黔产细锥香茶菜中化学成分的研究
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摘要
目的研究黔产细锥香茶菜Isodon coetsa的化学成分。方法采用硅胶、凝胶柱色谱、制备型HPLC等方法进行分离纯化,通过理化性质、光谱数据结合参考文献鉴定化合物结构。结果从细锥香茶菜95%甲醇提取物中分离得到了19个化合物,分别鉴定为β-谷甾醇(1)、豆甾醇(2)、β-胡萝卜苷(3)、亚麻酸甲酯(4)、油酸-1,3-甘油二酯(5)、熊果酸(6)、齐墩果酸(7)、3β-羟基-乌索-20-烯-28-酸(8)、白桦脂酸(9)、苦参黄素(10)、山楂酸(11)、2α羟基-熊果酸(12)、2α,3α-二羟基-12-烯-28-乌苏酸(13)、2α,3α,24-三羟基-12-烯-28-齐墩果酸(14)、2α,3α,24-三羟基-12-烯-28-熊果酸(15)、芒柄花素(16)、大黄素(17)、尿嘧啶(18)、蔗糖(19)。结论化合物2、4、5、9、11、13~19均为首次从该植物中分离得到,化合物11、17、19为首次从香茶菜属植物中分离得到。
Objective To investigate chemical constituents from Isodon coetsa distributed in Guizhou. Methods Chemical constituents were isolated and purified by chromatography with silica gel, Sephadex LH-20, and semi-preparative HPLC, and their structures were identified by analysis of spectroscopic evidences and physicochemical properties as well as relevant references. Results A total of 19 compounds were isolated from plant material extracted with 95% aqueous methanol, which were elucidated as β-sitosterol(1), stigmasterol(2), β-daucosterol(3), methyl linolenat(4), 9,12-octadecadienoic acid-2-hydroxy-1,3-propanedinyl ester(5), ursolic acid(6), oleanoic acid(7), 3β-hydroxy-urs-20-en-28-oic acid(8), betulinic acid(9), kurarinone(10), maslinic acid(11), 2α-hydroxy ursolic acid(12), 2α,3α-dihydroxy-urs-12-en-28-oic acid(13), 2α,3α,24-trihydrxyolean-12-en-28-oic acid(14), 2α,3β,24-trihydroxyolean-12-en-28-oic acid(15), formononetin(16), emodin(17), uracil(18), and sucrose(19). Conclusion Compounds 2, 4, 5, 9, 11, 13—19 are isolated from this plant for first time, and compounds 11, 17, 19 are isolated from the genus of Isodon for the first time.
Objective To investigate chemical constituents from Isodon coetsa distributed in Guizhou. Methods Chemical constituents were isolated and purified by chromatography with silica gel, Sephadex LH-20, and semi-preparative HPLC, and their structures were identified by analysis of spectroscopic evidences and physicochemical properties as well as relevant references. Results A total of 19 compounds were isolated from plant material extracted with 95% aqueous methanol, which were elucidated as β-sitosterol(1), stigmasterol(2), β-daucosterol(3), methyl linolenat(4), 9,12-octadecadienoic acid-2-hydroxy-1,3-propanedinyl ester(5), ursolic acid(6), oleanoic acid(7), 3β-hydroxy-urs-20-en-28-oic acid(8), betulinic acid(9), kurarinone(10), maslinic acid(11), 2α-hydroxy ursolic acid(12), 2α,3α-dihydroxy-urs-12-en-28-oic acid(13), 2α,3α,24-trihydrxyolean-12-en-28-oic acid(14), 2α,3β,24-trihydroxyolean-12-en-28-oic acid(15), formononetin(16), emodin(17), uracil(18), and sucrose(19). Conclusion Compounds 2, 4, 5, 9, 11, 13—19 are isolated from this plant for first time, and compounds 11, 17, 19 are isolated from the genus of Isodon for the first time.
引文
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[20]李延勋,栗章彭,颜世利,等.膜荚黄芪化学成分研究[J].中草药,2017,48(13):2601-2607.
[21]蒋亭,田黎,郭爱华,等.黄海葵附生真菌Penicillium thomii的化学成分[J].药学学报,2002,37(4):271-274.
[22]贾陆,李焕芬,敬林林.黄秋葵正丁醇部位化学成分的研究[J].中草药,2010,41(11):1771-1773.
[23]陈晓晓,杨尚军,白少岩.中华猕猴桃根化学成分研究[J].中草药,2011,42(5):841-843.
[2]陈一平,孙汉董,林中文.细锥香茶菜二萜的研究[J].植物学报,1990,32(4):292-296.
[3]吴征镒.新华本草纲要[M].上海:上海科学技术出版社,1988.
[4]Zou J,Pan L T,Li Q J,et al.Rubesanolides C-E:The abietane diterpenoids isolated from Isodon rubescens and evaluation of their anti-biofilm activity[J].Org Biomol Chem,2012,10(26):5039-5044.
[5]Li J X,Li Q J,Guan Y F,et al.Discovery of antifungal consti-tuents from the Miao medicinal plant Isodon flavidus[J].Ethnopharmacology,2016,191(1):372-378.
[6]黄泽豪,秦路平.华中五味子藤茎的化学成分研究[J].中草药,2016,47(19):3374-3378.
[7]Jun J,Zhang C F,Zhang M,Studies on the constituents of Senecio laetus Edgew[J].Modern Chin Med,2007,9(7):13-14.
[8]Tori K,Seo S,Yoshimura Y,et al.Glycosidation shifts in carbon 13 NMR spectroscopy:carbon-13 signal shifts from aglycone and glucose to glucoside[J].TetrahedronLett,l997,18(2):179-182.
[9]Chang M H,Wang G J,Kuo Y-H,et al.The Low polar constituents from Bidens Pilosa L.var.minor(Blume)Sherff[J].Chin Chem Soc,2013,47(5):1131-1136.
[10]杨辉,谢金伦,孙汉董.云木香化学成分研究II[J].云南植物研究,1997,19(1):92-96..
[11]Qin S X,Sun H D,Lobkovsky E,et al.Megathyrin B:a cytotoxic diterpene from Isodon megathyrsus[J].PlantaMed,1998,64(8):728-731.
[12]王建忠,王锋鹏.细锥香茶菜的化学成分研究[J].天然产物研究与开发,1988,10(3):15-19.
[13]Shashi B,Mahato A,Kundu P.13C NMR Spectra of pentacyclic triterpenoids a compilation a ndsome salientfeatures[J].Phytochemistry,1994,37(6):1517-1575.
[14]赵能武,李齐激,潘炉台,等.贵州紫云产黄花香茶菜的化学成分研究[J].西北植物学报,2011,31(8):1692-1694.
[15]Ryu Y B,Westwood I M,Kang N S,et al.Kurarinol,tyrosinase Inhibitor isolated from the root of Sophora flavescens[J].Phytomedicine,2008,15(8):612-618.
[16]Huang Y,Aisa H A,Isaev M I.Isoprenoids of Euphorbia sororia.I.Triterpenoids[J].Chem Nat Compds,2009,45(6):921-924.
[17]Yang M H,Blunden G,O’Neill M J,et al.Tormentic acid and 2alpha-hydroxyursolic acid from Arnebia euchroma[J].Phytochem Notes,1992,58(2):227-229.
[18]刘普,段宏泉,潘勤,等.委陵菜三萜成分研究[J].中国中药杂志,2006,31(22):1875-1879.
[19]Sashida Y,Ogawa K,Mori N,et al.Tsuyoshi Yamanouchi,triterpenoids from the fruit galls of Actinidia polygama[J].Phytochemistry,1992,31(8):2801-2804.
[20]李延勋,栗章彭,颜世利,等.膜荚黄芪化学成分研究[J].中草药,2017,48(13):2601-2607.
[21]蒋亭,田黎,郭爱华,等.黄海葵附生真菌Penicillium thomii的化学成分[J].药学学报,2002,37(4):271-274.
[22]贾陆,李焕芬,敬林林.黄秋葵正丁醇部位化学成分的研究[J].中草药,2010,41(11):1771-1773.
[23]陈晓晓,杨尚军,白少岩.中华猕猴桃根化学成分研究[J].中草药,2011,42(5):841-843.