CN112294782A - Pharmaceutical composition of dihydromyricetin and application - Google Patents

Pharmaceutical composition of dihydromyricetin and application Download PDF

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CN112294782A
CN112294782A CN202011262731.5A CN202011262731A CN112294782A CN 112294782 A CN112294782 A CN 112294782A CN 202011262731 A CN202011262731 A CN 202011262731A CN 112294782 A CN112294782 A CN 112294782A
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dihydromyricetin
pharmaceutical composition
curcumin
cancer
mass ratio
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张全
李锐
刘玉杰
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Chengdu Zhiyu Biology Technology Co ltd
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    • 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
    • A61K31/12—Ketones
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/02—Antidotes

Abstract

The invention relates to a pharmaceutical composition of dihydromyricetin and application thereof, wherein the pharmaceutical composition comprises curcumin and dihydromyricetin. The invention has the beneficial effects that: the pharmaceutical composition can remarkably improve the oral bioavailability of dihydromyricetin, thereby increasing the applications of the dihydromyricetin in relieving alcoholism, protecting liver and resisting tumor. Meanwhile, the curcumin in the composition also has the effects of protecting the liver and inhibiting tumors, so that the oral bioavailability of the curcumin can be improved while the oral bioavailability of dihydromyricetin is improved, and finally, the pharmaceutical composition consisting of the dihydromyricetin and the dihydromyricetin has stronger synergistic effect on the effects of relieving alcoholism, protecting the liver and resisting tumors.

Description

Pharmaceutical composition of dihydromyricetin and application
Technical Field
The application relates to the field of pharmacy, in particular to a dihydromyricetin pharmaceutical composition and application thereof.
Background
Dihydromyricetin is a flavonoid compound in Ampelopsis grossedentata extract, and has special effects in relieving alcoholism, preventing alcoholic liver and fatty liver, inhibiting hepatocyte deterioration, reducing incidence of liver cancer, resisting hypertension, inhibiting in vitro platelet aggregation and in vivo thrombosis, reducing blood lipid and blood sugar levels, improving SOD activity, and protecting liver. The wide and remarkable biological effect of the compound makes the compound have important development value. However, it has poor water solubility and very low oral bioavailability, and thus, clinical application of dihydromyricetin is greatly limited. How to improve the oral bioavailability of dihydromyricetin is a key factor influencing the clinical application of dihydromyricetin.
Curcumin is a natural pigment allowed to be used by the world health organization and the U.S. food and drug administration, and a large number of researches show that curcumin has extremely wide bioactivity and multiple health-care effects. Curcumin can promote bile secretion, help nutrient absorption, and treat harmful substances. Curcumin has an antioxidant effect, can protect cell tissues, can delay aging, resist depression, has a regulating effect on fat cells, and has certain benefits on slimming, but curcumin also has certain defects in the application process, such as low solubility, poor stability, low absorption rate, easy conversion into glucuronic acid, sulfonic acid and other compounds in intestinal tracts, fast metabolism, short half-life period, and the existence of the problems causes lower bioavailability and limits the application of curcumin in the fields of food and medicines.
Disclosure of Invention
The invention mainly aims to provide a dihydromyricetin pharmaceutical composition which can increase the absorption of dihydromyricetin in gastrointestinal tract and improve the oral bioavailability of dihydromyricetin.
In order to achieve the purpose, the invention adopts the following technical scheme:
a pharmaceutical composition of dihydromyricetin comprises curcumin and dihydromyricetin.
Curcumin is a diketone compound extracted from rhizomes of some plants in Zingiberaceae and Araceae, wherein curcumin contains about 3% -6% of curcumin, and is a rare pigment with diketone structure in plant world. Curcumin has effects of reducing blood lipid, resisting tumor, resisting inflammation, promoting bile flow, and resisting oxidation. In practical application, curcumin has certain defects, such as low solubility, poor stability, low absorption rate, easy conversion to complex such as glucuronic acid and sulfonic acid in intestinal tract, fast metabolism, short half-life period and the like, and the existence of the problems causes low bioavailability and limits the application of curcumin in the fields of food and medicines.
Preferably, the pharmaceutical composition contains curcumin and dihydromyricetin in a mass ratio of 1-20: 20-1.
Preferably, the composition contains curcumin and dihydromyricetin in a mass ratio of 1-5: 5-1.
Preferably, the composition contains curcumin and dihydromyricetin in a mass ratio of 1-5: 1.
Preferably, the composition contains curcumin and dihydromyricetin in a mass ratio of 1: 1.
Preferably, the curcumin and the dihydromyricetin are used separately or in the form of a mixture.
Preferably, the pharmaceutical composition further comprises a pharmaceutically acceptable carrier.
Preferably, the dosage form of the pharmaceutical composition is tablets, capsules, granules, emulsions, self-emulsifying preparations, suspensions, powders or dripping pills.
The second purpose of the invention is to provide the application of the dihydromyricetin pharmaceutical composition in the drugs for relieving alcoholism, protecting liver and resisting tumor.
Preferably, the tumor is liver cancer, intrahepatic cholangiocarcinoma, hepatocellular carcinoma, extrahepatic cholangiocarcinoma, gallbladder cancer, sarcoma, lung cancer, bronchial cancer, pleuropulmonary blastoma, prostate cancer, breast cancer, pancreatic cancer, islet cell carcinoma, gastric cancer, intestinal cancer, thyroid cancer, parathyroid cancer, or melanoma.
Compared with the prior art, the invention has the beneficial effects that:
the pharmaceutical composition can remarkably improve the oral bioavailability of dihydromyricetin, thereby increasing the applications of the dihydromyricetin in relieving alcoholism, protecting liver and resisting tumor. Meanwhile, the curcumin in the composition also has the effects of protecting the liver and inhibiting tumors, so that the oral bioavailability of the curcumin can be improved while the oral bioavailability of dihydromyricetin is improved, and finally, the pharmaceutical composition consisting of the dihydromyricetin and the dihydromyricetin has stronger synergistic effect on the effects of relieving alcoholism, protecting the liver and resisting tumors.
Drawings
FIG. 1 is a diagram: the time curve of dihydromyricetin in the rat body;
FIG. 2 is a diagram of: the time curve of curcumin in rats;
FIG. 3 is a diagram of: the influence of the pharmaceutical composition of dihydromyricetin on the alcohol concentration in the blood of a rat after drinking wine;
FIG. 4 is a diagram of: the pharmaceutical composition of dihydromyricetin has the influence on ALT in serum of an alcoholic liver injury mouse;
FIG. 5 is a diagram: the pharmaceutical composition of dihydromyricetin has the influence on AST in serum of mice with alcoholic liver injury.
Detailed Description
In order to make the technical solutions of the present invention better understood by those skilled in the art, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to examples, and it is obvious that the described embodiments are only some embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The pharmaceutical composition of dihydromyricetin comprises curcumin and dihydromyricetin, and the curcumin and the dihydromyricetin can be used respectively or in a mixture form in the using process;
in addition, the pharmaceutical composition also comprises a pharmaceutically acceptable carrier, and the pharmaceutically acceptable carrier can be any one of tablets, capsules, granules, emulsions, self-emulsifying preparations, suspensions, powders or dripping pills.
The curcumin used in the embodiment of the invention is from Xian super Bangbang biological technology company Limited, and the dihydromyricetin is from Shaanxi Xintianyuan biological technology company Limited.
Example 1
A pharmaceutical composition of dihydromyricetin comprises curcumin and dihydromyricetin, wherein the weight part of curcumin is 200mg, and the weight part of dihydromyricetin is 10 mg.
Example 2
A pharmaceutical composition of dihydromyricetin comprises curcumin and dihydromyricetin, wherein the weight part of curcumin is 200mg, and the weight part of dihydromyricetin is 20 mg.
Example 3
A pharmaceutical composition of dihydromyricetin comprises curcumin and dihydromyricetin, wherein the weight part of curcumin is 200mg, and the weight part of dihydromyricetin is 40 mg.
Example 4
A pharmaceutical composition of dihydromyricetin comprises curcumin and dihydromyricetin, wherein the weight part of curcumin is 200mg, and the weight part of dihydromyricetin is 80 mg.
Example 5
A pharmaceutical composition of dihydromyricetin comprises curcumin and dihydromyricetin, wherein the weight part of curcumin is 200mg, and the weight part of dihydromyricetin is 200 mg.
Example 6
A pharmaceutical composition of dihydromyricetin comprises curcumin and dihydromyricetin, wherein the weight part of curcumin is 100mg, and the weight part of dihydromyricetin is 200 mg.
Example 7
A pharmaceutical composition of dihydromyricetin comprises curcumin 40mg and dihydromyricetin 200 mg.
Example 8
A pharmaceutical composition of dihydromyricetin comprises curcumin and dihydromyricetin, wherein the weight part of curcumin is 20mg, and the weight part of dihydromyricetin is 200 mg.
Example 9
A pharmaceutical composition of dihydromyricetin comprises curcumin and dihydromyricetin, wherein the weight part of curcumin is 10mg, and the weight part of dihydromyricetin is 200 mg.
Comparative example 1
20mg of dihydromyricetin is weighed, added into 5mL of aqueous solution containing 1% of PEG400 (polyethylene glycol 400), and stirred and mixed evenly to obtain suspension of the pharmaceutical composition of the comparative example 1.
Comparative example 2
200mg of curcumin was weighed, added to 50mL of an aqueous solution containing 1% of PEG400 (polyethylene glycol 400), and mixed well with stirring to obtain a suspension of the pharmaceutical composition of comparative example 2.
Comparative example 3
500mg of curcumin and 10mg of dihydromyricetin are weighed and added into 50mL of aqueous solution containing 1% of PEG400 (polyethylene glycol 400), and the mixture is stirred and mixed evenly to obtain the pharmaceutical composition suspension of the comparative example 3.
Comparative example 4
10mg of curcumin and 500mg of dihydromyricetin are weighed and added into 50mL of aqueous solution containing 1% of PEG400 (polyethylene glycol 400), and the mixture is stirred and mixed evenly to obtain the pharmaceutical composition suspension of the comparative example 4.
The pharmaceutical compositions obtained in examples 1 to 9 were added to 50mL of aqueous solution of 1% PEG400 (polyethylene glycol 400), and mixed to obtain suspensions of the pharmaceutical compositions of test groups 1 to 9.
Test example 1: p glycoprotein inhibition assay
27 male Wistar rats (with a weight of 220 +/-20 g) were randomly and equally divided into 9 groups, after fasting for 12 hours (free drinking water), 45mg/kg of pentobarbital sodium was intraperitoneally injected, after general anesthesia of the rats, the rats were fixed while lying supine on the back under infrared light, the abdominal cavity was opened along the abdominal midline, bile ducts were ligated (influence of bile was eliminated), the upper end incision and the lower end incision of the duodenum were cannulated, the intestine was flushed with 37 ℃ physiological saline (10ml), air was evacuated, the lower end intubation and the apparatus were connected, the intestine was equilibrated with 37 ℃ blank Krebs-Ringer buffer at a rate of 0.2ml/min for 20min (during the experiment, the exposed intestine was covered with gauze wetted with 37 ℃ physiological saline, the exposed intestine was moisturized), and after evacuation, liquid medicines (test group 1 pharmaceutical composition suspension, test group 3 pharmaceutical composition suspension, test group 5 pharmaceutical composition suspension, respectively) were pumped at a rate of 0.2ml/min, Test group 7 suspension of the drug composition, test group 9 suspension of the drug composition, comparative example 1 suspension of the drug composition, comparative example 2 suspension of the drug composition, comparative example 3 suspension of the drug composition, and comparative example 4 suspension of the drug composition) were perfused for 2 hours (when the liquid in the pipeline enters the intestinal tract instantaneously, the drug solution was discharged by air (when the volume of the drug solution which does not enter the intestinal tract is calculated as V0 ═ V initial-V residual), the intestinal tract was flushed with a blank Krebs-Ringer buffer solution at 37 ℃ for several times, the flushing solution was combined and then the volume was adjusted to 25ml by methanol, and the drug concentration in the volumetric flask was used as the final concentration. Taking 1ml of the liquid after constant volume, using methanol to constant volume to 5ml, centrifuging at 12000rpm for 5min, and injecting 10 mul. After the experiment, the length and the inner diameter of the sausage section are measured by coordinate paper. The absorption rate constant (Ka) and the intestinal permeability coefficient (Papp) were calculated after the end of the experiment according to the following formulas, and the results are shown in table 1:
Ka＝(X0-Xt)/Ct0V
Papp＝Q·(Xin/Xout)/2πr·l
wherein, X0Is the initial total amount of the drug in the body intestine perfusion fluid; xtIs the residual total amount of the medicine in the body intestine perfusion liquid after 2 hours; ct0Is the initial drug concentration; v is the volume of the perfused intestinal segment; q is perfusion rate, XinAnd XoutThe amounts of the drugs flowing into and out of the intestinal segment, respectively; r and l are the diameter and length of the perfused intestinal segment.
TABLE 1 Effect of curcumin on Dihydromyricetin intestinal absorption Rate constants and effective osmotic coefficients
Figure BDA0002775166690000061
Figure BDA0002775166690000071
From table 1, it can be derived: in the presence of verapamil (a classical P glycoprotein inhibitor), Ka and PaPP of curcumin and dihydromyricetin are both significantly increased, indicating that dihydromyricetin and curcumin are both substrates of P glycoprotein. When the curcumin and the dihydromyricetin are used together, the Ka and PaPP of the curcumin and the dihydromyricetin are obviously improved compared with the two when the curcumin and the dihydromyricetin are used alone, which shows that the two can mutually reduce the effect of the curcumin and the dihydromyricetin on the efflux of the P glycoprotein when the curcumin and the dihydromyricetin are used together.
Test example 2: pharmacokinetic testing
15 male Wistar rats (weighing 220. + -.20 g) were randomly and equally divided into 3 groups. The liquid medicines of test group 5, comparative example 1 and comparative example 2 were administered, respectively, by gavage, the administration dose of test group 5 was 100mg dihydromyricetin/kg (weight of Wistar male rats) and 100mg curcumin/kg (weight of Wistar male rats), the administration dose of comparative example 1 was 100mg dihydromyricetin/kg (weight of Wistar male rats), and the administration dose of comparative example 2 was 100mg curcumin/kg (weight of Wistar male rats). Blood was collected via rat eye vein at 5min,10min,20min,40min, 60min,90min,120min,240min,480min,720min, and 1440min after administration. Placing whole blood in heparinized EP tube, centrifuging (5000rpm, 5min), and collecting supernatant to obtain blood plasma. The concentration of dihydromyricetin and curcumin in blood was determined by LC-MS/MS, and the results are shown in fig. 1 and 2:
from fig. 1 and 2, it can be derived that: when the dihydromyricetin and the curcumin are used together, the bioavailability of the dihydromyricetin and the curcumin is higher than that of the dihydromyricetin and the curcumin when the dihydromyricetin and the curcumin are used separately. This makes it possible to achieve better pharmacological effects by combining the two.
Test example 3: blood alcohol concentration determination
20 male Wistar rats (weighing 220 + -20 g) were randomly and evenly divided into 4 groups. After fasting for 12 hours, the animals were administered physiological saline 100mg/kg, dihydromyricetin 550 mg and curcumin 50mg, dihydromyricetin 150 mg and curcumin 250 mg by gavage, respectively. 2h after administration, each group of animals was given 50% ethanol by gavage at a dose of 0.16 mL/kg. After 1h of ethanol administration, the alcohol concentration in the rat blood was determined by headspace sampling using a gas chromatograph.
The results are shown in FIG. 3: as can be seen from FIG. 3, when dihydromyricetin is used alone, the removal of alcohol in blood can be accelerated to a certain extent. When the dihydromyricetin and the curcumin are used together, the metabolism speed of alcohol in blood can be remarkably increased. The results further demonstrate that curcumin in combination with dihydromyricetin can enhance absorption of dihydromyricetin, thereby enhancing the ability of dihydromyricetin to accelerate blood alcohol metabolism.
Test example 4: protective effect on alcoholic liver injury
25C 57BL/6 male mice (weighing 22. + -.2 g) were selected and randomly and equally divided into 5 groups. After fasting for 12 hours, two groups of animals were administered physiological saline by gavage, and the other three animals were administered 550 mg dihydromyricetin/kg and 50mg curcumin/kg, comparative example 150 mg dihydromyricetin/kg, and comparative example 250 mg curcumin/kg, respectively, to the test group. After 1h of administration, two groups of animals given physiological saline were given physiological saline (control group) and 50% ethanol (model group) at a dose of 0.16mL/kg, respectively, and gavage 3 times every 12 h; after 1 hour of administration, 50% ethanol was administered in a dose of 0.16mL/kg to three other groups of animals, and the animals were gavaged 3 times every 12 hours. The AST and ALT concentrations in the mouse serum were measured by ELLISA 4h after the last alcohol administration, and the results are shown in FIGS. 4 and 5:
as can be seen in fig. 4 and 5: when curcumin or dihydromyricetin is used alone, the protective effect on the liver injury caused by alcohol is limited, and when the curcumin or dihydromyricetin is used in combination, the protective effect on the alcoholic liver injury is obviously increased, and the result further proves that the oral absorption of the curcumin or dihydromyricetin can be mutually improved when the curcumin or dihydromyricetin is used together, so that a better liver protective effect is finally shown.
Remarking: AST and ALT are distributed mainly in hepatocytes, with a small proportion present in muscle cells. If the liver is damaged or destroyed, transaminases in the hepatocytes enter the blood and elevated levels of ALT and AST are present in the blood, signaling liver disease.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.

Claims (10)

1. A pharmaceutical composition of dihydromyricetin is characterized in that the pharmaceutical composition comprises curcumin and dihydromyricetin.
2. The pharmaceutical composition of dihydromyricetin according to claim 1, wherein the pharmaceutical composition comprises curcumin and dihydromyricetin in a mass ratio of 1-20: 20-1.
3. The pharmaceutical composition of dihydromyricetin according to claim 1, wherein the composition comprises curcumin and dihydromyricetin in a mass ratio of 1-5: 5-1.
4. The pharmaceutical composition of dihydromyricetin according to claim 1, wherein the composition comprises curcumin and dihydromyricetin in a mass ratio of 1-5: 1.
5. The pharmaceutical composition of dihydromyricetin according to claim 1, wherein the composition comprises curcumin and dihydromyricetin in a mass ratio of 1: 1.
6. A pharmaceutical composition of dihydromyricetin according to claim 1, wherein the curcumin and the dihydromyricetin are used separately or in the form of a mixture.
7. The pharmaceutical composition of claim 1, wherein said pharmaceutical composition further comprises a pharmaceutically acceptable carrier.
8. The pharmaceutical composition of dihydromyricetin according to claim 1, wherein the pharmaceutical composition is in the form of tablet, capsule, granule, emulsion, self-emulsifying formulation, suspension, powder or drop pill.
9. Use of a dihydromyricetin pharmaceutical composition according to any one of claims 1-8 in anti-hangover, hepatoprotective, and antitumor drugs.
10. The use of claim 9, wherein the tumor is liver cancer, intrahepatic cholangiocarcinoma, hepatocellular carcinoma, extrahepatic cholangiocarcinoma, gallbladder cancer, sarcoma, lung cancer, bronchial cancer, pleuropulmonary blastoma, prostate cancer, breast cancer, pancreatic cancer, islet cell carcinoma, gastric cancer, intestinal cancer, thyroid cancer, parathyroid cancer, or melanoma.
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Citations (2)

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Publication number Priority date Publication date Assignee Title
CN108653269A (en) * 2018-06-29 2018-10-16 浙江中医药大学 It is a kind of that there is the compound for reducing heart creatine kinase isozyme content function and its application
CN109125733A (en) * 2018-10-30 2019-01-04 成都先手生物科技有限公司 A kind of composition for the treatment of of arthritis and its application

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108653269A (en) * 2018-06-29 2018-10-16 浙江中医药大学 It is a kind of that there is the compound for reducing heart creatine kinase isozyme content function and its application
CN109125733A (en) * 2018-10-30 2019-01-04 成都先手生物科技有限公司 A kind of composition for the treatment of of arthritis and its application

Non-Patent Citations (4)

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Title
CHUNFENG LU等: "Curcumin Attenuates Ethanol-induced Hepatic Steatosis through Modulating Nrf2/FXR Signaling in Hepatocytes", 《IUBMB LIFE》 *
YI SHEN等: "Dihydromyricetin As a Novel Anti-Alcohol Intoxication", 《THE JOURNAL OF NEUROSCIENCE》 *
李玉倩等: "姜黄素抗肿瘤作用基础与临床研究进展", 《中国药理学与毒理学杂志》 *
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Application publication date: 20210202