CN102030790A - Preparation method of Homoplantagin - Google Patents
Preparation method of Homoplantagin Download PDFInfo
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- CN102030790A CN102030790A CN2010105201884A CN201010520188A CN102030790A CN 102030790 A CN102030790 A CN 102030790A CN 2010105201884 A CN2010105201884 A CN 2010105201884A CN 201010520188 A CN201010520188 A CN 201010520188A CN 102030790 A CN102030790 A CN 102030790A
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Abstract
The invention provides a preparation method of Homoplantagin, comprising the following steps of: smashing the raw material of common sage herbs; adding 60-80% ethanol water; heating for refluxing and extracting for 2-3 times; mixing extracting solutions; concentrating and adding water for dispersing, and filtering onto a macroporous resin column; carrying out gradient elution with ethanol water; collecting Homoplantagin fractions; concentrating eluent; adjusting pH to be 2-4; washing filtered precipitates with acetone; drying to obtain faint yellow powder; and separating and purifying with high speed countercurrent chromatography to obtain the product. The method is suitable for preparing high-content Homoplantagin.
Description
Technical field:
The invention belongs to the Separation of Natural Products field, especially relate to a kind of preparation method of Homoplantaginin.
Background technology:
Herba Salviae Plebeiae, another name snow see and grass, toad grass are the over-ground part of labiate Herba Salviae Plebeiae (svlvia plebeia r.br.).Cool in nature, bitter, suffering.It is heat-clearing that function cures mainly, detoxifcation, cool blood, diuresis.It is swollen to be mainly used in swelling and pain in the throat, bronchitis, nephritic edema, carbuncle; Control outward and be used for mazoitis, swelling and pain of hemorrhoid, hemorrhage etc.Wherein Homoplantaginin is the main function composition of Herba Salviae Plebeiae.
Homoplantaginin belongs to flavonoid compound, is soluble in methyl alcohol, ethanol, is slightly soluble in acetone, is insoluble in water.Molecular formula: C
22H
22O
11, its semihydrate is the yellow crystal thing.This product has bacteriostatic action, and external have the restraining effect of medium tenacity to chronic tracheitis common pathogenic bacteria Staphylococcus albus, pneumococcus etc., and streptococcus aureus is infected in animal body certain antagonistic action, can reduce mortality ratio 20%.Certain antibechic, expectorant effect are arranged, and the ability of eliminating the phlegm can be used for treating chronic tracheitis, and toxicity is less greater than ammonium chloride.Above pharmaceutical use report shows that Homoplantaginin has wide research prospect.
The extraction process of existing Homoplantaginin mainly is means separation and purification such as alcohol extracting, supersound extraction, ethyl acetate extraction, silicagel column, polyamide column chromatography, gel column.As " research of flavones ingredient in the Herba Salviae Plebeiae " that Xiang Lan etc. delivers, the disclosed extracting method of the document is alcohol extracting, and ethyl acetate extraction repeats polyamide column and separates, and it is long that this method prepares the Homoplantaginin cycle, only is suitable for the laboratory and prepares on a small quantity." chemical ingredients and the liver-protecting activity of hair Plantago depressa Willd " that also has Wu Fei China etc. to deliver in addition, the document is by alcohol extracting, n-butanol extraction, and repeatedly the method for silica gel column chromatography, gel column, C-18 post and recrystallization makes Homoplantaginin, various, the complicated operation of this method steps is not suitable for a large amount of preparations.And less to the research of extracting Homoplantaginin from Herba Salviae Plebeiae in the existing document, therefore a kind of method of extracting Homoplantaginin from Herba Salviae Plebeiae is provided is necessary.
Summary of the invention:
The technical problem to be solved in the present invention provides a kind of preparation method of Homoplantaginin.This method is simple to operate, the product content height.
Why the present invention adopts high speed adverse current chromatogram separation and purification Homoplantaginin, is because this separation method is easy and simple to handle, has also avoided the loss of sample simultaneously, compare with traditional separation means, overcome its complex operation, the shortcoming that separation cycle is long, and it is big to have a preparation amount, the advantage that product purity is high.
The present invention realizes by the following technical solutions:
A kind of preparation method of Homoplantaginin is characterized in that comprising following steps:
1) extract: with the Herba Salviae Plebeiae raw material pulverizing, add 8～12 times of amount 60-80% ethanol liquid heating and refluxing extraction 2～3 times, united extraction liquid, decompression recycling ethanol gets concentrated solution;
2) post separates: above-mentioned concentrated solution suitable quantity of water dilution is filtered, and last macroporous resin column is used the aqueous ethanolic solution gradient elution, and the thin layer monitoring is collected the Homoplantaginin flow point, concentrate eluant;
3) removal of impurities: above-mentioned concentrated solution is adjusted to acidity, leaches throw out, use washing with acetone, vacuum-drying gets pale yellow powder;
4) high speed adverse current chromatogram separation and purification: as the two-phase solvent system, getting is stationary phase mutually, is moving phase mutually down with ethyl acetate, alcohol and water, and with above-mentioned powder phased soln down, the effluent evaporated under reduced pressure promptly gets the Homoplantaginin product.
A kind of among the optional AB-8 of the model of the macroporous resin described step 2), D1300, HZ-816 and the LSA-8, the aqueous ethanolic solution gradient is 3-5BV20-40% → 4-6BV50-70%.
Adjustment of acidity can be that hydrochloric acid or vitriolic are a kind of in the described step 3), regulates pH2～4.
Two-phase solvent ethyl acetate in the described step 4): ethanol: the proportioning 4-3 of water: 1: 5.Chromatographic instrument rotating speed 700～1000r/min, flow rate of mobile phase 1.0～3.0ml/min.
In sum, there is following advantage in the present invention:
(1) treatment capacity of macroporous resin is big, and regeneration is simple, and is reusable;
(2) high speed adverse current chromatogram need not to use carrier, has reduced the loss of sample in the operating process, good separating effect, and preparation amount is big.
Further specify the present invention below in conjunction with embodiment, but the scope of protection of present invention is not limited to following embodiment.
Embodiment:
Tlc (with reference to " foundation of the extraction separation of Homoplantaginin and spectral chromatography characteristic spectrum in the Herba Salviae Plebeiae " documents such as Peng Miaomiao) is adopted in the monitoring of Homoplantaginin in the following embodiment, and concrete grammar is as follows:
The thin-layer chromatography condition:
Thin layer plate: silica gel g thin-layer plate.
Developping agent: chloroform-methanol (4: 1)
Developer: 1% AlCl3 ethanol liquid.
Launch back (exhibition is apart from 10cm), take out, dry, spray is with 1%AlCl
3Ethanol liquid, trial-product with the corresponding position of reference substance chromatogram on (Rf=0.48), the single spot of a same color is arranged.
Embodiment 1:
Get Herba Salviae Plebeiae crushed material 1Kg, 60% ethanolic soln that adds 10L extracted 2 hours, filter, filter residue extracts once by above-mentioned condition again, merging filtrate, decompression recycling ethanol, concentrated solution adds water-dispersion, filter, be added in the AB-8 type macroporous resin column that 600g is housed and adsorb, earlier with 1L water elution (discarding), use 5BV20% ethanol → 4BV50% ethanolic soln wash-out more successively, the Homoplantaginin flow point is collected in the thin layer monitoring, be concentrated into 0.5L, the sulphuric acid soln of adding 5% is adjusted to pH3, filters the throw out washing with acetone, vacuum-drying gets yellow powder 15.1g, again with ethyl acetate, ethanol, water is measured by 4: 1: 5 volume ratio, and ultrasonic mixing back adds in the separating funnel, leaves standstill to make, following phase layering, get as stationary phase, following to moving phase, with above-mentioned yellow powder phased soln down, use the full chromatographic column of phase pump again, go into moving phase with the flow pump of 2.5ml/min then, setting the chromatographic instrument rotating speed after the balance is 850r/min, and sample introduction separates, and collects the Homoplantaginin flow point, evaporated under reduced pressure promptly gets Homoplantaginin 2.4g, content 99.3%.
Embodiment 2:
Get Herba Salviae Plebeiae crushed material 1Kg, 75% ethanolic soln that adds 8L extracted 2 hours, filter, filter residue extracts twice by above-mentioned condition again, merging filtrate, decompression recycling ethanol, concentrated solution adds water-dispersion, filter, be added in the D1300 type macroporous resin column that 600g is housed and adsorb, earlier with 1L water elution (discarding), use 4BV30% ethanol → 4BV70% ethanolic soln wash-out more successively, the Homoplantaginin flow point is collected in the thin layer monitoring, be concentrated into 0.4L, the hydrochloric acid soln of adding 3% is adjusted to pH4, filters the throw out washing with acetone, vacuum-drying gets yellow powder 16.8g, again with ethyl acetate, ethanol, water is measured by 3: 1: 5 volume ratio, and ultrasonic mixing back adds in the separating funnel, leaves standstill to make, following phase layering, get as stationary phase, following to moving phase, with above-mentioned yellow powder phased soln down, use the full chromatographic column of phase pump again, go into moving phase with the flow pump of 2ml/min then, setting the chromatographic instrument rotating speed after the balance is 700r/min, and sample introduction separates, and collects the Homoplantaginin flow point, evaporated under reduced pressure promptly gets Homoplantaginin 2.2g, content 98.6%.
Embodiment 3:
Get Herba Salviae Plebeiae crushed material 1Kg, 80% ethanolic soln that adds 12L extracted 2 hours, filter, filter residue extracts twice by above-mentioned condition again, merging filtrate, decompression recycling ethanol, concentrated solution adds water-dispersion, filter, be added in the HZ-816 type macroporous resin column that 600g is housed and adsorb, earlier with 2L water elution (discarding), use 3BV40% ethanol → 5BV60% ethanolic soln wash-out more successively, the Homoplantaginin flow point is collected in the thin layer monitoring, be concentrated into 0.7L, the sulphuric acid soln of adding 3% is adjusted to pH2, filters the throw out washing with acetone, vacuum-drying gets yellow powder 18.5g, again with ethyl acetate, ethanol, water is measured by 4: 1: 5 volume ratio, and ultrasonic mixing back adds in the separating funnel, leaves standstill to make, following phase layering, get as stationary phase, following to moving phase, with above-mentioned yellow powder phased soln down, use the full chromatographic column of phase pump again, go into moving phase with the flow pump of 1ml/min then, setting the chromatographic instrument rotating speed after the balance is 700r/min, and sample introduction separates, and collects the Homoplantaginin flow point, evaporated under reduced pressure promptly gets Homoplantaginin 2.5g, content 98.4%.
Embodiment 4:
Get Herba Salviae Plebeiae crushed material 1Kg, 75% ethanolic soln that adds 8L extracted 2 hours, filter, filter residue extracts once by above-mentioned condition again, merging filtrate, decompression recycling ethanol, concentrated solution adds water-dispersion, filter, be added in the LSA-8 type macroporous resin column that 600g is housed and adsorb, earlier with 3L water elution (discarding), use 5BV30% ethanol → 4BV60% ethanolic soln wash-out more successively, the Homoplantaginin flow point is collected in the thin layer monitoring, be concentrated into 0.6L, the sulphuric acid soln of adding 5% is adjusted to pH4, filters the throw out washing with acetone, vacuum-drying gets yellow powder 16.1g, again with ethyl acetate, ethanol, water is measured by 3: 1: 5 volume ratio, and ultrasonic mixing back adds in the separating funnel, leaves standstill to make, following phase layering, get as stationary phase, following to moving phase, with above-mentioned yellow powder phased soln down, use the full chromatographic column of phase pump again, go into moving phase with the flow pump of 3ml/min then, setting the chromatographic instrument rotating speed after the balance is 1000r/min, and sample introduction separates, and collects the Homoplantaginin flow point, evaporated under reduced pressure promptly gets Homoplantaginin 2.5g, content 98.1%.
Claims (4)
1. the preparation method of a Homoplantaginin is characterized in that comprising following steps:
1) extract: with the Herba Salviae Plebeiae raw material pulverizing, add 8～12 times of amount 60-80% ethanol liquid heating and refluxing extraction 2～3 times, united extraction liquid, decompression recycling ethanol gets concentrated solution;
2) post separates: above-mentioned concentrated solution is added the suitable quantity of water dilution, filter, last macroporous resin column is used the aqueous ethanolic solution gradient elution, and the thin layer monitoring is collected the Homoplantaginin flow point, concentrate eluant;
3) removal of impurities: above-mentioned concentrated solution is adjusted to acidity, leaches throw out, use washing with acetone, vacuum-drying gets pale yellow powder;
4) high speed adverse current chromatogram separation and purification: as the two-phase solvent system, getting is stationary phase mutually, is moving phase mutually down with ethyl acetate, alcohol and water, and with above-mentioned powder phased soln down, the effluent evaporated under reduced pressure promptly gets the Homoplantaginin product.
2. the preparation method of Homoplantaginin as claimed in claim 1 is characterized in that described step 2) in the optional AB-8 of model, D1300, HZ-816 and the LSA-8 of macroporous resin in a kind of, the aqueous ethanolic solution gradient is 3-5BV20-40% → 4-6BV50-70%.
3. the preparation method of Homoplantaginin as claimed in claim 1, what it is characterized in that adjustment of acidity in the described step 3) can be that hydrochloric acid or vitriolic are a kind of, regulates pH2～4.
4. the preparation method of Homoplantaginin as claimed in claim 1 is characterized in that the two-phase solvent ethyl acetate in the described step 4): ethanol: the proportioning 4-3 of water: 1: 5.Chromatographic instrument rotating speed 700～1000r/min, flow rate of mobile phase 1.0～3.0ml/min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105201884A CN102030790A (en) | 2010-10-26 | 2010-10-26 | Preparation method of Homoplantagin |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105201884A CN102030790A (en) | 2010-10-26 | 2010-10-26 | Preparation method of Homoplantagin |
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| CN102030790A true CN102030790A (en) | 2011-04-27 |
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| CN2010105201884A Pending CN102030790A (en) | 2010-10-26 | 2010-10-26 | Preparation method of Homoplantagin |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102657698A (en) * | 2012-05-31 | 2012-09-12 | 南京中医药大学 | Extraction method and application of salvia plebeia general flavone extract |
| CN110787180A (en) * | 2019-12-19 | 2020-02-14 | 济南大学 | Application of homoplantaginoside and derivatives thereof as Nrf-2 activator |
-
2010
- 2010-10-26 CN CN2010105201884A patent/CN102030790A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102657698A (en) * | 2012-05-31 | 2012-09-12 | 南京中医药大学 | Extraction method and application of salvia plebeia general flavone extract |
| CN110787180A (en) * | 2019-12-19 | 2020-02-14 | 济南大学 | Application of homoplantaginoside and derivatives thereof as Nrf-2 activator |
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Application publication date: 20110427 |