CN102304160B - Preparation method and application of luteolin-7-O-gentibioside - Google Patents
Preparation method and application of luteolin-7-O-gentibioside Download PDFInfo
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- CN102304160B CN102304160B CN201110031474.9A CN201110031474A CN102304160B CN 102304160 B CN102304160 B CN 102304160B CN 201110031474 A CN201110031474 A CN 201110031474A CN 102304160 B CN102304160 B CN 102304160B
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Abstract
The invention discloses a method for preparing luteolin-7-O-gentibioside, which comprises the following process steps of: adding water to decoct a medicinal material of herb of sowthistleleaf ixeris twice, 1 hour for the first time and 0.5 hour for the second time, mixing decoction, concentrating until 1ml of decoction is equivalent to 0.5g of original raw medicine, naturally cooling to the temperature of below 40DEG C, adding 95 percent ethanol in an amount which is 2 to 4 times weight of the concentrated decoction with stirring to make the alcohol content is 50 to 70 percent, standing for 24 hours, and filtering; recovering ethanol from filtrate until alcohol smell is absent, making recovered liquid pass through a macroporous resin column, eluting 1 to 5 bed volume (BV) by using water, discarding aqueous eluant, eluting 5 to 10VB by using 30 percent ethanol, collecting eluant, and concentrating under reduced pressure; loading the concentrated solution on a polyamide column by using a dry process, eluting 5 to 10BV by using water, discarding aqueous eluant, eluting 5BV by using 30 percent ethanol, collecting 2 to 5BV of eluant, and concentrating under reduced pressure until dryness; and dissolving by using methanol, and performing high performance liquid chromatography (HPLC) separation preparation by applying 250*10mm semi-preparation column and taking acetonitrile and 1 percent glacial acetic acid in a ratio of 15:85 as mobile phases to obtain yellow amorphous powder. The process is simple and the purity of the product is over 98 percent.
Description
Technical field
The present invention relates to a kind of preparation method of luteolin-7-O-gentibioside, the invention still further relates to the application of luteolin-7-O-gentibioside aspect Herba Ixeritis Sonchifoliae and the control of the Herba Ixeritis Sonchifoliae quality of the pharmaceutical preparations, belong to pharmaceutical field.
Background technology
Herba Ixeritis Sonchifoliae, be commonly called as Herba Ixeritis Sonchifoliae, magnitude all over the sky, 2 years raw dry aerial parts for composite family gutweed Lepidium Herba Ixeritis Sonchifoliae [Ixeris sonchifolia (Bge) Hance], have clearing heat and detoxicating, the effect of blood-activating analgetic, clinical application is comparatively extensive with KUDIEZI ZHUSHEYE, is mainly used in treating the ischemic cardio cerebrovascular diseases such as coronary heart diseases and angina pectoris and myocardial infarction.Pharmacological research shows, the main pharmacodynamics composition of Herba Ixeritis Sonchifoliae is flavonoid compound and adenosine etc.In the national drug standards, the assay index of Herba Ixeritis Sonchifoliae is adenosine at present, but adenosine content is extremely low, and every milliliter only contains several micrograms, flavonoid compound is only had to the ultraviolet determination method of total flavones, and method specificity is poor, and accuracy is low.We have done following work for this reason, using and find a kind of new flavones ingredient as the index of Herba Ixeritis Sonchifoliae assay.
Summary of the invention
Object of the present invention, is to provide a kind of preparation method of luteolin-7-O-gentibioside.
Another object of the present invention is to provide the application of this luteolin-7-O-gentibioside aspect Ixeris sonchifolia Hance, the control of the Herba Ixeritis Sonchifoliae quality of the pharmaceutical preparations.
The technical scheme adopting is:
One, the preparation method of luteolin-7-O-gentibioside, comprises following processing step:
1. get Ixeris sonchifolia Hance, boiling secondary, 1 hour for the first time, 0.5 hour for the second time, collecting decoction, be concentrated into every 1ml and be equivalent to crude drug in whole 0.5g, let cool to below 40 ℃, under agitation add 2 ~ 4 times of amount 95% ethanol, make to reach 50 ~ 70% containing alcohol amount, place 24 hours, filter, filtrate recycling ethanol is extremely without alcohol taste.
2. reclaim liquid and pass through macroporous resin column, wash 1 ~ 5BV with water, discard water lotion, then use 30% ethanol elution 5 ~ 10BV, collect elutriant concentrating under reduced pressure, polyamide column in concentrated solution dry method, first wash 5 ~ 10BV with water, discard water lotion, then use 30% ethanol elution 5BV, collect 2 ~ 5BV elutriant, concentrating under reduced pressure.
3. through dissolve with methanol, apply the semipreparative column of 250 * 10mm, the acetonitrile of 15:85 of take carries out the separated preparation of HPLC with 1% Glacial acetic acid as moving phase, obtains yellow amorphous powder.Through HPLC, identify, purity is more than 98%.
This yellow amorphous powder dissolves in methyl alcohol, ethanol, is soluble in 50% ethanol, Mg-HCl reacting positive, and Molish reacting positive, illustrates that this compound is flavonoid glycoside compound.Acid hydrolysis detects glucose.?
1in H-NMR spectrum, 3 proton 7.44(1H in the ABX system of lower, dd, J=8.4,1.8Hz), 7.41(1H, d, J=1.8Hz) and 6.89(1H, d, J=8.4Hz) illustrate B ring be 3 ', 4 '-bis-replace, two proton 6.50(1H of high field, d, J=1.8Hz) and 6.80(1H, d, J=1.8Hz) be respectively 6,8 protons of A ring.6.70(1H, s) for C-3 be hydrogen signal.Carbon spectrum data comparison (Ternai B with document luteolin, Markham KR. Carbon-13 NMR studies of flavonoids-I flabones and flavonols. Tetrahedron, 1976,32:565-569), determine that aglycon is luteolin.And the C-7 of aglycon is to high field displacement 0.7, and C-6, C-8 and C-10 are respectively to low field displacement 0.8,1.0,1.6, thus explanation sugar chain is connected on C-7 position.
13c-NMR spectrum provides two glucose end group carbon signals 103.6 and 99.9. by more basically identical (the Kikuchi M of the gentiobiose base data of sugar moieties data and bibliographical information in anomeric spectrum district, Matsuda N. Flavone glycosides from Lonicera gracilipes. Journal of Natural Product, 1996,59 (3): 314-315), therefore, sugar moieties consists of β-D-Glucopyranose-(1 → 6)-β-D-glucopyranosyl.In sum, identify that this compound is luteolin-7-O-gentibioside.
Structural formula of compound:
Adopt luteolin-7-O-gentibioside purity that this method makes more than 98%, and be one of main active ingredient in Herba Ixeritis Sonchifoliae, can be used as the quantitative target of Ixeris sonchifolia Hance and preparation, adopt HPLC method measuring method favorable reproducibility, highly sensitive, specificity is strong.
Two, luteolin-7-O-gentibioside is for the quality control of Herba Ixeritis Sonchifoliae preparation, and concrete way is as follows:
Chromatographic condition and system suitability: with octadecylsilane chemically bonded silica, be weighting agent; Acetonitrile-0.4% phosphoric acid solution, acetonitrile and 0.4% phosphoric acid solution proportioning are 10:90, are moving phase; Detection wavelength is 330nm; Number of theoretical plate calculates and should be not less than 3000 with luteolin-7-O-gentibioside peak;
It is appropriate that the preparation precision of reference substance solution takes luteolin-7-O-gentibioside reference substance, adds methyl alcohol and make every 1ml containing the solution of 0.02mg, shakes up, and obtains;
It is appropriate that KUDIEZI ZHUSHEYE is got in need testing solution preparation, obtains;
Assay method: precision is drawn reference substance solution and each 10 μ l of need testing solution respectively, and injection liquid chromatography, measures, and obtains.
Methodological study experiment is as follows:
1 linear relationship is investigated accurate absorption reference substance storing solution (0.20mg/ml) 0.5ml, 1ml, 1.5ml, 2ml, 2.5ml, 3ml respectively and is put in the brown measuring bottle of 25ml, add methyl alcohol to scale, shake up, make the reference substance solution that concentration is respectively 4.0,8.0,12.0,16.0,20.0,24.0 μ g/ml, by the chromatographic condition of drafting, measure peak area, take peak area integrated value as ordinate zou, luteolin-7-O-gentibioside concentration is X-coordinate drawing standard curve, calculates regression equation: Y=1.8903X-104667 r
2=0.9995(table 1)
Table 1 linear relationship is investigated
| Experiment number | Sample concentration (μ g/ml) | Peak area |
| 1 | 4.0 | 6.6226 |
| 2 | 8.0 | 15.3445 |
| 3 | 12.0 | 23.6359 |
| 4 | 16.0 | 32.0870 |
| 5 | 20.0 | 39.5403 |
| 6 | 24.0 | 48.6373 |
Experiment shows that luteolin-7-O-gentibioside is good linear dependence within the scope of 4.0～24.0 μ g/ml.
The accurate need testing solution 10 μ l that draw of 2 precision tests, repeating 6 mensuration calculated by peak area relative standard deviations of sample introduction is RSD=0.99%. (table 2)
Table 2 Precision test result
| Experiment number | Peak area | RSD% |
| 1 | 26.3938 | ? |
| 2 | 25.8594 | ? |
| 3 | 26.4687 | 0.99 |
| 4 | 26.4917 | ? |
| 5 | 26.4435 | ? |
| 6 | 26.0814 | ? |
3 stability tests are got respectively with a need testing solution 10 μ l, by above-mentioned chromatographic condition, measure at regular intervals its content, investigate the stability of sample solution, calculate relative standard deviation, the results are shown in Table 3.
Table 3 sample stability result
| Time (h) | Peak area | RSD% |
| 0 | 26.3938 | ? |
| 2 | 26.189 | ? |
| 4 | 25.1625 | 1.89 |
| 6 | 26.1904 | ? |
| 8 | 26.1664 | ? |
| 12 | 26.5843 | ? |
More than experiment shows, in need testing solution, the content of luteolin-7-O-gentibioside is basicly stable in 12 hours.
4 circulation ratio test precisions take five parts, sample, make need testing solution, by the chromatographic condition of having drafted, measure peak area, calculate relative standard deviation < 5%, the results are shown in Table 4.
Table 4 reproducible test results
| Experiment number | Content (mg/10ml) | Average content (mg/ sheet) | RSD% |
| 1 | 0.131 | ? | ? |
| 2 | 0.134 | ? | ? |
| 3 | 0.138 | 0.134 | 1.96 |
| 4 | 0.134 | ? | ? |
| 5 | 0.13 | ? | ? |
| 6 | 0.135 | ? | ? |
5 recovery tests adopt application of sample absorption method, get the KUDIEZI ZHUSHEYE sample 2ml of known content, add respectively luteolin-7-O-gentibioside reference substance 2ml, shake up, and with millipore filtration (0.45 μ m), filter, and filtrate is as need testing solution.By above-mentioned chromatographic condition, measure, with following formula calculate recovery rate, the results are shown in table 5.
Rate of recovery %=(luteolin-7-O-gentibioside amount in actual measurement luteolin-7-O-gentibioside amount-sample)/add luteolin-7-O-gentibioside amount * 100%
.
Table 5 determination of recovery rates result
6 sample determinations difference accurate absorption reference substance solution and each 10 μ l of need testing solution, according to above-mentioned chromatographic condition mensuration, calculate the content of luteolin-7-O-gentibioside in KUDIEZI ZHUSHEYE with external standard method, average content is 0.13mg/10mL.
Three, luteolin-7-O-gentibioside is for the quality control of Ixeris sonchifolia Hance, and concrete grammar is as follows:
Chromatographic condition and system suitability: with octadecylsilane chemically bonded silica, be weighting agent; Acetonitrile-0.4% phosphoric acid solution, acetonitrile and 0.4% phosphoric acid solution proportioning are 8:92, are moving phase; Detection wavelength is 330nm; Number of theoretical plate calculates and should be not less than 5000 with luteolin-7-O-gentibioside peak;
It is appropriate that the preparation precision of reference substance solution takes luteolin-7-O-gentibioside reference substance, adds methyl alcohol and make every 1ml containing the solution of 0.2mg, shakes up, and obtains;
Ixeris sonchifolia Hance 30g is got in need testing solution preparation, cataclasm, mixes, and gets 5g, and accurately weighed, precision adds methyl alcohol 50ml, supersound process 30 minutes, and millipore filtration filters, and obtains;
Assay method: precision is drawn reference substance solution and each 10 μ l of need testing solution respectively, and injection liquid chromatography, measures, and obtains.
Measure according to the method described above different places of production medicinal material, measurement result is as following table:
The content of luteolin-7-O-gentibioside in the Ixeris sonchifolia Hance of the different places of production
| The place of production | Content (%) | The place of production | Content (%) |
| Haicheng City 090501 | 0.035 | Dandong 090502 | 0.030 |
| Haicheng City 090502 | 0.039 | Dandong 090503 | 0.026 |
| Haicheng City 090503 | 0.031 | Benxi 090501 | 0.035 |
| Haicheng City 090504 | 0.037 | Benxi 090502 | 0.029 |
| Dandong 090501 | 0.028 | Benxi 090503 | 0.026 |
Embodiment
Embodiment mono-
A preparation method for luteolin-7-O-gentibioside, comprises following processing step:
1. get Ixeris sonchifolia Hance, boiling secondary, 1 hour for the first time, 0.5 hour for the second time, collecting decoction, be concentrated into every 1ml and be equivalent to crude drug in whole 0.5g, let cool to below 40 ℃, under agitation add 3 times of amount 95% ethanol, make to reach 60% containing alcohol amount, place 24 hours, filter, filtrate recycling ethanol is extremely without alcohol taste.
2. reclaim liquid and pass through macroporous resin column, wash 5BV with water, discard water lotion, then use 30% ethanol elution 5 ~ 10BV, collect elutriant concentrating under reduced pressure, polyamide column in concentrated solution dry method, first wash 5 ~ 10BV with water, discard water lotion, then use 30% ethanol elution 5BV, collect 2 ~ 5BV elutriant, concentrating under reduced pressure.
3. through methyl alcohol, process, apply the semipreparative column of 250 * 10mm, the acetonitrile of 15:85 of take carries out the separated preparation of HPLC with 1% Glacial acetic acid as moving phase, obtains yellow amorphous powder.Through areas of peak normalization method, calculating its purity is 98.6%.
Compound of the present invention can reduce atherosclerotic rabbit Aortic Plaque area, reduces TXB
2, ET concentration, increase 6-keto-PGF
1 αconcentration, has inhibition atherogenesis, the effect of protection vascular endothelial cell.
The test of pesticide effectiveness is as follows:
1 materials and methods
1.1 animals and feed
Be sheerly Japanese white big ear rabbit, 48 male and female half and half, weight (2.5 ± 0.25) kg，You Shenyang Pharmaceutical University animal cultivation center provides.
1.2 experimental drug
Luteolin-7-O-gentibioside, Shuangding Pharmaceutical Co., Ltd., Shenyang produces;
1.3 experimental techniques and result
After 48 rabbit are raised 1 week, measure blood fat and weight, according to blood fat and weight, be divided into: Normal group, model control group, the compounds of this invention 2.5,5.0mg/kg group, 12 every group.Normal group: rabbit is only raised with normal diet; Model control group: every of rabbit every day give 50g high lipid food, then raise with normal diet 150g continuous 12 weeks; The compounds of this invention 2.5,5.0mg/kg group: rabbit gave high lipid food after 4 weeks, start through intraperitoneal injection continuous 4 weeks.When experiment finishes, heart extracting blood, measures plasma thromboxane (TXB
2), 6 ketone prostaglandin(PG) (6-keto-PGF
1 α), the index such as endothelin (ET).Taking-up is the aorta to common iliac artery bifurcation from heart, peels adventitia and fatty off around, along dorsal part median line, longitudinally cuts off, clean with 0.9% normal saline flushing, is laid on filter paper, with 15% formaldehyde, fixes.Calculate the per-cent of plaque area and whole piece aorta area.
The impact of the compounds of this invention on atherosclerotic rabbit Aortic Plaque area
| Group | n | Plaque area/aorta area (%) |
| Normal group | 12 | - |
| Model group | 12 | 56.1±22.5 |
| The compounds of this invention 2.5mg/kg | 12 | 32.3±15.1 * |
| The compounds of this invention 5.0mg/kg | 12 | 20.1±11.2 ** |
Experimental result shows, two dosage of the compounds of this invention all can suppress atherogenesis, compare with model group, have significant difference (P<0.05).
The compounds of this invention is to atherosclerotic rabbit blood plasma TXB
2, 6-keto-PGF
1 α, ET impact
| Group | n | TXB 2 | 6-keto-PGF 1α | ET |
| Normal group | 12 | 536.1±92.5 | 1038.5±160.1 | 39.1±12.5 |
| Model group | 12 | 633.5±34.5 | 814.14±140.6 | 65.1±12.9 |
| The compounds of this invention 2.5mg/kg | 12 | 581.5±81.3* | 1058.5±108.1* | 48.0±14.6* |
| The compounds of this invention 5.0mg/kg | 12 | 541.4±41.5* | 1154.8±81.8* | 40.8±11.2* |
Experimental result shows, two dosage of the compounds of this invention all can reduce thromboxane (TXB
2), endothelin (ET) concentration, increase by 6 ketone prostaglandin(PG) (6-keto-PGF
1 α) concentration, compare with model group, have and there is significant difference (P<0.05), illustrate that the compounds of this invention has clear and definite endotheliocyte provide protection.
Claims (1)
1. a preparation method for luteolin-7-O-gentibioside, is characterized in that comprising following processing step:
Get Ixeris sonchifolia Hance, boiling secondary, 1 hour for the first time, 0.5 hour for the second time, collecting decoction, be concentrated into every 1ml and be equivalent to crude drug in whole 0.5g, let cool to below 40 ℃, under agitation add 2～4 times of amount 95% ethanol, make to reach 50～70% containing alcohol amount, place 24 hours, filter, filtrate recycling ethanol is extremely without alcohol taste, reclaim liquid and pass through macroporous resin column, wash 1～5BV with water, discard water lotion, use again 30% ethanol elution 5～10BV, collect elutriant concentrating under reduced pressure, polyamide column in concentrated solution dry method, first wash 5～10BV with water, discard water lotion, use again 30% ethanol elution 5BV, collect 2～5BV elutriant, concentrating under reduced pressure, through dissolve with methanol, the semipreparative column of application 250 * 10mm, take acetonitrile and 1% Glacial acetic acid mixed solution carries out the separated preparation of HPLC as moving phase, obtain yellow amorphous powder, obtain,
The configuration proportion of above-mentioned acetonitrile and 1% Glacial acetic acid mixed solution is 15%:85%, and above-mentioned per-cent is mass percent.
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| CN103965274A (en) * | 2013-02-05 | 2014-08-06 | 河北以岭医药研究院有限公司 | Preparation method of apigenin-7-O-beta-D-glucuronide, and use of apigenin-7-O-beta-D-glucuronide |
| CN105175464B (en) * | 2015-06-17 | 2018-03-20 | 广东省农业科学院蚕业与农产品加工研究所 | The method that the O β glucosides of cyanidenon 5 are separated from arillus longan |
| CN109053836B (en) * | 2018-08-14 | 2021-12-03 | 南京中医药大学 | Luteolin 7-O-succinyl glucoside and apigenin-7-O-succinyl glucoside and application thereof |
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