艾蒿化学成分研究
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摘要
目的研究艾蒿Artemisia argyi的化学成分。方法采用溶剂萃取、硅胶柱色谱、高效液相色谱等方法进行分离纯化,通过理化性质及波谱数据分析鉴定结构。结果从艾蒿中分离得到34个化合物,分别鉴定为5-羟基-6,7,3′,4′-四甲氧基黄酮(1)、半齿泽兰素(2)、对羟基苯乙酮(3)、覆盆子酮(4)、姜酮(5)、7-羟基香豆素(6)、对羟基苯甲酸(7)、脱氢去乙酰氧母菊素(8)、3α-羟基-1(10),4,11(13)-吉马三烯-12,6α-内酯(9)、棕矢车菊素(10)、7-羟基松油醇(11)、顺-2,8-二羟基-对薄荷-1(7)-烯(12)、反-2,8-二羟基-对薄荷-1(7)-烯(13)、艾黄素(14)、东莨菪内酯(15)、艾蒿内酯C(16)、去乙酰母菊酮素(17)、1-表-4,5-二氢灰蒿素C(18)、11,13-脱氢去乙酰母菊酮素(19)、1,9-壬二酸(20)、3-methoxy-tanapartholide(21)、红花菜豆酸(22)、断愈创木酸(23)、5,3′,4′-三羟基-6,7-二甲氧基黄酮(24)、1,7-庚二酸(25)、10-epi-ajafinin(26)、3-epi-iso-seco-tanapartholide(27)、austroyunnane C(28)、刘寄奴内酯(29)、川芎内酯A(30)、seco-tanapartholide B(31)、3-dehydroxy-iso-seco-tanapartholide(32)、3α-hydroxyreynosin(33)、二氢红花菜豆酸(34)。结论化合物4、22、25、30、33、34为首次从蒿属植物中分离得到,化合物5、7、8、11～13、21、23、24、26～28为首次从艾蒿中分离得到。
Objective To study the chemical constituents of Artemisia argyi. Methods The chemical constituents were isolated by silica gel column chromatography and HPLC, and its structure were identified by their spectral data and physicochemical properties analysis. Results Thirty-four compounds were isolated from A. argyi with the structures identified as 5-hydroxy-6,7,3′,4′-tetramethoxyflavone(1), eupatorin(2), p-hydroxy-acetophenone(3), raspberry ketone(4), zingiberone(5), 7-hydroxycoumarin(6), p-hydroxybenzoic acid(7), desacetoxymatricarin(8), 3α-hydroxy-1(10),4,11(13)-triene-12,6α-olide(9), jaceosidin(10), 7-hydrxyterpineol(11), cis-2,8-dihydroxy-p-mentha-1(7)-en(12), trans-2,8-dihydroxy-p-mentha-1(7)-en(13), artemisetin(14), scopoletin(15), arteminolide C(16), desacetylmatricarin(17), artecalin(18), 11,13-dehydrodesacetylmatricarin(19), 1,9-azelaic acid(20), 3-methoxy-tanapartholide(21), phaseic acid(22), seco-guaiaretic acid(23), 5,3′,4′-trihydroxy-6,7-dimethoxy-flavone(24), 1,7-pimelic acid(25), 10-epi-ajafinin(26), 3-epi-iso-seco-tanapartholide(27), austroyunnane C(28), artanomaloide(29), ligustolide A(30), seco-tanapartholide B(31), 3-dehydroxy-iso-seco-tanapartholide(32), 3α-hydroxyreynosin(33), dihydrophaseic acid(34). Conclusion Compounds 4, 22, 25, 30, 33, 34 are separated from the Artemisia for the first time. Compounds 5, 7, 8, 11—13, 21, 23, 24, 26—28 are isolated from A. argyi for the first time.
Objective To study the chemical constituents of Artemisia argyi. Methods The chemical constituents were isolated by silica gel column chromatography and HPLC, and its structure were identified by their spectral data and physicochemical properties analysis. Results Thirty-four compounds were isolated from A. argyi with the structures identified as 5-hydroxy-6,7,3′,4′-tetramethoxyflavone(1), eupatorin(2), p-hydroxy-acetophenone(3), raspberry ketone(4), zingiberone(5), 7-hydroxycoumarin(6), p-hydroxybenzoic acid(7), desacetoxymatricarin(8), 3α-hydroxy-1(10),4,11(13)-triene-12,6α-olide(9), jaceosidin(10), 7-hydrxyterpineol(11), cis-2,8-dihydroxy-p-mentha-1(7)-en(12), trans-2,8-dihydroxy-p-mentha-1(7)-en(13), artemisetin(14), scopoletin(15), arteminolide C(16), desacetylmatricarin(17), artecalin(18), 11,13-dehydrodesacetylmatricarin(19), 1,9-azelaic acid(20), 3-methoxy-tanapartholide(21), phaseic acid(22), seco-guaiaretic acid(23), 5,3′,4′-trihydroxy-6,7-dimethoxy-flavone(24), 1,7-pimelic acid(25), 10-epi-ajafinin(26), 3-epi-iso-seco-tanapartholide(27), austroyunnane C(28), artanomaloide(29), ligustolide A(30), seco-tanapartholide B(31), 3-dehydroxy-iso-seco-tanapartholide(32), 3α-hydroxyreynosin(33), dihydrophaseic acid(34). Conclusion Compounds 4, 22, 25, 30, 33, 34 are separated from the Artemisia for the first time. Compounds 5, 7, 8, 11—13, 21, 23, 24, 26—28 are isolated from A. argyi for the first time.
引文
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[24]Ye G,Ma C H,Huang X Y,et al.Components of Sophora alopecuroides seeds[J].Chem Nat Compd,2009,45(4):545-546.
[2]谢建祥,王海东,林伟青.鼠曲草化学成分研究[J].中成药,2015,37(3):553-555.
[3]王金兰,易志聪,马耀玲,等.柳蒿化学成分研究[J].中草药,2016,47(13):2241-2245.
[4]马宏宇,孙奕,吕阿丽,等.茵陈蒿化学成分的分离与鉴定[J].中国药物化学杂志,2010,20(1):61-86.
[5]崔语涵,安潇,王海峰,等.姜黄化学成分研究[J].中草药,2016,47(7):1074-1078.
[6]张素挽,杨璐,顾政一.新疆一枝蒿化学成分的研究[J].新疆医科大学学报,2016,39(4):408-410.
[7]康洁,苏现明,张鹏,等.鸡眼藤地上部分的化学成分研究[J].中草药,2017,48(1):111-113.
[8]王金兰,马耀玲,王美娇,等.柳蒿中的倍半萜类化合物[J].中草药,2018,49(16):3758-3762.
[9]刘丹,师宁宁,吴叶红,等.冷蒿的化学成分研究[J].中草药,2017,48(24):5090-5098.
[10]Tan R X,Jakupovic J,Bojlmann F,et al.Sesquiterpene lactones and other constituents from Artemisia xerophytica[J].Phytochemistry,1991,30(2):583-587.
[11]Bolhmann F,Zdero C,Jakupovic J,et al.cis-Guajanolide aus Osmitopsis asteriscoides[J].Liebigs Ann Chem,1985,17(14):2342-2351.
[12]Lee S H,Kim H K,Seo J M,et al.Arteminolides B,C,and D,new inhibitors of farnesyl protein transferase from Artemisia argyi[J].J Org Chem,2002,67(22):7670-7675.
[13]Glasl S,Mucaji P,Werner I,et al.Sesqquiterpenes and flavonoid aglycones from a Hungarian Taxon of the Achillea millefolium group[J].Zeitschrift Für Naturforschung C,2002,57(12):976-982.
[14]Ahmed A A,Gati T,Hussein T A,et al.Ligustolide A and B,two novel sesquiterpenes with rare skeletons and three1,10-seco-guaianolide derivatives from Achillea ligustica[J].Tetrahedron,2003,59(21):3729-3735.
[15]Werner I,Glasl S,Presser A,et al.Sesquiterpenes from Achillea pannonica Scheele[J].Zeitschrift Für Naturforschung C,2003,58(6):303-307.
[16]郭丽娜,江黎明,吴立军,等.无梗五加茎叶化学成分的研究[J].沈阳药科大学学报,2017,19(3):180-182.
[17]魏伟,范春林,王贵阳,等.广王不留行的化学成分研究[J].中草药,2014,45(5):615-621.
[18]Wen J,Shi H M,Xu Z R,et al.Dimeric guaianolides and sesquiterpenoids from Artemisia anomala[J].J Nat Prod,2010,73(1):67-70.
[19]张启伟,张永欣,张颖,等.滨蒿化学成分的研究[J].中国中药杂志,2002,27(3):202-203.
[20]Marco J A,Sanz-Cervera J F,Manglano E,et al.Sesquiterpene lactones from Iranian Artemisia Species[J].Phytochemistry,1993,34(6):1561-1564.
[21]Chi J,Li B C,Dai W F,et al.Highly oxidized sesquiterpenes from Artemisia austro-yunnanesis[J].Fitoterapia,2016,115:182-188.
[22]Zan K,Chen X Q,Fu Q,et al.1,10-Secoguaianolides from Artemisia anomala(Asteraceae)[J].Biochem Syst Ecol,2010,38(3):431-434.
[23]Barrero A F,Oltra J E,Cuerva J M,et al.Effects of solvents and water in Ti(III)-mediated radical cyclizations of epoxygermacrolides.Straightforward synthesis and absolute stereochemistry of(+)-3α-hydroxyreynosin and related eudesmanolides[J].J Org Chem,2002,67(8):2566-2571.
[24]Ye G,Ma C H,Huang X Y,et al.Components of Sophora alopecuroides seeds[J].Chem Nat Compd,2009,45(4):545-546.