北極蒿與中藥常用蒿屬植物的化學成分比較_英文_

1、IntroductionThe genus artemisia belong to the Asteraceae familyand are widely distributed in the world.Artemisia borealis Pallas (A.campestris L.ssp.borealis (PallasH.M.et Clementsis mainly distributed in the Arctic area above northern latitude 60°and the local people use its leaves as healthy

2、tea for prevention and treatment of diabetes and atherosclerosis 1.However the research in the plants within the Arctic area was rarely engaged up to now.In China there are three generally used Artemisia species,A.annua Linn,A.argyi Levl,A.capillarae Thunb.In traditional Chinese medicine the aerial

3、part of A.annua is used as anti-malaria and fever-relieving agent,and artemisinin was discovered for the active constituent in anti-malaria.The leaves of A.argyi is applied for the treatment of uterus haemorrhage,dysmenorrheal,embryo protection and eczema,moreover ,the tender stems and leaves of A.c

4、apillaries is widely used for the prevention and treatment of hepatitis and cholecystitis.A.borealis is native to Arctic circle and shows stronger tolerance to cold.In Arctic,winter is longer than summer and polar day and night emerge alternately,Aurora borealisderived from the interaction between t

5、he solar windand the earth s magnetic field,always appears in the night sky.As we know sunlight cycle and temperature are important factors for growing of the plant,the growing condition of plant in Arctic region is much different from that in China.In order to explore and utilize the resources of A

6、.borealis and provide chemotaxonomic information,the chemical comparison of A.borealis and three other Chinese Artemisia species were conducted.Results and discussionArtemisinin detection in the four plantsArtemisinin is the characteristic and active component of A.annua and has been applied clinica

7、lly in China.Its detection in the four plants was carried out by TLC.The result indicated that only A.annua contains artemisinin.Essential oil of the leaves of A.borealisThe essential oil is also an important part for the bioactivity of A rtemisia plants,and is different in content and composition c

8、aused by the variation of cultivation places 2.The content of essential oil in the leaves of A.borealis was determined to be 0.1%byChemical comparison of Artemisia borealis and three ChineseArtemisia plantsFang Tian 1,Li Liu 1,De -Qiang Dou 1*,Ting -Guo Kang 1,and Smith David 21.College of Pharmacy,

9、Liaoning University of Traditional Chinese Medicine,Dalian 116620,China ;2.Alaska Green Gold,Anchorage,AK 99510,USAReceived date:2006!10!21.*Corresponding author:Tel 86!24!25857591,E -mail doudeqiang2003Abstract:Aim To compare the chemical constituents of Artemisia borealis with three other Artemisi

10、a plants which are generally used in traditional Chinese medicine.Method The chemical components of essential oil from the leaves of A.borealis were analyzed by GC -MS and the chemical components of water extracts of the four plants were compared by HPLC fingerprint method.Conclusion From the essent

11、ial oil of A.borealis,52peaks were separate,48of them were identified by GC -MS analysis,indicative that aromadendrane -4-ol is the highest constituent,which made up 24.73%of the total essential oil.In addition the chief constituents of the leaves of A.borealis are similar to the three other plants

12、but its pattern of HPLC fingerprint is different.The content of chlorogenic acid in aerial part of A.annus and A.scapillaries,leaves of A.borealis and A.argyi are 0.065,0.192,0.617and 0.178%respectively.Keywords:Artemisia;A.borealis;A.annua;A.argyi;A.capillaries CLC number:R284.1;R284.2Document code

13、:AArticle ID:1003!1057(2007!1-27-6Journal of Chinese Pharmaceutical Sciences27Table 1.Analytical results of chemical components of essential oil from the leaves of A.borealis38Aromadendrane -4-olC 15H 26O 24.73393-(2,6,6-Trimethyl-1-cyclohexen -1-y1-2-propenal C 12H 18O 1.26404,8-Dimethyl -1,7-nonad

14、ien -4-o1C 10H 18O 1.6341Oleic acid C 18H 34O 21.67421,3-Bis -(2-cyclopropy1,2-methylcyclopropy1-but -2-en -1-one C 18H 26O 0.79432,15,-HexadecanedioneC 16H 30O 21.53442,4,6,8-Tetramethy1-1-undeceneC 15H 300.4345Cetene C 16H 320.5346Heptadecane C 17H 360.9247Hexadecanoic acid C 16H 32O 25.5448Heneic

15、osane C 21H 441.1749Phytol C 20H 40O 2.9150Eicosane C 20H 240.8951Pentacosane C 25H 521.42524-M ethy -1-undeceneC 12H 240.48No.Name M olecular formulae Relative content/%12,6-Dimethyl -3,7-octadien -2-olC 10H 18O 3.192Isoart C 10H 16O 1.9733,3,6-Trimethyl -1,5-heptadien -4-olC 10H 18O 5.464Camphor C

16、 10H 16O2.935d -VerbenolC 10H 16O 1.946Borneol C 10H 18O0.747Bornyl acetate C 12H 20O 20.818(-M yrtenyl acetateC 12H 18O 21.589Cedrene C 15H 240.5210Isoboenyl acetate C 13H 22O 22.32111-M ethyl -3-methylene -8-(1-methylethyl -tricyclo 2,7decane C 15H 240.52121,4-Dimethyl -7-(1-methylethenyl -

17、1,2,3,5,6,7,8,8-octahydro -azuleneC 15H 240.4113Bornyl 2-propenateC 13H 20O 21.89143,7,11!Tremethyl "2,6,10-dodecatrien #1-olC 15H 26O 0.4715GermacreneD C 15H 240.3616Cedrol C 15H 26O1.0017Aromadendrene oxide C 15H 24O2.08182-Isopropyl $5-methyl -9-methylene %bicyclo 4.4.0dec &1-eneC 15H 24

18、1.1419Bornyl butanate C 15H 26O 23.2420Isothujol C 10H 18O 2.5021Davana ether C 15H 22O 22.67221,2,3,5,6,8-Hexahydro -4,7-dimethyl -1-(1-methylethyl -naphthalene C 15H 242.38235-Pentyloxy -2-penteneC 10H 20O 0.3524Unidentified 0.4225Nerolidol C 15H 26O1.8826Unidentified C 11H 20O 0.4927Unidentified

19、C 15H 240.41283,7,11-Trimethyl -1,6,10-dodecatrienC 15H 26O 0.9729Longipinene epoxide C 15H 24O1.12302-(5-Ethenyltetrahydro -5-methyl 2-furanyl -6-methyl -5-hepten -3-one C 15H 24O 22.15312,2,4-Trimethyl -3-carboxyisopropyl pentanoic acid isobutyl esterC 16H 30O 42.0932Diepi -cedrene epoxideC 15H 24

20、O 0.7433Unidentified 0.48347-(1-Hydroxy -cyclohexyl -2,2-dimethyl -hept -5-en -3-one C 15H 26O 21.5435-BisabololC 15H 26O 0.5236Isoaromadendrene epoxide C 15H 24O 0.4037Globulol C 15H 26O0.45F.Tian.et al./Journal of Chinese Pharmaceutical Sciences 2007(1627-322813.58995.324.984416.4880.72596.33*5.84

21、4856.815822.42375.61731.846.674161.657.365111.668.278648.37*9.4861699.515279.54821.34878.88*10.95780914783.53884.81874.59*11.966399.62931.21567.172701013.534160.411*14.2691274.28354.423451944.41216.699832.11317.867564.11418.6291399.71520.975613.81621.486559.81723.071167.81824.281420.513151925.762267

22、.62026.279138.91010.7A.annus A.borealis No.t Rarea area area area2129.137109.7782.3578.22230.096566.11248.42330.893297.624*31.8391132.88284.714702.92090.225*33.0435944850.910190.52191.42634.485531.81634.82922.72736.055135.82838.825192.62939.627252.21404.430*40.586884.27349.113907.12348.23141.6561273

23、242.612197.4852.13345.95895.11331.93447.545104.8787.13548.566200.7838.53649.42497.93754.992128.13157.73861.49190.73963.992109.84068.185116.5855.84169.011121.1A.argyi A.scapillaries water-steam distillation method.Fifty-two peaks were separated,of which 48were identified by GC-MS analysis and listed

24、in Table 1.The relative content calculated by area normalization indicated that peakNo.38(Aromadendrane-4-ol is the highest component in the leaves of A.borealis,accounted for 24.73%.In addition peaks No .4,6,8,9,10,15,20,41and 49existed in the leaves of A.borealis can be detected in A.argyi 3,4,No.

25、2,4,7,47and 49peaks can be detected in A.annua 2.HPL C fingerprints of water extract of the four plantsChlorogenic acid which is one of the active components of Artemisia plants could be detected in the water extracts of the four plants by retention time and UV chart in HPLC with DAD detector.So it

26、was selected as a reference substance in the HPLC fingerprint.As reported,UV detector at 326nm can give a good fingerprint of A.scapillariae 4,the comparison of HPLC fingerprint was also detected at this wavelength and shown i n Figure 1,the peak areas in the fingerprint were listed in Table 2.The r

27、esult indicated that the content of chlorogenic acid in aerial part of A.annus and A.scapillaries,leaves of A.borealis and A.argyi are 0.065,0.192,0.617and 0.178%respectively,indicating that in A.borealis chlorogenic acid content is the highest,but the peak numbers in the HPLC fingerprint are less t

28、han in the others.ConclusionThis research indicated that the major constituents in the leaves of A.borealis are similar to other three plants but its HPLC fingerprint pattern is different.The fact of less peaks in HPLC fingerprint and higher content of chlorogenic acid can conclude that A.borealis m

29、ay possess an unique bioactivity different from the three Chinese species.The bioactivity of A.borealis is under investigation.ExperimentalGeneral proceduresGV-MS wa s taken on a QP5050A GC-MS (Shimadzu Corporation with Class 5000MS database.The HPLC fingerprint was measured in Agilent 1100series HP

30、LCequipped with adiodearraydetector (DAD.Chlorogenic acid ,Artemisinin,leaves of A.argyi,aerial part of A.annus and A.scapillaries were purchased from Nation-al Institute for the Control of Pharmaceutical and Biological Product with standard serial number of No.753-9003,100202-200402,121345-200401,1

31、21016-200403and 120950-200305,respectively.The air-dried leaves of A.borealis was collected in Barrow,Alaska,USA,August 2005and identified by Mr.Smith David and Stoney J.Wright,director of Alaska Plant Material Center,Butte,Alaska,USA and its voucher specimen was stored in College of Pharmacy,Table

32、2.Peak area in the fingerprint of the four plants *Common peaks.F.Tian.et al./Journal of Chinese Pharmaceutical Sciences 2007(1627-3229F i g u r e 1.H P L C f i n g e r p r i n t o f t h e f o u r A r e m i s i a p l a n t s .N o t e :C A :c h l o r e g e n i e a c i d .F.Tian.et al./Journal of Chin

33、ese Pharmaceutical Sciences 2007(1627-3230Liaoning University of Traditional Chinese Medicine. The reagents are chromatographic grade and purchased from Yuwang corporation,China.Artemisinin detection in the four plantsSa mple preparation.Five hundred milligrames of leaves or aerial part of Artemisia

34、 materials was refluxed with petroleum ether(60-90for1h.After filtration, the extract was evaporated to dryness,and then the residues were redissolved in n-hexane and partitioned with10mL of acetonitrile(20%for three times.The acetonitrile layers were combined and evaporated to dryness and dissolved

35、 in0.5mL alcohol before TLC analysis.Preparation of artemisinin sample.Artemisinin was dissolved in EtOH to a concentration of0.5mgmL-1.TLC conditi on.TLC was performed on silica gel developed with petroleum-ethyl ether(32.An aliquot of15L of plant sample solution and5L of artemisinin solution were

36、applied on the TLC.After development,the TLC plate was taken out from chromatographic tank and evaporate to dryness,then sprayed with1%vanillin/sulfuric acid and heated under105till the spots exhibited clearly.Essential oil of leaves of Artemisia borealisExtraction of essential oil.The extraction of

37、 essential oil from the leaves of A.borealis was taken according to the water steam-distillation method in Chinese Pharmacopoeia5.Forty gram of the leaves of A.borealis was distilled with1000mL water for8h. And then the essential oil was collected and dried by sodium sulphate anhydrous to yield frag

38、rant dark green oil(0.1%.Conditions of GC-MS analysis.DB-5MS glass capil-lary column(30m×0.25mm×0.25mwas used. Column temperature programm:initial temperature at 80for5min,then temperature gradually increasing by4min-1,ended at250for10min;injection volume:0.2L.Injection mode:split with spl

39、it ration of10;injection temperature:200;Carrier gas:He; Column flow:1mLmin-1.Mass range:33-500amu; Scan rate:1000amus-1;interface temperature:230; detector:1.00KV.Peak identification was performed by comparison of standard MS spectra in class5000 database.HPLC fingerprints of water extract of the f

40、our plantsSamp le preparation.The method was taken accord-ing to reference6.One gram of pulverized60mesh samples(aerial part of A.annus and A.scapillaries, leaves of A.borealis and A.argyiwas refluxed with 25mL of water twice,the extracts were combined and evaporated in vacuo to20mL,50mL EtOH was ad

41、ded and kept in refrigerator for12h.After filtration, the filtrate was concentrated in vacuo to dryness,and the residue was then dissolved in water and transferred to10mL volumetric flask.The solution was filtrated using a0.45m milimembrane before HPLC analysis. Preparation of chlorogenic acid stand

42、ard solution. Chlorogenic acid was accurately weighed to make0.3 mgmL-1standard solution in20%MeOH. Conditions of HPLC.Agilent Eclipse XDB-C18(4.6 mm×150mm,5m,column temperature:25; detection wavelength:326nm;injection volume:10L;mobile phase:A-0.5%H3PO4of water solution, B-MeOH.Gradient elution:0-2.5min,10%-20%B;2.5-60min,20%-50%B;60-70min,50%-75%B.References1Wang Y,Toyota M,Krause F,et al.Polyacetylenes fromArtemisia bore