CN106117286B - A kind of method for detaching Guava Leaf Zhong avicularins and guaijaverin - Google Patents
A kind of method for detaching Guava Leaf Zhong avicularins and guaijaverin Download PDFInfo
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- CN106117286B CN106117286B CN201610432005.0A CN201610432005A CN106117286B CN 106117286 B CN106117286 B CN 106117286B CN 201610432005 A CN201610432005 A CN 201610432005A CN 106117286 B CN106117286 B CN 106117286B
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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
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
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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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Abstract
The invention discloses guaijaverin in a kind of separation Guava Leaf He the method for avicularin, belongs to biomedicine technical field.The method includes the extraction of pretreatment of raw material, avicularins and three steps of extraction of guaijaverin, the difference of Li avicularins and the guaijaverin solubility in petroleum ether and water of the present invention, and pass through the control of series of parameters, realize guaijaverin He both isomers of avicularin are nearly completely separated, use purity >=98.32% of the isolated avicularins of the method for the invention, purity >=98.68% of guaijaverin has the advantages that method is simple, efficient, purity is high.
Description
Technical field
The present invention relates in a kind of extracting method of active constituent in Guava Leaf more particularly to a kind of separation Guava Leaf
The method of avicularin and guaijaverin, belongs to biomedicine technical field.
Background technology
Guava Leaf position myrtle guava（Psidium guajava L.）Dried leaf and with leaf tender stem,
In contain there are many chemical composition, including compounds such as flavones, triterpene and tannins.Modern medicine study thinks that Guava Leaf has
The pharmacotoxicological effects such as hypoglycemic, anti-oxidant, antiviral, antibacterial and anti-nociceptive effects.Research shows that Quercetin -3- in Guava Leaf
O- Arabinosides (also known as guaijaverin guaijaverin), avicularins（avicularin）It is to be dropped in guava leaf extract
The main matter of sugared activity.In addition, external experiment in vitro shows：Guaijaverin, which has dipeptidyl peptidase IV activity, to be inhibited to make
With available for treating illness relevant with the activity of dipeptidyl peptidase IV or its similar enzyme or exception, such as metabolism obstacles of blood glucose, glycosuria
Disease, obesity, artery sclerosis etc..However, guaijaverin is He avicularin belongs to a kind of a pair of of isomers, the two molecule in structure
Measure identical, only difference is that the difference on glycosidic structure, formula one is the structural formula of guaijaverin, the knot of formula Er Wei avicularins
Structure formula, what the former connect with aglycon is arabopyranose, and the latter's connection is arabinofuranose.It is this just because of the two
Small difference causes to be difficult to detach both compounds.
Formula one：
Formula two：
State Intellectual Property Office discloses a notification number on March 25th, 2015 as CN104447915A, and entitled " one
The method and purposes of guaijaverin and auicularin kind are prepared from Guava Leaf " patent of invention, which mainly utilizes second
It after acetoacetic ester extraction, then carries out carrying out gradient elution to silicagel column using the eluant, eluent of different proportion, it is true then to add in low-carbon alcohols
Empty condensing crystallizing, filtration drying is up to guaijaverin, auicularin.The technique is as a result of the method for column chromatography, technique
Complexity, efficiency is low, and the period is long, of high cost, is not suitable for the guaijaverin and auicularin of prepare with scale high-purity.
Invention content
Present invention seek to address that exist in the separation of guaijaverin and its Yi Gou Ti avicularins, purification technique in the prior art
Complex process, efficiency is low, and the period is long, it is of high cost the problem of, propose it is a kind of using solvent extraction and separation, purifying Guava Leaf Zhong pivots
The method of glycosides and guaijaverin is stored, this method is simple, efficient, purity is high.
In order to achieve the above-mentioned object of the invention, technical scheme is as follows：
A kind of method for detaching Guava Leaf Zhong avicularins and guaijaverin, it is characterised in that：Include the following steps：
A. pretreatment of raw material
After Guava Leaf after drying is crushed, the ethyl alcohol of addition 3~5 times of weight of Guava Leaf, refluxing extraction 2~4 times,
5~7h every time is filtered and is merged multiple filtrate, and after being concentrated under reduced pressure into a quarter volume, it is standby to collect supernatant for filtering
With；
B. the extraction of avicularin
The water of supernatant addition 2~4 times of volumes of supernatant obtained to step a, the petroleum ether of 0.5~2 times of volume,
After 36~48h of laser heating refluxing extraction, upper strata is petroleum ether layer, and lower floor is water layer, and petroleum ether layer and water are detached with decantation
Layer, filtering oil ether layer obtain yellow-green precipitate, will precipitate the ethyl alcohol of 1.5~3 times of volumes of addition, after being completely dissolved, add water
Mass concentration 40~60% is diluted to, after crystallization, filtering is dried crystal, get Dao avicularin；
C. the extraction of guaijaverin
The water layer that step b is collected into filters, and the ethyl alcohol of 1.5~3 times of volumes is added in into the precipitation being obtained by filtration,
It is 40~60% that mass concentration is diluted with water to after being completely dissolved, and after crystallization, crystal is dried, obtains guaijaverin by filtering.
In order to be better achieved the present invention, above-mentioned steps a, step b, in step c, the water is preferably deionized water；
The volumetric concentration of ethyl alcohol is preferably 98%.
In step a, the fineness of the Guava Leaf after the crushing is 10~50 mesh.
In step b, the temperature of the refluxing extraction is 65~70 DEG C, is extracted within this temperature range, yield higher.
In step b and/or step c, the crystallization is stands for 24 hours under room temperature.
In step b and/or step c, the temperature of the drying is 55~65 DEG C, dries, can keep within this temperature range
The activity of product prevents its denaturation.
Using purity >=98.32% of above method get Dao avicularins, purity >=98.68% of guaijaverin, purity
Detection method is HPLC.
Beneficial effects of the present invention：
（1）Compared with the patent document CN104447915A in background technology, Li avicularins and guaijaverin of the present invention
The difference of solubility in petroleum ether and water, and pass through the control of series of parameters, realize guaijaverin He avicularin both
Isomer is nearly completely separated, and uses purity >=98.32% of the isolated avicularins of the method for the invention, kind stone
Purity >=98.68% of pomegranate glycosides.The method of the present invention is simple, it is easy to accomplish, it is at low cost, it is efficient, it is suitble to prepare with scale high-purity
Du avicularins and guaijaverin.
（2）The water used in separation process of the present invention is deionized water, avoid calcium ions and magnesium ions in tap water and activity into
The problem of dividing and combine, efficiency of pcr product is brought to reduce.
（3）In step a of the present invention, step b and step c, the volumetric concentration of the ethyl alcohol is 98%, and target product is in height
Solubility is big in the ethanol solution of concentration, can increase the yield of product using the ethyl alcohol of high concentration.
（4）In step a of the present invention, the fineness of the Guava Leaf after crushing is 10~50 mesh, meticulous directly to increase crushing
Cost influences efficiency, excessively thick to lead to that the extraction of later stage active ingredient is insufficient or extraction time is long again, brings product yield not
The problem of height, inefficiency, it is preferable that Guava Leaf is crushed to 10~50 mesh.
Specific embodiment
The present invention is described in further detail, but the implementation of the present invention is not limited to this with reference to embodiment.
Embodiment 1
A kind of method for detaching Guava Leaf Zhong avicularins and guaijaverin, includes the following steps：
A. pretreatment of raw material
After Guava Leaf after drying is crushed, the ethyl alcohol of addition 3 times of weight of Guava Leaf, refluxing extraction 2 times, every time
5h is filtered and is merged multiple filtrate, and after being concentrated under reduced pressure into a quarter volume, it is spare to collect supernatant for filtering；
B. the extraction of avicularin
The supernatant obtained to step a adds in the water of 2 times of volumes of supernatant, and the petroleum ether of 0.5 times of volume is continuous to add
After circumfluence distillation 36, upper strata is petroleum ether layer, and lower floor is water layer, and petroleum ether layer and water layer, filtering oil are detached with decantation
Ether layer obtains yellow-green precipitate, will precipitate the ethyl alcohol of 1.5 times of volumes of addition, after being completely dissolved, is diluted with water to mass concentration
40%, after crystallization, filtering is dried crystal, get Dao avicularin；
C. the extraction of guaijaverin
The water layer that step b is collected into filters, and the ethyl alcohol of 1.5 times of volumes is added in into the precipitation being obtained by filtration, complete
It is 40% that mass concentration is diluted with water to after fully dissolved, and after crystallization, crystal is dried, obtains guaijaverin by filtering.
Embodiment 2
A kind of method for detaching Guava Leaf Zhong avicularins and guaijaverin, includes the following steps：
A. pretreatment of raw material
After Guava Leaf after drying is crushed, the ethyl alcohol of 5 times of weight of Guava Leaf is added in, refluxing extraction 4 times, every time 5
~7h is filtered and is merged multiple filtrate, and after being concentrated under reduced pressure into a quarter volume, it is spare to collect supernatant for filtering；
B. the extraction of avicularin
The supernatant obtained to step a adds in the water of 4 times of volumes of supernatant, and the petroleum ether of 2 times of volumes is continuous to add
After circumfluence distillation 48h, upper strata is petroleum ether layer, and lower floor is water layer, and petroleum ether layer and water layer, filtering oil are detached with decantation
Ether layer obtains yellow-green precipitate, will precipitate the ethyl alcohol of 3 times of volumes of addition, after being completely dissolved, is diluted with water to mass concentration
60%, after crystallization, filtering is dried crystal, get Dao avicularin；
C. the extraction of guaijaverin
The water layer that step b is collected into filters, and the ethyl alcohol of 3 times of volumes is added in into the precipitation being obtained by filtration, completely
It is 60% that mass concentration is diluted with water to after dissolving, and after crystallization, crystal is dried, obtains guaijaverin by filtering.
In the present embodiment, in step a, b, c, water is deionized water, interference smaller.
Embodiment 3
A kind of method for detaching Guava Leaf Zhong avicularins and guaijaverin, includes the following steps：
A. pretreatment of raw material
After Guava Leaf after drying is crushed, the ethyl alcohol of addition 4 times of weight of Guava Leaf, refluxing extraction 3 times, every time
6h is filtered and is merged multiple filtrate, and after being concentrated under reduced pressure into a quarter volume, it is spare to collect supernatant for filtering；
B. the extraction of avicularin
The supernatant obtained to step a adds in the water of 3 times of volumes of supernatant, and the petroleum ether of 1.5 times of volumes is continuous to add
After circumfluence distillation 40h, upper strata is petroleum ether layer, and lower floor is water layer, and petroleum ether layer and water layer, filtering oil are detached with decantation
Ether layer obtains yellow-green precipitate, will precipitate the ethyl alcohol of 2 times of volumes of addition, after being completely dissolved, is diluted with water to mass concentration
50%, after crystallization, filtering is dried crystal, get Dao avicularin；
C. the extraction of guaijaverin
The water layer that step b is collected into filters, and the ethyl alcohol of 2 times of volumes is added in into the precipitation being obtained by filtration, completely
It is 50% that mass concentration is diluted with water to after dissolving, and after crystallization, crystal is dried, obtains guaijaverin by filtering.
In the present embodiment, in step a, b, c, water is deionized water；The volumetric concentration of ethyl alcohol is 98%.
Embodiment 4
A kind of method for detaching Guava Leaf Zhong avicularins and guaijaverin, includes the following steps：
A. pretreatment of raw material
After Guava Leaf after drying is crushed, the ethyl alcohol of addition 3 times of weight of Guava Leaf, refluxing extraction 2 times, every time
6h is filtered and is merged multiple filtrate, and after being concentrated under reduced pressure into a quarter volume, it is spare to collect supernatant for filtering；
B. the extraction of avicularin
The supernatant obtained to step a adds in the water of 2 times of volumes of supernatant, and the petroleum ether of 0.5 times of volume is continuous to add
After circumfluence distillation 42h, upper strata is petroleum ether layer, and lower floor is water layer, and petroleum ether layer and water layer, filtering oil are detached with decantation
Ether layer obtains yellow-green precipitate, will precipitate the ethyl alcohol of 3 times of volumes of addition, after being completely dissolved, is diluted with water to mass concentration
40%, after crystallization, filtering is dried crystal, get Dao avicularin；
C. the extraction of guaijaverin
The water layer that step b is collected into filters, and the ethyl alcohol of 3 times of volumes is added in into the precipitation being obtained by filtration, completely
It is 60% that mass concentration is diluted with water to after dissolving, and after crystallization, crystal is dried, obtains guaijaverin by filtering.
In the present embodiment, in step a, b, c, water is deionized water；The volumetric concentration of ethyl alcohol is 98%.
In step a, the fineness of the Guava Leaf after the crushing is 10 mesh.
Embodiment 5
A kind of method for detaching Guava Leaf Zhong avicularins and guaijaverin, includes the following steps：
A. pretreatment of raw material
After Guava Leaf after drying is crushed, the ethyl alcohol of addition 4 times of weight of Guava Leaf, refluxing extraction 2 times, every time
5.5h is filtered and is merged multiple filtrate, and after being concentrated under reduced pressure into a quarter volume, it is spare to collect supernatant for filtering；
B. the extraction of avicularin
The supernatant obtained to step a adds in the water of 2 times of volumes of supernatant, and the petroleum ether of 0.5 times of volume is continuous to add
After circumfluence distillation 40h, upper strata is petroleum ether layer, and lower floor is water layer, and petroleum ether layer and water layer, filtering oil are detached with decantation
Ether layer obtains yellow-green precipitate, will precipitate the ethyl alcohol of 2.5 times of volumes of addition, after being completely dissolved, is diluted with water to mass concentration
45%, after crystallization, filtering is dried crystal, get Dao avicularin；
C. the extraction of guaijaverin
The water layer that step b is collected into filters, and the ethyl alcohol of 2.5 times of volumes is added in into the precipitation being obtained by filtration, complete
It is 60% that mass concentration is diluted with water to after fully dissolved, and after crystallization, crystal is dried, obtains guaijaverin by filtering.
In the present embodiment, in step a, b, c, water is deionized water；The volumetric concentration of ethyl alcohol is 98%.
In step a, the fineness of the Guava Leaf after the crushing is 50 mesh.
In step b, the temperature of the refluxing extraction is 65 DEG C.
In step b, step c, the crystallization is stands for 24 hours under room temperature.
In step b, step c, the temperature of the drying is 55 DEG C.
Embodiment 6
The present embodiment and embodiment 5 difference lies in：
In step a, the fineness of the Guava Leaf after the crushing is 40 mesh.
In step b, the temperature of the refluxing extraction is 55 DEG C.
In step b, step c, the crystallization is stands under room temperature24h。
In step b, step c, the temperature of the drying is 65 DEG C.
Embodiment 7
A kind of method for detaching Guava Leaf Zhong avicularins and guaijaverin, includes the following steps：
A. pretreatment of raw material
After Guava Leaf after drying is crushed, the ethyl alcohol of addition 4 times of weight of Guava Leaf, refluxing extraction 3 times, every time
6h is filtered and is merged multiple filtrate, and after being concentrated under reduced pressure into a quarter volume, it is spare to collect supernatant for filtering；
B. the extraction of avicularin
The supernatant obtained to step a adds in the water of 2 times of volumes of supernatant, and the petroleum ether of 1.5 times of volumes is continuous to add
After circumfluence distillation 40h, upper strata is petroleum ether layer, and lower floor is water layer, and petroleum ether layer and water layer, filtering oil are detached with decantation
Ether layer obtains yellow-green precipitate, will precipitate the ethyl alcohol of 2 times of volumes of addition, after being completely dissolved, is diluted with water to mass concentration
45%, after crystallization, filtering is dried crystal, get Dao avicularin；
C. the extraction of guaijaverin
The water layer that step b is collected into filters, and the ethyl alcohol of 1.5 times of volumes is added in into the precipitation being obtained by filtration, complete
It is 50% that mass concentration is diluted with water to after fully dissolved, and after crystallization, crystal is dried, obtains guaijaverin by filtering.
In the present embodiment, in step a, b, c, water is deionized water；The volumetric concentration of ethyl alcohol is 98%.
In step a, the fineness of the Guava Leaf after the crushing is 50 mesh.
In step b, the temperature of the refluxing extraction is 60 DEG C.
In step b, step c, the crystallization is stands for 24 hours under room temperature.
In step b, step c, the temperature of the drying is 60 DEG C.
After testing, the purity of the present embodiment get Dao avicularins is 98.41%, and the purity of guaijaverin is 98.75%, purity
Detection method be HPLC.
Embodiment 8
A kind of method for detaching Guava Leaf Zhong avicularins and guaijaverin, includes the following steps：
A. pretreatment of raw material
After Guava Leaf after drying is crushed, the ethyl alcohol of addition 4 times of weight of Guava Leaf, refluxing extraction 3 times, every time
6h is filtered and is merged multiple filtrate, and after being concentrated under reduced pressure into a quarter volume, it is spare to collect supernatant for filtering；
B. the extraction of avicularin
The supernatant obtained to step a adds in the water of 2 times of volumes of supernatant, and the petroleum ether of 0.5 times of volume is continuous to add
After circumfluence distillation 48h, upper strata is petroleum ether layer, and lower floor is water layer, and petroleum ether layer and water layer, filtering oil are detached with decantation
Ether layer obtains yellow-green precipitate, will precipitate the ethyl alcohol of 2 times of volumes of addition, after being completely dissolved, is diluted with water to mass concentration
50%, after crystallization, filtering is dried crystal, get Dao avicularin；
C. the extraction of guaijaverin
The water layer that step b is collected into filters, and the ethyl alcohol of 2 times of volumes is added in into the precipitation being obtained by filtration, completely
It is 50% that mass concentration is diluted with water to after dissolving, and after crystallization, crystal is dried, obtains guaijaverin by filtering.
In the present embodiment, in step a, b, c, water is deionized water；The volumetric concentration of ethyl alcohol is 98%.
In step a, the fineness of the Guava Leaf after the crushing is 50 mesh.
In step b, the temperature of the refluxing extraction is 60 DEG C.
In step b, step c, the crystallization is stands for 24 hours under room temperature.
In step b, step c, the temperature of the drying is 60 DEG C.
After testing, the purity of the present embodiment get Dao avicularins is 98.32%, and the purity of guaijaverin is 98.68%, purity
Detection method be HPLC.
Claims (8)
- A kind of 1. method for detaching Guava Leaf Zhong avicularins and guaijaverin, it is characterised in that：Include the following steps：A. pretreatment of raw materialAfter Guava Leaf after drying is crushed, the ethyl alcohol of addition 3~5 times of weight of Guava Leaf, refluxing extraction 2~4 times, every time 5~7h is filtered and is merged multiple filtrate, and after being concentrated under reduced pressure into a quarter volume, it is spare to collect supernatant for filtering；B. the extraction of avicularinThe water of supernatant addition 2~4 times of volumes of supernatant obtained to step a, the petroleum ether of 0.5~2 times of volume, continuously After 36~48h of heating and refluxing extraction, detach petroleum ether layer with decantation and water layer, filtering oil ether layer obtain yellow-green precipitate, The ethyl alcohol for adding in 1.5~3 times of volumes will be precipitated, after being completely dissolved, be diluted with water to mass concentration 40~60%, after crystallization, mistake Filter, crystal is dried, get Dao avicularin；C. the extraction of guaijaverinThe water layer that step b is collected into filters, and the ethyl alcohol of 1.5~3 times of volumes is added in into the precipitation being obtained by filtration, completely It is 40~60% that mass concentration is diluted with water to after dissolving, and after crystallization, crystal is dried, obtains guaijaverin by filtering.
- 2. a kind of method for detaching Guava Leaf Zhong avicularins and guaijaverin as described in claim 1, it is characterised in that： In step b and c, the water is deionized water.
- 3. a kind of method for detaching Guava Leaf Zhong avicularins and guaijaverin as described in claim 1, it is characterised in that： Step a, in b and c, the volumetric concentration of the ethyl alcohol is 98%.
- 4. a kind of method for detaching Guava Leaf Zhong avicularins and guaijaverin as described in claim 1, it is characterised in that：Step In rapid a, the fineness of the Guava Leaf after the crushing is 10~50 mesh.
- 5. a kind of method for detaching Guava Leaf Zhong avicularins and guaijaverin as described in claim 1, it is characterised in that：Step In rapid b, the temperature of the refluxing extraction is 65~70 DEG C.
- 6. a kind of method for detaching Guava Leaf Zhong avicularins and guaijaverin as described in claim 1, it is characterised in that：Step In rapid b and/or step c, the crystallization is stands for 24 hours under room temperature.
- 7. a kind of method for detaching Guava Leaf Zhong avicularins and guaijaverin as described in claim 1, it is characterised in that：Step In rapid b and/or step c, the temperature of the drying is 55~65 DEG C.
- 8. the method for detaching Guava Leaf Zhong avicularins and guaijaverin as claim 1~7 any one of them is a kind of, special Sign is：Purity >=98.32% of the method get Dao avicularins, purity >=98.68% of guaijaverin.
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| CN104447915A (en) * | 2014-12-16 | 2015-03-25 | 华南农业大学 | Method for preparing guaijaverin and avicularin from guava leaf and use of method |
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| WO2006074278A2 (en) * | 2005-01-05 | 2006-07-13 | Mitsunori Ono | Compositions for treating diabetes or obesity |
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| CN103565928A (en) * | 2013-11-01 | 2014-02-12 | 华南农业大学 | Guava hypoglycemic active component, and preparation method and use thereof |
| CN104491016A (en) * | 2014-03-14 | 2015-04-08 | 浙江磐安巍峰植物原料厂 | Industrial production method for extraction of polygonum aviculare total flavone from polygonum aviculare herb |
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