CN104257715A - Artemisia sacrorum extract as well as preparation method and application thereof - Google Patents
Artemisia sacrorum extract as well as preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses an artemisia sacrorum extract which contains total-flavone compounds, wherein the total-flavone compounds comprise one or more of 6-methoxy-quercetagetin-7-O-beta-D-glucoside, quercetin-3-O-beta-D-glucoside, isorhamnetin, queretagetin-3-O-beta-D-glucoside, acacetin-7-O-beta-D-glucoside, rutin, 5,7,4'-trihydroxyflavone, 3,3',4',5,7-pentahydroxyflavone, 5,7,4'-trihydroxy-3'-methoxyflavone, kaempferol, 3,5,7,4'-tetrahydroxy-6-methoxyflavone, 3',4',5,7-tetrahydroxyflavone, 5,7,4'-trihydroxy-6,3'-dimethoxyflavone, 5,7,4'-trihydroxy-6-methoxyflavone, quercitrin, 7,3',4'-trimethyl quercetin, 5-hydroxy-7,4'-dimethoxyflavone, 5,4'-dihydroxy-7-methoxyflavone genkwanin, 5,7-dihydroxy-4'-methoxyflavone, 5,7,3'-dihydroxy-4-methoxyflavone and derivatives. The artemisia sacrorum extract has remarkable prevention and treatment effects on liver injury.
Description
Technical field
The present invention relates to medical art, particularly relate to Herba Artemisiae extract and its production and use.
Background technology
Compositae sagebruss more than about 350 kinds, be widely distributed in the Temperate Region in China in the Northern Hemisphere, Europe, Asia, North America, minority kind is distributed to the torrid areas such as Africa, South Asia and Central America, China's (do not comprise the thin,tough silk punt-pole separated and belong to Seriphidium (Bess.) Poljak.) has more than 170 kinds, various places are all produced, wherein as Herba Artemisiae annuae A.annua L, Herba Artemisiae Annuae A.apiacea Hance, Herba Artemisiae Scopariae A.capillaris Thunb. and A.argyi Levl.etVant. etc. are all used as medicine, the purposes of You Yiai is the widest, and Herba Artemisiae annuae can treating malaria disease, also can alcoholic cake.
Herba Artemisiae, draft, undershrub or undershrub, that rubs is often savory; Leaf alternate, often divides; Head inflorescence is little, the opposite sex, plate-like, normal curved vertical, lines up panicle, spike or raceme; Spend whole tubulose; Edge is spent female, 1 row, very thin, 2-3 fissure; Disc floret both sexes, solid or infertile; Receptacle of inflorescence is exposed or have holder hair; Achene is little, has rill, without pappus.Head inflorescence has separated containing the kind of homogamous flower and has separately stood as thin,tough silk artemisia.
Hepatic injury is the pathological state a kind of with conspicuous characteristics that multiple hepatic disease has, and human health in serious threat.Various harmful factor such as medicine, virus, ethanol, biology etc. may cause liver function to have infringement in various degree, thus make the removing toxic substances of liver, excretory function and stock to reduce with regeneration capacity, hepatic blood flow reduces, metabolic burden increases the weight of, thus it is disorderly that environment occurs, hepatic necrosis and apoptosis, and then cause hepatic injury.The hepatic injury that various harmful factor causes mainly contains the types such as drug induced hepatic injury, viral hepatic injury, alcoholic liver injury, immunologic liver injury, and the whole world has billions of people once or just to suffer from the misery of hepatic injury.For the hepatitis B virus in the viral hepatic injury cause of disease, the whole world has 2,000,000,000 people to infect hepatitis B virus (HBV), and wherein 3.78 hundred million people change into chronic infection, and 0.5-1.2 hundred million people dies from liver cirrhosis, liver failure, hepatocarcinoma etc.Drug induced hepatic injury, alcoholic liver injury patient are countless too.The long-term existence of hepatic injury often causes hepatic fibrosis, is and then brings out liver cirrhosis, liver failure, even the important initiating agent of hepatocarcinoma.Therefore prevention and therapy hepatocyte injury is one of important step of liver disease clinically, is the basis suppressing the Occurrence and development of diseases such as hepatic fibrosis, hepatic necrosis, fatty liver, cholestasis, liver cirrhosis and hepatocarcinoma.
Treatment and preventing liver injury, do not have particularly preferred way clinically.Therefore at present very strong to the demand of the low anti-liver injury medicament of clear curative effect, side effect clinically.Herba Artemisiae has one of distinguishing feature towards medicine on extensive application basis, Area of Yanbian of Jilin Province.Herba Artemisiae is the dry aerial parts of Compositae sagebruss Herba Artemisiae Artemisia sacrorum Ledeb., and at Changbaishan area application Herba Artemisiae unguentum, the various liver damage disease of prevention and therapy, has long Popular Utilization history.When treating the hepatitis symptoms such as hypochondriac pain, common people are ready to select Herba Artemisiae as choice drug.
Summary of the invention
The invention provides a kind of Herba Artemisiae extract and its production and use.
The present invention adopts following technical scheme:
Total flavones compound is comprised in Herba Artemisiae extract of the present invention.In Herba Artemisiae extract, total flavones compounds content is greater than 50% (weight percent content).
Described total flavones compound comprises one or more of following compounds: 6-methoxyl group-quercetagetin-7-O-β-D-Glucose glycosides, Quercetin-3-O-β-D glucoside, isorhamnetin, patuletin-3-O-β-D-Glucose glycosides, acacetin7OβDglucoside, rutin, 5, 7, 4 '-trihydroxyflavone, 3, 3 ', 4 ', 5, 7-pentahydroxyflavone, 5, 7, 4 '-trihydroxy-3 '-methoxy flavone, kaempferol, 3, 5, 7, 4 '-tetrahydroxy-6-methoxy-2-phenyl-4H-chromen-4-one, 3 ', 4 ', 5, 7-kaempferol, 5, 7, 4 '-trihydroxy-6, 3 '-dimethoxy flavone, 5, 7, 4 '-trihydroxy-6-methoxy-2-phenyl-4H-chromen-4-one, Quercitroside, 7, 3 ', 4 '-trimethyl Quercetin, 5-hydroxyl-7, 4 '-dimethoxy flavone, 5, 4 '-dihydroxy-7-methoxy flavone Flos Genkwa element, 5, 7-dihydroxy-4 '-methoxy flavone, 5, 7, 3 '-dihydroxy-4-methoxy flavone and derivant thereof.
The preparation method of Herba Artemisiae extract of the present invention is as follows: with the aerial parts of the Herba Artemisiae of Herba Artemisiae dry product or fresh collection for raw material, adopt solvent extraction method, solvent extraction, Flavonoids by Macroporous Adsorption Resin, Thin-layer chromatography, normal phase column chromatography method, reversed-phase column chromatography, one or more techniques in gel process, and be prepared into Herba Artemisiae extract in conjunction with concentrate drying, lyophilization, spraying dry.
In solvent extraction method and solvent extraction, one or more selecting in water, methanol, ethanol, n-butyl alcohol or other lower aliphatic alcohols do solvent, in room temperature lixiviate or supersound extraction, or the lower lixiviate of heating or reflux, extract, extraction time is once or repeatedly.
In Flavonoids by Macroporous Adsorption Resin, select normal pressure or pressurized column chromatography, resin adopts HPD-100, HPD-300, D-101, X-5, H103, AB-8, the resin of DA-201, HPD-400, NKA-9, S-8, HPD-500 model, eluting solvent adopts water, methanol, ethanol, acetone or containing one or more in aqueous methanol, aquiferous ethanol or aqueous acetone, is fixed eluting or the gradient elution of concentration during eluting.
In Thin-layer chromatography, select normal pressure or pressurized column chromatography, column packing used is polyamide, and eluting solvent adopts water, methanol, ethanol, acetone or containing one or more in aqueous methanol, aquiferous ethanol or aqueous acetone, is fixed eluting or the gradient elution of concentration during eluting.
In reversed-phase column chromatography, select normal pressure or pressurized column chromatography, eluting solvent adopts water, methanol, ethanol, acetone or containing one or more in aqueous methanol, aquiferous ethanol or aqueous acetone, is fixed eluting or the gradient elution of concentration during eluting.
In normal phase column chromatography method, select normal pressure or pressurized column chromatography, eluting solvent adopts methanol, ethanol, acetone, ethyl acetate, petroleum ether, n-butyl alcohol, dichloromethane, one or more in chloroform, is fixed eluting or the gradient elution of concentration during eluting.
Herba Artemisiae extract of the present invention has effect of prevention and therapy fatty liver, drug induced hepatic injury, viral hepatic injury, alcoholic liver injury and/or immunologic liver injury disease.
Herba Artemisiae extract of the present invention can make the health product or medicine that are used for the treatment of hepatic injury, described medicine is that described compound and pharmaceutically acceptable medicine are made liquid, solid, semisolid, oral or parenteral, pharmaceutically acceptable any dosage forms such as capsule, powder, pill, tablet, oral liquid, injection.
Medicine of the present invention can suppress generation and the development of the diseases such as hepatic fibrosis, hepatic necrosis, fatty liver, cholestasis, liver cirrhosis and hepatocarcinoma.
The active component of the medicine that the present invention obtains extracts from Herba Artemisiae to obtain, and its wide material sources, have significant curative effect to hepatic injury.
Accompanying drawing explanation
Fig. 1 is the schematic diagram of the impact of 95%EE (a Herba Artemisiae extract part) cell proliferation and accumulation of lipid.
HepG2 cell is with the 95%EE process 24h of variable concentrations (0,25,50,100 μ g/ml).Cell proliferation carries out testing (A) with MTS method.HepG2 cell, with the 95%EE process 24h of variable concentrations (0,25,50,100 μ g/ml), then dyes with Oil Red O.HepG2 cell is with the 95%EE process 24h of variable concentrations (0,25,50,100 μ g/ml), and content of triglyceride carries out testing with spectrophotography and is expressed as μ g triglyceride/mg protein (C).Tables of data reaches meansigma methods ± S.E.*, * * * represents respectively and compares p < 0.01 and p < 0.001 with untreated matched group.
Fig. 2 is 50%EE, 95%EE and WE (being the respectively a Herba Artemisiae extract part) schematic diagram on the impact of AMPK and ACC phosphorylation in HepG2 cell.
Cell processes 24h with 50%EE, 95%EE and WE respectively to indicate concentration.Extract protein and use pAMPK, AMPK, pACC, ACC, and β-actin antibody carries out western blot analysis.β-actin protein level is used as internal control.
Fig. 3 is the schematic diagram of 95%EE on the impact of AMPK and ACC phosphorylation in HepG2 cell.
Cell carries out processing (A) in the different sign time with 100 μ g/ml 95%EE.Cell is with the 95%EE process 24h (B) of different sign concentration.Cell with compound C pretreatment 2h, then with 95%EE process 24h (C, D).Extract protein and carry out western blot analysis with pAMPK, AMPK, pACC, ACC and β-actin.β-actin protein level is used as internal control.Tables of data reaches meansigma methods ± S.E (n=3), and * * representative is compared with undressed matched group, p < 0.01.
Detailed description of the invention
The following examples describe in further detail of the present invention.
The preparation method of embodiment 1. Herba Artemisiae extract
Get 500g dry product Herba Artemisiae and add water soaking 0.5-3h post-heating 0.5-3h, filter and obtain filtrate I, add water in residue and heat 0.5-3h again, obtain filtrate II, merging filtrate I and II, obtain Herba Artemisiae Aqueous extracts.Herba Artemisiae Aqueous extracts is splined in pretreated macroporous adsorptive resins, uses water and 10%-95% ethanol elution successively.10%-95% ethanol elution concentrates postlyophilization to dry, namely obtains Herba Artemisiae extract.
Determination of total flavonoids in embodiment 2. Herba Artemisiae extract
Flavone standard curve:
Reagent: rutin, methanol
Control substance of Rutin solution preparation
Precision takes 5.0mg rutin, adds methanol, dissolves and is settled to 100ml, obtains 50 μ g/ml.
Draw control substance of Rutin solution 0,1.0ml, 2.0ml, 3.0ml, 4.0ml, 5.0ml, 6.0ml, 7.0ml, in 10ml volumetric flask, add methanol to graduation mark, shake up, measure wavelength: 360nm.Result is as follows:
y＝0.1371x+0.0093?R
2＝0.9999
The preparation of test sample (Herba Artemisiae 50% ethanol elution thing) solution:
Extracting sample solution 1ml, in evaporating dish, adds the absorption of 1g Silon, in thermostatic drying chamber, 50 DEG C volatilize solvent, proceed in chromatographic column, with 30ml petroleum ether eluting, discard petroleum ether, use 100ml methanol-eluted fractions total flavones again, collect eluent, pressurization evaporate to dryness, residue dissolve with methanol, be settled in 25ml volumetric flask, obtain final product.
Test sample absorbance measurement:
Get the eluate of 1ml test sample Silon, put into 25ml volumetric flask, add methanol constant volume to 25ml, then take out 1ml from 25ml, add methanol dilution 10 times, surveying absorbance is 0.316, and calculating general flavone content is 28.115mg/ml.
Scaling results:
Total flavones component content is 68.2%.
The separation of chemical composition and Structural Identification in embodiment 3. Herba Artemisiae extract
Herba Artemisiae extract adopts the solution such as dichloromethane, ethyl acetate to extract, extract is respectively by various separation methods such as reverse phase silica gel post, SephadexLH-20 gel column, preparation HPLC, ODS lower pressure column, through system gradient elutions such as methanol-waters, be separated and obtain 20 flavone compounds.By wave spectrum analysis and document contrast, determine that its chemical constitution is respectively: 1) 6-methoxyl group-quercetagetin-7-O-β-D-Glucose glycosides, 2) Quercetin-3-O-β-D glucoside, 3) isorhamnetin, 4) patuletin-3-O-β-D-Glucose glycosides, 5) acacetin7OβDglucoside, 6) rutin, 7) 5,7,4 '-trihydroxyflavone, 8) 3,3',4',5,7-pentahydoroxyflavone, 9) 5,7,4 '-trihydroxy-3 '-methoxy flavone, 10) kaempferol, 11) 3,5,7,4 '-tetrahydroxy-6-methoxy-2-phenyl-4H-chromen-4-one, 12) Luteolin, 13) 5,7,4 '-trihydroxy-6,3 '-dimethoxy flavone, 14) 5,7,4 '-trihydroxy-6-methoxy-2-phenyl-4H-chromen-4-one, 15) Quercitroside, 16) 7,3 ', 4 '-trimethyl Quercetin, 17) 5-hydroxyl-7,4 '-dimethoxy flavone, 18) 5,4 '-dihydroxy-7-methoxy flavone Flos Genkwa elements, 19) 5,7-dihydroxy-4 '-methoxy flavones, 20) 5,7,3 '-dihydroxy-4-methoxy flavone and derivant etc. thereof.
In Herba Artemisiae extract, the spectral data of flavone compound is as follows respectively:
Compound 1:6-methoxyl group-quercetagetin-7-O-β-D-Glucose glycosides
1H-NMR(300MHz，(CD
3)
2CO)δppm：12.42(1H，s，5-OH)，7.89(1H，d，J＝2.01Hz，H-2’)，7.46(1H，dd，J＝2.04，8.34Hz，H-6’)，6.82(1H，d，J＝8.46Hz，H-5’)，6.47(1H，s，H-8)，5.12(1H，d，J＝7.26Hz，H-1”)，3.75(3H，s，6-OCH
3).
13C-NMR(75MHz，DMSO-d
6)δppm：145.26(C-2)，133.43(C-3)，178.11(C-4)，156.72(C-5)，131.70(C-6)，152.84(C-7)，94.22(C-8)，151.98(C-9)，104.76(C-10)，122.06(C-1′)，116.64(C-2′)，157.95(C-3′)，148.91(C-4′)，115.65(C-5′)，121.67(C-6′)，101.31(C-1″)，74.55(C-2″)，76.96(C-3″)，70.41(C-4″)，78.02(C-5″)，61.45(C-6″)，60.43(6-OCH
3).
Compound 2: Quercetin-3-O-β-D glucoside
1H-NMR(300MHz，CD
3OD)δppm：7.68(1H，dd，J＝2.10Hz，H-2’)，7.56(1H，dd，J＝2.1，9.00Hz，H-6’)，6.83(1H，d，J＝8.40Hz，H-5’)，6.36(1H，d，J＝2.10Hz，H-8)，6.17(1H，d，J＝2.10Hz，H-6)，5.23(1H，d，J＝7.20Hz，3-O-glu)，3.30-3.71(m-sugar-H).
13C-NMR(75MHz，CD
3OD)δppm：58.46(C-2)，135.60(C-3)，179.50(C-4)，163.06(C-5)，99.87(C-6)，166.02(C-7)，94.69(C-8)，159.00(C-9)，105.68(C-10)，123.06(C-1′)，115.99(C-2′)，145.91(C-3′)，149.85(C-4′)，117.54(C-5′)，123.19(C-6′)，104.20(C-1″)，75.72(C-2″)，78.10(C-3″)，71.20(C-4″)，78.39(C-5″)，62.53(C-6″).
Compound 3: isorhamnetin
1H-NMR(300MHz，CD
3OD)δppm：7.73(1H，d，J＝2.10Hz，H-2′)，7.63(1H，dd，J＝2.10，8.70Hz，H-6′)，6.88(1H，d，J＝8.70Hz，H-5′)，6.38(1H，d，J＝2.10Hz，H-8)，6.18(1H，d，J＝2.10Hz，H-6)，3.59(3H，s，-OCH
3).
13C-NMR(75MHz，CD
3OD)：148.78(C-2)，137.23(C-3)，177.34(C-4)，162.52(C-5)，99.28(C-6)，165.72(C-7)，94.43(C-8)，158.25(C-9)，104.49(C-10)，124.15(C-1’)，116.22(C-2’)，147.99(C-3’)，146.24(C-4’)，115.98(C-5’)，121.66(C-6’)，65.10(3’-OCH
3)。
Compound 4: patuletin-3-O-β-D-Glucose glycosides
1H-NMR(500MHz，CD
3OD)δppm：6.49(1H，s)，3.87(3H，s)，7.70(1H，d，J＝2.00Hz)，7.58(1H，dd，J＝2.00，2.00Hz)，6.86(1H，d，J＝8.50Hz)，5.27(1H，d，J＝7.50Hz)，5.27(1H，d，J＝7.50Hz)，3.26～3.57(m，suger-H)。
13C-NMR(125MHz，CD
3OD)：159.19(C-2)，135.34(C-3)，179.76(C-4)，153.87(C-5)，132.80(C-6)，159.07(C-7)，95.03(C-8)，153.87(C-9)，106.12(C-10)，123.22(C-1’)，117.60(C-2’)，145.92(C-3’)，149.66(C-4’)，116.03(C-5’)，123.15(C-6’)，104.37(C-1″)，75.75(C-2″)，78.39(C-3″)，71.29(C-4″)，78.14(C-5″)，62.62(C-6″)，60.96(6-OCH
3)。
Compound 5: acacetin7OβDglucoside
1H-NMR(500MHz，CD
3OD)δppm：8.04(2H，d，J＝8.00Hz)，7.11(2H，d，J＝8.00Hz)，5.08(1H，d，J＝7.50Hz)，3.87(3H，s，OCH
3)，3.22～3.81(m，sugar-H)。
13C-NMR(125MHz，CD
3OD)：158.94(C-2)，104.83(C-3)，179.14(C-4)，149.12(C-5)，103.58(C-6)，153.82(C-7)，77.57(C-8)，144.87(C-9)，1005.30(C-10)，123.00(C-1’)，134.77(C-2’)，117.49(C-3’)，145.19(C-4’)，116.41(C-5’)，123.40(C-6’)，104.73(C-1″)，70.51(C-2″)，75.05(C-3″)，61.82(C-4″)，77.14(C-5″)，61.40(C-6″)，49.83(4’-OCH
3)。
Compound 6: rutin
1H-NMR(500MHz，CD
3OD)δppm：8.03(1H，d，J＝9.00Hz)，7.58(1H，dd，J＝1.00，1.00Hz)，6.95(1H，d，J＝8.50Hz)，4.98(1H，d，J＝8.00Hz)，4.54(1H，br?s)，1.08(3H，d，J＝6.0Hz，OCH
3)，3.35～4.52(m，sugar-H)。
13C-NMR(125MHz，CD
3OD)：149.40(C-2)，133.30(C-3)，178.87(C-4)，154.01(C-5)，101.88(C-6)，158.90(C-7)，77.18(C-8)，152.56(C-9)，106.89(C-10)，123.59(C-1’)，116.40(C-2’)，134.54(C-3’)，145.07(C-4’)，117.60(C-5’)，123.10(C-6’)，104.78(C-1″)，73.19(C-2″)，76.31(C-3″)，71.42(C-4″)，75.00(C-5″)，61.37(C-6″)，103.65(C-1′″)，69.60(C-2′″)，70.84(C-3′″)，71.57(C-4′″)，68.29(C-5′″)，17.54(C-6′″)。
Compound 7:5,7,4 '-trihydroxyflavone
1H-NMR(500MHz，DMSO-d
6)δppm：6.19(1H，d，J＝2.1Hz，H-6)，6.48(1H，d，J＝2.1Hz，H-8)，6.74(1H，s，H-3)，6.92(2H，d，J＝8.8Hz，H-3′，H-5′)，，7.90(2H，d，J＝8.8Hz，H-2′，H-6′).
13C-NMR(125MHz，DMSO-d
6)δppm：164.17(C-2)，103.04(C-3)，181.77(C-4)，157.48(C-5)，98.90(C-6)，163.88(C-7)，94.16(C-8)，161.22(C-9)，103.77(C-10)，121.38(C-1′)，128.56(C-2′)，116.05(C-3′)，161.06(C-4′)，116.05(C-5′)，128.56(C-6′).
Compound 8:3,3 ', 4 ', 5,7-pentahydroxyflavone
1H-NMR(300MHz，CD
3OD)δppm：6.18(1H，d，J＝2.0Hz，H-6)，6.38(1H，d，J＝2.0Hz，H-8)，7.73(1H，d，J＝2.1Hz，H-2′)，6.88(1H，d，J＝8.52Hz，H-5′)，7.63(1H，dd，J＝2.19，8.52Hz，H-6′).
13C-NMR(75MHz，CD
3OD)δppm：147.99(C-2)，137.24(C-3)，177.34(C-4)，158.23(C-5)，99.22(C-6)，162.52(C-7)，94.39(C-8)，165.58(C-9)，104.52(C-10)，148.77(C-1′)，115.98(C-2′)，124.14(C-3′)，146.22(C-4′)，116.22(C-5′)，121.67(C-6′).
Compound 9:5,7,4 '-trihydroxy-3 '-methoxy flavone
1H-NMR(500MHz，CD
3OD)δppm：3.97(3H，s，-OCH
3)，6.19(1H，d，J＝2.0Hz，H-6)，6.44(1H，d，J＝2.0Hz，H-8)，6.61(1H，s，H-3)，6.90(1H，d，J＝8.5Hz，H-5′)，7.48(1H，d，J＝2.0Hz，H-2′)，7.52(1H，dd，J＝8.5，2.0Hz，H-6′).
13C-NMR(125MHz，CD
3OD)δppm：160.89(C-2)，104.15(C-3)，183.79(C-4)，163.13(C-5)，123.75(C-6)，166.09(C-7)，95.31(C-8)，156.19(C-9)，105.39(C-10)，124.69(C-1′)，110.70(C-2′)，149.58(C-3′)，152.52(C-4′)，116.86(C-5′)，121.77(C-6′)，56.72(-OCH
3).
Compound 10: kaempferol
1H-NMR(500MHz，CD
3OD)δppm：6.18(1H，d，J＝2.0Hz，H-6)，6.40(1H，d，J＝2.0Hz，H-8)，6.90(2H，d，J＝9.0Hz，H-3′，H-5′)，8.09(2H，d，J＝9.0Hz，H-2′，H-6′).
13C-NMR(125MHz，CD
3OD)δppm：148.15(C-2)，137.17(C-3)，177.44(C-4)，158.35(C-5)，99.38(C-6)，165.77(C-7)，94.55(C-8)，162.53(C-9)，104.56(C-10)，123.81(C-1′)，130.69(C-2′)，116.35(C-3′)，160.57(C-4′)，116.35(C-5′)，130.69(C-6′).
Compound 11:3,5,7,4 '-tetrahydroxy-6-methoxy-2-phenyl-4H-chromen-4-one
1H-NMR(500MHz，CD
3OD)δppm：3.87(3H，s，-OCH
3)，6.48(1H，s，H-8)，6.89(2H，d，J＝8.8Hz，H-3′，H-5′)，8.07(2H，d，J＝8.8Hz，H-2′，H-6′).
13C-NMR(125MHz，CD
3OD)δppm：148.39(C-2)，136.85(C-3)，177.64(C-4)，153.67(C-5)，132.27(C-6)，158.50(C-7)，94.80(C-8)，152.98(C-9)，105.01(C-10)，123.77(C-1′)，130.72(C-2′)，116.33(C-3′)，160.60(C-4′)，116.33(C-5′)，130.72(C-6′)，60.99(-OCH
3).
Compound 12:3 ', 4 ', 5,7-kaempferol
1H-NMR(500MHz，CD
3OD)δppm：7.42(1H，dd，J＝2.0，8.0Hz，H-6′)，7.39(1H，d，J＝2.0Hz，H-2′)，6.94(1H，d，J＝8.5Hz，H-5′)，6.75(1H，s，H-3)，6.44(1H，d，J＝2.0Hz，H-8)，6.20(1H，d，J＝2.0Hz，H-6).
13C-NMR(125MHz，CD
3OD)δppm：164.73(C-2)，104.62(C-3)，183.66(C-4)，162.33(C-5)，99.78(C-6)，165.61(C-7)，94.75(C-8)，158.25(C-9)，103.89(C-10)，122.31(C-1′)，114.22(C-2′)，146.78(C-3′)，150.71(C-4′)，116.01(C-5′)，120.46(C-6′).
Compound 13:5,7,4 '-trihydroxy-6,3 '-dimethoxy flavone
1H-NMR(500MHz，CD
3OD)δppm：3.96(3H，s，-OCH
3)，3.88(3H，s，-OCH
3)，6.56(1H，s，H-3)，6.61(1H，s，H-8)，7.45(1H，d，J＝2.0Hz，H-2′)，6.92(1H，d，J＝8.35Hz，H-5′)，7.49(1H，dd，J＝2.0，8.35Hz，H-6′).
13C-NMR(125MHz，CD
3OD)δppm：166.24(C-2)，103.80(C-3)，184.23(C-4)，154.70(C-5)，132.97(C-6)，158.90(C-7)，95.38(C-8)，154.70(C-9)，105.78(C-10)，123.78(C-1′)，110.75(C-2′)，149.52(C-3′)，152.13(C-4′)，116.81(C-5′)，121.76(C-6′)，56.71(-OCH
3)，60.94(-OCH
3).
Compound 14:5,7,4 '-trihydroxy-6-methoxy-2-phenyl-4H-chromen-4-one
1H-NMR(500MHz，CD
3OD)δppm：3.89(3H，s，-OCH
3)，6.58(1H，s，H-3)，6.67(1H，s，H-8)，6.92(2H，d，J＝8.75Hz，H-3′，H-5′)，7.84(2H，d，J＝8.75Hz，H-2′，H-6′).
13C-NMR(125MHz，CD
3OD)δppm：164.46(C-2)，102.46(C-3)，184.31(C-4)，152.69(C-5)，131.70(C-6)，，157.66(C-7)，94.17(C-8)，152.69(C-9)，104.87(C-10)，122.14(C-1′)，128.45(C-2′)，1116.15(C-3′)，161.32(C-4′)，116.15(C-5′)，128.45(C-6′).
Compound 15: Quercitroside
1H-NMR(300MHz，Acetone-d
6)δppm：6.25(1H，d，J＝2.07Hz，H-6)，6.46(1H，d，J＝2.07Hz，H-8)，7.49(1H，d，J＝2.07Hz，H-2′)，7.39(1H，dd，J＝2.1，8.34Hz，H-6′)，6.98(1H，d，J＝8.34Hz，H-5′)，5.28(1H，d，J＝1.5Hz，H-1″)，3.72(1H，dd，J＝3.4，9.4Hz，H-3″)，3.34-3.43(2H，m，H-4″，H-5″)，0.91((3H，d，J＝5.7Hz，-CH3).
13C-NMR(75MHz，Acetone-d
6)δppm：158.15(C-2)，135.63(C-3)，179.18(C-4)，163.06(C-5)，99.35(C-6)，164.77(C-7)，94.35(C-8)，157.63(C-9)，105.75(C-10)，122.43(C-1′)，115.99(C-2′)，145.68(C-3′)，148.85(C-4′)，116.56(C-5′)，122.73(C-6′)，102.57(C-1″)，71.26(C-2″)，71.97(C-3″)，72.86(C-4″)，71.19(C-5″)，17.63(C-6″).
Compound 16:7,3 ', 4 '-trimethyl Quercetin
1H-NMR(300MHz，CDCl
3)δppm：13.08(1H，s，5-OH)，7.53(1H，dd，J＝8.50，2.00Hz，H-6′)，7.34(1H，d，J＝2.00Hz，H-2′)，6.98(1H，d，J＝8.50Hz，H-5′)，6.61(1H，s，H-8)，6.58(1H，s，H-6)，4.05(3H，s，OCH
3)，3.98(3H，s，OCH
3)，3.97(3H，s，OCH
3).
Compound 17:5-hydroxyl-7,4 '-dimethoxy flavone
1H-NMR(300MHz，CDCl
3)δppm：7.87(2H，d，J＝8.85Hz，H-2′，6′)，7.04(2H，d，J＝8.85Hz，H-3′，5′)，6.60(1H，s，H-3)，6.51(1H，d，J＝2.10Hz，H-8)，6.39(1H，d，J＝2.10Hz，H-6)，3.91(3H，s，OCH
3)，3.90(3H，s，OCH
3).
13C-NMR(75MHz，DMSO-d
6)δppm：164.51(C-2)，104.41(C-3)，182.47(C-4)，162.24(C-5)，98.04(C-6)，165.29(C-7)，92.64(C-8)，157.06(C-9)，104.92(C-10)，123.63(C-1′)，128.06(C-2′)，114.65(C-3′)，162.61(C-4′)，114.52(C-5′)，128.06(C-6′)，55.79(OCH
3)，55.54(OCH
3).
Compound 18:5,4 '-dihydroxy-7-methoxy flavone
1H-NMR(300MHz，DMSO-d
6)δppm：3.86(3H，s，OCH
3)，6.37(1H，d，J＝2.08Hz，H-6)，6.76(1H，d，J＝2.08Hz，H-8)，6.86(1H，s，H-3)，7.11(2H，d，J＝8.85Hz，H-3′，5′)，8.02(2H，d，J＝8.85Hz，H-2′，6′)，10.63(1H，br.s，4′-OH)，12.93(1H，s，5-OH).
Compound 19:5,7-dihydroxy-4 '-methoxy flavone
1H-NMR(300MHz，DMSO-d
6)δppm：3.87(3H，s，OCH
3)，6.20(1H，d，J＝1.80Hz，H-6)，6.50(1H，d，J＝1.80Hz，H-8)，6.84(1H，s，H-3)，6.93(2H，d，J＝8.70Hz，H-3′，5′)，7.95(2H，d，J＝8.70Hz，H-2′，6′)，10.63(1H，br.s，4′-OH)，12.97(1H，s，5-OH).
Compound 20:5,7,3 '-dihydroxy-4-methoxy flavones
1H-NMR(300M?Hz，ACETONE)δppm：6.14(1H，s，6-H)，6.44(1H，s，8-H)，6.50(1H，s，3-H)，7.00(1H，d，J＝8.40Hz，5′-H)，7.37(1H，d，J＝1.80Hz，2′-H)，7.41(1H，m，6′-H)，12.86(1H，s，5-OH)，3.82(3H，s，4′-OCH
3).
In Herba Artemisiae extract, the chemical structural formula of flavone compound is as follows:
The activity assay of embodiment 4. Herba Artemisiae extract and the therapeutical effect to hepatic injury
1) Herba Artemisiae extract 95%EE part is on lipopectic impact
In order to observe the impact of 95%EE on lipid accumulation, process HepG2 cell 24hr then with Oil Red O dyeing with the 95%EE (0,25,50,100 μ g/ml) of variable concentrations.As shown in Figure 1 C, 95%EE suppresses accumulation of lipid and presents dose dependent.In addition, after the 95%EE (0,25,50,100 μ g/ml) with variable concentrations processes HepG2 cell 24hr, the content of triglyceride in cell is tested.As shown in Figure 1B, 95%EE obviously lowers content of triglyceride and presents dose dependent.Compare with non-administered group, 95%EE (the 25 μ g/ml of variable concentrations, 50 μ g/ml, 100 μ g/ml) make lipid storage decrease 13.2% (p < 0.01) respectively, 14.6% (p < 0.01), 19.0% (p < 0.001).These results show that 95%EE can suppress accumulation of lipid.
2) impact of Herba Artemisiae extract 95%EE part on AMPK phosphorylation
In order to filter out the effective site of AMPK phosphorylation, test WE by western blotting, 50%EE, and 95%EE is on the impact of AMPK activity.95%EE obviously promotes the phosphorylation of AMPK and ACC and presents dose dependent (Fig. 2).Therefore, in this experiment, 95%EE part is selected further to study.In order to inquire into the impact of 95%EE on AMPK phosphorylation, in the different sign time, HepG2 cell is processed respectively with the 95%EE of 100 μ g/ml concentration.After processing, collecting cell also extracts cytolysate at every turn.The state of activation of AMPK α and ACC adopts the antibody of phosphorylation to be tested by western blotting.Result shows that 95%EE have activated AMPK α-Thr172 in HepG2 cell and presentative time dependency (Fig. 3 A).Consistent with the AMPK activity added, ACC-Ser79 phosphorylation (the characteristic site of AMPK phosphorylation most) have also been obtained to be increased and presentative time dependency.
Then, the 95%EE process 24hr of HepG2 cell variable concentrations.As shown in Figure 3 B, 95%EE promotes the phosphorylation of AMPK and ACC and presents dose dependent.Therefore, in order to confirm the impact of 95%EE on AMPK activity, we attempt to suppress AMPK and ACC active by pharmacological methods.When with a kind of AMPK inhibitor, compound C (10 μMs), after carrying out pretreatment to HepG2 cell, AMPK and ACC phosphorylation degree caused by 95%EE is obviously weakened (Fig. 3 C, 3D).These results show that 95%EE passes through to activate the AMPK activity of HepG2 cell and plays a role.
Although illustrate and describe embodiments of the invention, for the ordinary skill in the art, be appreciated that and can carry out multiple change, amendment, replacement and modification to these embodiments without departing from the principles and spirit of the present invention, scope of the present invention is by claims and equivalents thereof.
Claims (10)
1. Herba Artemisiae extract, is characterized in that: containing total flavones compound in described Herba Artemisiae extract.
2. Herba Artemisiae extract as claimed in claim 1, is characterized in that: in Herba Artemisiae extract, total flavones compounds content is greater than 50%.
3. Herba Artemisiae extract as claimed in claim 1, is characterized in that: described total flavones compound comprises one or more of following compounds: 6-methoxyl group-quercetagetin-7-O-β-D-Glucose glycosides, Quercetin-3-O-β-D glucoside, isorhamnetin, patuletin-3-O-β-D-Glucose glycosides, acacetin7OβDglucoside, rutin, 5,7,4 '-trihydroxyflavone, 3,3',4',5,7-pentahydoroxyflavone, 5,7,4 '-trihydroxy-3 '-methoxy flavone, kaempferol, 3,5,7,4 '-tetrahydroxy-6-methoxy-2-phenyl-4H-chromen-4-one, Luteolin, 5,7,4 '-trihydroxy-6,3 '-dimethoxy flavone, 5,7,4 '-trihydroxy-6-methoxy-2-phenyl-4H-chromen-4-one, Quercitroside, 7,3 ', 4 '-trimethyl Quercetin, 5-hydroxyl-7,4 '-dimethoxy flavone, 5,4 '-dihydroxy-7-methoxy flavone Flos Genkwa elements, 5,7-dihydroxy-4 '-methoxy flavone, 5,7,3 '-dihydroxy-4-methoxy flavone and derivant thereof.
4. the preparation method of the Herba Artemisiae extract as described in any one of claim 1-3, it is characterized in that: with the aerial parts of the Herba Artemisiae of Herba Artemisiae dry product or fresh collection for raw material, adopt solvent extraction method, solvent extraction, Flavonoids by Macroporous Adsorption Resin, Thin-layer chromatography, normal phase column chromatography method, reversed-phase column chromatography, one or more techniques in gel process, and be prepared into Herba Artemisiae extract in conjunction with concentrate drying, lyophilization, spraying dry.
5. preparation method as claimed in claim 4, it is characterized in that: in solvent extraction method and solvent extraction, one or more selecting in water, methanol, ethanol, n-butyl alcohol or other lower aliphatic alcohols do solvent, in room temperature lixiviate or supersound extraction, or the lower lixiviate of heating or reflux, extract, extraction time is once or repeatedly.
6. preparation method as claimed in claim 4, it is characterized in that: in Flavonoids by Macroporous Adsorption Resin, select normal pressure or pressurized column chromatography, resin adopts HPD-100, HPD-300, D-101, X-5, H103, AB-8, the resin of DA-201, HPD-400, NKA-9, S-8, HPD-500 model, eluting solvent adopts water, methanol, ethanol, acetone or containing one or more in aqueous methanol, aquiferous ethanol or aqueous acetone, is fixed eluting or the gradient elution of concentration during eluting.
7. preparation method as claimed in claim 4, it is characterized in that: in Thin-layer chromatography, select normal pressure or pressurized column chromatography, column packing used is polyamide, eluting solvent adopts water, methanol, ethanol, acetone or containing one or more in aqueous methanol, aquiferous ethanol or aqueous acetone, is fixed eluting or the gradient elution of concentration during eluting.
8. preparation method as claimed in claim 4, it is characterized in that: in reversed-phase column chromatography, select normal pressure or pressurized column chromatography, eluting solvent adopts water, methanol, ethanol, acetone or containing one or more in aqueous methanol, aquiferous ethanol or aqueous acetone, is fixed eluting or the gradient elution of concentration during eluting.
9. preparation method as claimed in claim 4, it is characterized in that: in normal phase column chromatography method, select normal pressure or pressurized column chromatography, eluting solvent adopts methanol, ethanol, acetone, ethyl acetate, petroleum ether, n-butyl alcohol, dichloromethane, one or more in chloroform, is fixed eluting or the gradient elution of concentration during eluting.
10. the purposes of the Herba Artemisiae extract as described in any one of claim 1-3 in prevention and therapy fatty liver, drug induced hepatic injury, viral hepatic injury, alcoholic liver injury and/or immunologic liver injury disease.
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