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Abstract
The invention discloses a preparation method of secoxyloganin. The preparation method includes the steps of firstly, taking a honeysuckle medicinal material, adding ethyl alcohol for reflux extraction, conducting filtration, combining filtrate, conducting concentration, putting the concentrate on a macroporous resin column to be eluted with water and then eluted with ethyl alcohol with the concentration of 20-95% in a gradient mode, and collecting eluted parts containing secoxyloganin; secondly, conducting separation through industrial preparative chromatography, wherein preparation is conducted through the inverse industrial preparative chromatography, methyl alcohol and water are used as the flowing phase, an elution curve is monitored under the wavelength of 242 nm so that product collection can be guided, and secoxyloganin is obtained by concentrating collected liquid. According to the preparation method, the optimal extraction method and the optimal macroporous resin purification method are screened out through system experiments, and high-purity secoxyloganin is prepared through optimal industrial preparative chromatography purification. The method is industrially reasonable, and is particularly large in preparation amount, high in efficiency and high in preparation yield, and obtained secoxyloganin is high in purity and suitable for large-scale preparation.
Description
Technical field
The present invention relates to a kind of preparation method of disconnected oxidation loganin, be specifically related to a kind of method of preparing fast disconnected oxidation loganin from honeysuckle.
Background technology
Disconnected oxidation loganin is to be honeysuckle (FlosLoniceraejaponicae), to extract the refining product obtaining from the dry flower of caprifoliaceae plant honeysuckle (LonicerajaponicaThunb.). Disconnected oxidation loganin is iridoid, is a kind of active ingredient of honeysuckle. Modern pharmacological research is found; iridoid has the pharmacological actions such as nervous system protective effect, anti-inflammatory, antibacterial, antiviral, antitumor, hepatic cholagogic, hypoglycemic, spasmolysis and analgesia, also can be used for the material medicine of Cardiovarscular, diabetes and complication thereof. Bibliographical information, disconnected oxidation loganin is under the dosage of 20mg/kg, to CCl4Cause hepatic injury mouse and show significant liver-protecting activity, therefore, disconnected oxidation loganin has very large development prospect, and the separation to disconnected oxidation loganin and purifying become the key technology of disconnected oxidation loganin deep development.
In existing investigative technique, document about disconnected oxidation loganin preparation method is little, and the separation and purification of disconnected oxidation loganin is also only limited under laboratory condition and is studied, generally from medicinal material extract through extraction or macroporous resin purification to silica gel, gel and reversed phase column chromatography purifying etc. will through 5～6 steps even more multi-step just can obtain the compound that purity is higher, step is more loaded down with trivial details, and consumption of organic solvent is large. According to bibliographical information, as Bi Yuefeng (Bi Yuefeng, field, Pei Shanshan, Liu Hongmin. secoiridoid glycoside chemical components research in honeysuckle. Chinese herbal medicine [J] .2008,39 (1): 18～21.) utilize D101, SephadexLH-20, silica gel isochrome spectrometry to separate from 1.5kg honeysuckle and obtain the disconnected oxidation of 21mg loganin; Song Weixia (Song Weixia. honeysuckle water-soluble chemical component research [D]. China Concord Medical Science University, 2008.) from 12kg honeysuckle, separate and obtain disconnected oxidation loganin 13.1mg; Field (field. honeysuckle chemical constitution study [D]. the .2007. of Zhengzhou University) from 1.5kg honeysuckle by extraction, macroreticular resin and repeatedly the method such as silica gel column chromatography separate and obtain disconnected oxidation loganin 21mg; Li Chang (Li Chang, Dai Yi, Zhang Jinbo, Liu Mingli, Yao new life. 1 new iridoid glycoside compounds in honeysuckle. Chinese herbal medicine [J] .2013,44 (21): 2951～2954.) from 1kg honeysuckle, separate and obtain disconnected oxidation loganin 186.2mg by multiple column chromatographys such as HP-20 macroreticular resin, ODS, HW-40; Chen Yu (Chen Yu, Zhao Youyi, Wu Shuan, Wang Ming, Feng Xu, Liang Jingyu. Buds of Lonicera macranthoides water-soluble chemical component research. Chinese medicine [J] .2012,35 (2): 231～234.) adopt the methods such as D101, SephadexLH-20 and reversed phase column chromatography repeatedly to separate from 8kg Buds of Lonicera macranthoides and obtain the disconnected loganin 121mg that is oxidized. But, problem of ubiquity in above research, disconnected oxidation loganin all finds in chemical constitution study process, and the amount of the disconnected oxidation loganin obtaining is very little, and poor reproducibility is difficult to amplify. In addition, in most refining purge processes, use SephadexLH-20 filler, this filler volume containing the sample is few, flow velocity is little, length consuming time, and extensive amplification is difficult to operation, and this filler is expensive, and cost is high, is not suitable for industrialization promotion.
Therefore, necessary on the basis of prior art, research and develop a kind of preparation efficiency high, speed is fast, and production cost is low, without using a large amount of organic solvents, has the method for preparing fast disconnected oxidation loganin from honeysuckle of good application prospect.
Summary of the invention
Goal of the invention: the object of the invention is in order to solve the deficiencies in the prior art, through great many of experiments screening, provide the method for preparing fast disconnected oxidation loganin from honeysuckle. Preparation method provided by the invention, taking honeysuckle as crude drug, adopts the absorption of preferred resin post, and with the ethanol elution of preferred concentration, finally preparing chromatograph in industry purifying under the process conditions of optimizing, whole technique preparation efficiency is high, and especially preparation amount is large, yield is high, the disconnected oxidation loganin purity preparing is high, and production cost is low, workable, be applicable to extensive preparation, there is good application prospect.
Technical scheme: in order to realize above object, the present invention adopts following technical scheme:
A preparation method for disconnected oxidation loganin, comprises the following steps:
(1) extracting honeysuckle medicinal material, adding 8～16 times of amount volumetric concentrations of medicinal material is that 70%～85% alcohol reflux extracts 1～3 time, filter, merging filtrate, concentrated, upper macroporous resin column, first washes with water, the ethanol gradient elution that is 20%～95% by concentration again, collects the wash-out position of containing disconnected oxidation loganin;
(2) preparing chromatograph in industry separates: prepared by the oxidation loganin position preparing chromatograph in industry that will break, chromatographic column is taking anti-phase C18 as filler, methyl alcohol taking volume ratio as 10～35:90～65: water is mobile phase, under 242nm wavelength, monitor that elution curve collects with guide product, collect liquid and after concentrate drying, obtain disconnected oxidation loganin.
As preferred version, the above-described method of preparing fast disconnected oxidation loganin from honeysuckle, the chromatographic condition that described preparing chromatograph in industry separates is: chromatographic column is with anti-phase C18For filler (30～250 × 250～1000mm), flow velocity is 10～1000mL/min, and sample size is 0.2g～20.0g, and wavelength is 242nm, and mobile phase is that volume ratio is the first alcohol and water of 25:75, and each sample treatment time is 30～60min.
Preparation technology's screening test
1, the screening of resin model
Choosing 3 kinds of each 5g of pretreated resin (D101, HP20, HPD100) puts in 100ml tool plug conical flask, extracting honeysuckle extracts concentrate and adds in bottle, leave standstill 24h in room temperature, after adsorption equilibrium, elimination resin, quantitatively pipette clear liquid, measure the content of disconnected oxygen loganin, calculate adsorption rate. Result adsorption rate is followed successively by 72.1%, 64.3%, 67.7%, and therefore the present invention selects D101 type macroporous absorbent resin, and purification efficiency is higher.
2, the selection of eluting solvent
Get 5 parts and carry out after sample absorption according to preferred D101 resin is parallel, first wash with water to efflux be colourless after, then carry out wash-out with 10%, 20%, 30%, 40%, 60% ethanolic solution respectively, and follow the tracks of and detect with HPLC, calculate eluting rate, efflux reduced pressure concentration is also dry, measures disconnected oxygen Determination of Loganin, the results are shown in Table 1.
Eluting rate and the content of table 1 different concentration ethanol to disconnected oxygen loganin
As shown in Table 1, the disconnected oxygen Determination of Loganin of 10% ethanol eluate is the highest, but wash-out is incomplete, though 30%, 40% and 60% ethanol eluate eluting rate is high, but impurity is also many, therefore select 20% ethanol as eluting solvent, not only eluting rate is high, and the content of eluent interruption oxygen loganin is also high.
As preferred version, the above-described method of preparing fast disconnected oxidation loganin from honeysuckle, extracting honeysuckle medicinal material, adding 8 times of amount volumetric concentrations of medicinal material is that 70% alcohol reflux extracts 2 times, filtration, merging filtrate, upper D101 macroporous resin column.
3, preparing chromatograph in industry separation condition is selected
Adopt Agilent1260 analytic type high performance liquid chromatograph, with methanol-water, methyl alcohol-0.5% formic acid water, acetonitrile-water and acetonitrile-0.5% formic acid water are respectively mobile phase, and experimental result shows, with methyl alcohol-0.5% formic acid water, when acetonitrile-water and acetonitrile-0.5% formic acid water are mobile phase, system separating effect is poor, and elution speed is slow, peak shape is not good, and therefore to select methanol-water be eluant, eluent in the present invention.
Determine after eluant, eluent, the present invention again by great many of experiments to methyl alcohol: the concrete volume ratio of water has been carried out a large amount of experiment screenings, and result shows, methyl alcohol: when water=25:75 (V/V), there is good elute effect, and can in 40 minutes, separate wash-out and obtain disconnected oxidation loganin. Elution speed is fast, and efficiency is high.
As preferred version, the above-described method of preparing fast disconnected oxidation loganin from honeysuckle, the purity that step (2) prepares disconnected oxidation loganin reaches more than 98%, and gained purity is higher compared to existing technology.
Beneficial effect: the present invention compared with prior art has the following advantages:
The method of preparing fast disconnected oxidation loganin from honeysuckle provided by the invention, screen best extracting method and macroporous resin purification method through system experimentation, and obtain highly purified disconnected oxidation loganin through the preferred anti-phase preparing chromatograph in industry purification of great many of experiments, advantage of the present invention is only to adopt macroreticular resin and preparing chromatograph in industry two-step purifying can obtain highly purified disconnected oxidation loganin, avoid prior art through extraction or purification on normal-phase silica gel repeatedly, numerous and diverse steps such as gel and normal pressure reversed phase column chromatography, elution time is long, consumption of organic solvent is large, the shortcomings such as yield is low, technique is reasonable, simple to operate, reproducible, error is little, especially normal pressure column chromatography relatively, manufacturing cycle is short, preparation amount is large, output is high, the disconnected oxidation loganin purity obtaining is high, be applicable to extensive preparation, obtain good technique effect.
Brief description of the drawings
Fig. 1 is the liquid chromatogram of the disconnected oxidation loganin prepared of the present invention.
Fig. 2 is the liquid chromatogram of disconnected oxidation loganin reference substance.
Detailed description of the invention
According to following embodiment, the present invention may be better understood. But, those skilled in the art will readily understand, the described concrete material proportion of embodiment, process conditions and result thereof be only for the present invention is described, and should also can not limit the present invention described in detail in claims.
Embodiment 1
1, a preparation method for disconnected oxidation loganin, it comprises the following steps:
(1) extracting honeysuckle medicinal material 5kg, adding 8 times of amount volumetric concentrations of medicinal material is that 70% alcohol reflux extracts 2 times, each 2 hours, filters, merging filtrate, concentrated, upper D101 macroporous resin column, first wash with water, then the ethanol gradient elution that is 20% by concentration, 20% alcohol elution collected;
(2) preparing chromatograph in industry preparation separates: the oxidation loganin position preparing chromatograph in industry that will break is prepared, and chromatographic column is anti-phase C18Chromatographic column (50 × 250mm), flow velocity is 20mL/min, wavelength is 242nm, mobile phase is that volume ratio is the first alcohol and water of 25:75, sample size is 1.0g, monitors that elution curve collects with guide product under 242nm wavelength, collects liquid after concentrate drying, obtaining purity is 99.2% disconnected oxidation loganin 12.24g, and the rate of recovery is 92.0%.
As shown in Figure 1, the disconnected oxidation loganin liquid chromatogram preparing for the present invention. Fig. 2 is the liquid chromatogram of disconnected oxidation loganin reference substance.
The disconnected oxidation loganin structure elucidation that the present invention prepares: white powder (methyl alcohol), HR-ESI-MSm/z:403.1267[M-H]-，807.2610[2M-H]-, molecular formula is C17H24O11。1H-NMR(400MHz,CD3OD)δ：7.47(1H,d,J＝1.8Hz,H-3),5.49(1H,d,J＝3.8Hz,H-1),4.66(1H,d,J＝7.9Hz,H-1′),3.68(3H,s,-OCH3),5.65(1H,ddd,J＝10.1,9.9,17.1Hz,H-8),2.95(1H,dd,J＝16.5,4.9Hz,H-6),2.27(1H,dd,J＝9.0,16.5Hz,H-6),2.82(1H,m,H-9).13C-NMR(100MHz,CD3OD)δ:176.7(s,C-7),169.4(s,C-11),154.1(d,C-3),135.0(d,C-8),121.0(t,C-10),110.6(s,C-4),100.5(d,C-1′),98.1(d,C-1),78.9(d,C-5′),78.5(d,C-3′),75.1(d,C-2′),72.0(d,C-4′),63.2(t,C-6′),52.1(q,-OCH3),45.8(d,C-9),35.6(t,C-6),29.1(d,C-5)。
Embodiment 2
1, a method of preparing fast disconnected oxidation loganin from honeysuckle, it comprises the following steps:
(1) extracting honeysuckle medicinal material 10kg, adding 16 times of amount volumetric concentrations of medicinal material is that 80% alcohol reflux extracts 3 times, each 2 hours, filters, merging filtrate, concentrated, upper D101 macroporous resin column, first wash with water, then the ethanol gradient elution that is 20% by concentration, 20% alcohol elution collected;
(2) preparing chromatograph in industry preparation separates: the oxidation loganin position preparing chromatograph in industry that will break is prepared, and chromatographic column is anti-phase C18Chromatographic column (80 × 600mm), flow velocity is 60mL/min, wavelength is 242nm, mobile phase is that volume ratio is the first alcohol and water of 25:75, sample size is, sample size 5.0g monitors that under 242nm wavelength elution curve collects with guide product, it is 98.7% disconnected oxidation loganin 24.13g that collection liquid obtains purity after concentrate drying, and the rate of recovery is 90.6%.
The disconnected oxidation loganin structure elucidation that the present invention prepares: white powder (methyl alcohol), HR-ESI-MSm/z:403.1267[M-H]-，807.2610[2M-H]-, molecular formula is C17H24O11。1H-NMR(400MHz,CD3OD)δ：7.47(1H,d,J＝1.8Hz,H-3),5.49(1H,d,J＝3.8Hz,H-1),4.66(1H,d,J＝7.9Hz,H-1′),3.68(3H,s,-OCH3),5.65(1H,ddd,J＝10.1,9.9,17.1Hz,H-8),2.95(1H,dd,J＝16.5,4.9Hz,H-6),2.27(1H,dd,J＝9.0,16.5Hz,H-6),2.82(1H,m,H-9).13C-NMR(100MHz,CD3OD)δ:176.7(s,C-7),169.4(s,C-11),154.1(d,C-3),135.0(d,C-8),121.0(t,C-10),110.6(s,C-4),100.5(d,C-1′),98.1(d,C-1),78.9(d,C-5′),78.5(d,C-3′),75.1(d,C-2′),72.0(d,C-4′),63.2(t,C-6′),52.1(q,-OCH3),45.8(d,C-9),35.6(t,C-6),29.1(d,C-5)。
Embodiment 3
1, a method of preparing fast disconnected oxidation loganin from honeysuckle, it comprises the following steps:
(1) extracting honeysuckle medicinal material 20kg, adding 8 times of amount volumetric concentrations of medicinal material is that 70% alcohol reflux extracts 3 times, each 2 hours, filters, merging filtrate, concentrated, upper D101 macroporous resin column, first wash with water, then the ethanol elution that is 20% by concentration, 20% alcohol elution collected;
(2) preparing chromatograph in industry separates: the oxidation loganin position preparing chromatograph in industry that will break is prepared, chromatographic column is anti-phase C18 chromatographic column (150 × 600mm), flow velocity is 1L/min, wavelength is 242nm, mobile phase is that volume ratio is the first alcohol and water of 25:75, sample size is 20g, under 242nm wavelength, monitor that elution curve collects with guide product, it is 98.9% disconnected oxidation loganin white powder 48.21g that collection liquid obtains purity after concentrate drying, and the rate of recovery is 90.1%.
The disconnected oxidation loganin structure elucidation that the present invention prepares: white powder (methyl alcohol), HR-ESI-MSm/z:403.1267[M-H]-，807.2610[2M-H]-, molecular formula is C17H24O11。1H-NMR(400MHz,CD3OD)δ：7.47(1H,d,J＝1.8Hz,H-3),5.49(1H,d,J＝3.8Hz,H-1),4.66(1H,d,J＝7.9Hz,H-1′),3.68(3H,s,-OCH3),5.65(1H,ddd,J＝10.1,9.9,17.1Hz,H-8),2.95(1H,dd,J＝16.5,4.9Hz,H-6),2.27(1H,dd,J＝9.0,16.5Hz,H-6),2.82(1H,m,H-9).13C-NMR(100MHz,CD3OD)δ:176.7(s,C-7),169.4(s,C-11),154.1(d,C-3),135.0(d,C-8),121.0(t,C-10),110.6(s,C-4),100.5(d,C-1′),98.1(d,C-1),78.9(d,C-5′),78.5(d,C-3′),75.1(d,C-2′),72.0(d,C-4′),63.2(t,C-6′),52.1(q,-OCH3),45.8(d,C-9),35.6(t,C-6),29.1(d,C-5)。
The above is only the preferred embodiment of the present invention; it should be pointed out that for those skilled in the art, under the premise without departing from the principles of the invention; can also make some improvements and modifications, these improvements and modifications also should be considered as protection scope of the present invention.
Claims (5)
1. a preparation method for disconnected oxidation loganin, is characterized in that comprising the following steps:
(1) extracting honeysuckle medicinal material, adding 8～16 times of amount volumetric concentrations of medicinal material is that 70%～85% alcohol reflux extracts 1～3 time, filterCross, merging filtrate, concentrated, upper macroporous resin column, first washes with water, then the ethanol gradient elution that is 20%～95% by concentration,The wash-out position that collection contains disconnected oxidation loganin;
(2) preparing chromatograph in industry separates: the anti-phase preparing chromatograph in industry in oxidation loganin position that will break is prepared, with volumeThan being the methyl alcohol of 10～30:90～70: water is mobile phase, under 242nm wavelength, monitor that elution curve collects with guide product,Collect liquid and after concentrate drying, obtain disconnected oxidation loganin.
2. the preparation method of disconnected oxidation loganin according to claim 1, is characterized in that, look is prepared in described industryThe chromatographic condition of spectrum is: chromatographic column is anti-phase C18Chromatographic column, flow velocity is 10～1000mL/min, wavelength is 242nm, flowsThe first alcohol and water that is 25:75 for volume ratio mutually, sample size is 0.2g～20g.
3. the preparation method of disconnected oxidation loganin according to claim 1, is characterized in that, extracting honeysuckle medicinal material, addsEntering 8 times of amount volumetric concentrations of medicinal material is that 70% alcohol reflux extracts 2 times, filters merging filtrate, upper D101 macroporous resin column.
4. the preparation method of disconnected oxidation loganin according to claim 1, is characterized in that, described in step (1)The wash-out position of containing disconnected oxidation loganin be 20% alcohol elution.
5. the method for preparing fast disconnected oxidation loganin from honeysuckle according to claim 1, is characterized in that stepSuddenly the purity that (2) prepare disconnected oxidation loganin reaches more than 98%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510864523.5A CN105585600B (en) | 2015-11-30 | 2015-11-30 | A kind of preparation method of disconnected oxidation loganin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510864523.5A CN105585600B (en) | 2015-11-30 | 2015-11-30 | A kind of preparation method of disconnected oxidation loganin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105585600A true CN105585600A (en) | 2016-05-18 |
| CN105585600B CN105585600B (en) | 2019-03-08 |
Family
ID=55925537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510864523.5A Active CN105585600B (en) | 2015-11-30 | 2015-11-30 | A kind of preparation method of disconnected oxidation loganin |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105585600B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106117284A (en) * | 2016-07-11 | 2016-11-16 | 山东省分析测试中心 | The method of six kinds of iridoid glycoside constituents in Extraction and enrichment Flos Lonicerae while of a kind of |
| CN110849998A (en) * | 2019-12-05 | 2020-02-28 | 吴海靖 | Liquid chromatography method for separating epiloganin hemiacetal lactone and secologanin hemiacetal lactone |
| CN110849999A (en) * | 2019-12-05 | 2020-02-28 | 吴海靖 | Liquid chromatography method for separating 8-epiloganin and loganin |
| CN116549476A (en) * | 2023-07-10 | 2023-08-08 | 暨南大学附属第一医院（广州华侨医院） | Compound, composition and application thereof in preparation of drugs with tumor angiogenesis inhibiting effect |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101085795A (en) * | 2006-06-07 | 2007-12-12 | 石家庄汉康生化药品有限公司 | Honeysuckle extract and its preparation method and application |
| WO2013023340A1 (en) * | 2011-08-12 | 2013-02-21 | 甘肃普源医药科技有限公司 | Honeysuckle extract, and pharmaceutical composition comprising the same and use of the same |
| WO2013023338A1 (en) * | 2011-08-12 | 2013-02-21 | 甘肃普源医药科技有限公司 | Pharmaceutical composition containing honeysuckle extract and antibiotics, pharmaceutical kit, and use of honeysuckle extract for preparation of drug |
| CN105017353A (en) * | 2015-06-12 | 2015-11-04 | 沈阳药科大学 | Iridoid compounds in lonicera japonica, preparation method therefor and use thereof |
-
2015
- 2015-11-30 CN CN201510864523.5A patent/CN105585600B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101085795A (en) * | 2006-06-07 | 2007-12-12 | 石家庄汉康生化药品有限公司 | Honeysuckle extract and its preparation method and application |
| WO2013023340A1 (en) * | 2011-08-12 | 2013-02-21 | 甘肃普源医药科技有限公司 | Honeysuckle extract, and pharmaceutical composition comprising the same and use of the same |
| WO2013023338A1 (en) * | 2011-08-12 | 2013-02-21 | 甘肃普源医药科技有限公司 | Pharmaceutical composition containing honeysuckle extract and antibiotics, pharmaceutical kit, and use of honeysuckle extract for preparation of drug |
| CN105017353A (en) * | 2015-06-12 | 2015-11-04 | 沈阳药科大学 | Iridoid compounds in lonicera japonica, preparation method therefor and use thereof |
Non-Patent Citations (5)
| Title |
|---|
| RITA MEHROTRA，ET AL.: ""ISOLATION OF SECOXYLOGANIN FROM LONICERA JAPONICA AND ITS CONVERSION INTO SECOLOGANIN"", 《JOURNAL OF NATURAL PRODUCTS》 * |
| 倪付勇，等: ""金银花中抗补体活性酚酸类成分的研究"", 《中国中药杂志》 * |
| 宋亚玲，等: ""金银花中酚酸类成分及其抗炎活性研究"", 《中草药》 * |
| 李畅，等: ""金银花中1个新的环烯醚萜苷类化合物"", 《中草药》 * |
| 毕跃峰，等: ""金银花中裂环环烯醚萜苷类化学成分研究"", 《中草药》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106117284A (en) * | 2016-07-11 | 2016-11-16 | 山东省分析测试中心 | The method of six kinds of iridoid glycoside constituents in Extraction and enrichment Flos Lonicerae while of a kind of |
| CN106117284B (en) * | 2016-07-11 | 2019-01-11 | 山东省分析测试中心 | A kind of method of six kinds of iridoid glycoside constituents in while Extraction and enrichment honeysuckle |
| CN110849998A (en) * | 2019-12-05 | 2020-02-28 | 吴海靖 | Liquid chromatography method for separating epiloganin hemiacetal lactone and secologanin hemiacetal lactone |
| CN110849999A (en) * | 2019-12-05 | 2020-02-28 | 吴海靖 | Liquid chromatography method for separating 8-epiloganin and loganin |
| CN110849999B (en) * | 2019-12-05 | 2022-12-06 | 江西永通科技股份有限公司 | Liquid chromatography method for separating 8-epiloganin and loganin |
| CN116549476A (en) * | 2023-07-10 | 2023-08-08 | 暨南大学附属第一医院（广州华侨医院） | Compound, composition and application thereof in preparation of drugs with tumor angiogenesis inhibiting effect |
| CN116549476B (en) * | 2023-07-10 | 2023-09-19 | 暨南大学附属第一医院（广州华侨医院） | Compound, composition and application thereof in preparation of drugs with tumor angiogenesis inhibiting effect |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105585600B (en) | 2019-03-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107337586A (en) | A kind of method of extraction purification cannabidiol in fiber crops from the Chinese | |
| CN103145677B (en) | Method for separating active ingredients from aquilaria sinensis lamina by utilizing high-speed countercurrent chromatography | |
| CN105585600A (en) | Preparation method of secoxyloganin | |
| CN103570779A (en) | Method for preparing glycyrrhizin by simulated moving bed separation | |
| Zhu et al. | Ultrahigh pressure extraction of lignan compounds from Dysosma versipellis and purification by high-speed counter-current chromatography | |
| CN104892687A (en) | Method for separating and purifying monomeric compound from Chinese mahonia leaves through high-speed counter-current chromatography | |
| CN114988979B (en) | Method for preparing high-purity lycopene by macro separation | |
| CN101357933B (en) | Method for separating isoflavones monomeric compound in Belamcanda chinensis by high speed countercurrent chromatography | |
| CN102936275A (en) | Method for separating and purifying impurities in sodium tanshinone IIA sulfonate crude drug | |
| CN101255182B (en) | Extraction separating method for bupleurum root saponin b2 | |
| CN107936033A (en) | The method that industrially prepared liquid chromatogram isolates and purifies koumine | |
| CN1268631C (en) | Technique for preparing general flavone of Chinese globeflower with short petal some medicinal substances in high purity | |
| CN108101923B (en) | Separation and purification method of glabridin monomer | |
| CN102617674A (en) | Preparation method of scopolin monomer in anisodus tanguticus root | |
| CN102908371A (en) | Method for preparing high-purity ferulic acid from angelica sinensis | |
| CN101220066B (en) | Separation purification process of monomeric compound in whitethorn leaf | |
| CN105434539A (en) | Composition of lotus flavones | |
| CN102503998B (en) | Method for rapidly separating quercetin from flos albiziae | |
| CN104926659A (en) | Method for preparing rosmarinic acid chemical reference substance from three types of high mountain salvias | |
| CN104557471A (en) | Method for simultaneously preparing gram-grade high-purity tyrosol, renulatin and salidroside from rhodiola crenulata | |
| CN105061212B (en) | A kind of preparation method of neochlorogenic acid | |
| CN104945391B (en) | The method and system of extraction separation Schaftoside from Desmodium styracifolium | |
| CN101906091B (en) | Method for preparing and separating tectorigenin from iris in high-speed countercurrent chromatography by one step | |
| CN103450212A (en) | Preparation method of deoxyelephantopin | |
| CN102464635B (en) | Separation and purification method of arctigenin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |