CN108484695A - A method of extracting benzyl carbinol glycosides and flavone compound simultaneously from butterflybush flower - Google Patents
A method of extracting benzyl carbinol glycosides and flavone compound simultaneously from butterflybush flower Download PDFInfo
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- CN108484695A CN108484695A CN201810305434.0A CN201810305434A CN108484695A CN 108484695 A CN108484695 A CN 108484695A CN 201810305434 A CN201810305434 A CN 201810305434A CN 108484695 A CN108484695 A CN 108484695A
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- C—CHEMISTRY; METALLURGY
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
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- 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
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- 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
- C07H17/06—Benzopyran radicals
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- C07H17/07—Benzo[b]pyran-4-ones
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Abstract
The method that the present invention relates to a kind of to extract benzyl carbinol glycosides and flavone compound simultaneously from butterflybush flower, includes the following steps：(1) take butterflybush flower ethanol extract, be splined on HPD BJQH type macroreticular resins, be washed to it is colourless after, the ethanol water for being 65~75% using concentration of volume percent is eluted as mobile phase, collect eluent, after concentration concentrate；(2) concentrate is splined on 100 type macroreticular resins of HPD, be washed to it is colourless after, successively with concentration of volume percent be respectively 10~15%, 25~30%, 32~38% and 65~75% ethanol water elute；Collect a concentration of 25~30% eluent, the as active component of benzyl carbinol glycosides；Collect a concentration of 65~75% eluent, the as active component of flavone compound.The present invention isolates and purifies benzyl carbinol glycosides in butterflybush flower and flavone effective part using 100 macroreticular resin joint technology of HPD BJQH and HPD, and the process stabilizing of acquisition is feasible, and reference is provided for the research of butterflybush flower new Chinese medicine active component and production.
Description
Technical field
The present invention relates to field of natural product extraction, and in particular to one kind extracting benzyl carbinol glycosides and Huang simultaneously from butterflybush flower
The method of ketone compounds.
Background technology
Butterflybush flower (Buddleja officinalis Maxim) is the dry flower of Loganiaceae Genus Buddleja L butterflybush flower
Flower bud and inflorescence.Its is sweet in flavor, cold nature, Return liver, gallbladder channel, has dispelling wind and heat, swollen for hot eyes the effect of nourishing the liver to improve visual acuity, move back screen
Bitterly, more tear photophobia, screen of looking unfamiliar film, hepatasthenia dim eyesight, the diseases such as blurring of vision.Clinically it is mainly used for xerophthalmia, diabetic retina
The eye diseases such as lesion, conjunctivitis, it is significant in efficacy.Studies have shown that being rich in benzyl carbinol glycosides and flavones ingredient, content in butterflybush flower
It is significantly higher than other ingredients, the former includes verbascoside, Isoverbascoside, salidroside, echinacoside, forsythiaside B etc.；The latter
Including the new glycosides of linarin, butterflybush flower, robinin, cyanidenon, apiolin etc., wherein verbascoside and Determination of Linarin protrude,
It is significantly higher than other ingredients, benzyl carbinol glycoside and flavones ingredient all have bacteriostatic activity in butterflybush flower, can inhibit aldose reduction
Diabetic retinopathy is effectively relieved in enzyme；Flavonoids also can effectively treat the xerophthalmia caused by androgen levels decline, it is seen that
Benzyl carbinol glycoside and flavones ingredient are the material bases that butterflybush flower plays clinical efficacy.
Invention content
The purpose of the present invention is overcoming the deficiencies of existing technologies, and provides a kind of using macroreticular resin while isolating and purifying close illiteracy
The optimised process for spending two active components of middle benzyl carbinol glycosides and flavones, to obtain the verbascoside and illiteracy of best eluting rate and purity
Flower glycosides provides reference for the research of butterflybush flower new Chinese medicine active component and production.
Specifically, the present invention provides a kind of from butterflybush flower while extracting the side of benzyl carbinol glycosides and flavone compound
Method, described method includes following steps：
(1) take butterflybush flower ethanol extract, be splined on HPD-BJQH type macroreticular resins, be washed to it is colourless after, with volume hundred
It is that mobile phase is eluted to divide the ethanol water that specific concentration is 70~80%, collects eluent, and concentrate is obtained after concentration；
(2) concentrate is splined on HPD-100 type macroreticular resins, be washed to it is colourless after, use percent by volume successively
Concentration is respectively 10~15%, 25~30%, 32~38% and 65~75% ethanol water elution；
Collect a concentration of 25~30% eluent, the as active component of benzyl carbinol glycosides；
Collect a concentration of 65~75% eluent, the as active component of flavone compound.
Method provided by the invention creatively uses HPD-BJQH and HPD-100 macroreticular resin joint technology to butterflybush flower
Middle benzyl carbinol glycosides and flavone effective part are isolated and purified.
For butterflybush flower, verbascoside and linarin are benzyl carbinol glycoside compound and flavonoid in the plant
Typical Representative in object, therefore, method provided by the invention with verbascoside and linarin with respect to the content of crude drug, eluting rate,
The parameters such as purity and eluent total solid substance yield are evaluation index.
The present invention can effectively elute benzene second in separation butterflybush flower by largely putting into practice discovery, HPD-100 types macroreticular resin
Alcohol glycosides and flavone effective part, it is especially excellent to the eluting rate and refining effect of verbascoside and linarin, often compared with other
The similar macroreticular resin (such as HPD-300, X-5, AB-8 macroreticular resin) seen is to the good separating effect of the two.But if only with list
One HPD-100 type macroreticular resins are isolated and purified, and the retention rate of target product is relatively low, and purity is also not achieved 50%；And
Although HPD-BJQH type macroreticular resins detach verbascoside and linarin is ineffective, using the ethyl alcohol of concentration 70~80%
Can simultaneously the two be eluted, eluting rate is up to 80% or more, and impurity-eliminating effect is preferable, can effectively clean and retain effectively at
Point.Therefore, after the present invention creatively first carries out preliminary purification removal of impurities using HPD-BJQH types macroreticular resin, then HPD- is used
The best elution processes of 100 macroreticular resins isolate and purify benzyl carbinol glycosides and flavone effective part.Using HPD-100 type macroreticular resins
When being eluted, the present invention first uses 10~15% ethanol solution to carry out first time removal of impurities, then collect a concentration of 25~
30% eluent is the active component of benzyl carbinol glycosides；It uses 32~38% ethanol solution to carry out second again to clean, then
The eluent for collecting a concentration of 65~75% is the active component of flavone compound.
Butterflybush flower ethanol extract of the present invention is using butterflybush flower medicinal material as raw material, with ethyl alcohol using known in the art
For method extraction.As the preferred embodiment of the present invention, the butterflybush flower ethanol extract is that extraction obtains with the following method：
Take butterflybush flower medicinal material, it is that 55~65% ethanol waters extract 30~60min that concentration of volume percent, which is added, add with before
Extract same concentrations ethanol water extract 15~45min, merge twice extraction gained extracting solution, concentration to get.It is preferred that
Ground, the butterflybush flower ethanol extract are that extraction obtains with the following method：Butterflybush flower medicinal material is taken, 10 times of amounts are added for the first time
60% ethanol solution extracts 45min, and second of addition, 8 times of 60% ethanol solutions of amount extract 30min, and merging filtrate recycles ethyl alcohol,
To obtain the final product.
The present invention carries out the parameters such as applied sample amount, mobile phase elution volume and elution speed in extraction process comprehensively excellent
Choosing, to improve the yield and purity of benzyl carbinol glycosides and flavone compound simultaneously.Specifically：
In the preferably described step (1) of the present invention：
A concentration of 0.12~0.13g/ml of ethanol extract of loading.The present invention is had found by putting into practice, when sample solution quality
Concentration in the range when, the eluting rate higher of target product；Especially, in corresponding eluent the eluting rate of verbascoside than dense
The eluting rate of verbascoside significantly improves 1.5~2 times when contracting liquid mass concentration is 0.1g/ml or 0.2g/ml, can be more effectively
Verbascoside is eluted.
The applied sample amount of the butterflybush flower ethanol extract is 1 with the mass ratio of HPD-BJQH type macroreticular resins:1.5~2.5.
The present invention is had found by putting into practice, when applied sample amount and macroreticular resin mass ratio 1:1 or 1:When 1.5, verbascoside and linarin have
Leakage, when applied sample amount reaches 1.5~2.5 with macroreticular resin mass ratio, verbascoside and linarin are substantially without leakage.
The mobile phase elution volume is 11~13BV.The present invention is had found by putting into practice, using a concentration of 70~80%
Ethanol water can fully elute two class target products by the elution of 11~13BV.
The flow velocity of the mobile phase elution is 2~3BV/h.The present invention is had found by putting into practice, with the increasing of eluant, eluent flow velocity
Greatly, the eluting rate of verbascoside reduces, and linarin eluting rate slightly reduces after then increasing first increase with elution rate, and adopts
When with 2~3BV/h elution flow rates, there was no significant difference for the eluting rate of verbascoside and linarin.
In the preferably described step (2) of the present invention：
The concentrate mass concentration of loading is 0.12~0.13g/ml.The present invention is had found by putting into practice, when sample solution quality
Concentration in the range when, the eluting rate higher of target product；Especially, in corresponding eluent the eluting rate of verbascoside than dense
The eluting rate of verbascoside significantly improves 1.5~2 times when contracting liquid mass concentration is 0.1g/ml or 0.2g/ml, can be more effectively
Verbascoside is eluted.
The applied sample amount of the concentrate is 1 with the mass ratio of HPD-100 type macroreticular resins:1.5~2.5.The present invention passes through
Practice is found, when applied sample amount and macroreticular resin mass ratio 1:1 or 1:When 1.5, verbascoside and linarin have leakage, work as loading
When amount reaches 1.5~2.5 with macroreticular resin mass ratio, verbascoside and linarin are substantially without leakage.
The elution volume of the mobile phase of described a concentration of 10~15%, 25~30%, 32~38% and 65~75% point
It is not：7~9BV, 17~19BV, 11~13BV and 11~13BV.Using above-mentioned specific elution volume, it can be ensured that use
It cleans when 10~15% and 32~38% concentration abundant, and is produced using target when 25~30% and 65~75% concentration
Object is fully eluted.
The flow velocity of the mobile phase elution is 2~3BV/h.The present invention is had found by putting into practice, with the increasing of eluant, eluent flow velocity
Greatly, the eluting rate of verbascoside reduces, and linarin eluting rate slightly reduces after then increasing first increase with elution rate, and adopts
When with 2~3BV/h elution flow rates, there was no significant difference for the eluting rate of verbascoside and linarin.
As a kind of specific preferred embodiment of the present invention, described method includes following steps：
(1) it is 0.125g/mL butterflybush flower ethanol extracts to take mass concentration, is splined on HPD-BJQH type macroreticular resins, on
Sample amount is 1 with resin quality ratio:2；Be washed to it is colourless after, with 12BV concentration of volume percent be 70% ethanol water stream
Speed is eluted, and eluent is collected, and the concentrate that mass concentration is 0.125g/mL is obtained after concentration；
(2) concentrate is splined on HPD-100 type macroreticular resins, applied sample amount is 1 with resin quality ratio:2；It is washed to
After colourless, use the ethanol water of 8BV a concentration of 12%, the ethanol water of 18BV a concentration of 28%, 12BV a concentration of successively
The ethanol water solution of 35% ethanol water and 12BV a concentration of 70% is with 3BVh-1Flow velocity eluted；
Collect a concentration of 28% eluent, the as active component of benzyl carbinol glycosides；
Collect a concentration of 70% eluent, the as active component of flavone compound.
" BV " represents column volume, i.e., the chromatography cylinder being filled in macroreticular resin after chromatographic column in scheme of the present invention
Product, practically equals to the volume of macroreticular resin.
United separation and purification is carried out to butterflybush flower through macroreticular resin HPD-BJQH and HPD-100 using provided by the invention
Afterwards, verbascoside and linarin retention rate reach 80% or more in benzyl carbinol glycosides active component and flavone effective part, purity
Also reach 50% or more.
The present invention is for the first time with content, eluting rate, purity and the eluent total solid substance of verbascoside and the opposite crude drug of linarin
Yield is evaluation index, using HPD-BJQH types and HPD-100 type macroreticular resin joint technology to benzyl carbinol glycosides in butterflybush flower and
Flavone effective part is isolated and purified, and the process stabilizing of acquisition is feasible, is studied for butterflybush flower new Chinese medicine active component and raw
Production provides reference.
Specific implementation mode
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..
Embodiment
It present embodiments provides a kind of from butterflybush flower while the method for extracting benzyl carbinol glycosides and flavone compound.
The butterflybush flower ethanol extract that the present embodiment uses extracts with the following method to be obtained：Take butterflybush flower medicinal material, first
Secondary that 10 times of amount 60% ethanol solutions extraction 45min are added, second of addition, 8 times of 60% ethanol solutions of amount extract 30min, merging filter
Liquid, recycling ethyl alcohol to get.
It is described to extract benzyl carbinol glycosides and the method for flavone compound is specially simultaneously from butterflybush flower：
(1) it is 0.125g/mL butterflybush flower ethanol extracts to take mass concentration, is splined on HPD-BJQH type macroreticular resins, on
Sample amount is 1 with resin quality ratio:2；Be washed to it is colourless after, with 12BV concentration of volume percent be 70% ethanol water stream
Speed is eluted, and eluent is collected, and the concentrate that mass concentration is 0.125g/mL is obtained after concentration；
(2) concentrate is splined on HPD-100 type macroreticular resins, applied sample amount is 1 with resin quality ratio:2；It is washed to
After colourless, use the ethanol water of 8BV a concentration of 12%, the ethanol water of 18BV a concentration of 28%, 12BV a concentration of successively
The ethanol water solution of 35% ethanol water and 12BV a concentration of 70% is with 3BVh-1Flow velocity eluted；
Collect a concentration of 28% eluent, the as active component of benzyl carbinol glycosides；Collect described a concentration of 70%
Eluent, the as active component of flavone compound.
The present embodiment is further in the verbascoside and flavone compound in the active component of gained benzyl carbinol glycosides
The content of linarin be measured.Determination condition includes：
A, chromatographic condition chromatographic column：Welchrom C18(250mm × 4.6mm, 5 μm)；Mobile phase：- 0.1% phosphorus of acetonitrile (A)
Aqueous acid (B), gradient elution：0~10min, A 20%, 10~20min, A 20%~40%, 20~30min, A 40%
~60%；Detection wavelength：327nm；Flow velocity：1.0mL·min-1；Column temperature：25℃；Sample size：10μL.Under these conditions, hair
Stamen spends the theoretical cam curve of glycosides, linarin to be not less than 5000.
B, the configuration precision of reference substance solution weighs verbascoside reference substance 10.14mg, linarin reference substance 10.32mg,
It is respectively placed in 100mL brown volumetric flasks, proper amount of methanol solution ultrasonic dissolution is added, it is cooling, it is used in combination methanol constant volume to scale, shakes
It is even to get 101.40 μ gmL of verbascoside-1, 103.20 μ gmL of linarin-1Reference substance storing solution.5.0mL is pipetted respectively
Above-mentioned reference substance storing solution is added methanol constant volume to scale, shakes up to get 20.28 μ g of verbascoside in 25mL volumetric flasks
mL-1, 20.64 μ gmL of linarin-1Mixed reference substance solution.
C, precision pipettes in eluent 2.0mL to 25mL volumetric flasks respectively for the preparation of test solution, absolute ethyl alcohol constant volume
It to scale, shakes up, filters, subsequent filtrate is taken to cross 0.45 μm of miillpore filter to get test solution.
D, the investigation of linear relationship dilutes above-mentioned reference substance solution, and a series of reference substance for obtaining different quality concentration is molten
Liquid.Precision draws the 10 μ L sample introductions of reference substance solution of 6 kinds of concentration, and peak area is measured by 2.1.1 lower chromatographic conditions.With reference substance
Mass concentration (X) is abscissa, and peak area (Y) is ordinate, draws standard curve, obtains the recurrence of verbascoside and linarin
Equation is respectively：Y=11.9923X-21.1340, r=0.9995 (n=6)；Y=19.3013X+13.1770, r=0.9999
(n=6).Show verbascoside and linarin reference substance respectively in 10.14~101.40 μ gmL-1, 10.32~103.20 μ g
mL-1In range, good linear relationship is presented with corresponding peak area.
After testing, through the content of verbascoside and linarin in the method butterflybush flower ethanol extract before purification,
The content of verbascoside and linarin in reservation degree and purity (as a contrast) and the present embodiment products therefrom, reservation degree and
The results are shown in Table 1 for purity.
Table 1：The content of verbascoside and linarin, reservation degree and purity
The above result shows that method provided by the invention may be implemented to verbascoside and linarin efficiently separate and
Purification.
Although above having used general explanation, specific implementation mode and experiment, the present invention is made to retouch in detail
It states, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Range.
Claims (10)
1. a kind of method for extracting benzyl carbinol glycosides and flavone compound simultaneously from butterflybush flower, which is characterized in that including as follows
Step：
(1) take butterflybush flower ethanol extract, be splined on HPD-BJQH type macroreticular resins, be washed to it is colourless after, with percent by volume
A concentration of 70~80% ethanol water is that mobile phase is eluted, and collects eluent, concentrate is obtained after concentration；
(2) concentrate is splined on HPD-100 type macroreticular resins, be washed to it is colourless after, use concentration of volume percent successively
The ethanol water of respectively 10~15%, 25~30%, 32~38% and 65~75% elutes；
Collect a concentration of 25~30% eluent, the as active component of benzyl carbinol glycosides；
Collect a concentration of 65~75% eluent, the as active component of flavone compound.
2. according to the method described in claim 1, it is characterized in that, the butterflybush flower ethanol extract extracts with the following method
It obtains：Butterflybush flower medicinal material is taken, it is that 55~65% ethanol waters extract 30~60min that concentration of volume percent, which is added, is added
15~45min is extracted with the ethanol water for extracting same concentrations before, merges the extracting solution of extraction gained twice, concentrates, i.e.,
.
3. method according to claim 1 or 2, which is characterized in that in step (1), the butterflybush flower ethyl alcohol for loading carries
It is 0.12~0.13g/ml to take the mass concentration of object.
4. according to the method described in claims 1 to 3 any one, which is characterized in that in the step (1), the butterflybush flower
The applied sample amount of ethanol extract is 1 with the mass ratio of HPD-BJQH type macroreticular resins:1.5~2.5.
5. according to the method described in Claims 1 to 4 any one, which is characterized in that in the step (1), mobile phase elution
Volume is 11~13BV.
6. according to the method described in Claims 1 to 5 any one, which is characterized in that in the step (1), mobile phase elution
Flow velocity be 2~3BV/h.
7. according to the method described in claim 1~6 any one, which is characterized in that in step (2), be used for the concentration of loading
The mass concentration of liquid is 0.12~0.13g/ml.
8. according to the method described in claim 1~7 any one, which is characterized in that in the step (2), the concentrate
The mass ratio of applied sample amount and HPD-100 type macroreticular resins be 1:1.5~2.5.
9. according to the method described in Claims 1 to 4 any one, which is characterized in that in the step (2), a concentration of 10~
15%, the elution volume of 25~30%, 32~38% and 65~75% mobile phase is respectively：7~9BV, 17~19BV, 11
~13BV and 11~13BV.
10. according to method as described in any one of claim 1 to 9, which is characterized in that in the step (2), mobile phase elution
Flow velocity be 2~3BV/h.
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| CN109765314A (en) * | 2019-01-29 | 2019-05-17 | 北京中医药大学 | A kind of method of quality control of butterflybush flower medicinal material |
| CN109824739A (en) * | 2019-04-02 | 2019-05-31 | 中国药科大学 | A method of quick separating preparation high-purity acteoside and linarin from butterflybush flower |
| CN114507264A (en) * | 2022-01-06 | 2022-05-17 | 湖南中医药大学 | Monomer chrysanthemin A extracted from golden-silk chrysanthemums and extraction method and application thereof |
| CN114736251A (en) * | 2022-03-22 | 2022-07-12 | 湖南中医药大学 | Monomer chrysanthemin B extracted from golden-silk chrysanthemums and extraction method and application thereof |
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| CN109765314A (en) * | 2019-01-29 | 2019-05-17 | 北京中医药大学 | A kind of method of quality control of butterflybush flower medicinal material |
| CN109824739A (en) * | 2019-04-02 | 2019-05-31 | 中国药科大学 | A method of quick separating preparation high-purity acteoside and linarin from butterflybush flower |
| CN109824739B (en) * | 2019-04-02 | 2022-02-18 | 中国药科大学 | Method for separating and preparing verbascoside and linarin from flos Buddlejae |
| CN114507264A (en) * | 2022-01-06 | 2022-05-17 | 湖南中医药大学 | Monomer chrysanthemin A extracted from golden-silk chrysanthemums and extraction method and application thereof |
| CN114736251A (en) * | 2022-03-22 | 2022-07-12 | 湖南中医药大学 | Monomer chrysanthemin B extracted from golden-silk chrysanthemums and extraction method and application thereof |
| CN114736251B (en) * | 2022-03-22 | 2024-04-19 | 湖南中医药大学 | Extraction monomer chrysanthemin B of golden silk chrysanthemums, extraction method and application thereof |
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