CN112746089A - Preparation method of narirutin - Google Patents
Preparation method of narirutin Download PDFInfo
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- CN112746089A CN112746089A CN202011617288.9A CN202011617288A CN112746089A CN 112746089 A CN112746089 A CN 112746089A CN 202011617288 A CN202011617288 A CN 202011617288A CN 112746089 A CN112746089 A CN 112746089A
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- narirutin
- naringin
- rhamnose
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- rhamnosidase
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- HXTFHSYLYXVTHC-AJHDJQPGSA-N narirutin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C=C3O[C@@H](CC(=O)C3=C(O)C=2)C=2C=CC(O)=CC=2)O1 HXTFHSYLYXVTHC-AJHDJQPGSA-N 0.000 title claims abstract description 29
- HXTFHSYLYXVTHC-ZPHOTFPESA-N narirutin Natural products C[C@@H]1O[C@H](OC[C@H]2O[C@@H](Oc3cc(O)c4C(=O)C[C@H](Oc4c3)c5ccc(O)cc5)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O HXTFHSYLYXVTHC-ZPHOTFPESA-N 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000001606 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one Substances 0.000 claims abstract description 33
- DFPMSGMNTNDNHN-ZPHOTFPESA-N naringin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C3O[C@@H](CC(=O)C3=C(O)C=2)C=2C=CC(O)=CC=2)O[C@H](CO)[C@@H](O)[C@@H]1O DFPMSGMNTNDNHN-ZPHOTFPESA-N 0.000 claims abstract description 33
- 229940052490 naringin Drugs 0.000 claims abstract description 33
- 229930019673 naringin Natural products 0.000 claims abstract description 33
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims abstract description 20
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 claims abstract description 20
- PNNNRSAQSRJVSB-BXKVDMCESA-N aldehydo-L-rhamnose Chemical compound C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O PNNNRSAQSRJVSB-BXKVDMCESA-N 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 15
- 108010044879 alpha-L-rhamnosidase Proteins 0.000 claims abstract description 14
- 125000003275 alpha amino acid group Chemical group 0.000 claims description 3
- 239000002299 complementary DNA Substances 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 12
- GHCZTIFQWKKGSB-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;phosphoric acid Chemical compound OP(O)(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O GHCZTIFQWKKGSB-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000008055 phosphate buffer solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 101100223920 Caenorhabditis elegans rha-1 gene Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 241001093501 Rutaceae Species 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000003147 glycosyl group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 244000183685 Citrus aurantium Species 0.000 description 1
- 235000007716 Citrus aurantium Nutrition 0.000 description 1
- 244000276331 Citrus maxima Species 0.000 description 1
- 235000001759 Citrus maxima Nutrition 0.000 description 1
- 235000000228 Citrus myrtifolia Nutrition 0.000 description 1
- 235000016646 Citrus taiwanica Nutrition 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000004530 effect on cardiovascular disease Effects 0.000 description 1
- 230000000225 effect on diabetes Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 239000000348 glycosyl donor Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- 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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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Abstract
The invention discloses a preparation method of narirutin, which comprises the following steps: adding alpha-L-rhamnosidase into naringin solution, reacting at 50-70 deg.C and pH of 5.0-7.0 for 10min, adding L-rhamnose, and reacting at 400rpm for 24h to obtain narirutin. The method has simple operation and low cost, can obtain high-purity narirutin, and has high efficiency of synthesizing the narirutin.
Description
Technical Field
The invention relates to the technical field of biology, and particularly relates to a preparation method of narirutin.
Background
Naringin is a dihydroflavonoid compound mainly found in fruit of Citrus grandis of Rutaceae, Citrus aurantium of Rutaceae, and cultivar thereof. Research shows that the narirutin is a natural antioxidant, has the functions of eliminating free radicals, resisting cancer, bacteria, viruses, inflammation, allergy and the like, and also has certain curative effect on cardiovascular diseases and diabetes.
At present, narirutin is mainly obtained by two methods, namely plant extraction and chemical synthesis. The narirutin is extracted from plants, so that high-purity narirutin is difficult to obtain and the extraction rate is low; the chemical synthesis of the narirutin is time-consuming and labor-consuming.
Disclosure of Invention
In order to solve the problems, the invention provides a preparation method of narirutin, which is simple to operate, low in cost, capable of obtaining high-purity narirutin and high in efficiency of synthesizing the narirutin.
In order to achieve the above purpose, the technical solution adopted by the invention to solve the technical problem is as follows:
a method for preparing narirutin, which comprises the following steps:
adding alpha-L-rhamnosidase into naringin solution, reacting at 50-70 deg.C and pH of 5.0-7.0 for 10min, adding L-rhamnose, and reacting at 400rpm for 24h to obtain narirutin.
According to the preparation method of the naringin, the naringin is hydrolyzed by alpha-L-rhamnosidase to generate the pulutinine, then the L-rhamnose is taken as a glycosyl donor, the pulutinine is taken as a glucoside acceptor, and the naringin is synthesized by utilizing the glycosyl transfer activity of the pulutinine; therefore, the high-purity narirutin can be obtained at low cost under the condition of avoiding using expensive compounds, and the efficiency of synthesizing the narirutin is high.
In addition, the preparation method of the narirutin provided by the embodiment of the invention can also have the following additional technical characteristics:
alternatively, the cDNA sequence (2062bp, NCBI accession No. KC750908.1), amino acid sequence (655AA) of said alpha-L-rhamnosidase.
Optionally, the concentration of the naringin solution is 0.005mol/L-0.07mol/L, the concentration of alpha-L-rhamnosidase is 50 μ g/mL, and the concentration of L-rhamnose is 0.05mol/L-1.5 mol/L.
Optionally, the concentration of the naringin solution is 0.03mol/L, and the concentration of the L-rhamnose is 1.0 mol/L.
Optionally, the naringin solution, the alpha-L-rhamnosidase and the L-rhamnose are added in a ratio of 6:1: 6.
Alternatively, the temperature is 60 ℃ and the pH is 6.0.
Additional aspects and advantages of the invention will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the invention.
Drawings
FIG. 1 is a liquid chromatogram of a product according to an embodiment of the present invention with naringin and a naringin standard (note: A: naringin standard; B: naringin standard; C: a glycosyl transfer reaction sample of embodiment 3; D: naringin added at the same concentration to the sample of embodiment 3);
FIG. 2 is a liquid chromatogram of the product of example 1 according to the invention;
FIG. 3 is a liquid chromatogram of the product of example 2 according to the invention;
FIG. 4 is a liquid chromatogram of the product of example 3 according to the invention;
FIG. 5 is a graph of the yield of narirutin in accordance with an embodiment of the present invention.
Detailed Description
The technical solution of the present invention is illustrated by specific examples below. It is to be understood that one or more method steps mentioned in the present invention do not exclude the presence of other method steps before or after the combination step or that other method steps may be inserted between the explicitly mentioned steps; it should also be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Moreover, unless otherwise indicated, the numbering of the various method steps is merely a convenient tool for identifying the various method steps, and is not intended to limit the order in which the method steps are arranged or the scope of the invention in which the invention may be practiced, and changes or modifications in the relative relationship may be made without substantially changing the technical content.
In order to better understand the above technical solutions, exemplary embodiments of the present invention are described in more detail below. While exemplary embodiments of the invention have been shown, it should be understood that the invention may be embodied in various forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the invention to those skilled in the art.
The test materials adopted by the invention are all common commercial products and can be purchased in the market.
Wherein, the alpha-L-rhamnosidase rRhha 1cDNA sequence (2062bp, NCBI accession number is KC750908.1), and the amino acid sequence (655 AA).
The invention will now be described with reference to specific examples, which are intended to be illustrative only and not to be limiting in any way.
Example 1
0.29mg of naringin was dissolved in 1mL of 0.02mol/L citric acid-phosphate buffer solution with pH of 3.0 to obtain a 0.005mol/L naringin solution.
9.1mg of L-rhamnose was dissolved in 1mL of 0.02mol/L citric acid-phosphate buffer solution with pH 3.0 to obtain a 0.05mol/L L-rhamnose solution.
And (3) placing 300 mu L of the naringin solution at 50 ℃ for incubation for 10min, adding 50 mu L of alpha-L-rhamnosidase Rha1 of 50 mu g/mL for reaction, adding 300 mu L of the L-rhamnose solution after reaction for 10min, reacting at 400rpm, and boiling in 100 ℃ boiling water for 10min after reaction for 24h to stop the reaction.
Example 2
40.6mg of naringin was dissolved in 1mL of 0.02mol/L citric acid-phosphate buffer solution with pH of 7.0 to obtain a 0.07mol/L naringin solution.
273.2mg of L-rhamnose was dissolved in 1mL of 0.02mol/L citric acid-phosphate buffer solution with pH 7.0 to obtain a 1.5mol/L L-rhamnose solution.
And (3) placing 300 mu L of the naringin solution at 70 ℃ for incubation for 10min, adding 50 mu L of alpha-L-rhamnosidase Rha1 of 50 mu g/mL for reaction, adding 300 mu L of the L-rhamnose solution after reaction for 10min, reacting at 400rpm, and boiling in 100 ℃ boiling water for 10min after reaction for 24h to stop the reaction.
Example 3
Dissolving 17.4mg of naringin in 1mL of 0.02mol/L citric acid-phosphate buffer solution with pH of 6.0 to obtain 0.03mol/L naringin solution.
182mg of L-rhamnose is dissolved in 1mL of 0.02mol/L citric acid-phosphate buffer solution with the pH value of 6.0 to obtain 1.0mol/L L-rhamnose solution.
And (3) placing 300 mu L of the naringin solution at 60 ℃ for incubation for 10min, adding 50 mu L of alpha-L-rhamnosidase Rha1 of 50 mu g/mL for reaction, adding 300 mu L of the L-rhamnose solution after reaction for 10min, reacting at 400rpm, and boiling in 100 ℃ boiling water for 10min after reaction for 24h to stop the reaction.
Test examples
HPLC detection of the products obtained in examples 1 to 3, naringin standard, narirutin standard, and the addition of 0.03mol/L of narirutin to the samples of example 3.
The samples were separately injected through 0.22 μm aqueous filters into 1.5mL liquid bottles for detection by Agilent 1260 liquid chromatograph. Temperature injection: 35 ℃, injection volume: 20 μ L. The pump of the mobile phase A is water, the pump of the B is methanol, the pump of the C is acetonitrile, the flow rate is 1mL/min, and the wavelength is 280 nm. The elution procedure is shown in table 1:
TABLE 1 liquid phase elution conditions
Each value is the average of three experiments.
Examples 1, 2, 3 narirutin yield calculation formula: naringin yield ═ naringin molar amount/naringin molar amount × 100%
10mL of each of the narirutin prepared in examples 1, 2 and 3 was collected, concentrated to 1mL by rotary evaporation, purified by using a preparative liquid phase, and analyzed by HPLC after purification to check the purity, wherein the ratio of the peak area of the narirutin to the total peak area was the purity of the narirutin.
The results are shown in FIGS. 2-4, which show that the naringin purity is highest at 98% and the yield is maximum at 28.3% at pH 6.0, 60 deg.C, L-rhamnose concentration of 1.0mol/L and naringin concentration of 0.03 mol/L.
In the description herein, references to the description of the term "one embodiment," "some embodiments," "an example," "a specific example," or "some examples," etc., mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above should not be understood to necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples. Furthermore, various embodiments or examples described in this specification can be combined and combined by those skilled in the art.
Although embodiments of the present invention have been shown and described above, it is understood that the above embodiments are exemplary and should not be construed as limiting the present invention, and that variations, modifications, substitutions and alterations can be made to the above embodiments by those of ordinary skill in the art within the scope of the present invention.
Claims (6)
1. A preparation method of narirutin is characterized by comprising the following steps:
adding alpha-L-rhamnosidase into naringin solution, reacting at 50-70 deg.C and pH of 5.0-7.0 for 10min, adding L-rhamnose, and reacting at 400rpm for 24h to obtain narirutin.
2. The method of claim 1, wherein: the cDNA sequence (2062bp, NCBI accession number KC750908.1) of the alpha-L-rhamnosidase, and the amino acid sequence (655 AA).
3. The method of claim 1, wherein: the concentration of the naringin solution is 0.005mol/L-0.07mol/L, the concentration of alpha-L-rhamnosidase is 50 mu g/mL, and the concentration of L-rhamnose is 0.05mol/L-1.5 mol/L.
4. The method of claim 1, wherein: the concentration of the naringin solution is 0.03mol/L, and the concentration of the L-rhamnose is 1.0 mol/L.
5. The method of claim 1, wherein: the adding ratio of the naringin solution to the alpha-L-rhamnosidase to the L-rhamnose is 6:1: 6.
6. The method of claim 1, wherein: the temperature was 60 ℃ and the pH was 6.0.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115300521A (en) * | 2022-09-20 | 2022-11-08 | 吉林大学 | Application of narirutin in preparation of Sortase A sortase and PLY hemolysin inhibitor |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101089187A (en) * | 2006-06-14 | 2007-12-19 | 浙江工业大学 | Method for hydrolytic preparing biological tangeritin by enzyme |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101089187A (en) * | 2006-06-14 | 2007-12-19 | 浙江工业大学 | Method for hydrolytic preparing biological tangeritin by enzyme |
Non-Patent Citations (2)
| Title |
|---|
| KYOUNG HOON JEONG ET AL.: "Naringin attenuates autophagic stress and neuroinflammation in kainic acid-treated hippocampus in vivo", 《EVID BASED COMPLEMENT ALTERNAT MED》, pages 1 - 9 * |
| 谭舒舒等: "枳壳中芸香柚皮苷和橙皮苷配伍对正常小鼠小肠推进作用的影响", 《江西中医药大学学报》, pages 73 - 75 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115300521A (en) * | 2022-09-20 | 2022-11-08 | 吉林大学 | Application of narirutin in preparation of Sortase A sortase and PLY hemolysin inhibitor |
| CN115300521B (en) * | 2022-09-20 | 2024-02-27 | 吉林大学 | Application of naringin in preparation of Sortase A sortase and PLY hemolysin inhibitor |
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