CN103275049B - Method for preparing myricetin by using vine tea and application of pyrosulfite - Google Patents
Method for preparing myricetin by using vine tea and application of pyrosulfite Download PDFInfo
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- CN103275049B CN103275049B CN201310189757.5A CN201310189757A CN103275049B CN 103275049 B CN103275049 B CN 103275049B CN 201310189757 A CN201310189757 A CN 201310189757A CN 103275049 B CN103275049 B CN 103275049B
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- pyrosulfite
- vine tea
- ampelopsin
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- myricetin
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Abstract
The invention discloses a method for preparing myricetin by using vine tea and an application of pyrosulfite. The method comprises the following steps of: extracting the ground vine tea with hot water, filtering while the vine tea is hot, concentrating the filter liquor and cooling to separate out sediments; carrying out suction filtration, dissolving the sediment residue with absolute ethyl alcohol, filtering to remove undissolved substances, and concentrating the ethanol solution obtained from filtration to obtain ethyl alcohol extract; adding the ethyl alcohol extract into the pyrosulfite solution for reaction, then pouring the reaction liquid into an ice-water mixture, and crystallizing, filtering, washing and drying to obtain the myricetin. According to the application, the pyrosulfite is applied to the vine tea as a dehydrogenation oxidizing agent for dehydrogenation transformation from dihydromyricetin to myricetin, and the transformation efficiency is high. By using the method, materials are low in cost and can be easily obtained. The method is simple, pollution-free and low in equipment requirement and can be widely applied to industrial production. The yield of the prepared myricetin reaches 21% in comparison with materials, and the purity reaches 96%.
Description
Technical field:
The present invention relates to and prepare the method for ampelopsin and the application of pyrosulfite with vine tea, belong to extraction and the enrichment preparation field of natural product active ingredient.
Background technology
All containing flavone component ampelopsin and dibydro myricetrin in the plant of Vitaceae Ampelopsis, wherein the highest with content in Ampelopsis grossedentata, the processed goods of Ampelopsis grossedentata cauline leaf is commonly called as vine tea, is rich in various active composition in vine tea, as dibydro myricetrin, ampelopsin, catechin, gallic acid, amino acid, polysaccharide etc., wherein the highest with dihydromyricetin cellulose content, ampelopsin is lower.According to existing document and patent report, most research focuses on the extraction and purification to the high dibydro myricetrin of content in vine tea, and it is less to the research of ampelopsin, relevant patent documentation has: a kind of method CN200510032918.5 extracting dibydro myricetrin from vine tea, the preparation method CN201110093346.7 of dihydromyricetin from Ampelopsis grossedentata, non-patent literature is more (Qin Jieping etc., Chinese Journal of New Drugs then, 2004, NO.10; Li Wei etc., Food science, 2004, NO.11, etc.).But at present, ampelopsin is widely used in medicine, food, healthcare products and makeup by U.S. FDA (united States food and drug administration (U.S.Food and Drug Administration)), and be expected to the anti-inflammatory medication it being developed as further special population, thus alleviate the toxic side effect of western medicine antibiotics to human body.Source-the Hairy Waxmyrtle of ampelopsin is the peculiar resource of China, but, due to reasons such as extraction processes, at present vine tea is mainly derived to the research of ampelopsin, and considerably less to the research of Hairy Waxmyrtle.From the result of study of some scientific research personnel, we can find out: in vine tea, main component is dibydro myricetrin, its content accounts for about 25%, and ampelopsin only accounts for about 2%, even lower (guangdong agricultural science, 2012, NO.15, the people such as Zhang Mingsheng obtain the mixture of dibydro myricetrin and ampelopsin by supersound extraction, and wherein the former accounts for about 25%, and the latter is less than 1%; Herbal medicine, the people such as 2003, NO.34, Li Yingqi utilize the content of the dibydro myricetrin in hplc simultaneous determination vine tea and ampelopsin to be 25%, 2% respectively), this makes the development and utilization of ampelopsin have some limitations.See domestic and foreign literature, only have the investigator of only a few to carry out modification to dihydromyricetin from Ampelopsis grossedentata up to now thus realize ampelopsin enrichment preparation, relevant patent documentation has: refer to a kind of method extracting ampelopsin in a kind of preparation method CN200610019693.4 of ampelopsin, purity brings up to 95%, but productive rate is very low, only have 5%, the novel preparation method CN200810050893.5 of ampelopsin refer to a kind of conversion by alkaline transforming agent, dibydro myricetrin being carried out to mechanism, achieve the ampelopsin that purity is higher, but wherein the yield of ampelopsin is up to about 8%.
Summary of the invention
The present invention is directed to ampelopsin resource shortage, prior art is to the extraction of ampelopsin and to prepare productive rate low, be up to 8%, be difficult to the problem tackling suitability for industrialized production, so object is being to provide the low vine tea of a kind of cost to prepare the method for high yield, high purity ampelopsin; The method cheaper starting materials is easy to get, method is simple, pollution-free, low for equipment requirements, can extensive suitability for industrialized production.
Another object of the present invention provides the application of pyrosulfite as dehydrogenation oxidation agent, using pyrosulfite as dehydrogenation oxidation agent can by dibydro myricetrin in vine tea class plant almost all dehydrogenation change into ampelopsin, obtain high yield, highly purified ampelopsin.
The invention provides the method preparing ampelopsin with vine tea, the method is by the vine tea pulverized with 90 ~ 100 DEG C of hot water extraction, after filtered while hot, by concentrated for filtrate be placed on 0 ~ 5 DEG C at cooling separate out precipitation; Suction filtration, precipitation filter residue anhydrous alcohol solution, refilters removing insolubles, and the ethanolic soln filtering gained obtains ethanol extract after concentrated; Ethanol extract is joined in pyrosulphite salts solution, react at 80 ~ 100 DEG C, after having reacted, reaction solution is poured in mixture of ice and water, after crystallization, filtration, washing, drying, to obtain final product; Described pyrosulfite add-on is 1 ~ 3 times of vine tea quality, and wherein, in pyrosulphite salts solution, the mass content of pyrosulfite is 10 ~ 40%.
Described pyrosulfite comprises one or more in potassium pyrosulfite, Sodium Pyrosulfite or ammonium pyrosulfite.
Described pyrosulphite salts solution is the aqueous solution of pyrosulfite.
Joined by ethanol extract in pyrosulphite salts solution in aforesaid method, at 80 ~ 100 DEG C, the time of reaction is 4 ~ 8h.
Vine tea powder in aforesaid method: the solid-liquid ratio of hot water is 1:20 ~ 40, and unit is g/mL.
In aforesaid method, extracting times is 2 ~ 4 times, and each extraction time is 0.5 ~ 2h.
In aforesaid method after lixiviate for several times, united extraction liquid, then carry out concentration operation.
In aforesaid method, filtrate is concentrated to 1/4 ~ 2/5 of former filtrate volume.
In aforesaid method, ethanolic soln is concentrated into 1/4 ~ 2/5 of former volumes of aqueous ethanol after concentrated.
In aforesaid method, after crystallization, the ampelopsin crystal filtering separation of gained out uses frozen water repetitive scrubbing afterwards; By pyrosulfite washes clean complete for unreacted.
Vine tea powder in aforesaid method: the solid-liquid ratio (g:mL) of dehydrated alcohol is 1:5 ~ 15.
Pass through repeatedly recrystallization in aforesaid method and can improve purity further.
Method of the present invention is applicable to any material of vegetable origin containing dibydro myricetrin.
Present invention also offers the application of pyrosulfite, this application pyrosulfite is applied to dibydro myricetrin in vine tea class plant as dehydrogenation oxidation agent transform to the dehydrogenation of ampelopsin.
Described pyrosulfite comprises one or more in potassium pyrosulfite, Sodium Pyrosulfite or ammonium pyrosulfite.
The method that vine tea of the present invention prepares ampelopsin comprises the following steps:
(1) by vine tea finished product crushed after being dried in vacuum drying oven, with 90 ~ 100 DEG C of hot water extraction 2 ~ 4 times, united extraction liquid, while hot suction filtration, filtrate, through underpressure distillation, is concentrated into 1/4 ~ 2/5 of former filtrate volume, leaves standstill separate out precipitation at 0 ~ 5 DEG C; Suction filtration, precipitation filter residue anhydrous alcohol solution, leave standstill suction filtration to remove insoluble composition, filtrate reduced in volume, to 1/4 ~ 2/5 of former volumes of aqueous ethanol, obtains ethanol extract;
(2) above-mentioned gained ethanol extract is joined in the aqueous solution of pyrosulfite, under 80 ~ 100 DEG C of conditions, after reaction 4 ~ 8h, reaction solution is poured in mixture of ice and water, crystallize out, suction filtration, frozen water repetitive scrubbing, vacuum-drying, obtain ampelopsin crystal;
Described pyrosulfite add-on is 1 ~ 3 times of vine tea quality, and wherein, in pyrosulphite salts solution, the mass content of pyrosulfite is 10 ~ 40%.
Beneficial effect of the present invention: instant invention overcomes the extraction of ampelopsin in prior art and prepare the low defect of productive rate, bibliographical information dihydromyricetin from Ampelopsis grossedentata content accounts for about 25wt%, and ampelopsin 2wt%, prior art extract from material of vegetable origin or prepare ampelopsin the highest yield 8%; The present invention finds through contriver's lot of experiments, conversion one step that pyrosulphite can be able to make dibydro myricetrin carry out structure as dehydrogenation oxidation agent generates ampelopsin, when conversion reaction is reacted under the temperature condition of 80 ~ 100 DEG C, transformation efficiency is given prominence to, temperature is crossed low-yield and is reduced, the too high product of temperature can be further oxided, particularly 95 ~ 100 DEG C of transformation efficiencies best (as can be seen from Figure 3, dibydro myricetrin is almost all converted into ampelopsin); The present invention adopts and extracts and the continuous processing method of dehydrogenation thaumatropy integration, is extracted by the plant material of the cheapnesss such as the vine tea containing dibydro myricetrin by simple method, then dehydrogenation transforms a step and directly obtains high yield, highly purified ampelopsin; The inventive method productive rate reaches 21%, and purity reaches more than 96%; The method is pollution-free, low for equipment requirements, can extensive suitability for industrialized production.
Accompanying drawing explanation
The high performance liquid chromatography spectrogram that [Fig. 1] is dibydro myricetrin and ampelopsin reference substance: 1 is dibydro myricetrin, and 2 is ampelopsin.
[Fig. 2] is the high performance liquid chromatography spectrogram of crude extract before embodiment 2 dehydrogenation reaction: 1 is dibydro myricetrin, and 2 is ampelopsin.
[Fig. 3] is the high performance liquid chromatography spectrogram of embodiment 2 ampelopsin product: 1 is dibydro myricetrin, and 2 is ampelopsin.
Embodiment
Following examples further illustrate of the present invention, instead of restriction the present invention.
Chromatographic condition: chromatographic column: Kromasil C18 post (250mm × 4.6mm, 5 μm), moving phase: methyl alcohol: water: Glacial acetic acid=50:50:1; Determined wavelength: 292nm, 375nm; Detect column temperature: 30 DEG C; Sample size: 20 μ L; Flow velocity: 1.0mLmin
– 1;
Embodiment 1
1, the extraction of vine tea
Take dry vine tea powder 20g, add about 200mL water, be heated to 95 DEG C of lixiviate 1h, filtered while hot, filter residue repeats aforesaid operations twice, merges three filtrates, be concentrated into 200mL, after in 0 ~ 5 DEG C leave standstill separate out light-yellow precipitate, suction filtration, filter precipitation uses 300mL anhydrous alcohol solution, leave standstill suction filtration, filtrate reduced in volume, to 100mL, obtains the ethanol extract of extract, for subsequent use;
2, the dehydrogenation reaction of dibydro myricetrin
Above-mentioned 100mL concentrated extract is joined the Na of 250mL20%
2s
2o
5in the aqueous solution, at 100 DEG C, react 4h; Terminate reaction, mixed solution is poured in mixture of ice and water, leave standstill separate out precipitation, suction filtration, frozen water is washing precipitation repeatedly, after carry out drying in 40 DEG C, vacuum, obtain greenish yellow solid, i.e. ampelopsin, product yield is 21%.
The yellow-green colour material obtained in aforesaid operations is initially identified as ampelopsin by thin-layer chromatography; Carry out qualitative and quantitative analysis through high performance liquid chromatography, confirm that gained material is ampelopsin, and high purity 96%.
Embodiment 2
1. the extraction of vine tea:
Take dry vine tea powder 20g, add 200mL water, be heated to 95 DEG C of lixiviate 1h, filtered while hot, filter residue repeats aforesaid operations twice, merges three filtrates, is concentrated into 200mL; After to leave standstill in 0 ~ 5 DEG C and separate out light-yellow precipitate, suction filtration, filter precipitation use 300mL anhydrous alcohol solution, and standing suction filtration, filtrate reduced in volume, to 100mL, obtains the ethanol extract of extract, for subsequent use.
2. the dehydrogenation reaction of dibydro myricetrin:
Above-mentioned 100mL concentrated extract is joined the K of 250mL20%
2s
2o
5in the aqueous solution, at 100 DEG C, react 4h; Terminate reaction, mixed solution is poured in mixture of ice and water, leave standstill separate out precipitation, suction filtration, frozen water is washing precipitation repeatedly, after carry out drying in 40 DEG C, vacuum, obtain greenish yellow solid, i.e. ampelopsin, product yield is 21%.
The yellow-green colour material obtained in aforesaid operations is initially identified as ampelopsin by thin-layer chromatography; Carry out qualitative and quantitative analysis through high performance liquid chromatography, confirm that gained material is ampelopsin, and high purity 96%.
Claims (7)
1. prepare the method for ampelopsin with vine tea, it is characterized in that, by the vine tea pulverized with 90 ~ 100 DEG C of hot water extraction, after filtered while hot, by concentrated for filtrate be placed on 0 ~ 5 DEG C at cooling separate out precipitation; Suction filtration, precipitation filter residue anhydrous alcohol solution, refilters removing insolubles, and the ethanolic soln filtering gained obtains ethanol extract after concentrated; Ethanol extract is joined in pyrosulphite salts solution, react at 80 ~ 100 DEG C, after having reacted, reaction solution is poured in mixture of ice and water, after crystallization, filtration, washing, drying, to obtain final product; Described pyrosulfite add-on is 1 ~ 3 times of vine tea quality, and wherein, in pyrosulphite salts solution, the mass content of pyrosulfite is 10 ~ 40%; Described pyrosulfite is one or more in potassium pyrosulfite, Sodium Pyrosulfite, ammonium pyrosulfite.
2. the method for claim 1, is characterized in that, is joined by ethanol extract in pyrosulphite salts solution, and at 80 ~ 100 DEG C, the time of reaction is 4 ~ 8h.
3. the method for claim 1, is characterized in that, vine tea powder: the solid-liquid ratio of hot water is 1:20 ~ 40, and unit is g/mL.
4. method as claimed in claim 3, it is characterized in that, extracting times is 2 ~ 4 times, and each extraction time is 0.5 ~ 2h.
5. the method for claim 1, is characterized in that, filtrate is concentrated to 1/4 ~ 2/5 of former filtrate volume; Ethanolic soln is concentrated into 1/4 ~ 2/5 of former volumes of aqueous ethanol after concentrated.
6. the method as described in any one of Claims 1 to 5, is characterized in that, after crystallization, the ampelopsin crystal filtering separation of gained out uses frozen water repetitive scrubbing afterwards.
7. the application of pyrosulfite, is characterized in that, pyrosulfite is applied to dihydromyricetin from Ampelopsis grossedentata as dehydrogenation oxidation agent and transforms to the dehydrogenation of ampelopsin; Described pyrosulfite is one or more in potassium pyrosulfite, Sodium Pyrosulfite, ammonium pyrosulfite.
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| CN108586409A (en) * | 2018-04-12 | 2018-09-28 | 铜仁学院 | A kind of preparation method being converted into myricetin with efficient dihydromyricetin |
| CN110627761A (en) * | 2019-10-12 | 2019-12-31 | 上海尹胜咨询管理合伙企业(有限合伙) | Method for synthesizing myricetin |
| CN111903812A (en) * | 2020-07-20 | 2020-11-10 | 上海中医药大学 | Instant strawberry tea extract, preparation method and application thereof |
| CN112851614A (en) * | 2020-12-28 | 2021-05-28 | 江苏天晟药业股份有限公司 | Preparation method of myricetin |
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| KR100883757B1 (en) * | 2007-03-12 | 2009-02-12 | 성균관대학교산학협력단 | Polyphenol compounds with modulating neurotransmitter release |
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