CN104997768B - Application of the rotenone in hypoglycemic drug is prepared - Google Patents
Application of the rotenone in hypoglycemic drug is prepared Download PDFInfo
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- CN104997768B CN104997768B CN201510439208.8A CN201510439208A CN104997768B CN 104997768 B CN104997768 B CN 104997768B CN 201510439208 A CN201510439208 A CN 201510439208A CN 104997768 B CN104997768 B CN 104997768B
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- 229940080817 rotenone Drugs 0.000 title claims abstract description 64
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 239000003472 antidiabetic agent Substances 0.000 title claims abstract description 8
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 17
- 239000003814 drug Substances 0.000 claims abstract description 12
- 229940122355 Insulin sensitizer Drugs 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract description 37
- 239000008103 glucose Substances 0.000 abstract description 36
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- 230000002218 hypoglycaemic effect Effects 0.000 abstract description 9
- 206010022489 Insulin Resistance Diseases 0.000 abstract description 4
- 208000013016 Hypoglycemia Diseases 0.000 abstract description 3
- 239000002131 composite material Substances 0.000 abstract description 3
- 229940000406 drug candidate Drugs 0.000 abstract description 2
- 239000002547 new drug Substances 0.000 abstract description 2
- 230000005787 mitochondrial ATP synthesis coupled electron transport Effects 0.000 abstract 1
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- 238000012360 testing method Methods 0.000 description 19
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- 238000012545 processing Methods 0.000 description 12
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- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 8
- 102000004877 Insulin Human genes 0.000 description 7
- 108090001061 Insulin Proteins 0.000 description 7
- 210000003494 hepatocyte Anatomy 0.000 description 7
- WITLAWYGGVAFLU-UHFFFAOYSA-N 3-(6-methoxy-1,3-benzodioxol-5-yl)-8,8-dimethylpyrano[2,3-f]chromen-4-one Chemical compound C1=CC(C)(C)OC2=CC=C(C(C(C3=CC=4OCOC=4C=C3OC)=CO3)=O)C3=C21 WITLAWYGGVAFLU-UHFFFAOYSA-N 0.000 description 6
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- 238000002474 experimental method Methods 0.000 description 6
- 229940125396 insulin Drugs 0.000 description 6
- 235000015097 nutrients Nutrition 0.000 description 6
- 230000034659 glycolysis Effects 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 210000005229 liver cell Anatomy 0.000 description 5
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 4
- 108010019160 Pancreatin Proteins 0.000 description 4
- 230000004110 gluconeogenesis Effects 0.000 description 4
- 239000007928 intraperitoneal injection Substances 0.000 description 4
- 235000014655 lactic acid Nutrition 0.000 description 4
- 239000004310 lactic acid Substances 0.000 description 4
- 229940055695 pancreatin Drugs 0.000 description 4
- 210000002363 skeletal muscle cell Anatomy 0.000 description 4
- 102100036009 5'-AMP-activated protein kinase catalytic subunit alpha-2 Human genes 0.000 description 3
- 101000783681 Homo sapiens 5'-AMP-activated protein kinase catalytic subunit alpha-2 Proteins 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 210000000107 myocyte Anatomy 0.000 description 3
- SPFMQWBKVUQXJV-BTVCFUMJSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;hydrate Chemical compound O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O SPFMQWBKVUQXJV-BTVCFUMJSA-N 0.000 description 2
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- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
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- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000008121 dextrose Substances 0.000 description 2
- 229960000673 dextrose monohydrate Drugs 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
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- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical compound O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 description 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- 206010068676 Pneumoretroperitoneum Diseases 0.000 description 1
- 208000001280 Prediabetic State Diseases 0.000 description 1
- 208000005727 Retropneumoperitoneum Diseases 0.000 description 1
- 210000000683 abdominal cavity Anatomy 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
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- 230000010534 mechanism of action Effects 0.000 description 1
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- 239000000203 mixture Substances 0.000 description 1
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- 201000009104 prediabetes syndrome Diseases 0.000 description 1
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- JUVIOZPCNVVQFO-HBGVWJBISA-N rotenone Chemical compound O([C@H](CC1=C2O3)C(C)=C)C1=CC=C2C(=O)[C@@H]1[C@H]3COC2=C1C=C(OC)C(OC)=C2 JUVIOZPCNVVQFO-HBGVWJBISA-N 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The present invention relates to new application of the rotenone in hypoglycemic medicament is reduced.Rotenone acts on suppression mitochondrial electron transport chain composite I and substantially reduces blood glucose in animal body, also significantly improves insulin sensitivity.The present invention provides application of the rotenone in hypoglycemic drug is prepared, so as to provide a kind of new drug candidate in treating diabetes, the shortcomings that overcoming secondary failure in existing medicine or inject repeatedly and cause hypoglycemia.
Description
Technical field
The present invention relates to application of the rotenone in medicine is prepared, and in particular to rotenone is one in hypoglycemic drug is prepared
The new application of kind.
Background technology
China is the big country of world population first, and the big country of diabetes first.According to the latest report of 2010, Chinese population
In diabetes morbidity be up to 9.7%, prediabetes is up to 15.5%, the two addition, China have people more than 200,000,000 by or
It will be endangered by diabetes, diabetes have turned into China or even a global great public health problem.Diabetes
The course of disease is very long, although existing a variety of hypoglycemic medicines at present, meeting secondary failure after oral medicine long-term use, and insulin needs
Inject repeatedly, and when often result in hypoglycemia, bring pain to patient, therefore, exploitation novel blood sugar lowing medicine be still treatment sugar
Urinate the key of disease.
Research was thought in the past, and the conventional hypoglycemic medicine melbine of clinic and jamaicin play glycolipid tune because activating AMPK
Section acts on.However, there is scholar's proposition in recent years, the blood sugar reducing function of melbine is not rely on AMPK, suppresses Mitochondrial electron and passes
It is probably its real mechanism of action to pass chain cpd I.Applicants have found that the blood sugar reducing function of jamaicin equally independent of
AMPK, it is equally the key that jamaicin plays curative effect to suppress electron transport chain composite I.Therefore, applicant is begun attempt to each
The inhibitor of kind of compound carries out hypoglycemic experiment, it is found that rotenone has obvious curative effect of medication at hypoglycemic aspect.
Rotenone (rotenone), also known as malicious trifoliate jewelvine (Tubatoxin) is a kind of nothing separated from natural plants
Color, tasteless ketone crystalline compounds, its structural formula are as follows：
Rotenone can extract from the seed of a variety of pulse families and liana (such as trifoliate jewelvine), stem and root.Rotenone is
A kind of specific inhibitor of mitochondrial respiratory chain composite I, have highly lipophilic, it is not necessary to rely on DAT just
It can be directly entered in kytoplasm, and optionally suppress the Respiratory Chain Complex I of mitochondria.
The content of the invention
Present invention aims at application of the rotenone in hypoglycemic drug is prepared is provided, so as to be carried in treating diabetes
For a kind of new drug candidate, the shortcomings that overcoming secondary failure in existing medicine or inject repeatedly and cause hypoglycemia.
The technical solution adopted in the present invention is：Application of the rotenone in hypoglycemic drug is prepared.
Above-mentioned described application, can be specifically the insulin sensitivity that rotenone significantly improves diabetic.
Further, above-mentioned described application can be specifically the composition that rotenone is made to hypoglycemic drug.
Brief description of the drawings
Fig. 1：Rotenone increases the glucose utilization of liver cell
Fig. 2：Rotenone increases the glucose utilization of Skeletal Muscle Cell
Fig. 3：Rotenone suppresses the gluconeogenesis of primary hepatocyte
Fig. 4：Rotenone increases the glycolysis of liver cell
Fig. 5：Rotenone increases the glycolysis of Skeletal Muscle Cell
Fig. 6：Blood sugar concentration curve in contrast test Mice Body after six hours on an empty stomach
Fig. 7：Insulin tolerance test Area under the curve of blood glucose block diagram after six hours on an empty stomach
Fig. 8：Blood sugar concentration curve in contrast test Mice Body after fasted overnight
Fig. 9：Six hours insulin tolerance test Area under the curve of blood glucose block diagrams after fasted overnight
Embodiment
Unless otherwise defined, all technologies and the implication and the technical field of the invention of scientific terminology that the present invention uses
The implication that those of ordinary skill is generally understood that is identical.Generally, the name and following experimental methods that the present invention uses all are this areas
It is known or conventional.
In order that technical problem solved by the invention, technical scheme and beneficial effect are more clearly understood, below in conjunction with
Specific embodiment, the present invention is further illustrated.Rotenone is bought from sigma (article No. R8875) in the present invention；db/db
Mouse is bought from Shanghai Slac Experimental Animal Co., Ltd.；Hepatic cell line HepG2 comes from Shanghai City diabetes study institute；Flesh is thin
Born of the same parents system C2C12 comes from Shanghai City diabetes study institute；Primary hepatocyte is bought from Shanghai Slac Experimental Animal Co., Ltd.
8 week old C57B6 mouse.
Embodiment 1
Rotenone increases the glucose utilization of liver cell
The present embodiment is in hepatic cell line HepG2, using glucose consumption testing, the rotenone processing of detection various concentrations
After 24h, the glucose utilization of cell.Experiment is divided into control group and rotenone group, and control group is not added with any processing, rotenone group
Be respectively adopted 4 various concentrations (0.02 μm of ol/L, 0.05 μm of ol/L, 0.1 μm of ol/L,
0.2 μm of ol/L), each 8 samples of concentration.When disk inner cell density reaches 70-80%, digested, spread with pancreatin
In 96 orifice plates, residual blank well does not plant cell and is used to determine background, and cell covers with substantially after 24 hours, changes with containing 0.25%
The DMEM nutrient solutions culture of BSA, 15mmol/L glucose and various concentrations rotenone 24 hours.As a result it is thin that HepG2 livers are shown in
Intracellular, the processing of various concentrations rotenone make grape cell sugar consumption amount (p significantly raised compared with control group<0.001), difference has system
Meter learns meaning, as shown in Figure 1.
Embodiment 2
Rotenone increases the glucose utilization of Skeletal Muscle Cell
The present embodiment is in myocyte system C2C12, using glucose consumption testing, the rotenone processing of detection various concentrations
After 24h, the glucose utilization of cell.Experiment is divided into control group and rotenone group, and control group is not added with any processing, rotenone group
4 various concentrations (0.02 μm of ol/L, 0.05 μm of ol/L, 0.1 μm of ol/L, 0.2 μm of ol/L), each 8 samples of concentration are respectively adopted
This.When disk inner cell density reaches 70-80%, digested with pancreatin, be laid on 96 orifice plates, residual blank well is not planted cell and is used for
Background is determined, cell covers with substantially after 24 hours, changes with containing 0.25%BSA, 15mmol/L glucose and various concentrations rotenone
DMEM nutrient solutions culture 24 hours.As a result it is shown in C2C12 myocyte, 0.05 μm of ol/L, 0.1 μm of ol/L and 0.2 μm of ol/
The processing of L rotenone also makes grape cell sugar consumption amount raise (p compared with control group<0.01), difference has statistical significance, such as Fig. 2
It is shown.
Embodiment 3
Rotenone suppresses the gluconeogenesis of primary hepatocyte
This implementation uses gluconeogenesis Inhibition test, and primary hepatocyte is inoculated into 12 orifice plates (ten thousand/ml of 25-30), adherent 4-6
Hour, change low sugar culture medium, overnight starvation into.Next day, first gently wash cell once with PBS, after rotenone is handled 6 hours, survey
Nutrient solution glucose content.As a result show, the nutrient solution glucose content of various concentrations rotenone treatment group is obvious compared with control group
Reduce (p<0.001), as shown in Figure 3.Illustrate that rotenone has the gluconeogenesis for suppressing primary hepatocyte.
Embodiment 4
Rotenone increases the glycolysis of liver cell
Lactic acid is the primary product of cell anaerobic respiration (glycolysis), to understand shadow of the rotenone to cellular respiration function
Ring, after the present embodiment have detected 4 kinds of various concentrations rotenone processing 24h, the change of cell lactic acid synthetic quantity.Experiment is divided into control
Group and rotenone group, control group are not added with any processing, and 4 various concentrations (0.02 μm of ol/L, 0.05 μ is respectively adopted in rotenone group
Mol/L, 0.1 μm of ol/L, 0.2 μm of ol/L), each 8 samples of concentration.When disk inner cell density reaches 70-80%, pancreatin is used
Digestion, is laid on 96 orifice plates, cell covers with substantially after 24h, changes with containing 0.25%BSA, 15mmol/L glucose and various concentrations medicine
The DMEM nutrient solution cultures 24h of thing.Test result indicates that the processing of various concentrations rotenone makes cell newborn in HepG2 liver cells
Sour synthetic quantity raises compared with control group, and difference has statistical significance (p<0.001), as shown in Figure 4.
Embodiment 5
Rotenone increases the glycolysis of Skeletal Muscle Cell
After the present embodiment have detected 4 kinds of various concentrations rotenone processing 24h, the change of cell lactic acid synthetic quantity.Experiment point
For control group and rotenone group.Control group is not added with any processing, rotenone group be respectively adopted 4 various concentrations (0.02 μm of ol/L,
0.05 μm of ol/L, 0.1 μm of ol/L, 0.2 μm of ol/L), each 8 samples of concentration.When disk inner cell density reaches 70-80%,
Digested with pancreatin, be laid on 96 orifice plates, cell covers with substantially after 24h, changes with containing 0.25%BSA, 15mmol/L glucose and difference
The DMEM nutrient solution cultures 24h of acute drug.Test result indicates that the processing of various concentrations rotenone makes in C2C12 myocyte
Cell lactic acid synthetic quantity raises compared with control group, and difference has statistical significance (p<0.001), as shown in Figure 5.
Above test result indicates that rotenone has good hypoglycemic effect in vitro.
Embodiment 6
Rotenone significantly improves the insulin sensitivity of diabetic mice
Diabetes B db/db mouse are divided into control group and rotenone treatment group, every group 6.By two groups of db/db mouse
After fasting 6h, basal plasma glucose value is determined, regular insulin solution is injected intraperitoneally by 1unit/Kg dosage, determines and records injection
Before (0 minute) and injection after 15 minutes, 30 minutes, 60 minutes and 120 minutes blood glucose values.Test result indicates that intraperitoneal injection pancreas
Before the element of island (0 minute) and injection after 15 minutes, 30 minutes, 60 minutes and 120 minutes when, the blood sugar level of rotenone treatment group is equal
Less than control group, there is significant difference (p<0.05), as shown in Figure 6.The insulin tolerance test blood glucose of rotenone treatment group is bent
Area is again smaller than control group, the statistically significant (p of difference under line<0.001), as shown in Figure 7.Experimental result fully proves trifoliate jewelvine
Ketone treats the insulin sensitivity that can improve diabetic mice.
The blood glucose concentration value unit of two groups of mouse of insulin tolerance test after fasting 6 hours：mmol/L
| Time | Control group | Experimental group |
| 0min | 15.7±2.50 | 12.5±0.79 |
| 15min | 14.83±2.86 | 11.81±1.67 |
| 30min | 14.38±3.08 | 10.65±2.10 |
| 60min | 13.75±2.91 | 8.80±0.41 |
| 120min | 13.33±3.09 | 8.22±0.80 |
After fasting 6 hours in 0-120min two groups of mouse insulin tolerance test Area under the curve of blood glucose
| Group | Control group | Experimental group |
| Area value | 1681.25±354.77 | 1126.65±58.53 |
Embodiment 7
Rotenone significantly reduces the blood glucose of diabetic mice
Diabetes B db/db mouse are divided into control group and rotenone treatment group, every group 6.Daily rotenone is given to control
Treatment group mouse peritoneal injection 1mg/kg rotenone, continuous 14 days.Mouse overnight fasting, proceed by abdominal cavity glucose the next morning
Tolerance test, every mouse press 0.1g/kg body weight intraperitoneal injection glucose solutions, before injectable dextrose monohydrate (0 minute),
Tail vein is cut within 15 minutes, 30 minutes, 60 minutes and 120 minutes after intraperitoneal injection glucose and takes blood 0.5ml, blood glucose meter measure blood glucose
Value.Test result indicates that before intraperitoneal injection glucose (0 minute) and injection after 15 minutes, 30 minutes, 60 minutes and 120 minutes
When, the blood sugar level of rotenone treatment group is below control group, there is statistics difference (p<0.05), as shown in Figure 8.Rotenone is controlled
The dextrose tolerance test Area under the curve of blood glucose for the treatment of group is again smaller than control group, the statistically significant (p of difference<0.001), as schemed
Shown in 9.Rotenone can make the fasting blood-glucose of db/db mouse be down to 6.5mmol/L from 10mmol/L, after making glucose load 2 hours
Blood glucose 9.6mmol/L is down to by 14.4mmol/L, it can be seen that rotenone, which is treated, can significantly reduce the blood glucose of diabetic mice,
Improve sugar tolerance.
The blood glucose concentration value unit of overnight fasting pneumoretroperitoneum injectable dextrose monohydrate two groups of mouse of tolerance test：mmol/L
| Time | Control group | Experimental group |
| 0min | 10.10±2.37 | 5.72±1.53 |
| 15min | 26.71±1.70 | 19.44±5.25 |
| 30min | 32.5±4.06 | 24.9±4.91 |
| 60min | 32.9±3.44 | 23.6±5.62 |
| 120min | 14.5±2.85 | 8.65±1.65 |
After overnight fasting in 0-120min two groups of mouse dextrose tolerance test Area under the curve of blood glucose
| Group | Control group | Experimental group |
| Area value | 3017.55±109.76 | 2153.06±327.00 |
It should be noted that although the present invention is disclosed above with preferred embodiment, so it is not limited to the present invention, appoints
What is familiar with this those skilled in the art, without departing from the spirit and scope of the present invention, all any modification, equivalent and improvement made
Deng should be included in the scope of the protection.
Claims (3)
1. application of the rotenone in hypoglycemic drug is prepared.
2. application as claimed in claim 1, it is characterised in that prepare the application in treatment diabetes medicament.
3. application as claimed in claim 1, it is characterised in that application of the rotenone as insulin sensitizer.
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| CN106362168A (en) * | 2016-11-15 | 2017-02-01 | 南京市儿童医院 | Experimental method for medicament capable of treating hyperuresis caused by lithium salt |
| CN107296824A (en) * | 2017-06-30 | 2017-10-27 | 广西民族大学 | Comospore trifoliate jewelvine ligroin extraction and its preparation and inflammatory applications |
| CN108524492A (en) * | 2018-06-22 | 2018-09-14 | 南京市儿童医院 | Application of the rotenone in preparing medicine for treating diabetic nephropathy |
| CN108514557B (en) * | 2018-07-04 | 2019-04-12 | 南京市儿童医院 | Application of the rotenone in pancreas islet protection |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101805333A (en) * | 2010-04-16 | 2010-08-18 | 湖南大学 | Cyclorotenoid, preparation method and application thereof |
| CN102076854A (en) * | 2008-07-03 | 2011-05-25 | 桑塔里斯制药公司 | Rna antagonist compounds for inhibition of expression of mitochondrial glycerol-3-phosphate acyltransferase 1 (mtgpat1) |
| TW201125497A (en) * | 2010-01-19 | 2011-08-01 | Univ Taipei Medical | Method of generating animal fatty liver model |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102076854A (en) * | 2008-07-03 | 2011-05-25 | 桑塔里斯制药公司 | Rna antagonist compounds for inhibition of expression of mitochondrial glycerol-3-phosphate acyltransferase 1 (mtgpat1) |
| TW201125497A (en) * | 2010-01-19 | 2011-08-01 | Univ Taipei Medical | Method of generating animal fatty liver model |
| CN101805333A (en) * | 2010-04-16 | 2010-08-18 | 湖南大学 | Cyclorotenoid, preparation method and application thereof |
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