赫章产毛萼香茶菜化学成分的研究
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摘要
目的研究毛萼香茶菜Isodoneriocalyx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。结果从毛萼香茶菜醋酸乙酯部位中分离得到了20个化合物,分别鉴定为毛萼晶D(1)、isothymusin(2)、假细锥甲素(3)、毛萼晶A(4)、5,4′-二羟基-6,7-二甲氧基黄酮(5)、牡荆素(6)、α-香树脂醇(7)、β-胡萝卜苷(8)、毛叶香茶菜丁素(9)、蓟黄素(10)、毛萼晶N(11)、epi-macoecrystalP(12)、海松酸(13)、laxiflorin R(14)、enmelol(15)、毛萼晶B(16)、柳穿鱼黄素(17)、neolaxiflorin V(18)、毛萼甲素(19)、新香茶菜素(20)。结论化合物2、5～7、13～15、17、18均为首次从该植物中分离得到,化合物5、6为首次从香茶菜属中分离得到。
Objective To study the chemical constituents of Isodon eriocalyx. Methods The 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 data and physicochemical properties as well as relevant references. Results A total of 20 constituents were isolated from I. eriocalyx, plant material extracted with ethyl aceta, and they were elucidated as maoecrystal D(1), isothymusin(2), coetsoidin A(3), maoecrystal A(4), 5,4′-dihydroxy-6,7-dimethoxy flavone(5), vitexin(6), α-amyrin(7), β-daucosterol(8),odinicin(9), cirsimaritin(10), maoecrystal N(11), epi-macoecrystal P(12), pimaric acid(13), laxiflorin R(14), enmelol(15),maoecrystal B(16), pectolarigenin(17), neolaxiflorin V(18), eriocalyxin A(19), and neorabdosin(20). Conclusion Compounds 2,5—7, 13—15, 17, 18 are isolated from this plant for the first time, and compounds 5 and 6 are isolated from the plants of Isodon for the first time.
Objective To study the chemical constituents of Isodon eriocalyx. Methods The 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 data and physicochemical properties as well as relevant references. Results A total of 20 constituents were isolated from I. eriocalyx, plant material extracted with ethyl aceta, and they were elucidated as maoecrystal D(1), isothymusin(2), coetsoidin A(3), maoecrystal A(4), 5,4′-dihydroxy-6,7-dimethoxy flavone(5), vitexin(6), α-amyrin(7), β-daucosterol(8),odinicin(9), cirsimaritin(10), maoecrystal N(11), epi-macoecrystal P(12), pimaric acid(13), laxiflorin R(14), enmelol(15),maoecrystal B(16), pectolarigenin(17), neolaxiflorin V(18), eriocalyxin A(19), and neorabdosin(20). Conclusion Compounds 2,5—7, 13—15, 17, 18 are isolated from this plant for the first time, and compounds 5 and 6 are isolated from the plants of Isodon for the first time.
引文
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[19]陶晨,李齐激,叶林虎,等.黔产毛萼香茶菜二萜成分[J].天然产物研究与开发,2015,27(1):26-30.
[20]Chen Y N,Tian M Q,Wu R,et al.Two new diterpenoids from Isodon eriocalyx[J].J Chin Chem Soc,1999,10(1):31-32.
[21]Norihisa K,Tatsuya A,Yuichi H,et al.Antitermitic activities of Abietane type dite-rpenes from Taxodium distichum cones[J].J Chem Ecol,2009,35(5):635-642.
[22]Wang W G,Li X N,Du X,et al.Laxiflorolides A and B,epimeric bishomoditerpene lactones from Isodon eriocalyx[J].J Nat Prods,2012,75(5):1102-1107.
[23]Zhao Y,Niu X M,Qian L P,et al.Synthesis and cytotoxicity of some new eriocalyxin B derivatives[J].Eur J Med Chem,2007,42(4):494-502.
[24]Zeng Q,Chang R J,Qin J J,et al.New glycosides from Dracocephalum tanguticum Maxim[J].Arch Pharm Res,2011,34(12):2015-2020.
[25]Wang W G,Yang J,Wu H Y,et al.ent-Kauranoids isolated from Isodon eriocalyx var.laxiflora and their structure activity relationship analyses[J].Tetrahedron,2015,71(9):9161-9171.
[26]王佳,赵勤实,林中文,等.毛萼香茶菜中的三个新的对映-贝壳杉烷型二萜[J].云南植物研究,1997,19(2):191-195.
[27]孙汉董,林中文,王德祖,等.新香茶菜素的结构[J].化学学报,1985,43(5):481-483.
[2]舒晔,王懋德,宋骥鹏,等.毛尊香茶菜提出物的抗炎抑菌作用[J].云南中医学院学报,1995,18(4):9-12.
[3]丁兰,李昊聪,王保强,等.甘肃产4种香茶菜的主要次生代谢产物的抑菌活性[J].西北师范大学学报,2017,53(2):82-87.
[4]齐玉明,王春丽,冯社军.毛萼乙素通过调节STAT3抑制宫颈癌C-33A细胞survivin的表达[J].西部医学,2016,28(5):625-627.
[5]雷雯.毛萼乙素靶向NF-κB信号通路抑制非霍奇金淋巴瘤细胞增殖机制研究[D].郑州:郑州大学,2014.
[6]王舟.表毛萼甲素与电离辐射诱导结直肠癌细胞凋亡的相关分子机制研究[D].济南:山东大学,2015.
[7]李惠兰,王懋德,王宗玉,等.毛萼香茶菜对豚鼠肠平滑肌作用的分析[J].天津药学,1994,6(3):16-20.
[8]李惠兰,王懋德,李肇玖.毛萼香茶菜对血压及血管平滑肌的作用[J].中药通报,1988,13(10):46-50.
[9]李春葆,孙汉董,周俊.毛萼香茶菜的新二萜化合物,毛萼晶甲-戊的结构[J].云南植物研究,1985,7(1):115-116.
[10]Apichart S,Ponsuda P,Nuntana A,et al.Antimycobacterial and antioxidant flavones from Limnophila geoffrayi[J].Arch Pharm Res,2003,26(10):816-820.
[11]王雪芬,卢文杰,郑启泰,等.假细锥香茶菜新二萜成分--假细锥甲素的结构[J].药学学报,1989,24(7):522-524.
[12]Xuemei N,Shenghong L,Qinshi Z,et al.Novel ent-abietane diterpenoids from Isodon eriocalyx var.Laxiflora[J].Helv Chim Acta,2003,86(1):299-306.
[13]余正文,朱海燕,杨小生,等.毛子草化学成分及其促PC-12细胞的分化作用研究I[J].中国中药杂志,2005,30(17):1335-1338.
[14]程伟贤,陈鸿雁,张义平,等.山牡荆的化学成分研究[J].天然产物研究与开发,2007,19(2):244-246.
[15]周雯,王霞,付思红,等.羊耳菊的化学成分研究[J].中国药学杂志,2017,52(1):25-30.
[16]周大颖,杨小生,杨波,等.黔产毛子草化学成分研究[J].天然产物研究与开发,2007,19(5):807-808.
[17]Fu L Y,Lan Q G,Su P B,et al.Two new diterpenoids and other constituents from Isodon nervosus[J].J Chin Chem Soc,2008,55(4):933-936.
[18]侯爱君,杨辉,姜北,等.疏花毛萼香茶菜中一新的对映-贝壳杉烷型二萜[J].云南植物研究,2000,16(3):337-342.
[19]陶晨,李齐激,叶林虎,等.黔产毛萼香茶菜二萜成分[J].天然产物研究与开发,2015,27(1):26-30.
[20]Chen Y N,Tian M Q,Wu R,et al.Two new diterpenoids from Isodon eriocalyx[J].J Chin Chem Soc,1999,10(1):31-32.
[21]Norihisa K,Tatsuya A,Yuichi H,et al.Antitermitic activities of Abietane type dite-rpenes from Taxodium distichum cones[J].J Chem Ecol,2009,35(5):635-642.
[22]Wang W G,Li X N,Du X,et al.Laxiflorolides A and B,epimeric bishomoditerpene lactones from Isodon eriocalyx[J].J Nat Prods,2012,75(5):1102-1107.
[23]Zhao Y,Niu X M,Qian L P,et al.Synthesis and cytotoxicity of some new eriocalyxin B derivatives[J].Eur J Med Chem,2007,42(4):494-502.
[24]Zeng Q,Chang R J,Qin J J,et al.New glycosides from Dracocephalum tanguticum Maxim[J].Arch Pharm Res,2011,34(12):2015-2020.
[25]Wang W G,Yang J,Wu H Y,et al.ent-Kauranoids isolated from Isodon eriocalyx var.laxiflora and their structure activity relationship analyses[J].Tetrahedron,2015,71(9):9161-9171.
[26]王佳,赵勤实,林中文,等.毛萼香茶菜中的三个新的对映-贝壳杉烷型二萜[J].云南植物研究,1997,19(2):191-195.
[27]孙汉董,林中文,王德祖,等.新香茶菜素的结构[J].化学学报,1985,43(5):481-483.