CN108451960B - Application of beta-ethoxy rutinose in preparation of liver protection product - Google Patents
Application of beta-ethoxy rutinose in preparation of liver protection product Download PDFInfo
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- CN108451960B CN108451960B CN201810578545.9A CN201810578545A CN108451960B CN 108451960 B CN108451960 B CN 108451960B CN 201810578545 A CN201810578545 A CN 201810578545A CN 108451960 B CN108451960 B CN 108451960B
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- ethoxy rutinose
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- OVVGHDNPYGTYIT-VHBGUFLRSA-N Robinobiose Natural products O(C[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](C)O1 OVVGHDNPYGTYIT-VHBGUFLRSA-N 0.000 title claims abstract description 20
- -1 beta-ethoxy rutinose Chemical compound 0.000 title claims abstract description 20
- 210000004185 liver Anatomy 0.000 title abstract description 17
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 206010067125 Liver injury Diseases 0.000 claims abstract description 10
- 239000003814 drug Substances 0.000 claims abstract description 9
- 231100000753 hepatic injury Toxicity 0.000 claims abstract description 8
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 6
- 238000010253 intravenous injection Methods 0.000 claims description 3
- 239000006186 oral dosage form Substances 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims 1
- 241000700159 Rattus Species 0.000 abstract description 7
- 229940079593 drug Drugs 0.000 abstract description 4
- 238000012827 research and development Methods 0.000 abstract description 4
- 230000036541 health Effects 0.000 abstract description 2
- 230000001681 protective effect Effects 0.000 abstract description 2
- 230000001154 acute effect Effects 0.000 abstract 1
- 238000011161 development Methods 0.000 abstract 1
- 238000001727 in vivo Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 244000130270 Fagopyrum tataricum Species 0.000 description 6
- 235000014693 Fagopyrum tataricum Nutrition 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000013642 negative control Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 210000005228 liver tissue Anatomy 0.000 description 4
- 238000010186 staining Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 125000000953 rutinose group Chemical group 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000219050 Polygonaceae Species 0.000 description 2
- 244000269722 Thea sinensis Species 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 210000003494 hepatocyte Anatomy 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 101100116778 Arabidopsis thaliana GSH3 gene Proteins 0.000 description 1
- 241000219051 Fagopyrum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 238000012333 histopathological diagnosis Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Mycology (AREA)
- Gastroenterology & Hepatology (AREA)
- Epidemiology (AREA)
- Nutrition Science (AREA)
- Molecular Biology (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Botany (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
the invention belongs to the field of biological medicine, and discloses application of beta-ethoxy rutinose in preparation of a liver protection product. In vivo experiments on rats show that the beta-ethoxy rutinose has a protective effect on acute alcoholic liver injury. The invention provides a certain experimental basis for the research and development of new liver injury drugs and the development of health care products.
Description
Technical Field
The invention belongs to the technical field of biological medicines, and particularly relates to application of beta-ethoxy rutinose in preparation of a liver protection product.
Background
Liver diseases seriously threaten human health and reduce the quality of life of people, and the incidence and the death rate are high. Alcohol, drugs and infection can damage liver cells, causing liver damage. Alcohol is a common beverage for people, and diseases finally induced by liver injury caused by alcohol are more and more valued. Research and development of liver-protecting drugs and health-care products with liver-protecting function are hot spots in research and development.
Fagopyrum tataricum (Fagopyrum tataricum) of Polygonaceae (Polygonaceae) genus Fagopyrum (Fagopyrum tataricum)Fagoyrum tataricum (L.) Gaertn) plants are recognized as excellent dual-purpose plants for both food and medicine by the International food and agriculture organization, and the efficacy of the plants in ancient medical science of China is mostly explained. Researchers at Baotou medical college nutrition research institute found that the tartary buckwheat tea can effectively reduce the influence of aging on the liver tissue SOD and MDA of mice (Li Ying, xu Xiu, Duyang. research on the influence of the tartary buckwheat tea on the liver tissue SOD and MDA of aging mice [ J]Food research and development 2015, 36(18): 42-43).
In the previous research, a simple and rapid method for extracting and purifying beta-ethoxy rutinose from tartary buckwheat is invented. We find that the beta-ethoxy rutinose has a better protective effect on alcoholic liver injury.
Disclosure of Invention
The invention aims to provide application of beta-ethoxy rutinose in preparation of a liver protection product.
The invention aims to realize the application of beta-ethoxy rutinose in preparing products for protecting liver, wherein the structural formula of the beta-ethoxy rutinose is as follows:
A medicine for protecting liver comprises beta-ethoxyrutinose.
The dosage form is oral dosage form or intravenous injection.
Drawings
FIG. 1 is the chemical structural formula of beta-ethoxy rutinose prepared by the invention
Detailed Description
The present invention is further illustrated by the following figures and examples, but is not limited thereto in any way, and any variations or modifications based on the teachings of the present invention are within the scope of the present invention.
The application of beta-ethoxy rutinose in preparing a product for protecting liver, wherein the structural formula of the beta-ethoxy rutinose is as follows:
A medicine for protecting liver comprises beta-ethoxyrutinose.
The dosage form is oral dosage form or intravenous injection.
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail by examples and experimental data. It should be understood that the specific embodiments described herein are merely illustrative of the invention and do not limit the scope of the invention.
Example 1
Preparation of beta-ethoxy rutinose:
(1) Weighing 1kg of radix Et rhizoma Fagopyri Tatarici, adding 5L of 5% ethanol, extracting at 20 deg.C for 3 times with stirring, each time for 4 hr, filtering, and mixing filtrates; concentrating under reduced pressure at 60-70 deg.C to 1/10 volume to obtain low alcohol extract.
(2) Macroporous adsorption resin D101 column chromatography: separating with macroporous adsorbent resin D101 column, eluting with water, discarding the first 1.5 times of column water eluate, eluting with 2 times of column volume water, collecting and concentrating to obtain beta-ethoxy rutinose crude product (TLC shows main spot as target component).
(3) Flash silica gel column chromatography: chloroform after saturation with water: and (3) performing silica gel column chromatography on the beta-ethoxy rutinose crude product by taking methanol as an eluent at the ratio of 3:1, collecting fractions with the volume from 5 th to 8 th columns, and concentrating to obtain pure beta-ethoxy rutinose.
The beta-ethoxy rutinose is determined by mass spectrum and nuclear magnetic resonance spectrum to be colorless transparent liquid, EI-MSm/z: 355 [M＋H]+Molecular formula C14H26O10。1H-NMR（500MHz, D2O）δ H: 1.08（3H, t, J = 7.1Hz, H-2’’），1.15（3H, d,J = 6.3Hz, H-6’），4.31（1H, d, J = 7.8Hz, H-1）；13C-NMR（125MHz, D2O）δ C: 101.9（d, C-1），72.0（d, C-2）， 75.7（d, C-3）， 69.7（d, C-4）， 74.7（d, C-5），66.9（t,C-6），100.6（d, C-1’），70.0（d, C-2 '), 70.1 (d, C-3 '), 73.0 (d, C-4 '), 68.6 (d, C-5 '), 16.6 (q, C-6 '), 14.3 (q, C-2 ' '), 66.2 (t, C-1 ' '). Nuclear magnetic data and literature data (Xudefing. preparation method of beta-ethoxy rutinose and application thereof in reducing blood sugar, CN 101519457B [ P ]]2011.) is consistent.
Example 2
Female SD rats were randomly divided into 5 groups of 10 animals each, negative control group, model control group, and high, medium, and low three dose groups. Wherein the three dose groups are respectively a low-dose beta-ethoxy rutinose group, a medium-dose beta-ethoxy rutinose group and a high-dose beta-ethoxy rutinose group; the doses were 2.5, 5, 10g/kgBW, respectively. The negative control group is distilled water control group, and the model control group is 50% ethanol model control group. The dose is adjusted by adopting an alcoholic liver injury model method, wherein the test substances with different doses are given to three dose groups, distilled water is given to a negative control group and a model control group, the test substances are intragastrically administered for 1 time/d by mouth according to 10ml/kg. BW, the test substances are continuously administered for 30d, and the weight is weighed for 2 times/w. At the end of the test, the model control group and the three dose groups are orally administered with 50% absolute ethyl alcohol once, the dose is 14ml/kg.BW, the negative control group is administered with distilled water with the same volume, after fasting for 16h, the animals are sacrificed, the livers are taken and weighed, the visceral body ratio is calculated, and the livers are used for carrying out biochemical index detection and histopathological examination.
taking a cross section from the middle part of the left lobe of the liver of a rat, slicing, staining and observing the distribution, range and area of lipid droplets in the liver under a mirror. The liver tissue of each animal was observed continuously with 40-fold objective lens, and scored according to the number of positive cells and the distribution range, on a scale of 0, 1, 2, 3, 4. The average of the obtained scores was taken as the fatty staining score of the liver tissue in this example. The evaluation standard is positive indexes of MDA, TG and GSH3 of the liver; or MDA, TG and GSH are positive in any two indexes and liver histopathological diagnosis results are positive, and the tested sample can be judged to have the auxiliary protection function on alcoholic liver injury.
From the indexes of rat body weight, liver body ratio and the like, the three dose groups have no statistical significance compared with the model control group (p > 0.05). The contents of MDA and TG in liver homogenate of the rat in the model control group are obviously increased (about 0.01) compared with those in the negative control group, and the content of GSH is obviously reduced (about 0.01), which indicates that the model is successful and the experimental system is reliable.
Compared with the model control group, the MDA, GSH and TG contents of the three dose groups are remarkably reduced, the GSH is remarkably increased (about 0.05), and the TG of the three dose groups is not remarkably different (p is more than 0.05).
The hepatocyte fat staining score of the model control group rats is obviously increased compared with that of the negative control group (p is less than 0.01), and the hepatocyte fat staining score of the rats in the three dose groups is reduced and has obvious difference (p is less than 0.01) compared with that of the model control group in the medium and high dose groups.
therefore, the beta-ethoxyrutinose can be judged to have an auxiliary protection function on alcoholic liver injury.
Claims (2)
1. The application of beta-ethoxy rutinose in preparing a product with auxiliary protection effect on alcoholic liver injury has the following structural formula:
。
2. The use according to claim 1, wherein the medicament is in the form of an oral dosage form or an intravenous injection.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810578545.9A CN108451960B (en) | 2018-06-07 | 2018-06-07 | Application of beta-ethoxy rutinose in preparation of liver protection product |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810578545.9A CN108451960B (en) | 2018-06-07 | 2018-06-07 | Application of beta-ethoxy rutinose in preparation of liver protection product |
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| Publication Number | Publication Date |
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| CN108451960A CN108451960A (en) | 2018-08-28 |
| CN108451960B true CN108451960B (en) | 2019-12-17 |
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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 |
| CN103829122A (en) * | 2014-01-09 | 2014-06-04 | 山西春阳生物科技有限公司 | Production method of capsule rich in beta-ethoxy rutinose |
-
2018
- 2018-06-07 CN CN201810578545.9A patent/CN108451960B/en active Active
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 |
| CN103829122A (en) * | 2014-01-09 | 2014-06-04 | 山西春阳生物科技有限公司 | Production method of capsule rich in beta-ethoxy rutinose |
Non-Patent Citations (3)
| Title |
|---|
| a-l-Rhamnosyl-b-d-glucosidase (Rutinosidase) from Aspergillus niger: Characterization and Synthetic Potential of a Novel Diglycosidase;Michael Kotik,et al;《Adv.Synth.Catal》;20151231;第357卷;第107-117页 * |
| Hepatoprotective effects of kaempferol 3-O-rutinoside and kaempferol 3-O-glucoside from Carthamus tinctorius L. on CCl4-induced oxidative liver injury in mice;Yu Wang,et al;《Journal of food and drug analysis》;20141203;第310-317页 * |
| Protective effect of blueberry anthocyanins in a CCL4-induced liver cell model;Jian Chen,et al;《LWT - Food Science and Technology》;20141029;第60卷;第1105-1112页 * |
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