CN103012356A - 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 the alpha-glycosidase enzymolysis activity from having of ZANGYINCHEN compound and preparation method thereof and the application in preparation treatment diabetes medicament.
Background technology
ZANGYINCHEN is the rare medicinal herbs that prevents and treat hepatitis, liver injury, hepatic fibrosis, fatty liver diseases in the Tibetan medicine.Chemical research shows, contains Secoiridoid Glycosides, flavones and glycoside thereof, mountain ketone and the Multiple components such as glycoside, triterpenes thereof in the ZANGYINCHEN class main Chinese medicinal materials (Swertia mussotii Franch., Indian Herba Swertiae bimaculatae, Swertia franchetiana H.Smith and flower anchor).
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 a kind of method of separating ketone composition in mountain in the ZANGYINCHEN, comprises the extraction ZANGYINCHEN extract aqueous solution, extracts rough segmentation and three processing steps of column chromatographic isolation and purification according to polarity gradient.
Bibliographical information is arranged, 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).Studies show that, wherein xanthones compounds Swerchirin, methylswertianin and bellidifolin are 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, also separates obtaining in ZANGYINCHEN.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 to obtain from the herb of ZANGYINCHEN.
A further object of the present invention is that the compound with alpha-glucoside inhibiting activity that provides above-mentioned is preparing the application for the treatment of in the carbohydrate metabolism disturbance disease medicament, the especially application in preparation treatment type ii diabetes medicine.
Purpose of the present invention is achieved through the following technical solutions:
A kind of compound with alpha-glucoside inhibiting activity, its structure is suc as formula shown in the I:
(formula I)
In formula I, R
1, R
2, R
3, R
4, R
5Be 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 may further comprise the steps:
With ZANGYINCHEN herb grind into powder, with 50～95% ethanol percolate extraction several times, filter cleaner behind the united extraction liquid, revolve to steam and remove ethanol, obtain medicinal extract after the drying again; Medicinal extract is soluble in water, use dichloromethane extraction; The dichloromethane extraction product adopts silica gel column chromatography to separate, and uses the petroleum ether-ethyl acetate gradient elution, and sherwood oil is 30:1 with the original volume ratio of ethyl acetate, is transitioned at last 0:1; The compound polarity size that shows according to thin-layer chromatography (TLC) obtains 8 thick cuts according to the ascending order merging elutriant of polarity, is labeled as respectively F1～F8; Cut F3 prepares compound ZYC-01 and ZYC-02 by silica gel column chromatography in conjunction with the 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, preferred Swertia mussotii Franch. (Swertia mussotii Franch).
It is active to experimental results show that below the present invention utilizes that above-mentioned compound has a good inhibition to alpha-glycosidase: mensuration xanthones compounds (being compound of the present invention) is to the inhibiting rate of alpha-glycosidase enzymolysis activity take 4-nitrophenol-α-D-glucopyranoside (PNPG) as substrate, with clinical medicine acarbose (Acarbose) as positive control.The 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; Level (IC near acarbose
50=0.99mmol/L).
Experiment shows in the body of artificial diabetes NOD mouse, 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 preparing the medicine for the treatment of carbohydrate metabolism disturbance disease, especially can be used for preparing the medicine for the treatment of type ii diabetes.
The present invention has following advantage and effect with respect to prior art:
ZANGYINCHEN is take the research and development Antihepatitis medicament as main direction traditionally.Compound of the present invention is active and be applied as reported first in preparation treatment diabetes medicament to the inhibition of alpha-glycosidase.
Description of drawings
Fig. 1 is 3,4-dimethoxy-1,7, the mass spectrum of 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
The present invention is described in further detail below in conjunction with embodiment and accompanying drawing, but embodiments of the present invention are not limited to this.
Embodiment 1
Have the extraction separation and purification of the compound of alpha-glucoside inhibiting activity, may further comprise the 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, and then 60 ℃ of vacuum chamber dryings, gets dry extract 509.7g.Medicinal extract is ground, soluble in water, repeatedly extract with isopyknic methylene dichloride, obtain dichloromethane extract 92g.Get dichloromethane extract and adopt silica gel column chromatography to separate, use the petroleum ether-ethyl acetate gradient elution, sherwood oil is 30:1 with the original volume ratio of ethyl acetate, is transitioned at last 0:1; The compound polarity size that shows according to thin-layer chromatography (TLC) obtains 8 thick cuts according to the ascending order merging elutriant of polarity, is labeled as respectively F1～F8.Cut F3 prepares compound ZYC-01 and ZYC-02 by silica gel column chromatography in conjunction with the 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 seen Fig. 1.The 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 seen 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
-1ESI-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 seen 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), the proof product is 1,3-dihydroxyl-7,8-dimethoxy xanthenone (ZYC-05).
It is active to the inhibition of alpha-glycosidase that embodiment 1 extracts the compound that separates
In the present embodiment, people source alpha-glycosidase is available from Sigma company; 4-nitrophenol-α-D-glucopyranoside (PNPG) is available from Merk company.
At first (this system contains 67mmol/L potassium phosphate buffer (pH6.8) 1.7ml to the enzyme activity determination system of potassium phosphate buffer, 1mg/mL gsh 50 μ l) add people source alpha-glucosidase 5 μ l(concentration in: 20mg/mL), 37 ℃ of insulation 10min, after adding 0.116mol/L PNPG50 μ l, 37 ℃ of reaction 10min add Na
2CO
3Termination reaction is measured the absorbancy of the nitrophenol that discharges under the enzyme effect at the 400nm place, and then gets embodiment 1 and extract in the compound adding enzyme activity determination system that separates, and first with 37 ℃ of insulations of enzyme 5min, adds PNPG in 37 ℃ of reaction 10min again, adds Na
2CO
3Termination reaction, the absorbancy of the nitrophenol that under the mensuration enzyme effect of 400nm place, discharges.At last twice absorbance compared and namely got inhibition percentage.
Experimental result sees Table 1.
Table 1 ZANGYINCHEN effective component is active to the inhibition of people source alpha-glycosidase
As can be seen from Table 1, embodiment 1 extracts the compound that separates all has preferably 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, near positive control medicine acarbose.
Embodiment 3
Embodiment 1 extracts the hypoglycemic activity of the compound that separates
Experiment material: the NOD mouse, available 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 behind the 72h is measured respectively blood sugar and Regular Insulin.All blood sugar concentrations〉13mmol/L, glucose in urine be positive, and the many foods of many drinks occur 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 is freely drunk water, and every day is with the distilled water gavage; Every mouse administration of positive controls 50mg/kg gavage; Every mouse administration 20 of medication therapy groups, 40,60mg/kg, respectively gavage.Each organizes mouse respectively at 1d, 10d, 20d empty stomach venous blood sampling, measures blood sugar and insulin concentration.
Behind the diabetic mice last administration fasting 8h, pluck eyeball and get blood, get blood plasma after centrifugal and adopt the GOD-PAP method to measure blood sugar, with serum measured by radioimmunoassay Regular Insulin TC and TG, measure and operate by the explanation on the test kit.
All data are all used
Expression, data statistics is relatively checked with t between group by the SPSS10.0 software processes.
Experimental result: see Table 2.Analyzed as seen by table 2, embodiment 1 extracts the compound (ZYC-01 and ZYC-02) that separates 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 of regulating carbohydrate metabolism and treatment artificial diabetes.
Every biochemical indicator after each group experiment of table 2 (
Mmol/L; N=10)
Embodiment 4
Embodiment 1 extracts the acute toxicity test of the compound that separates
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, in 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, in continuous 1 week, observes the 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 preferably prospect in medicine.
Above-described embodiment is the better 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 the principle, substitutes, combination, simplify; all should be the substitute mode of equivalence, be included within protection scope of the present invention.
Claims (7)
1. compound with alpha-glucoside inhibiting activity is characterised in that its structure is suc as formula shown in the I:
2. the compound with alpha-glucoside inhibiting activity according to claim 1, it is characterized in that: described compound with alpha-glucoside inhibiting activity is 1,7,8-trihydroxy--3,4-dimethoxy xanthenone, 1,3,5,8-tetrahydroxy mountain ketone, 1,3,7,8-tetrahydroxy mountain ketone, 1,7-dihydroxyl-3-methoxyl xanthone and 1,3-dihydroxyl-7, the 8-dimethoxy xanthenone.
3. claim 1 or 2 described preparation methods with compound of alpha-glucoside inhibiting activity is characterized in that may further comprise the steps:
With ZANGYINCHEN herb grind into powder, with 50～95% ethanol percolate extraction several times, filter cleaner behind the united extraction liquid, revolve to steam and remove ethanol, obtain medicinal extract after the drying again; Medicinal extract is soluble in water, use dichloromethane extraction; The dichloromethane extraction product adopts silica gel column chromatography to separate, and uses the petroleum ether-ethyl acetate gradient elution, and sherwood oil is 30:1 with the original volume ratio of ethyl acetate, is transitioned at last 0:1; The compound polarity size that shows according to thin-layer chromatography obtains 8 thick cuts according to the ascending order merging elutriant of polarity, is labeled as respectively F1～F8; Cut F3 prepares compound ZYC-01 and ZYC-02 by silica gel column chromatography in conjunction with the 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.
4. the preparation method with compound of alpha-glucoside inhibiting activity according to claim 3 is characterized in that: described ZANGYINCHEN refers to Swertia mussotii Franch., Indian Herba Swertiae bimaculatae, Swertia franchetiana H.Smith and flower anchor.
5. the preparation method with compound of alpha-glucoside inhibiting activity according to claim 3, it is characterized in that: described ZANGYINCHEN is Swertia mussotii Franch..
6. claim 1 or the 2 described application of compound in the medicine of preparation treatment carbohydrate metabolism disturbance disease with alpha-glucoside inhibiting activity.
7. claim 1 or the 2 described application of compound in the medicine of preparation treatment type ii diabetes with alpha-glucoside inhibiting activity.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| CN106632216A (en) * | 2016-12-30 | 2017-05-10 | 中山大学 | Xanthone sulfonamide derivative as well as preparation method and application 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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| CN103012356B (en) | 2014-12-03 |
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