CN103393637B - Use of flavonoid compound in preparation of metabolic disease resistance medicines - Google Patents
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Abstract
The invention belongs to the technical field of medicines, and relates to a use of a compound having a structure represented by formula (I), and concretely relates to a use of the compound (5aR,10aS)-5a,10a-dihydro-1,3,8,10a-tetrahydroxy-2,5a-di(3-methyl-2-butenyl)-11H-benzofuranyl[3,2-b][1]benzopyranyl-11-one in the treatment of metabolic diseases. The compound is separated from Morus nigra. Experiments prove that the compound has very strong adipocyte differentiation promotion, diabetic mouse insulin sensitivity increasing and blood sugar and blood fat reducing effects, and can be further processed to prepare insulin sensitizers, sugar reducing medicines and lipid reducing medicines which can be applied to the medicine field. The formula (I) is shown in the specification.
Description
The application is denomination of invention: flavone compound is preparing the purposes in antimetabolic disease medicament, application number: 201110001869.4, the applying date: the division on January 6th, 2011.
Technical field
The invention belongs to medical art, relate to the medicinal usage that flavone compound is new, be specifically related to the purposes being separated the flavone compound obtained from black Mulberry.Particularly relate to compound (5a
r, 10a
s)-5a, 10a-dihydro-1,3,8,10a-tetrahydroxy-2,5a-bis-(3-methyl-2-butene base)-11H-benzofuran [3,2-b] [1] .alpha.-5:6-benzopyran-11-ketone is improving the purposes in insulin sensitivity, treatment diabetes and hyperlipemia.
Background technology
In recent years, due to factors such as the change of growth in the living standard, dietary structure, the rhythm of life be becoming tight day and few dynamic life style of sitting more, whole world onset diabetes rate rapid development, diabetes have become the disease of the third-largest serious threat human health after tumor, cardiovascular and cerebrovascular disease.Estimate according to World Health Organization (WHO), by 2025, global maturity-onset diabetes patient numbers will increase to 300,000,000.
Type 2 diabetes mellitus accounts for 90% of total diabetes, and its main pathogenesis is insulin resistant, islet beta cell function exhaustion and insulin secretion obstacle.Type 2 diabetes mellitus patient is attended by obesity, high triglyceride or hypercholesterolemia more, and hyperlipidemia is the one of the main reasons of insulin resistant and islet beta cell function disorder.Diabetes can cause various acute and chronic complicating diseases, as ketoacidosis, cardiovascular and cerebrovascular disease, nephropathy etc., constitute a serious threat to human health.Antidiabetic drug conventional at present has: insulin, sulfonylurea drugs, non-sulphanylureas Insulin secretagogues, biguanides, euglycemic agent etc., this a few class antidiabetic drug effect is fast, good effect but toxic and side effects is strong, to the organ injury such as liver, kidney, part of diabetes mellitus people shows obvious Drug resistance to insulin.Diabetes are lifelong participation disease, need Long-term taking medicine, therefore, find new antidiabetic medicine be safely and effectively present society in the urgent need to.
Fatty tissue is the main portions that GLPP absorbs, adipose cell energy high level expression glucose transporter 4 (Glut4) of differentiation.Glut4 is a kind of glycoprotein, to have glucose transport under the effect of insulin to the function in adipose cell.The expression increasing Glut4 albumen can increase the transhipment of fatty tissue to glucose, improves the opposing of the glucose uptake to insulin stimulating.In diabetics body, Glut4 expresses minimizing, displacement obstacle, it is the main cause of insulin resistant, therefore, find promotion Adipocyte Differentiation, improve Glut4 expression, increase insulin sensitivity and promote that the medicine of glucose transport has important clinical meaning to treatment type 2 diabetes mellitus.There is the history of abundant natural pharmaceutical resources and long application Chinese herbal medicine in China, and each ethnic groups with the struggle of disease in have accumulated valuable ethnic drug, these all become the important source of drug discovery.
Black Mulberry (
morus nigralinn.) be Moraceae (Moraceae) Mulberry plant, originate in Iran, after import China into, present Kashi, Aksu Prefecture are extensively cultivated.Black Mulberry is applied already in uighur medicine, is commonly called as " medicine Mulberry ", and root bark and stem branch have the effects such as blood pressure lowering, defying age, anti-inflammatory analgetic.Structure compound Radix Mori alcohol F (sanggenol F) is as shown in the formula (I) separated and obtains (list of references: Fu great Xu etc. from black Mulberry, " chemical constitution study of black Mulberry ", Chinese herbal medicine, 2005,36 (9), 1296-1299).Separately have bibliographical information, Fukai T. etc. from Mulberry plant Hua Sang (
morus cathayanahemsl.) the compound sanggenol F(Phytochemistry obtained as shown in the formula (I) is separated in first, 1997,47 (2), 273-280).Have no the bioactivity research report of this compound.
Summary of the invention
The object of this invention is to provide the medicinal usage that flavone compound is new, particularly relate to compound (5a
r, 10a
s)-5a, 10a-dihydro-1,3,8,10a-tetrahydroxy-2,5a-bis-(3-methyl-2-butene base)-11H-benzofuran [3,2-b] [1] .alpha.-5:6-benzopyran-11-ketone is improving the purposes in insulin sensitivity, treatment diabetes and hyperlipemia.
Flavone compound of the present invention is from black Mulberry, be separated the native compound obtained.This flavone compound has the structure as shown in the formula (I),
（I）
The compound of formula of the present invention (I) structure, especially compound (5a
r, 10a
s)-5a, 10a-dihydro-1,3,8,10a-tetrahydroxy-2,5a-bis-(3-methyl-2-butene base)-11H-benzofuran [3,2-b] [1] .alpha.-5:6-benzopyran-11-ketone, confirm through experiment, it has very strong promotion Adipocyte Differentiation, increase the expression of Glut4 albumen and the effect that increases insulin sensitivity and promote glucose transport, and have and reduce effect of blood fat, euglycemic agent can be further used as, hypoglycemic medicine, fat-reducing medicament be applied to field of medicaments.
Flavone compound of the present invention is from black Mulberry, be separated the native compound obtained, and prepares by the following method:
By black Mulberry
morus nigralinn. after stem branch is pulverized, with organic solvent or/and water extraction prepares total extract, organic solvent used can adopt alcohols, as ethanol, methanol etc., wherein preferred 95%(volume ratio) ethanol, after total extract is water-soluble, with petroleum ether extraction, get petroleum ether phase, after recycling design, be drying to obtain ligroin extraction;
Ligroin extraction is carried out silica gel column chromatography separation, use petroleum ether, petroleum ether-acetone gradient elution respectively, wherein petroleum ether-acetone 4: 1 elution fraction carries out silica gel column chromatography separation, with chloroform-ether (5: 1) eluting, and then carry out ODS pillar layer separation, with methanol-water gradient elution, obtain compound (5a
r, 10a
s)-5a, 10a-dihydro-1,3,8,10a-tetrahydroxy-2,5a-bis-(3-methyl-2-butene base)-11H-benzofuran [3,2-b] [1] .alpha.-5:6-benzopyran-11-ketone, identify its structure with spectral method, such as formula (
) structure.
Formula (
) compound carried out db/db mice carbohydrate metabolism, lipid metabolism related experiment in external Adipocyte Differentiation, glucose transport and body, result shows, described compound (I) has very strong promotion Adipocyte Differentiation, strengthens the adipose cell glucose transport of insulin stimulating and increase the effect of insulin sensitivity, and there is the effect of blood fat reducing, can be used as euglycemic agent, blood sugar lowering, blood lipid-lowering medicine and be applied to field of medicaments.
Further, the compound (5a of formula (I)
r, 10a
s)-5a, 10a-dihydro-1,3,8,10a-tetrahydroxy-2,5a-bis-(3-methyl-2-butene base)-11H-benzofuran [3,2-b] [1] .alpha.-5:6-benzopyran-11-ketone can be used as the effective ingredient of medicine, prepares the medicine of antimetabolic disease.Described medicine is euglycemic agent, hypoglycemic drug or blood lipid-lowering medicine.
Accompanying drawing explanation
Fig. 1 be in embodiment 2 the compounds of this invention (I) on the impact of 3T3-L1 PECTORAL LIMB SKELETON differentiation.
Fig. 2 be in embodiment 3 the compounds of this invention (I) on the impact of the glucose transport of insulin stimulating.
Fig. 3 be in embodiment 4 the compounds of this invention (I) on the impact of db/db Mouse oral carbohydrate tolerance (OGTT).
Fig. 4 be in embodiment 4 the compounds of this invention (I) on the impact of db/db mice OGTT area under curve.
Fig. 5 be in embodiment 5 the compounds of this invention (I) on db/db mouse islets element tolerance (ITT) impact.
Fig. 6 be in embodiment 5 the compounds of this invention (I) on the impact of db/db mice ITT area under curve.
Fig. 7 be in embodiment 6 the compounds of this invention (I) on the impact of db/db mouse adipose tissue gene aP2, C/EBP α, PPARg and Glut4 expression.
Fig. 8 be in embodiment 7 the compounds of this invention (I) on the impact of db/db mice serum triglyceride (TG), cholesterol (TC) level.
In Fig. 1 to Fig. 8, *
p< 0.05 and * *
p< 0.01(is compared with matched group).
Detailed description of the invention
Below in conjunction with concrete embodiment, the present invention is further elaborated, but do not limit the present invention.
embodiment 1the compounds of this invention (I) is extracted from black Mulberry
(1) extract: the dry stem branch of black Mulberry pulverize after coarse powder 2 kilograms, 95% aquiferous ethanol room temperature lixiviate three times, obtain respectively extracting solution 8 liters, 6 liters, 4 liters, merge extractive liquid, is evaporated to dry, obtains extractum 204 grams.By water-soluble for this extractum suspension, with petroleum ether extraction, recycling design is concentrated into dry, obtains ligroin extraction 47 grams.
(2) be separated: ligroin extraction 47 grams is carried out silica gel column chromatography separation, use petroleum ether, petroleum ether-acetone (30: 1 → 20: 1 → 10: 1 → 9: 1 → 6: 1 → 4: 1) gradient elution respectively, each gradient consumption 3000 milliliters, collects stream part, obtains component 1 ~ 17 part.Petroleum ether-acetone 4: 1 eluting obtains component 15 ~ 17, wherein component 15(800 milligram) be separated through silica gel column chromatography, chloroform-ether (5: 1) eluting 700 milliliters, obtains component 15.1 ~ 15.3; By component 15.2(450 milligram) carry out ODS pillar layer separation, methanol-water (7: 3 → 8: 2 → 9: 1) gradient elution, each gradient consumption 500 milliliters, collect stream part, methanol-water (8: 2) stream part obtains compound (I) (5a
r, 10a
s)-5a, 10a-dihydro-1,3,8,10a-tetrahydroxy-2,5a-bis-(3-methyl-2-butene base)-11H-benzofuran [3,2-b] [1] .alpha.-5:6-benzopyran-11-ketone 201 milligrams.
(3) physicochemical property of compound (I) and spectroscopic data are as following: molecular formula is C
25h
26o
7, its character is Yellow amorphous powder, specific rotation: [a]
20 d+ 165.6 ° (
c1.03, Me
2cO), electron impact mass spectra (mass-to-charge ratio): 438 [M]
+, proton nmr spectra (500 MHz) data (chemical shift: ppm, coupling constant: Hz, solvent: deuterated acetone): δ 11.91(1H, s, OH-5), 9.12(2H, br s, OH-7,4 '), 7.35(1H, d,
j=8.2 Hz, H-6 '), 7.03(1H, br s, OH-3), 6.52(1H, dd,
j=1.6,8.2 Hz, H-5 '), 6.40(1H, d,
j=1.6 Hz, H-3 '), 5.92(1H, s, H-8), 5.25(1H, br t,
j=7.0 Hz, H-2 "), 5.19(1H, br t,
j=7.0 Hz, H-10), 3.23 (2H, br d,
j=7.0 Hz, H
2-1 "), 3.12(1H, br dd,
j=8.8,14.7 Hz, H-9a), 2.78(1H, br dd,
j=6.1,14.7 Hz, H-9b), 1.73,1.623(each 3H, br s, H
3-4 ", 5 "), 1.615,1.52 (each 3H, br s, H
3-12,13), (the chemical shift: ppm of carbon-13 nmr spectra (100 MHz) data, solvent: deuterated acetone): d 188.2 s(C-4), 166.6 s(C-7), 162.7 s(C-5), 161.6 s(C-8a), 161.3 s(C-2 ￠), 161.2 s(C-4 ￠), 136.5 s(C-11), 131.4 s(C-3 ￠ ￠), 125.6 d(C-6 ￠), 123.3 d(C-2 ￠ ￠), 121.4 s(C-1 ￠), 118.7 d(C-10), 109.7 d(C-5 ￠), 109.1 s(C-6), 102.6 s(C-3), 100.2 s(C-4a), 99.5 d(C-3 ￠), 95.3 s(C-8), 91.8 s(C-2), 31.9 t(C-9), 25.8 q(C-13, 5 ￠ ￠), 21.5 t(C-1 ￠ ￠), 18.1 q(C-12), 17.8 q(C-4 ￠ ￠).
embodiment 2the impact (oil red staining) that the compounds of this invention (I) breaks up 3T3-L1 PECTORAL LIMB SKELETON
3T3-L1 cell is inoculated in 48 orifice plates, with containing 10% NCS(calf serum) height sugar H-DMEM culture medium culturing.Use instead after 2 days containing 125 μMs of IBMX(3-isobutyl group-1-methylxanthine), 1 μM of Dex(dexamethasone), 20 μ g/ml Insulin(insulins) 10% FBS(hyclone) culture medium is differentiation-inducing, and adds the compound (I) of variable concentrations.Break up after 2 days, the culture medium of noble cells is used instead containing 20 μ g/ml Insulin, the FBS of 10% and the height sugar H-DMEM culture medium of variable concentrations compound (I), within every 2 days, changes liquid once, changes three times continuously.Cell differentiation abandoned culture medium after 8 days, used PBS(phosphate buffered saline (PBS)) to wash once, every hole carefully adds 10% formalin (final concentration is 4% formaldehyde) of 300 μ l, hatches 15 minutes for 37 DEG C.Abandon 10% formalin, wash twice with PBS, blot PBS, oil red O dyes 30 minutes, abandons supernatant, adds the PBS of 300 μ l, takes pictures.Result confirms that the compounds of this invention (I) can the content that drips of the increase 3T3-L1 cell lactone of dose dependent, obviously can promote that 3T3-L1 cell is to Adipocyte Differentiation (as shown in Figure 1).
embodiment 3the compounds of this invention (I) is on the impact breaking up 3T3-L1 adipose cell glucose transport
3T3-L1 cell is inoculated in 48 orifice plates, and differentiation and cultivation process is identical with oil red staining, and cell differentiation, after 8 days, discards culture medium, washes one time with serum-free DMEM, and 1ml/ hole adds the DMEM containing 0.1% BSA (bovine serum albumin), 300 μ l/ holes.37 DEG C of incubation 3-5h.Discard culture medium, wash one time with HRP buffer, add HRP buffer(and shift to an earlier date 37 DEG C of incubations, containing 10 ng/ml insulins), 200 μ l/ holes, 37 DEG C of incubation 15min.Add HRP buffer(and contain 2-deoxy-d-[1,2-3H]-glucose, final concentration dilutes 2000 times), 100 μ l/ holes, 37 DEG C of incubation 10min.Discard all liq in plate, the HRP buffer(300 μ l/hole with ice-cold) wash one time, sop up, add HRP buffer (400-500 μ l/ hole) and wash one time again, discard.Add HRP buffer(and contain 0.1-0.5% TritonX-100), 200 μ l/ holes, cracking of spending the night.Add scintillation solution 800 μ l/ hole, detect.Result confirms that the compounds of this invention (I) can promote the glucose transport of insulin stimulating and strengthen the sensitivity of insulin by dose dependent, when its concentration is 10 μMs, effect is slightly better than hypoglycemic medicine rosiglitazone (Rosiglitazone) (as shown in Figure 2).
embodiment 4the compounds of this invention (I) is on the impact of db/db diabetic mice oral glucose tolerance (OGTT)
The db/db mice in 8 week age is divided into two groups by body weight blood glucose: matched group (every day lumbar injection olive oil, 0.1ml/ is only) and the administration group (compound (I) that every day, lumbar injection olive oil dissolved, 5 mg/kg, 0.1ml/ is only), often organize 6, administration 21 days, within 22nd day, survey oral glucose tolerance (OGTT): fasting 12h, survey matched group and administration group blood glucose, body weight, when being designated as 0 according to body weight gavage glucose (1g/kg), after gavage, survey 60,90,120,150 min blood glucose respectively.Result shows, give gavage glucose with the db/db its mouse oral of the compounds of this invention (I) after blood glucose lower than matched group, area under curve is significantly less than matched group, illustrates that the compounds of this invention (I) can improve db/db mouse glucose tolerance (as shown in Figure 3 and Figure 4).
embodiment 5the compounds of this invention (I) is on the impact of db/db diabetic mice insulin tolerance (ITT)
Db/db mice administration 18 days (method is the same), within 19th day, survey insulin tolerance (ITT): fasting 6h, survey matched group and administration group blood glucose, body weight, when being designated as 0 according to body weight lumbar injection insulin (1U/kg), after gavage, survey 30,60,90,120 min blood glucose respectively.Result shows, and give with the db/db mice of the compounds of this invention (I) under same dose insulin effect, blood glucose is starkly lower than matched group, illustrates that the compounds of this invention (I) can improve db/db mouse islets element sensitivity (as shown in Figure 5 and Figure 6).
embodiment 6the compounds of this invention (I) is on the impact of db/db diabetic mice fatty tissue gene expression dose
Db/db mice is given and after three weeks (method is the same) with the compounds of this invention (I), dissects, get fatty tissue, with TRIzol method extracting mRNA.100 mg tissues add 1ml TRIzol, and vortex oscillator adds after mixing the chloroform of about 1/5 volume, and fully after mixing, room temperature leaves standstill 5 min; Then in centrifugal 15 min of 4 ° of C, 12000 rpm; Proceeded to by supernatant in 1.5 ml centrifuge tubes, add isopyknic isopropyl alcohol, after mixing, room temperature leaves standstill 5 min; In centrifugal 10 min of 4 ° of C, 12000 rpm; Suck supernatant, in precipitation, add 70% ethanol of 2/5 volume, the centrifugal 15 min washing precipitations of 4 ° of C, 12000 rpm; Suck supernatant, be deposited in the water adding appropriate RNase-free after room temperature is dried naturally, abundant dissolution precipitation; Get 1-2 ml to dilute, measure OD
260, RNA concentration calculates as follows: A
260× 40 × extension rate (μ g/ μ l).With M-MLV reverse transcriptase, mRNA reverse transcription is become cDNA ,-80 ° of C Refrigerator stores are stand-by.Adopt SYBR
?premix Ex Taq
?iI(Takara) real-time fluorescence quantitative PCR analysis is carried out to sample reverse transcription product.ABI 7500 Fast real-time fluorescence quantitative PCR instrument is utilized to measure, do melt curve analysis simultaneously and judge primer quality, with β-actin for contrast, calculate aP2(fatty tissue fatty acid binding protein), C/EBP α (CAAT/ enhancer binding protein α), PPARg(peroxidase precursor multiplication agent activated receptor g) and Glut4(glucose transporter 4) expression.Result shows, give with the expression of db/db mouse adipocytes gene aP2, C/EBP α, PPARg and Glut4 of the compounds of this invention (I) apparently higher than matched group, illustrate that the compounds of this invention (I) can improve the expression of db/db mouse adipocytes gene aP2, C/EBP α, PPAR γ and Glut4, confirm that the compounds of this invention (I) can promote the transhipment (as shown in Figure 7) of Adipocyte Differentiation and glucose further at molecular level.
embodiment 7the compounds of this invention (I) is on the impact of db/db mice serum triglyceride (TG), cholesterol (TC) level
Db/db mice is given with the compounds of this invention (I) after three weeks (method is the same), tail venous blood sampling, centrifugal, draw upper serum, survey serum TG content with GPO-peroxidase method, survey serum TC content with cholesterol oxidase-peroxidase method.Result confirms, the compounds of this invention (I) can reduce the content (as shown in Figure 8) of db/db mice serum TG, TC.
Above-mentioned experimental result shows, the compounds of this invention (I) has the effect of the expression obviously promoting Adipocyte Differentiation, raising Glut4, the glucose transport increasing insulin stimulating, raising diabetic mice insulin sensitivity, reduction blood glucose, reduction blood fat.Therefore, the compounds of this invention (I) can be used as euglycemic agent, hypoglycemic drug and blood lipid-lowering medicine for field of medicaments.
Claims (2)
1. compound (the 5aR of formula (I), 10aS)-5a, 10a-dihydro-1,3,8,10a-tetrahydroxy-2,5a-bis-(3-methyl-2-butene base)-11H-benzofuran [3,2-b] [1] .alpha.-5:6-benzopyran-11-ketone as single-activity composition preparation treatment hyperlipidemia in purposes
2., by the purposes of claim 1, it is characterized in that described medicine is blood lipid-lowering medicine.
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Non-Patent Citations (4)
| Title |
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| 桑属植物化学成分及药理活性研究进展;黎琼红等;《沈阳药科大学学报》;20030930;第20卷(第5期);386-390 * |
| 植物次生代谢物黄酮类化合物的研究进展;王军妮等;《桑业科学》;20071231;第33卷(第3期);499-505 * |
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