CN103012356B - Compound with alpha-glycosidase inhibitory activity, as well as preparation method and application of compound - Google Patents
Compound with alpha-glycosidase inhibitory activity, as well as preparation method and application of compound Download PDFInfo
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Abstract
The invention discloses a kind of compound and its preparation method and application with alpha-glucoside inhibiting activity,The structure of the compound is shown in formula I,It is to extract 50~95% ethanol percolations of Swertia mussotii herb,Combined extract,Revolving removes ethyl alcohol,Medicinal extract is obtained after re-dry; Medicinal extract is soluble in water,It is extracted with dichloromethane; Methylene chloride is extracted product and is separated using silica gel column chromatography,With petroleum ether-ethyl acetate gradient elution,The compound polarity size shown according to thin-layer chromatography merges eluent according to the ascending sequence of polarity and obtains 8 thick fractions,It is respectively labeled as F1~F8; Compound ZYC-01 and ZYC-02 is prepared by the separation of silica gel column chromatography combination preparative high performance liquid chromatography in fraction F3; ZYC-04 is prepared by gel filtration chromatography in fraction F4; ZYC-03 and ZYC-05 is prepared by gel filtration chromatography in fraction F5. Traditionally Swertia mussotii is to research and develop Antihepatitis medicament as Main way. The compound of the present invention is to report for the first time to the inhibitory activity of alpha-glucosidase and the application in preparation treatment diabetes medicament.
Description
Technical field
The invention belongs to pharmaceutical field, be specifically related to a kind of extraction suppresses alpha-glycosidase enzymolysis activity compound and preparation method thereof and the application in preparation treatment diabetes medicament from having of ZANGYINCHEN.
Background technology
ZANGYINCHEN is in Tibetan medicine, to prevent and treat the rare medicinal herbs of hepatitis, liver injury, hepatic fibrosis, fatty liver diseases.Chemical research shows, in ZANGYINCHEN class main Chinese medicinal materials (Swertia mussotii Franch., Indian Herba Swertiae bimaculatae, Swertia franchetiana H.Smith and flower anchor), contains the Multiple components such as Secoiridoid Glycosides, flavones and glycoside thereof, mountain ketone and glycoside, triterpenes.
Chinese patent (application number 200710163097.8) discloses ZANGYINCHEN extract and preparation method thereof, pharmaceutical composition and purposes, its extract comprises swertiamarin, gentiopicrin, sweroside, Mangiferin, five kinds of compositions of Lutonaretin, be mainly used in improving liver injury, promote the reverse of liver fibrosis process.
Chinese patent (application number 92108809.4) discloses a kind of production method of extraction process, equipment and ZANGYINCHEN tablet of ZANGYINCHEN effective constituent.
Chinese patent CN101845037B discloses the method for mountain ketone composition in a kind of separated ZANGYINCHEN, comprises the extraction ZANGYINCHEN extract aqueous solution, according to polarity gradient, extracts rough segmentation and three processing steps of column chromatographic isolation and purification.
There is bibliographical information, the Darjeeling in India Sillim and the Himalayas, people utilize Indian Herba Swertiae bimaculatae (Swertia chirayita) treatment diabetes (Chhetri, D.R. traditionally, Parajuli, P., Subba, G.C.Antidiabetic plants used by Sikkim and Darjeeling Himalayan tribes, India.J.Ethnopharmacol., 2005,99,199-202).Research shows, xanthones compounds Swerchirin, methylswertianin and bellidifolin are wherein its effective components, have good hypoglycemic effect (Tian, L.-Y., Bai, X., Chen, X.-Y., et al.Anti-diabetic effect of methylswertianin and bellidifolin from Swertia punicea Hemsl.and its potential mechanism.Phytomedicine, 2010,17,533-539).On the other hand, Mangiferin is a kind of mountain ketoside, and also in ZANGYINCHEN, separation obtains.Miura etc. reported its function of polysaccharide (Miura, T., Ichiki, H., Hashimoto, I., et al.Antidiabetic activity of a xanthone compound, mangiferin.Phytomedicine, 2001,8,85-87).
Summary of the invention
Primary and foremost purpose of the present invention is to provide a kind of compound with alpha-glucoside inhibiting activity.
The preparation method of the compound with alpha-glucoside inhibiting activity that another object of the present invention is to provide above-mentioned, above-mentioned compound is to extract and obtain from the herb of ZANGYINCHEN.
The application of the compound with alpha-glucoside inhibiting activity that a further object of the present invention is to provide above-mentioned in preparation treatment carbohydrate metabolism disturbance disease medicament, the especially application in preparation treatment type ii diabetes medicine.
Object of the present invention is achieved through the following technical solutions:
A compound with alpha-glucoside inhibiting activity, its structure is suc as formula shown in I:
(formula I)
In formula I, R
1, R
2, R
3, R
4, R
5for H, OH or OCH
3;
Preferably, the above-mentioned compound with alpha-glucoside inhibiting activity is 1,7,8-trihydroxy--3,4-dimethoxy xanthenone (code name is ZYC-01), 1,3,5,8-tetrahydroxy mountain ketone (ZYC-02), 1,3,7,8-tetrahydroxy mountain ketone (ZYC-03), 1,7-dihydroxyl-3-methoxyl xanthone (ZYC-04) and 1,3-dihydroxyl-7,8-dimethoxy xanthenone (ZYC-05);
The preparation method of the above-mentioned compound with alpha-glucoside inhibiting activity, comprises the following steps:
By ZANGYINCHEN herb grind into powder, with 50～95% ethanol percolate extraction several times, filter cleaner after united extraction liquid, revolve to steam and remove ethanol, then obtain medicinal extract after dry; Medicinal extract is soluble in water, with dichloromethane extraction; Dichloromethane extraction product adopts silica gel column chromatography separated, uses petroleum ether-ethyl acetate gradient elution, and sherwood oil is 30:1 with the original volume ratio of ethyl acetate, is finally transitioned into 0:1; The compound polarity size showing according to thin-layer chromatography (TLC) merges elutriant according to the ascending order of polarity and obtains 8 thick cuts, is labeled as respectively F1～F8; Cut F3 prepares compound ZYC-01 and ZYC-02 by silica gel column chromatography in conjunction with preparative high performance liquid chromatography separation; Cut F4 prepares ZYC-04 by gel filtration chromatography; Cut F5 prepares ZYC-03 and ZYC-05 by gel filtration chromatography;
Described ZANGYINCHEN refers to Swertia mussotii Franch., Indian Herba Swertiae bimaculatae, Swertia franchetiana H.Smith and flower anchor, preferably Swertia mussotii Franch. (Swertia mussotii Franch).
The present invention utilizes that following to experimental results show that above-mentioned compound has good inhibition to alpha-glycosidase active: take 4-nitrophenol-α-D-glucopyranoside (PNPG) for the inhibiting rate of substrate mensuration xanthones compounds (being compound of the present invention) to alpha-glycosidase enzymolysis activity, using clinical medicine acarbose (Acarbose) as positive control.Result shows, 1,7,8-trihydroxy--3, and 4-dimethoxy xanthenone (ZYC-01) and 1,3,5,8-tetrahydroxy mountain ketone (ZYC-02) are best to the inhibition activity of people source alpha-glycosidase, IC
50value is respectively 1.43mmol/L and 1.64mmol/L; Approach the level (IC of acarbose
50=0.99mmol/L).
In the body of artificial diabetes NOD mouse, experiment shows, 1,7,8-trihydroxy--3, and 4-dimethoxy xanthenone (ZYC-01) and 1,3,5,8-tetrahydroxy mountain ketone (ZYC-02) is reducing blood glucose, TC, TG concentration significantly, improves serum insulin level.
Therefore, the above-mentioned compound with alpha-glucoside inhibiting activity can be used for the medicine of preparation treatment carbohydrate metabolism disturbance disease, especially can be used for the medicine of preparation treatment type ii diabetes.
The present invention has following advantage and effect with respect to prior art:
Traditionally ZANGYINCHEN take research and development Antihepatitis medicament be main direction.Compound of the present invention is to the inhibition activity of alpha-glycosidase and treat the reported first that is applied as in diabetes medicament in preparation.
Accompanying drawing explanation
Fig. 1 is 3,4-dimethoxy-1, the mass spectrum of 7,8-trihydroxy diphenylene ketone oxide (ZYC-01).
Fig. 2 is the mass spectrum of 1,3,5,8-tetrahydroxy mountain ketone (ZYC-02).
Fig. 3 is the mass spectrum of 1,3,7,8-tetrahydroxy mountain ketone (ZYC-03).
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention are not limited to this.
Embodiment 1
The extraction separation and purification with the compound of alpha-glucoside inhibiting activity, comprises the following steps:
Swertia mussotii Franch. herb 2.5kg, is ground into powder, and with 75% ethanol percolate extraction 3 times, each 2h, 2h and 1h, filter, and extracting solution is merged, and revolves to steam and removes, then dry at 60 ℃ of vacuum chambers, obtains dry extract 509.7g.Medicinal extract is ground, soluble in water, with isopyknic methylene dichloride, repeatedly extract, obtain dichloromethane extract 92g.Get dichloromethane extract and adopt silica gel column chromatography to carry out separation, use petroleum ether-ethyl acetate gradient elution, sherwood oil is 30:1 with the original volume ratio of ethyl acetate, is finally transitioned into 0:1; The compound polarity size showing according to thin-layer chromatography (TLC) merges elutriant according to the ascending order of polarity and obtains 8 thick cuts, is labeled as respectively F1～F8.Cut F3 prepares compound ZYC-01 and ZYC-02 by silica gel column chromatography in conjunction with preparative high performance liquid chromatography separation.Cut F4 prepares ZYC-04 by gel filtration chromatography.Cut F5 prepares ZYC-03 and ZYC-05 by gel filtration chromatography.
1,7,8-trihydroxy--3,4-dimethoxy xanthenone (ZYC-01): light yellow solid powder.UV (MeOH) λ
max: 239,268,313,344nm; IR (KBr) υ
max: 3396,1645,1606,1505cm
-1; ESI-MS (m/z): 303.2[M-H]
-;
1h NMR (300MHz, DMSO-d
6) δ: 7.27 (1H, d, J=9Hz, H-6), 6.90 (1H, d, J=9Hz, H-5), 6.55 (1H, s, H-2), 3.93 (3H, s ,-OCH
3), 3.77 (3H, s ,-OCH
3);
13c NMR (300MHz, DMSO-d
6) δ: 157.67 (C-1), 95.03 (C-2), 160.25 (C-3), 128.24 (C-4), 148.97 (C-4a), 148.01 (C-4b), 106.04 (C-5), 124.02 (C-6), 140.65 (C-7), 147.34 (C-8), 101.21 (C-8a), 107.16 (C-8b), 184.29 (C-9), 60.91,56.62 (OCH
3); Its mass spectrum is shown in Fig. 1.Control reference document (Silveira, E.R.,
, M.J.C., Menezes, et al.Pentaoxygenated xanthones from Bredemeyera Floribunda.Phytochemistry, 1995,39 (6), 1433-1436), prove that product is 1,7,8-trihydroxy--3,4-dimethoxy xanthenone (ZYC-01).
1,3,5,8-tetrahydroxy mountain ketone (ZYC-02): light yellow solid powder.UV (MeOH) λ
max: 239,264,331,381nm; IR (KBr) υ
max: 3383,1640,1606,1506cm
-1; ESI-MS (m/z): 259.2[M-H]
-;
1h NMR (300MHz, CD
3oD) δ: 7.15(1H, d, J=9Hz, H-6), 6.56(1H, d, J=9Hz, H-7) and, 6.16(1H, d, J=3Hz, H-2), 6.30(1H, d, J=3Hz, H-4);
13cNMR (300MHz, CD
3oD) δ: 164.26 (C-1), 99.45 (C-2), 167.93 (C-3); 95.41 (C-4); 159.26 (C-4a), 145.08 (C-4b), 138.25 (C-5); 124.63 (C-6); 110.41 (C-7), 154.28 (C-8), 108.63 (C-8a); 102.73 (C-8b), 185.71 (C-9); Its mass spectrum is shown in Fig. 2.Control reference document (Qing, Z.Liu, Y.-W., 2003.Studies on the constituents of Swertia kauitchensis Franch.Hubei College of Traditional Chinese Medicine, Hubei), prove that product is 1,3,5,8-tetrahydroxy mountain ketone (ZYC-02).
1,3,7,8-tetrahydroxy mountain ketone (ZYC-03): light yellow solid powder.UV (MeOH) λ
max: 238,265,331,386nm; IR (KBr) υ
max: 3355,1661,1612,1518,1475cm
-1; ESI-MS(m/z): 259.2[M-H]
-;
1h NMR (300MHz, DMSO-d
6) δ: 11.87 (1H, s ,-OH), 11.70 (1H, s;-OH), 11.16 (1H, s ,-OH), 9.36 (1H; s ,-OH), 7.26(1H, d, J=6Hz; H-6), 6.87(1H, d, J=6Hz, H-5); 6.20(1H, d, J=3Hz, H-2); 6.34(1H, d, J=3Hz, H-4);
13c NMR (300MHz, DMSO-d
6) δ: 162.15 (C-1), 98.15 (C-2), 166.37 (C-3); 94.01 (C-4); 157.77 (C-4a), 147.86 (C-4b), 105.95 (C-5); 123.92 (C-6); 140.37 (C-7), 147.01 (C-8), 107.19 (C-8a); 100.80 (C-8b), 183.89 (C-9); Its mass spectrum is shown in Fig. 3.Control reference document (Li, S., Shi, Y.Shang, X. – Y., et al.Triterpenoids from the roots of Pterospermum heterophyllum Hance.J Asian Nat.Prod.Res., 2009,11 (7), 652-657), prove that product is 1,3,7,8-tetrahydroxy mountain ketone (ZYC-03).
1,7-dihydroxyl-3-methoxyl xanthone (ZYC-04): light yellow solid powder.UV(MeOH)λ
max:239,262,325,382nm；IR(KBr)υ
max:3382，1657，1606，1478cm
-1;ESI-MS(m/z):259.2[M+H]
+;
1H?NMR(300MHz,DMSO-d
6)δ:12.86(1H，s，-OH)，7.42（1H,d，J=3Hz，H-8），7.30（1H,d，J=9Hz，H-6），7.49（1H,d，J=9Hz，H-5），6.58（1H,d，J=3Hz，H-4），6.36（1H,d，J=3Hz，H-2）δ3.87(3H，s，-OCH
3);
13C?NMR(300MHz，DMSO-d
6)δ:162.47(C-1)，96.84(C-2)，166.30(C-3)，92.46(C-4)，149.00(C-4a)，157.38(C-4b)，119.02(C-5)，124.77(C-6)，154.07(C-7)，107.95(C-8)，120.39(C-8a)，102.79(C-8b)，180.06(C-9)。Control reference document (Hidehiro, A., Yasuaki, H., Mikio, F., et al.The chemical constituents of fresh Gentian root.J.Nat.Med., 2007,61 (3), 269-279), prove that product is 1,7-dihydroxyl-3-methoxyl xanthone (ZYC-04).
1,3-dihydroxyl-7,8-dimethoxy xanthenone (ZYC-05): light yellow solid powder.UV (MeOH) λ
max: 237,264,328,385nm; IR (KBr) υ
max: 3390,1645,1608,1479cm
-1; ESI-MS (m/z): 289[M+H]
+;
1h NMR (300MHz, DMSO-d
6) δ: 13.26 (1H, s ,-OH), 7.5 (1H, d, J=9Hz, H-6), 7.28 (1H, d, J=9Hz, H-5), 6.07 (1H, s, H-2), 6.22 (1H, s, H-4), 3.85 (3H, s ,-OCH
3, 3.79 (3H, s ,-OCH
3);
13c NMR (300MHz, DMSO-d
6), δ: 163.13 (C-1), 97.89 (C-2), 165.57 (C-3), 93.24 (C-4), 156.78 (C-4a), 149.90 (C-4b), 112.76 (C-5), 120.60 (C-6), 147.53 (C-7), 149.01 (C-8), 114.81 (C-8a), 102.29 (C-8b), 180.17 (C-9), 60.99 (OCH
3), 56.56 (OCH
3); Control reference document (Cortez, D.A.G., Young, M.C.M., Marston, A., et al.Xanthones, triterpenes and a biphenyl from Kielmeyera coriacea.Phytochemistry, 1998,47 (7), 1367-1374), proof product is 1,3-dihydroxyl-7,8-dimethoxy xanthenone (ZYC-05).
Embodiment 2
The embodiment 1 separated compound that extracts is active to the inhibition of alpha-glycosidase
In the present embodiment, people source alpha-glycosidase is purchased from Sigma company; 4-nitrophenol-α-D-glucopyranoside (PNPG) is purchased from Merk company.
First to the enzyme activity determination system of potassium phosphate buffer, (this system is containing 67mmol/L potassium phosphate buffer (pH6.8) 1.7ml, 1mg/mL gsh 50 μ l) in, add people source alpha-glucosidase 5 μ l(concentration: 20mg/mL), 37 ℃ of insulation 10min, add after 0.116mol/L PNPG50 μ l, 37 ℃ of reaction 10min, add Na
2cO
3termination reaction, measures the absorbancy of the nitrophenol discharging under enzyme effect at 400nm place, and then gets the embodiment 1 separated compound that extracts and add in enzyme activity determination system, first by 37 ℃ of insulation 5min of enzyme, then adds PNPG and reacts 10min in 37 ℃, adds Na
2cO
3termination reaction, the absorbancy of the nitrophenol discharging under the mensuration enzyme effect of 400nm place.Finally inhibition percentage is compared and obtained to twice absorbance.
Experimental result is in Table 1.
Table 1 ZANGYINCHEN effective component is active to the inhibition of people source alpha-glycosidase
As can be seen from Table 1, the embodiment 1 separated compound that extracts all has good inhibition active to people source alpha-glycosidase, wherein 1,7,8-trihydroxy--3,4-dimethoxy xanthenone (ZYC-01) and 1,3, the inhibition of 5,8-tetrahydroxy mountain ketone (ZYC-02) is active best, approaches positive control medicine acarbose.
Embodiment 3
The hypoglycemic activity of the embodiment 1 separated compound that extracts
Experiment material: NOD mouse, purchased from Guangdong Province's Experimental Animal Center.
Experimental technique:
After mouse is bought, feed with high lipid food, wherein carbohydrate 40%, protein 15%, and fat 40%, other is 5% years old.Feed continuously after 3 months disposable celiac injection streptozotocin (STZ, 60mg/kg).Tail venous blood sampling after 72h, measures respectively blood sugar and Regular Insulin.All blood sugar concentration >13mmol/L, glucose in urine are positive, also occur many drinks are eaten more and diuresis phenomenon person is diabetes model.
Get diabetic mice, be divided at random 8 groups, 10 every group, and diabetic model group, positive controls (acarbose), ZYC-01(1,7,8-trihydroxy--3,4-dimethoxy xanthenone) treatment group, ZYC-02(1,3,5,8-tetrahydroxy mountain ketone) treatment group.Model group feeding normal diet, freely drinks water, and every day is with distilled water gavage; Every mouse administration 50mg/kg gavage of positive controls; Every mouse administration of medication therapy groups 20,40,60mg/kg, respectively gavage.Each organizes mouse respectively at 1d, 10d, 20d empty stomach venous blood sampling, measures blood sugar and insulin concentration.
After diabetic mice last administration fasting 8h, pluck eyeball and get blood, get blood plasma after centrifugal and adopt GOD-PAP method to measure blood sugar, with serum measured by radioimmunoassay Regular Insulin TC and TG, measure and operate by the explanation on test kit.
All data are all used
represent, data statistics, by SPSS10.0 software processes, is relatively checked with t between group.
Experimental result: in Table 2.From table 2, analyzed, the embodiment 1 separated compound that extracts (ZYC-01 and ZYC-02) can significantly reduce blood sugar, TC and the TG concentration of tissue of experimental diabetic mice, and obviously improves plasma insulin level.This shows that compound of the present invention has the effect that regulates carbohydrate metabolism and treatment artificial diabetes.
Every biochemical indicator after each group experiment of table 2 (
mmol/L; N=10)
Embodiment 4
The acute toxicity test of the embodiment 1 separated compound that extracts
Oral administration
Healthy male mice, body weight 18-23g, is made into aqueous solution gavage 1.0g/kg with ZYC-01 and ZYC-02 respectively, continuous 1 week, has no dead mouse.
Drug administration by injection
Healthy male mice, body weight 18-23g, is made into the aqueous solution with ZYC-01 and ZYC-02 respectively and carries out abdominal injection, continuous 1 week, observes dead mouse situation.
The LD50 of experimental result: ZYC-01 is 5.32 ± 0.26g/kg; The LD50 of ZYC-02 is 4.82 ± 0.74g/kg.
Experimental result discloses, and the toxicity of ZYC-01 and ZYC-02 is less, and pharmacological action is stronger, has good prospect in medicine.
Above-described embodiment is preferably embodiment of the present invention; but embodiments of the present invention are not restricted to the described embodiments; other any do not deviate from change, the modification done under spirit of the present invention and principle, substitutes, combination, simplify; all should be equivalent substitute mode, within being included in protection scope of the present invention.
Claims (1)
1. a preparation method with the compound of a-glucoside inhibiting activity, is characterized in that comprising the following steps:
By ZANGYINCHEN herb grind into powder, with 50 ~ 95% ethanol percolate extraction several times, filter cleaner after united extraction liquid, revolve to steam and remove ethanol, then obtain medicinal extract after dry; Medicinal extract is soluble in water, with dichloromethane extraction; Dichloromethane extraction product adopts silica gel column chromatography separated, uses petroleum ether-ethyl acetate gradient elution, and sherwood oil is 30:1 with the original volume ratio of ethyl acetate, is finally transitioned into 0:1; The compound polarity size showing according to thin-layer chromatography merges elutriant according to the ascending order of polarity and obtains 8 thick cuts, is labeled as respectively F1 ~ F8; Cut F3 prepares compound ZYC-01 and ZYC-02 by silica gel column chromatography in conjunction with preparative high performance liquid chromatography separation; Cut F4 prepares ZYC-04 by gel filtration chromatography; Cut F5 prepares ZYC-03 and ZYC-05 by gel filtration chromatography;
Described ZANGYINCHEN is Swertia mussotii Franch.;
Described ZYC-01 is 1,7,8-trihydroxy--3,4-dimethoxy
ketone, ZYC-02 is 1,3,5,8-tetrahydroxy
ketone, ZYC-03 is 1,3,7,8-tetrahydroxy
ketone, ZYC-04 is 1,7-dihydroxyl-3-methoxyl group
ketone, ZYC-05 is 1,3-dihydroxyl-7,8-dimethoxy
ketone.
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| CN103724313A (en) * | 2013-11-28 | 2014-04-16 | 江苏康缘药业股份有限公司 | Antineoplastic compound extracted from cambogia and preparation method and application of antineoplastic compound |
| CN107226801A (en) * | 2016-03-25 | 2017-10-03 | 中国海洋大学 | A kind of xanthone classes compound and its preparation method of monocrystalline and the application as alpha-glucosidase restrainer |
| CN106008446A (en) * | 2016-04-29 | 2016-10-12 | 广州药本君安医药科技股份有限公司 | Xanthone derivatives, and preparation methods and use of xanthone and derivatives thereof |
| CN106632216B (en) * | 2016-12-30 | 2019-11-15 | 中山大学 | Xanthene one sulfonamide derivatives and its preparation method and application |
| CN108402255A (en) * | 2018-05-23 | 2018-08-17 | 广西中医药大学 | A kind of Camellia nitidissima leaf Hypoylycemic health tea and its preparation method and application |
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| JPH07206673A (en) * | 1994-01-12 | 1995-08-08 | Tsuneo Nanba | Blood sugar reducing agent |
| CN101480422A (en) * | 2009-02-27 | 2009-07-15 | 中央民族大学 | Tibetan oriental wormwood extract as well as preparation method and use thereof |
| CN101845037B (en) * | 2010-05-19 | 2012-05-02 | 重庆市中药研究院 | Method for separating xanthione chemical component in Swertia mussoti |
| CN102516219B (en) * | 2011-10-28 | 2014-12-03 | 沈阳药科大学 | Halogenated polyhydroxy xanthene derivatives, preparation method and use thereof |
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| CN110128396B (en) * | 2019-06-11 | 2021-05-18 | 中山大学 | Xanthone bridged sulfonamide derivative and preparation method and application thereof |
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