CN102151281B - Flavonoid compound for preventing and treating diabetes and medicament application thereof - Google Patents
Flavonoid compound for preventing and treating diabetes and medicament application thereof Download PDFInfo
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- CN102151281B CN102151281B CN201110024707.2A CN201110024707A CN102151281B CN 102151281 B CN102151281 B CN 102151281B CN 201110024707 A CN201110024707 A CN 201110024707A CN 102151281 B CN102151281 B CN 102151281B
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Abstract
The invention belongs to the technical field of pharmacy. The invention discloses a flavonoid compound for preventing and treating the diabetes and medicament application thereof, wherein the flavonoid compound is homoplantagin and hispidulin and is separated from the whole Salvia plebeia R. Br. The homoplantagin and the hispidulin can be used for obviously reducing the blood sugar of the mouse which suffer from the alloxan diabetes, reducing the serum total cholesterol content and the triglyceride content, obviously reducing the generation of the nitrogen oxide in the endothelial cell caused by free fatty acid, improving the insulin resistance caused by the free fatty acid, and protecting the endothelial cell of the blood vessel. Therefore, the homoplantagin and the hispidulin have good functions for reducing the blood sugar and the blood fat, and protecting the endothelial cell of the blood vessel, and can be used for preparing the medicament for preventing and curing the diabetes and the cardiovascular disease such as the lipid metabolism dysfunction, the atherosclerosis, the coronary disease and the like caused by the diabetes.
Description
One, technical field
The invention belongs to pharmaceutical technology field, relate to the preparation method of flavone compound Homoplantaginin and aglycon dinatin thereof, and relate to Homoplantaginin and dinatin in the application preventing and treating aspect the cardiovascular disease such as disorders of lipid metabolism that diabetes, diabetes cause and atherosclerosis, coronary heart disease.
Two, background technology
Diabetes are the one group of Developmental and Metabolic Disorder syndromes being caused by h and E factor interaction, take hyperglycemia as feature, and metabolism disorder is for performance, closely related with insulin secretion.Diabetes can be divided into insulin dependent diabetes mellitus (IDDM) (Insulin Dependent Diabetes Mellitus, IDDM claims again 1 type) and non-insulin-dependent diabetes mellitus (Noinsulin Dependent Diabetes Mellitus, NIDDM claims again II type), the latter accounts for the 95%-99% of patient's sum.The main harm of diabetes is its vascular complication, and the probability of the concurrent cardiovascular and cerebrovascular disease of diabetics will be far away higher than ND.Current research thinks that the complication (as cardiovascular disease) that diabetes cause is the main cause that causes death, is the noninfectious of the third-largest serious threat human health after cardiovascular and tumor.Therefore, prevention and treatment diabetes have now become global hygienic issues.
Free fatty is to connect fat and the topmost tie of diabetes.Free fatty synthesizes, promotes glyconeogenesis, causes hyperinsulinemia and activate oxidative stress process to cause insulin resistant (Insulin Resistance, IR) by inhibition glucose oxidase, inhibition muscle glycogen.And insulin resistant is common pathophysiological basis or " the common soil " that causes Developmental and Metabolic Disorder and cardiovascular disease, it is the basis that causes other abnormal change in metabolism syndrome.At vascular endothelial cell; insulin is realized the protective effect to blood vessel by activating the generation of phosphatidyl-inositol 3-kinase (PI3K) path stimulating endothelial nitric oxide (NO); as NO can cause vasodilation; thereby increase its blood flow, increase skeletal muscle and the utilization of fatty tissue to glucose.But, during IR, the NO synthesis system of blood vessel endothelium is impaired, NO is synthetic to be reduced, Dysfunction of vascular endothlial cells, cause that vasoconstriction spasm, platelet are activated, the pathological process such as the attached wall of leukocyte, smooth muscle cell proliferation and vascular remodeling, finally cause the cardiovascular disease such as atherosclerosis and coronary heart disease.
The medicine for the treatment of diabetes mainly contains sulphanylureas, biguanides, insulin, alpha-glucosidase inhibitor, Thiazolidine ketone etc. at present.These medicines can cause that some side effect are as hypoglycemia, liver toxicity, lactic acidosis and diarrhoea.And Chinese medicine and natural drug treatment diabetes are too many levels, multipath, many target spots, and there is abundant, the comparatively safe and cheap feature in medicine source.Therefore, exploitation Chinese medicine and natural drug have vast potential for future development as the medicine of prevention and treatment diabetes.
Herba Salviae Plebeiae (Salvia plebeia R.Br.) is Labiatae salvia, another name green vegetable seven, snow are shown in grass, cross Ilicis Purpureae etc., have heat-clearing and toxic substances removing, cool the blood dissipate blood stasis, the effects such as inducing diuresis to remove edema, are used for the treatment of acute tonsillitis, chronic tracheitis, oedema due to nephritis, swelling and pain of hemorrhoid etc.Herba Salviae Plebeiae herb is containing compounds such as Homoplantaginin (Homoplantaginin), dinatins (dinatin Hispidulin); bibliographical information Homoplantaginin and dinatin have antioxidation, protect the liver isoreactivity; but it is generated and reduced at the vascular endothelial cell NO due to blood sugar lowering, blood fat reducing, antagonism free fatty; thereby improve insulin resistant and protection Endothelial Cell Function due to free fatty, there is not yet report.
Three, summary of the invention
The invention provides a kind of method of preparing Homoplantaginin and dinatin from Herba Salviae Plebeiae; and Homoplantaginin and dinatin in blood sugar lowering, blood fat reducing, improve insulin resistant and protection Endothelial Cell Function due to free fatty, and in the application preventing and treating aspect the cardiovascular disease such as disorders of lipid metabolism that diabetes, diabetes cause and atherosclerosis, coronary heart disease.
1, the separated and Structural Identification of the extraction of Homoplantaginin and dinatin
(1) Herba Salviae Plebeiae herb is dry, pulverizing;
(2) by ethanol or methanol or propanol or their aqueous reflux, extract,, or dipping extraction, extracting solution concentrating under reduced pressure;
(3) extracting solution concentrating under reduced pressure, extracts concentrated extract 3～4 times by petroleum ether, ethyl acetate successively;
(4) acetic acid ethyl acetate extract is evaporated to dry, recycle silicon glue post carries out column chromatography;
(5) with chloroform: methanol (100: 2) eluting, collect eluent, concentrated, recrystallization obtains dinatin.
(6) with chloroform: methanol (100: 8) eluting, collect eluent, concentrated, recrystallization obtains Homoplantaginin.
The condition and range of above-mentioned preparation method is: in step (2), the concentration of ethanol or methanol or propanol is 10～90%, and extracting method is for refluxing, flooding; Also available chloroform in step (5): acetone (100: 5) eluting; Also available chloroform in step (6): acetone (100: 15) eluting.
Homoplantaginin, yellow powder, C
22h
22o
11, 240～242 ℃ of mp, UV (CH
3oH) λ
maxnm:275.6,331.2.ESI-MS?m/z：461.1[M-H]
-，446.0[M-H-CH
3]
-，298.9[M-C
6H
10O
5]
-。IR(KBr)υ：3405(OH)，1642(C＝O)，1599，1565，1100cm
-1。
1h NMR (300MHz, DMSO-d
6) δ: 6.85 (1H, s, C
3-H), 12.96 (1H, s, C
5-OH), 7.03 (1H, s, C
8-H), 3.78 (3H, s, C
6-OCH
3), 7.96 (2H, d, J=8.8Hz, C
2 'and C
6 '-H), 6.95 (2H, d, J=8.8Hz, C
3 'and C
5 '-H), 5.12 (1H, d, J=7.6Hz, C
1 "-H), δ 3.21-3.78 (6H, m, H-2 ", 3 ", 4 " and, 5 ", 6 ").
13C?NMR(75MHz，DMSO-d
6)δ：164.3(C-2)，102.8(C-3)，182.2(C-4)，152.4(C-5)，132.5(C-6)，152.1(C-7)，94.4(C-8)，156.4(C-9)，105.7(C-10)，60.3(6-OCH
3)，121.2(C-1’)，128.5(C-2’，6’)，161.2(C-4’)，115.9(C-3’，5’)，100.2(C-1”)，73(C-2”)，76.5(C-3”)，69.5(C-4”)，77.2(C-5”)，60.5(C-6”)。Above data, with basically identical with Homoplantaginin physicochemical property and the spectroscopic data of bibliographical information, are accredited as Homoplantaginin (Homoplantaginin).Its structural formula is as follows:
Dinatin, yellow acicular crystal, C
16h
12o
6, mp:284～286 ℃ (methanol), ESI-MS m/z:299[M-H]
+, 283[M-CH
3]
+.UV(CH
3OH)λ
maxnm：274.2，334.8。IR(KBr)υ：3446(OH)，1659(C＝O)，1614，1572，1496cm
-1。
1h NMR (300MHz, DMSO-d
6) δ: 6.60 (1H, s, C
3-H), 13.08 (1H, s, C
5-OH), 6.77 (1H, s, C
8-H), 3.77 (3H, s, C
6-OCH
3), 7.92 (2H, d, J=8.8Hz, C
2 'and C
6 '-H), 6.93 (2H, d, J=8.8Hz, C
3 'and C
5 '-H), δ 10.50 (2H, br.s C
7-OH and C
4 '-OH).
13C?NMR(75MHz，DMSO-d
6)δ：157.3(C-2)，102.5(C-3)，182.2(C-4)，152.9(C-5)，131.5(C-6)163.9(C-7)，94.3(C-8)，152.5(C-9)，104.2(C-10)，60.1(6-OCH
3)，121.4(C-1’)，128.6(C-2’，6’)，161.3(C-4’)，116.3(C-3’，5’)。Above data are consistent with dinatin physicochemical property and the spectroscopic data of bibliographical information, therefore be accredited as dinatin (Hispidulin).Its structural formula is as follows:
Homoplantaginin of the present invention and dinatin can mix with conventional adjuvant and/or excipient, are prepared into various dosage forms, for prevention or treatment.Injection, capsule, tablet, granule, dragee, solution etc. are all alternative pharmaceutical dosage form.The dosage forms such as capsule, tablet, granule, dragee, solution can be prepared by known conventional method.
The dosage forms such as capsule, tablet, granule, dragee can contain one or more conventional excipient-filler and solubilizing agents: as starch, and microcrystalline cellulose etc.; Binding agent: as carboxymethyl cellulose, polyvinylpyrrolidone etc.; Humectant: as glycerol; Disintegrating agent: as calcium carbonate etc.; Absorbent: as Kaolin etc.; Lubricant: as Pulvis Talci etc.
Medicinal excipient can be the various forms such as solid, semisolid, liquid, and formula adjuvant can be various types of.
Solution can contain general solvent, solubilizing agent, emulsifying agent, antiseptic etc., as water, ethanol, glycerol, Polyethylene Glycol, benzyl benzoate etc.
2, Homoplantaginin and dinatin blood sugar lowering, blood fat reducing and protection vascular inner skin cell activity
The impact on alloxan diabetes mice fasting glucose, T-CHOL (TC), triglyceride (TG) of 2.1 Homoplantaginins and dinatin
Random take out 10 of mices as normal group, after all the other mice fasting 15-16h, tail vein injection alloxan 62mg/kg, after injection, 72h eye socket rear vein beard is got blood, separation of serum, prediction blood glucose, select 70 of the mices of fasting glucose > 11.5mM, be divided at random 7 groups, by 10ml/kg body weight per os, give Homoplantaginin 50,100mg/kg respectively, dinatin 35,70mg/kg; Metformin (Metformin) 200mg/kg, normal group and model group give isopyknic 0.1%CMC-Na, once a day, successive administration 10 days.1.5h after last administration (fasting 5h), mouse orbit rear vein beard is got blood, and separation of serum is measured blood glucose, TC, TG with kit method.
Blood glucose experimental result as shown in Figure 1, is compared with normal group, the blood glucose of model group alloxan diabetes mice extremely obviously raise (P < 0.01).Compare with model group, Homoplantaginin 50mg/kg obviously reduces the blood glucose (P < 0.05) of diabetic mice; Homoplantaginin 100mg/kg, dinatin 35,70mg/kg and metformin 200mg/kg all can extremely obviously reduce the blood glucose (P < 0.01) of diabetic mice.
T-CHOL experimental result as shown in Figure 2, is compared with normal group, model group alloxan diabetes mice T-CHOL obviously raise (P < 0.05).Compare with model group, Homoplantaginin 50,100mg/kg, dinatin 35mg/kg and metformin 200mg/kg dosage group all reduce the serum total cholesterol content (P < 0.05) of diabetic mice significantly; The dinatin 70mg/kg dosage group utmost point reduces the serum total cholesterol content (P < 0.01) of diabetic mice significantly.
The experimental result of triglyceride as shown in Figure 3, is compared with normal group, and model group alloxan diabetes mice triglyceride has the trend of rising.Compare with model group, Homoplantaginin 100mg/kg, dinatin 70mg/kg and metformin 200mg/kg group all reduce the serum triglycerides content (P < 0.05) of diabetic mice significantly.
The impact that 2.2 Homoplantaginins and dinatin generate endotheliocyte NO due to Palmic acid (Palmitic acid, PA)
The trophophase HUVEC that takes the logarithm is digested to single cell suspension and is inoculated in 96 porocyte culture plates (1 * 10
4cell/well), 37 ℃, 5%CO
2under condition, cultivate after 24h, be replaced by serum-free RPMI 1640 culture medium, continue to cultivate 24h, abandon supernatant, with phosphate buffer PBS (pH7.4), wash 3 times, every hole adds 5 μ M 4-Amino, 5-aminomethyl-2 ', 7 ' difluorescein, diacetate (DAF-FM DA, NO fluorescent probe) 100 μ l, hatch 20min in 37 ℃ of cell culture incubators, with PBS, wash three times, fully to remove, do not enter intracellular DAF-FM DA.Afterwards, each hole replaces serum-free medium to continue to cultivate with PBS, and experiment is grouped into:
1) normal group (Normal): be naturally cultivating of HUVEC;
2) Norma/Insulin matched group: be first naturally cultivating of HUVEC, cultivate altogether 15min with Insulin 0.1 μ M afterwards;
3) model group (Control): HUVEC and PA 500 μ M cultivate 3h altogether; Cultivate altogether 15min with Insulin 0.1 μ M again;
4) Homoplantaginin group: Homoplantaginin 0.1,1 μ M and HUVEC cultivate after 30min altogether, continues to cultivate 3h with PA 500 μ M; Cultivate altogether 15min with Insulin 0.1 μ M again;
5) dinatin group: dinatin 0.1,1 μ M and HUVEC cultivate after 30min altogether, continues to cultivate 3h with PA 500 μ M; Cultivate altogether 15min with Insulin 0.1 μ M again;
6) sodium salicylate group (Salicylate): Salicylate 5mM and HUVEC cultivate after 30min altogether, continues to cultivate 3h with PA 500 μ M; Cultivate altogether 15min with Insulin 0.1 μ M again.
Except normal group, after each is organized Insulin and is disposed, in fluorescence inverted microscope (Olympus, I * 51 S8F-3) is lower, observes NO release conditions and take the photograph sheet immediately.Excitation wavelength 488nm, wavelength of transmitted light 515nm.Experiment repeats 3 times, each 3 multiple holes.
Experimental result is as shown in Figure 4: compare with normal group, the fluorescence intensity of Norma/Insulin group obviously strengthens, and shows that endotheliocyte NO generates showed increased, and the fluorescence intensity of model group obviously weakens, and prompting PA endothelial cell injury, causes NO to generate obviously and reduce.Compare with model group; Homoplantaginin (0.1; 1 μ M), dinatin (0.1; 1 μ M) and the fluorescence intensity of sodium salicylate (5mM) obviously strengthen; show that each medicine group all can obviously increase endotheliocyte NO and generate, prompting Homoplantaginin and dinatin and salicylic acid all can improve insulin resistant and the protection Endothelial Cell Function due to free fatty.
Of the present invention, Homoplantaginin and dinatin can be used for the medicine of the cardiovascular disease such as disorders of lipid metabolism that preparation prevention and treatment diabetes, diabetes cause and atherosclerosis, coronary heart disease.
Four, accompanying drawing explanation
The impact on alloxan diabetes mice fasting glucose of Fig. 1 Homoplantaginin and dinatin
Random take out 10 of mices as normal group, after all the other mice fasting 15-16h, tail vein injection alloxan 62mg/kg, after injection, 72h eye socket rear vein beard is got blood, select 70 of the mices of fasting glucose > 11.5mM, be divided at random model group, Homoplantaginin 50,100mg/kg, dinatin 35,70mg/kg; Metformin 200mg/kg, once a day, successive administration 10 days.1.5h after last administration (fasting 5h), gets blood, with kit method, measures serum fasting glucose, result with
represent.
##P＜0.01?vs?Normal；
*P＜0.05，
**P＜0.01?vs?Control(Student’s-t?test).
The impact on alloxan diabetes mice serum T-CHOL of Fig. 2 Homoplantaginin and dinatin
Random take out 10 of mices as normal group, after all the other mice fasting 15-16h, tail vein injection alloxan 62mg/kg, after injection, 72h eye socket rear vein beard is got blood, select 70 of the mices of fasting glucose > 11.5mM, be divided at random model group, Homoplantaginin 50,100mg/kg, dinatin 35,70mg/kg; Metformin 200mg/kg, once a day, successive administration 10 days.1.5h after last administration (fasting 5h), gets blood, with kit method, measures serum total cholesterol.Result with
represent.
#P＜0.05?vs?Normal；
*P＜0.05，
**P＜0.01?vs?Control(Student’s-t?test).
The impact on alloxan diabetes mice serum triglyceride of Fig. 3 Homoplantaginin and dinatin
Random take out 10 of mices as normal group, after all the other mice fasting 15-16h, tail vein injection alloxan 62mg/kg, after injection, 72h eye socket rear vein beard is got blood, select 70 of the mices of fasting glucose > 11.5mM, be divided at random model group, Homoplantaginin 50,100mg/kg, dinatin 35,70mg/kg; Metformin 200mg/kg, once a day, successive administration 10 days.1.5h after last administration (fasting 5h), gets blood, with kit method, measures serum triglycerides.Result with
represent.
*P＜0.05?vs?Control(Student’s-t?test).
The impact that Fig. 4 Homoplantaginin and dinatin generate endotheliocyte NO due to PA
Exponential phase HUVEC is digested to single cell suspension (1 * 10
4individual/hole) be inoculated in 96 porocyte culture plates, after cultivating 24h, be replaced by serum-free RPMI 1640 culture medium, continue to cultivate 24h, abandon supernatant, with PBS, wash 3 times, every hole adds 5 μ MDAF-FM DA 100 μ l, hatch 20min for 37 ℃, with PBS, wash three times, afterwards, each hole replaces serum-free medium to continue to cultivate with PBS, experiment is grouped into: what normal group was HUVEC cultivates naturally, Normal/Insulin matched group is after naturally cultivating of HUVEC and Insulin 0.1 μ M cultivates 15min altogether, model group (Control) is cultivated 3h altogether for HUVEC and 500 μ M PA, cultivate altogether 15min with Insulin 0.1 μ M afterwards, medicine group is Homoplantaginin 0.1, 1 μ M, dinatin 0.1, 1 μ M and sodium salicylate 0.5mM cultivate 30min altogether with HUVEC respectively, cultivate altogether 3h with PA 500 μ M afterwards, cultivate altogether 15min with Insulin 0.1 μ M again.Except normal group, after each is organized Insulin and is disposed, under fluorescence inverted microscope, observe immediately NO and generate situation and take the photograph sheet.Excitation wavelength 488nm, wavelength of transmitted light 515nm.Experiment repeats 3 times, each 3 multiple holes.
Five, the specific embodiment
Below in conjunction with example, describe the present invention.But the present invention is not limited to these given examples.
the preparation of embodiment 1. Homoplantaginins and dinatin:
Get the dry Herba Salviae Plebeiae herb of 10kg, pulverize, with 85% alcohol reflux of 10 times of amounts 3 times, merge extractive liquid,, concentrating under reduced pressure, by concentrated solution, successively with the petroleum ether of 4 times of amounts, ethyl acetate extraction 4 times, by after acetic acid ethyl acetate extract concentrating under reduced pressure, through silica gel column chromatography repeatedly, with chloroform: methanol (100: 2) eluting, collect eluent, concentrated, recrystallization, obtain dinatin, yield is 0.08 ‰; With chloroform: methanol (100: 8) eluting, obtain Homoplantaginin, yield is 0.29 ‰.
embodiment 2: the preparation of Homoplantaginin and dinatin:
Get the dry Herba Salviae Plebeiae herb of 10kg, pulverize, with 80% alcohol reflux of 12 times of amounts 3 times, merge extractive liquid,, concentrating under reduced pressure, by concentrated solution, by petroleum ether, the ethyl acetate of 5 times of amounts, extract 4 times successively, by after acetic acid ethyl acetate extract concentrating under reduced pressure, through silica gel column chromatography repeatedly, with chloroform: acetone (100: 5) eluting, obtain dinatin, yield is 0.09 ‰; With chloroform: acetone (100: 15) eluting, collect eluent, concentrated, recrystallization, obtains Homoplantaginin, and yield is 0.34 ‰.
Claims (4)
1. Homoplantaginin application in the medicine of preparation prevention and treatment diabetes, disorders of lipid metabolism that diabetes cause, coronary heart disease that diabetes cause as unique active component; it is characterized in that in described application that Homoplantaginin is by blood sugar lowering, blood fat reducing, the blood vessel endothelium insulin resistant and the protection vascular endothelial cell that improve due to free fatty play a role.
2. application according to claim 1, is characterized in that the preparation method of Homoplantaginin is wherein:
(1) Herba Salviae Plebeiae herb is dry, pulverizing;
(2) by ethanol or methanol or propanol or their aqueous reflux, extract,, or dipping extraction, extracting solution concentrating under reduced pressure;
(3) extracting solution concentrating under reduced pressure, extracts concentrated extract 3～4 times by petroleum ether, ethyl acetate successively;
(4) acetic acid ethyl acetate extract is evaporated to dry, recycle silicon glue post carries out column chromatography;
(5) with chloroform: methanol 100: 8 or chloroform: 100: 15 eluting of acetone, collect eluent, concentrated, recrystallization obtains Homoplantaginin;
The condition and range of above-mentioned preparation method is: in step (2), the concentration of ethanol or methanol or propanol is 10～90%, and extracting method is for refluxing, flooding.
3. application according to claim 1, is characterized in that described Homoplantaginin and one or more adjuvant and/or mixed with excipients make pharmaceutically acceptable dosage form.
4. application according to claim 3, is characterized in that dosage form is solution, capsule, tablet, granule, dragee.
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| CN103063634A (en) * | 2012-12-25 | 2013-04-24 | 华南师范大学 | Flow cytometry detection method of nitric oxide level of shrimp blood corpuscles |
| CN109010352B (en) * | 2018-11-07 | 2019-09-13 | 黑龙江中医药大学 | A kind of fatigue-resistant drug composition and its preparation method and application |
| CN110787180A (en) * | 2019-12-19 | 2020-02-14 | 济南大学 | Application of homoplantaginoside and derivatives thereof as Nrf-2 activator |
| CN112156091A (en) * | 2020-09-30 | 2021-01-01 | 中山大学附属第一医院 | Application of hispidulin in preparation of medicine for treating and/or preventing cardiovascular diseases |
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| CN101474251A (en) * | 2008-12-19 | 2009-07-08 | 华东理工大学 | Common sage herb total flavone extract as well as preparation method and application thereof |
| WO2009152453A2 (en) * | 2008-06-12 | 2009-12-17 | The Board Of Trustees Of The University Of Illinois | Compositions and methods for treating pulmonary hypertension |
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| WO2009152453A2 (en) * | 2008-06-12 | 2009-12-17 | The Board Of Trustees Of The University Of Illinois | Compositions and methods for treating pulmonary hypertension |
| KR20100035471A (en) * | 2008-09-26 | 2010-04-05 | 허병주 | Manufacturing method of the pill-type gombo-baechu |
| CN101474251A (en) * | 2008-12-19 | 2009-07-08 | 华东理工大学 | Common sage herb total flavone extract as well as preparation method and application thereof |
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