CN112746089B - Preparation method of naringin - Google Patents
Preparation method of naringin Download PDFInfo
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- CN112746089B CN112746089B CN202011617288.9A CN202011617288A CN112746089B CN 112746089 B CN112746089 B CN 112746089B CN 202011617288 A CN202011617288 A CN 202011617288A CN 112746089 B CN112746089 B CN 112746089B
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- naringin
- rhamnose
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- rhamnosidase
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- 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 title claims abstract description 57
- 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 title claims abstract description 57
- 229940052490 naringin Drugs 0.000 title claims abstract description 57
- 229930019673 naringin Natural products 0.000 title claims abstract description 57
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims abstract description 19
- 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 19
- 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 19
- 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 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 abstract description 10
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 17
- 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
- 239000007788 liquid 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 compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- DLIKSSGEMUFQOK-SFTVRKLSSA-N naringenin 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C(C(=O)C[C@H](O2)C=3C=CC(O)=CC=3)C2=C1 DLIKSSGEMUFQOK-SFTVRKLSSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 239000008055 phosphate buffer solution Substances 0.000 description 3
- RXVLWCCRHSJBJV-UHFFFAOYSA-N prunin Natural products OCC1OC(O)C(Oc2cc(O)c3C(=O)CC(Oc3c2)c4ccc(O)cc4)C(O)C1O RXVLWCCRHSJBJV-UHFFFAOYSA-N 0.000 description 3
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 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
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 2
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin 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(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 2
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 2
- 235000005493 rutin Nutrition 0.000 description 2
- 229960004555 rutoside Drugs 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 244000183685 Citrus aurantium Species 0.000 description 1
- 235000007716 Citrus aurantium Nutrition 0.000 description 1
- 235000000228 Citrus myrtifolia Nutrition 0.000 description 1
- 235000016646 Citrus taiwanica Nutrition 0.000 description 1
- 240000000560 Citrus x paradisi Species 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
- 241001093501 Rutaceae Species 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
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 239000000348 glycosyl donor Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
Classifications
-
- 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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- Chemical & Material Sciences (AREA)
- 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)
- General Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention discloses a preparation method of naringin, which comprises the following steps: adding alpha-L-rhamnosidase into naringin solution, reacting at 50-70deg.C and pH of 5.0-7.0, reacting for 10min, adding L-rhamnose, and reacting at 400rpm for 24 hr to obtain naringin. The method is simple to operate, low in cost, capable of obtaining the naringin with higher purity, and high in naringin synthesis efficiency.
Description
Technical Field
The invention relates to the technical field of biology, in particular to a preparation method of naringin.
Background
Naringin is a dihydroflavonoid compound which is mainly present in the fruits of pomelo in the family Rutaceae, citrus aurantium and its cultivars. Studies show that the naringin is a natural antioxidant, has the effects of scavenging free radicals, resisting cancer, bacteria and viruses, resisting inflammation, resisting allergy and the like, and has certain curative effects on cardiovascular diseases and diabetes.
At present, the naringin is mainly obtained by two methods of plant extraction and chemical synthesis. The naringin with higher purity is difficult to obtain by extracting from plants, and the extraction rate is low; the chemical synthesis of naringin is time-consuming and laborious.
Disclosure of Invention
In order to solve the problems, the invention provides a preparation method of the naringin, which is simple to operate, low in cost, capable of obtaining the naringin with higher purity and high in naringin synthesis efficiency.
In order to achieve the above object, the technical scheme adopted by the invention for solving the technical problems is as follows:
a method for preparing naringin, which comprises the following steps:
adding alpha-L-rhamnosidase into naringin solution, reacting at 50-70deg.C and pH of 5.0-7.0, reacting for 10min, adding L-rhamnose, and reacting at 400rpm for 24 hr to obtain naringin.
According to the preparation method of the naringin, disclosed by the embodiment of the invention, naringin is hydrolyzed by alpha-L-rhamnosidase to generate the prunin, then L-rhamnose is taken as a glycosyl donor, the prunin is taken as a glycoside acceptor, and the glycosyl transfer activity of the prunin is utilized to synthesize the naringin; thus, the rutin with higher purity can be obtained at low cost without using expensive compounds, and the efficiency of synthesizing the rutin is high.
In addition, the preparation method of the naringin provided by the embodiment of the invention can also have the following additional technical characteristics:
alternatively, the cDNA sequence of the alpha-L-rhamnosidase (2062 bp, NCBI accession No. KC 750908.1), amino acid sequence (655 AA).
Optionally, the concentration of the naringin solution is 0.005mol/L-0.07mol/L, the concentration of alpha-L-rhamnosidase is 50 mug/mL, and the concentration of L-rhamnose is 0.05mol/L-1.5mol/L.
Optionally, the naringin solution has a concentration of 0.03mol/L and L-rhamnose has a concentration of 1.0mol/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 naringin standard (note: A: naringin standard; B: naringin standard; C: sample of the glycosyl transfer reaction of example 3; D: addition of the same concentration of naringin to sample of example 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 yield of naringin according to an embodiment of the present invention.
Detailed Description
The technical scheme of the invention is described below through specific examples. It is to be understood that the mention of one or more method steps of the present invention does not exclude the presence of other method steps before and after the combination step or that other method steps may be interposed between these explicitly mentioned steps; it should also be understood that these examples are illustrative of the present invention and are not intended to limit the scope of the present invention. Moreover, unless otherwise indicated, the numbering of the method steps is merely a convenient tool for identifying the method steps and is not intended to limit the order of arrangement of the method steps or to limit the scope of the invention in which the invention may be practiced, as such changes or modifications in their relative relationships may be regarded as within the scope of the invention without substantial modification to the technical matter.
In order to better understand the above technical solution, exemplary embodiments of the present invention are described in more detail below. While exemplary embodiments of the invention are shown, it should be understood that the invention may be embodied in various forms and should not be 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, alpha-L-rhamnosidase rRsha 1cDNA sequence (2062 bp, NCBI accession No. KC 750908.1), 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 limiting in any way.
Example 1
0.29mg naringin was dissolved in 1mL of 0.02mol/L citric acid-phosphate buffer solution having pH 3.0 to obtain 0.005mol/L naringin solution.
9.1mg of L-rhamnose was dissolved in 1mL of 0.02mol/L citric acid-phosphate buffer having a pH of 3.0 to obtain 0.05mol/L L-rhamnose solution.
300 mu L of the naringin solution is taken to be incubated for 10min at 50 ℃, 50 mu L of 50 mu g/mL of alpha-L-rhamnosidase Rha1 is added to react, 300 mu L of the L-rhamnose solution is added to react for 10min, the reaction is carried out at 400rpm, and the reaction is terminated after 24h of reaction, the reaction is boiled in boiling water at 100 ℃.
Example 2
40.6mg of naringin was dissolved in 1mL of 0.02mol/L citric acid-phosphate buffer solution having pH of 7.0 to obtain 0.07mol/L naringin solution.
273.2mg of L-rhamnose was dissolved in 1mL of 0.02mol/L citric acid-phosphate buffer pH 7.0 to obtain 1.5mol/L L-rhamnose solution.
300 mu L of the naringin solution is taken to be incubated for 10min at 70 ℃, 50 mu L of 50 mu g/mL of alpha-L-rhamnosidase Rha1 is added to react, 300 mu L of the L-rhamnose solution is added to react for 10min, the reaction is carried out at 400rpm, and the reaction is terminated after 24h of reaction, the reaction is boiled in boiling water at 100 ℃.
Example 3
17.4mg of naringin was dissolved in 1mL of 0.02mol/L citric acid-phosphate buffer solution having pH of 6.0 to obtain 0.03mol/L naringin solution.
182mg of L-rhamnose was dissolved in 1mL of 0.02mol/L citric acid-phosphate buffer pH 6.0 to obtain 1.0mol/L L-rhamnose solution.
300 mu L of the naringin solution is taken to be incubated for 10min at 60 ℃, 50 mu L of 50 mu g/mL of alpha-L-rhamnosidase Rha1 is added to react, 300 mu L of the L-rhamnose solution is added to react for 10min, the reaction is carried out at 400rpm, and the reaction is terminated after 24h of reaction, the reaction is boiled in boiling water at 100 ℃.
Test examples
HPLC detection of the products obtained in examples 1-3, naringin standard, sample of example 3, and addition of 0.03mol/L naringin.
Samples were each injected through a 0.22 μm aqueous filter into 1.5mL liquid bottles and detected by agilent 1260 liquid chromatograph. And (3) temperature injection: 35 ℃, sample injection volume: 20. Mu.L. The mobile phase A pump is water, the mobile phase B pump is methanol, the mobile phase C pump is acetonitrile, the flow rate is 1mL/min, and the wavelength is 280nm. 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 naringin yield calculation formula: yield of naringin = molar amount of naringin/molar amount of naringin x 100%
And respectively collecting 10mL of the naringin prepared in the examples 1, 2 and 3, concentrating to 1mL by rotary evaporation, purifying by using a preparation liquid phase, performing HPLC analysis after purification, and checking the purity, wherein the ratio of the peak area of the naringin to the total peak area is the purity of the naringin.
As shown in FIGS. 2 to 4, it was revealed that the purity of naringin was 98% at the highest and the yield was 28.3% at pH 6.0, at 60℃and at a concentration of L-rhamnose of 1.0mol/L and at a naringin concentration of 0.03 mol/L.
In the description of the present specification, a description referring to terms "one embodiment," "some embodiments," "examples," "specific examples," or "some examples," etc., means 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 present invention. In this specification, schematic representations of the above terms should not be understood as necessarily being directed 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. Further, one skilled in the art can engage and combine the different embodiments or examples described in this specification.
While embodiments of the present invention have been shown and described above, it will be understood that the above embodiments are illustrative and not to be construed as limiting the invention, and that variations, modifications, alternatives and variations may be made to the above embodiments by one of ordinary skill in the art within the scope of the invention.
Claims (3)
1. The preparation method of the naringin is characterized by comprising the following steps:
adding alpha-L-rhamnosidase into naringin solution, reacting at 60 ℃ and pH of 6.0 for 10min, adding L-rhamnose, and reacting at 400rpm for 24h to obtain naringin;
the NCBI accession number of the cDNA sequence of the alpha-L-rhamnosidase is KC750908.1, the cDNA sequence is 2062bp, and the amino acid sequence is 655AA;
the concentration of naringin solution is 0.03mol/L, and the concentration of L-rhamnose is 1.0mol/L.
2. The method of manufacturing according to claim 1, wherein: the concentration of alpha-L-rhamnosidase was 50. Mu.g/mL.
3. The method of manufacturing according to claim 1, wherein: the addition ratio of the naringin solution, the alpha-L-rhamnosidase and the L-rhamnose is 6:1:6.
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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 |
|---|
| Naringin attenuates autophagic stress and neuroinflammation in kainic acid-treated hippocampus in vivo;Kyoung Hoon Jeong et al.;《Evid Based Complement Alternat Med》;第1-9页 * |
| 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;谭舒舒等;《江西中医药大学学报》;第73-75页 * |
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