CN108530499A - A kind of preparation method of the β of the extraction purification from bitter buckwheat-beta-ethoxy rutinose - Google Patents
A kind of preparation method of the β of the extraction purification from bitter buckwheat-beta-ethoxy rutinose Download PDFInfo
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- CN108530499A CN108530499A CN201810527024.0A CN201810527024A CN108530499A CN 108530499 A CN108530499 A CN 108530499A CN 201810527024 A CN201810527024 A CN 201810527024A CN 108530499 A CN108530499 A CN 108530499A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
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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 preparation method of the invention discloses a kind of from bitter buckwheat extraction purification β beta-ethoxy rutinoses.Using bitter buckwheat as raw material, through low alcohol extracting, macroporous absorbent resin D101 column chromatographies, Flash silica column chromatography, β beta-ethoxy rutinoses are obtained.Preparation method of the present invention is simple and quick, and solvent is less, is good for the environment and cost reduction.
Description
Technical field
The invention belongs to food production applied technical fields, and in particular to one kind extraction purification β-ethyoxyl rue from bitter buckwheat
The preparation method of fragrant sugar.
Background technology
Duck wheat is Liao Ke（Polygonaceae）Fagopyrum（Fagoyrum tataricum (L.) Gaertn）Plant,
It is a kind of cereal, refers to its seed, also known as " bitter buckwheat ", annual herb more, there is cultivation in China various regions, and virgin soil, roadside etc. to be had more
It is wild.Bitter buckwheat is the generally acknowledged outstanding medicine-food two-purpose crop of international food and agricultural organization, and effect Chinese dynasties Gu medical skill is described more.It is existing
Show that bitter buckwheat has the multiple biological activities such as anti-oxidant, anti-inflammatory, hypoglycemic, reducing blood lipid, antitumor for pharmacology, medical research.
Bitter buckwheat active constituent report is more, mostly flavonoids, phenolic acid class, fatty acid, carbohydrate etc..Carbohydrate content contributes to blood in bitter buckwheat
The reduction of sugar, the effect of being reported especially with β-beta-ethoxy rutinose with blood glucose is reduced.β-beta-ethoxy rutinose（Ethyl α-L-
rhamnopyranosyl-(1→6)-β-D-glucoside；β ethoxy-rutinoside）It is a disaccharides in structure（Figure
1）, polarity is larger.Currently, there is patent to prepare β-beta-ethoxy rutinose in bitter buckwheat, but process is excessively cumbersome.Therefore,
Develop it is a kind of it is more easy, quickly the method for extraction purification β-beta-ethoxy rutinose is extremely important from bitter buckwheat.
We to bitter buckwheat water extract after carrying out macroporous adsorption resin chromatography, it has unexpectedly been found that low alcohol（10% ethyl alcohol）
Sample is eluted, finds that, there are one main spot, purified, Structural Identification, which is β-ethoxy through TLC detections
Base rutinose.Based on this, the side of extraction purification β-beta-ethoxy rutinose we have invented a kind of simplicity, quickly from bitter buckwheat
Method.
Invention content
The object of the present invention is to provide a kind of preparation methods of β-beta-ethoxy rutinose.
The object of the present invention is achieved like this, using bitter buckwheat as raw material, through low alcohol extracting, macroporous absorbent resin D101 columns
Chromatography, Flash silica column chromatography and etc., β-beta-ethoxy rutinose is obtained, following steps are specifically included：
（1）Low alcohol extracting：By bitter buckwheat, solid-liquid ratio is 1 based on kg/L：5-1：10 are added the ethyl alcohol of mass concentration 5%-15%,
It extracts 3-4 hours, filters in 20-60 DEG C of temperature, slag repeats extraction once, and filtering merges secondary filtrate；In 60-70
It is concentrated under reduced pressure under the conditions of DEG C, is concentrated into 1/10 volume, obtain low alcohol extracting thing；
（2）Macroporous absorbent resin D101 column chromatographies：By step（1）Macroporous absorbent resin D101 column layers in middle minuent alcohol extracting thing
Analysis, is eluted with water, and abandons preceding 1.5 times of column volume water elutions, later with 2 times of column volume water elutions, collects and is concentrated to give β-ethoxy
Base rutinose crude product；
（3）Flash silica column chromatography：With the chloroform after water saturation：Methanol 3:1 for eluent to β-beta-ethoxy rutinose crude product into
Row silica gel column chromatography collects the 5th to the 8th column volume fraction, and pure β-beta-ethoxy rutinose is obtained after concentration.
Step（2）Described in the dosage of macroporous absorbent resin D101 be 10-20 times of low alcohol extracting thing volume.
Step（3）Described in silica gel be 60-100 mesh.
Step（3）Described in the dosage of silica gel be 10-20 times of β-beta-ethoxy rutinose crude product.
Advantages of the present invention：
The present invention is directed to bitter buckwheat（Tartary buckwheat powder or tartary buckwheat bran）Middle effect of lowering blood sugar ingredient β-beta-ethoxy rutinose carries out
Extraction purification, preparation method is simple and quick, and solvent is less, is good for the environment and cost reduction.
Description of the drawings
Fig. 1 is the chemical structural formula for β-beta-ethoxy rutinose that the present invention is prepared；
Fig. 2 is β-beta-ethoxy rutinose nuclear magnetic resonance spectroscopy that the present invention is prepared（1H NMR）Figure；
Fig. 3 is β-beta-ethoxy rutinose carbon-13 nmr spectra that the present invention is prepared（13C NMR）Figure.
Specific implementation mode
The invention will be further described with reference to the accompanying drawings and embodiments, but is not limited in any way the present invention
System, be based on present invention teach that made by any transformation or improvement, each fall within protection scope of the present invention.
Using bitter buckwheat as raw material, through steps such as low alcohol extracting, macroporous absorbent resin D101 column chromatographies, Flash silica column chromatographies
Suddenly, β-beta-ethoxy rutinose is obtained, following steps are specifically included：
（1）Low alcohol extracting：By bitter buckwheat, solid-liquid ratio is 1 based on kg/L：5-1：10 are added the ethyl alcohol of mass concentration 5%-15%,
It extracts 3-4 hours, filters in 20-60 DEG C of temperature, slag repeats extraction once, and filtering merges secondary filtrate；In 60-70
It is concentrated under reduced pressure under the conditions of DEG C, is concentrated into 1/10 volume, obtain low alcohol extracting thing；
（2）Macroporous absorbent resin D101 column chromatographies：By step（1）Macroporous absorbent resin D101 column layers in middle minuent alcohol extracting thing
Analysis, is eluted with water, and abandons preceding 1.5 times of column volume water elutions, later with 2 times of column volume water elutions, collects and is concentrated to give β-ethoxy
Base rutinose crude product；
（3）Flash silica column chromatography：With the chloroform after water saturation：Methanol 3:1 for eluent to β-beta-ethoxy rutinose crude product into
Row silica gel column chromatography collects the 5th to the 8th column volume fraction, and pure β-beta-ethoxy rutinose is obtained after concentration.
Step（2）Described in the dosage of macroporous absorbent resin D101 be 10-20 times of low alcohol extracting thing volume.
Step（3）Described in silica gel be 60-100 mesh.
Step（3）Described in the dosage of silica gel be 10-20 times of β-beta-ethoxy rutinose crude product.
In order to make the purpose , technical scheme and advantage of the present invention be clearer, by the following examples and experiment number
According to the present invention is described in further detail.It should be appreciated that specific embodiment described herein is only used to explain this hair
It is bright, it is not limited to the technical solution.
Embodiment 1
（1）1kg bitter buckwheats are weighed, 5 liter of 5% ethyl alcohol, 20 DEG C of stirrings is added to extract 4 hours, filtering, slag repeats extraction once,
Filtering, merges secondary filtrate；It is concentrated under reduced pressure under the conditions of 60-70 DEG C, is concentrated into 1/10 volume, obtain low alcohol extracting thing.
（2）Macroporous absorbent resin D101 column chromatographies：Upper macroporous absorbent resin D101 column chromatographies, are eluted with water, and abandon preceding 1.5
Times column volume water elution, later with 2 times of column volume water elutions, collection is concentrated to give β-beta-ethoxy rutinose crude product（TLC display masters
It is target component to want spot）.
（3）Flash silica column chromatography：With the chloroform after water saturation：Methanol 3:1 is thick to β-beta-ethoxy rutinose for eluent
Product carry out silica gel column chromatography, collect the 5th to the 8th column volume fraction, and pure β-beta-ethoxy rutinose is obtained after concentration.
Embodiment 2
（1）1kg bitter buckwheats are weighed, add 10 liter of 5% ethyl alcohol, 60 DEG C of stirrings to extract 3 hours, filtering, slag repeats extraction one
Secondary, filtering merges secondary filtrate；It is concentrated under reduced pressure under the conditions of 60-70 DEG C, is concentrated into 1/10 volume, obtain low alcohol extracting
Object.
（2）Macroporous absorbent resin D101 column chromatographies：Upper macroporous absorbent resin D101 column chromatographies, are eluted with water, and abandon preceding 1.5
Times column volume water elution, later with 2 times of column volume water elutions, collection is concentrated to give β-beta-ethoxy rutinose crude product（TLC display masters
It is target component to want spot）.
（3）Flash silica column chromatography：With the chloroform after water saturation：Methanol 3:1 is thick to β-beta-ethoxy rutinose for eluent
Product carry out silica gel column chromatography, collect the 5th to the 8th column volume fraction, and pure β-beta-ethoxy rutinose is obtained after concentration.
Claims (4)
1. a kind of preparation method of β-beta-ethoxy rutinose is inhaled it is characterized in that using bitter buckwheat as raw material through low alcohol extracting, macropore
Attached resin D101 column chromatographies, Flash silica column chromatography and etc., β-beta-ethoxy rutinose is obtained, following steps are specifically included：
（1）Low alcohol extracting：By bitter buckwheat, solid-liquid ratio is 1 based on kg/L：5-1：10 are added the ethyl alcohol of mass concentration 5%-15%,
It extracts 3-4 hours, filters in 20-60 DEG C of temperature, slag repeats extraction once, and filtering merges secondary filtrate；In 60-70
It is concentrated under reduced pressure under the conditions of DEG C, is concentrated into 1/10 volume, obtain low alcohol extracting thing；
（2）Macroporous absorbent resin D101 column chromatographies：By step（1）Macroporous absorbent resin D101 column layers in middle minuent alcohol extracting thing
Analysis, is eluted with water, and abandons preceding 1.5 times of column volume water elutions, later with 2 times of column volume water elutions, collects and is concentrated to give β-ethoxy
Base rutinose crude product；
（3）Flash silica column chromatography：With the chloroform after water saturation：Methanol 3:1 for eluent to β-beta-ethoxy rutinose crude product into
Row silica gel column chromatography collects the 5th to the 8th column volume fraction, and pure β-beta-ethoxy rutinose is obtained after concentration.
2. according to the method described in claim 1, it is characterized in that step（2）Described in macroporous absorbent resin D101 dosage
It is 10-20 times of low alcohol extracting thing volume.
3. according to the method described in claim 1, it is characterized in that step（3）Described in silica gel be 200-300 mesh.
4. according to the method described in claim 1, it is characterized in that step（3）Described in silica gel dosage be β-ethyoxyl rue
30-50 times of fragrant sugar crude product.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114287557A (en) * | 2021-12-30 | 2022-04-08 | 江南大学 | Edible plant micro powder with high ethoxy rutinose content and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101519457A (en) * | 2009-03-17 | 2009-09-02 | 徐德平 | Method for preparing beta-ethoxy rutinose and application thereof for reducing blood glucose |
| CN103755751A (en) * | 2014-01-09 | 2014-04-30 | 山西春阳生物科技有限公司 | Method for enriching beta-ethyoxyl rutinose |
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2018
- 2018-05-29 CN CN201810527024.0A patent/CN108530499A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101519457A (en) * | 2009-03-17 | 2009-09-02 | 徐德平 | Method for preparing beta-ethoxy rutinose and application thereof for reducing blood glucose |
| CN103755751A (en) * | 2014-01-09 | 2014-04-30 | 山西春阳生物科技有限公司 | Method for enriching beta-ethyoxyl rutinose |
Non-Patent Citations (3)
| Title |
|---|
| LE ZHOU，等: "Syntheses of R-beta-rutinosides by rutin-degrading reaction", 《JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH》 * |
| PHAM THANH KY，等: "Benzyl Glycosides from the Aerial Parts of Gynostemma laxum and Their NF-κB Inhibitory Activity in HepG2 Cells", 《BULL. KOREAN CHEM. SOC.》 * |
| 徐宝才，等: "色谱法分析检测苦荞籽粒中的可溶性糖(醇)", 《色谱》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114287557A (en) * | 2021-12-30 | 2022-04-08 | 江南大学 | Edible plant micro powder with high ethoxy rutinose content and preparation method thereof |
| CN114287557B (en) * | 2021-12-30 | 2023-10-03 | 江南大学 | Edible plant micro powder with high ethoxy rutinose content and preparation method thereof |
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Application publication date: 20180914 |