北细辛苗在不同生长阶段与成熟期的主要化学成分分析
|
摘要
目的:研究北细辛苗在生长过程中主要化学成分的变化规律。方法:分别采集生长1周和2周的北细辛苗以及生长3个月的北细辛植株,均分成地上(茎、叶)与地下部分(根),采用HPLC-TOF-MS对其次生代谢产物进行定性鉴别,以细辛脂素作为指标成分进行定量鉴别。结果:从北细辛地下部分共鉴定6个已知化合物,分别为α-细辛醚(1),N-isobutyl-2,4,8,10-dodecatetraenamide(2),9-methoxyaristolactamⅣ(3),细辛脂素(4),caulesnarinside(6)和chalcononaringenin 2’,4’-di-O-β-Dglucopyranoside(7),峰面积数值表明其含量随着生长时间的增长逐渐增加;从北细辛地上部分共鉴定出4个已知化合物,分别为N-isobutyl-2,4,8,10-dodecatetraenamide(2),caulesauroneside(5),caulesnarinside(6)或chalcononaringenin 2’,4’-di-O-β-Dglucopyranoside(7)和peonidin 3-caffeoylgentiobioside(8)。仅在生长3个月的北细辛地下部分鉴定出了细辛脂素,其质量分数155.4μg·g~(-1)。结论:北细辛地上与地下部分次生代谢产物种类与含量存在较大差异;在北细辛苗的不同生长阶段,相同部位的次生代谢产物的种类和含量也存在较大差异,其主要成分的含量基本呈现随生长时间增加而增加的趋势。
Objective: To analyze the change rule of main chemical components in Asarum heterotropoides var. mandshuricum seedling during the growing process. Method: Whole seedling samples( one week and two weeks) and the mature plant( three months) of A. heterotropoides var. mandshuricum were collected and every sample was divided to aerial part( stems and leaves) and underground part( roots). The secondary metabolites were qualitatively identified by HPLC-TOF-MS and the quantitative identification was carried out at the same time with asarinin as index component. Result: A total of 6 known compounds were identified from the underground part of A. heterotropoides var. mandshuricum as α-asarone( 1), N-isobutyl-2,4,8,10-dodecatetraenamide( 2),9-methoxyaristolactam Ⅳ( 3),asarinin( 4),caulesnarinside( 6) and chalcononaringenin 2’,4’-di-O-β-D-glucopyranoside( 7), respectively, the peak area values showed that the contents of these compounds increased gradually with the growth time. A total of 4 known compounds were identified from the aerial part of this herb as N-isobutyl-2, 4, 8, 10-dodecatetraenamide( 2), caulesauroneside( 5), caulesnarinside( 6) or chalcononaringenin 2’,4’-di-O-β-D-glucopyranoside( 7) and peonidin 3-caffeoylgentiobioside( 8). Asarinin was identified only in the underground part of mature plant,its content was 155. 4 μg·g~(-1). Conclusion: The species and contents of secondary metabolites are quite different in the aerial and underground parts of A.heterotropoides var. mandshuricum. At different growth stages of A. heterotropoides var. mandshuricum seedling,the types and contents of secondary metabolites in the same site are also different, while the contents of main components show an increasing trend with the growth time.
Objective: To analyze the change rule of main chemical components in Asarum heterotropoides var. mandshuricum seedling during the growing process. Method: Whole seedling samples( one week and two weeks) and the mature plant( three months) of A. heterotropoides var. mandshuricum were collected and every sample was divided to aerial part( stems and leaves) and underground part( roots). The secondary metabolites were qualitatively identified by HPLC-TOF-MS and the quantitative identification was carried out at the same time with asarinin as index component. Result: A total of 6 known compounds were identified from the underground part of A. heterotropoides var. mandshuricum as α-asarone( 1), N-isobutyl-2,4,8,10-dodecatetraenamide( 2),9-methoxyaristolactam Ⅳ( 3),asarinin( 4),caulesnarinside( 6) and chalcononaringenin 2’,4’-di-O-β-D-glucopyranoside( 7), respectively, the peak area values showed that the contents of these compounds increased gradually with the growth time. A total of 4 known compounds were identified from the aerial part of this herb as N-isobutyl-2, 4, 8, 10-dodecatetraenamide( 2), caulesauroneside( 5), caulesnarinside( 6) or chalcononaringenin 2’,4’-di-O-β-D-glucopyranoside( 7) and peonidin 3-caffeoylgentiobioside( 8). Asarinin was identified only in the underground part of mature plant,its content was 155. 4 μg·g~(-1). Conclusion: The species and contents of secondary metabolites are quite different in the aerial and underground parts of A.heterotropoides var. mandshuricum. At different growth stages of A. heterotropoides var. mandshuricum seedling,the types and contents of secondary metabolites in the same site are also different, while the contents of main components show an increasing trend with the growth time.
引文
[1]国家药典委员会.中华人民共和国药典.一部[M].北京:中国医药科技出版社,2015:230-231.
[2]舒娜.锦鸡儿化学成分、含量及其变化研究[D].上海:复旦大学,2006.
[3]谭玲玲.药用柴胡的结构发育与主要药用成分积累关系的研究[D].西安:西北大学,2008.
[4]滕红梅.药用远志的结构发育与主要要用成分积累关系的研究[D].西安:西北大学,2009.
[5]刘辉.川贝母产地适应性分析及基于成分分析的采收加工方法研究[D].成都:成都中医药大学,2008.
[6]刘凤波.黄芪药材质量的差异及影响因素研究[D].北京:北京中医药大学,2013.
[7]Quang T H,Ngan N T,Minh C V,et al.Antiinflammatory and PPAR transactivational effects of secondary metabolites from the roots of Asarum sieboldii[J].Bioorg Med Chem Lett,2012,22(7):2527-2533.
[8]Kopyt'Ko Y F,Shchurevich N N,Sokol'Skaya T A,et al.Uses,chemical composition,and standardization of plant raw material and medicinal substances from plants of the genus Asarum L.[J].Pharm Chem J,2013,47(3):157-168.
[9]臧埔,武晓琳,郜玉钢,等.不同产地细辛有效成分与毒性成分的比较研究[J].中国现代应用药学,2014,31(4):416-421.
[10]古一帆,刘忠,何明,等.华细辛中药有效成分与土壤理化性质的相关性研究[J].上海交通大学学报:农业科学版,2010,28(4):361-372.
[11]杜成智,陈玉萍,覃洁萍,等.不同产地细辛挥发油的GC-MS分析[J].中国实验方剂学杂志,2011,17(7):57-59.
[12]刘雅婧,李春杰,周英亮,等.不同产地细辛中有效成分与马兜铃酸I含量差异比较[J].中国执业药师,2010,7(12):29-33.
[13]刘东吉,刘春生.不同产地栽培辽细辛的挥发油研究[J].中国实验方剂学杂志,2010,16(9):79-82.
[14]万昶宸,刘艳艳,杨浩天,等.HPLC-MS/MS法同时测定紫菀中9种化学成分[J].中草药,2016,47(14):2354-2539.
[15]王亚丹,何轶,戴忠,等.HPLC-MS-MS同时测定山银花中10种活性成分的含量[J].中国中药杂志,2016,41(10):1870-1875.
[16]秦语欣,张先灵,王蕾,等.HPLC-MS法研究川乌炮制前后化学成分的变化[J].北京中医药大学学报,2016,39(4):298-303.
[17]毛叶勤,姚鑫,陈琳.HILIC-HPLC-MS/MS测定酸枣仁内氨基酸类成分的含量[J].中国实验方剂学杂志,2016,22(21):67-72.
[18]张巧月,刘艳艳,万昶宸,等.HPLC-ESI-MS/MS法测定连翘心中的8种化学成分[J].中草药,2017,48(1):192-196.
[19]南泽东,任华忠,赵明波,等.HPLC-MS鉴定塔中栽培肉苁蓉药材的17个成分[J].中国实验方剂学杂志,2018,24(20):62-67.
[20]董捷鸣,崔健,赵小梅,等.2种颜色拳参饮片HPLCMS指纹图谱比较研究[J].药物分析杂志,2017,37(8):1503-1508.
[21]毛思浩,陈碧莲,唐登峰.毛叶香茶菜HPLC指纹图谱的建立及其液-质联用分析[J].中国现代应用药学,2018,35(4):556-560.
[22]秦建平,吴建雄,郎悦,等.痛宁凝胶的HPLC-MS指纹图谱研究[J].现代药物与临床,2016,31(4):427-430.
[23]艾鑫卫,胡思平,龚姮姮,等.高效液相色谱-串联质谱法测定各生长期紫苏中酚类物质的含量[J].食品科学,2016,37(18):126-131.
[24]陈伟,刘玉玲,贺玖明,等.液相色谱-串联质谱法测定兔血浆中α-细辛脑的浓度[J].药物分析杂志,2006,26(10):1364-1368.
[25]ZHOU L,QI W,XU C,et al.A rapid method for simultaneous determination of 52 marker compounds in Xiao-Qing-Long-Tang by ultra high performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry[J].J Sep Sci,2014,37(22):3260-3267.
[26]GUO T,LI Y H.Determination of four lignanoids in roots,stems and leaves of Zanthoxylum armatum DC by HPLC-DAD with HPLC-ESI-QTOF-MS confirmation[J].J Anal Chem,2016,71(5):527-533.
[27]ZHANG S X,Tani T,Yamaji S,et al.Glycosyl flavonoids from the roots and rhizomes of Asarum longerhizomatosum[J].J Asian Nat Prod Res,2003,5(1):25-30.
[28]Ishikura N.Anthocyanins of Asarum asaroides[J].Phytochemistry,1971,10(12):3297-3298.
[29]于营,朴向民,欧阳艳飞,等.北细辛种苗分级标准研究[J].特产研究,2017,40(4):1-5.
[30]国家药典委员会.中华人民共和国药典.一部[M].北京:化学工业出版社,2005:159.
[2]舒娜.锦鸡儿化学成分、含量及其变化研究[D].上海:复旦大学,2006.
[3]谭玲玲.药用柴胡的结构发育与主要药用成分积累关系的研究[D].西安:西北大学,2008.
[4]滕红梅.药用远志的结构发育与主要要用成分积累关系的研究[D].西安:西北大学,2009.
[5]刘辉.川贝母产地适应性分析及基于成分分析的采收加工方法研究[D].成都:成都中医药大学,2008.
[6]刘凤波.黄芪药材质量的差异及影响因素研究[D].北京:北京中医药大学,2013.
[7]Quang T H,Ngan N T,Minh C V,et al.Antiinflammatory and PPAR transactivational effects of secondary metabolites from the roots of Asarum sieboldii[J].Bioorg Med Chem Lett,2012,22(7):2527-2533.
[8]Kopyt'Ko Y F,Shchurevich N N,Sokol'Skaya T A,et al.Uses,chemical composition,and standardization of plant raw material and medicinal substances from plants of the genus Asarum L.[J].Pharm Chem J,2013,47(3):157-168.
[9]臧埔,武晓琳,郜玉钢,等.不同产地细辛有效成分与毒性成分的比较研究[J].中国现代应用药学,2014,31(4):416-421.
[10]古一帆,刘忠,何明,等.华细辛中药有效成分与土壤理化性质的相关性研究[J].上海交通大学学报:农业科学版,2010,28(4):361-372.
[11]杜成智,陈玉萍,覃洁萍,等.不同产地细辛挥发油的GC-MS分析[J].中国实验方剂学杂志,2011,17(7):57-59.
[12]刘雅婧,李春杰,周英亮,等.不同产地细辛中有效成分与马兜铃酸I含量差异比较[J].中国执业药师,2010,7(12):29-33.
[13]刘东吉,刘春生.不同产地栽培辽细辛的挥发油研究[J].中国实验方剂学杂志,2010,16(9):79-82.
[14]万昶宸,刘艳艳,杨浩天,等.HPLC-MS/MS法同时测定紫菀中9种化学成分[J].中草药,2016,47(14):2354-2539.
[15]王亚丹,何轶,戴忠,等.HPLC-MS-MS同时测定山银花中10种活性成分的含量[J].中国中药杂志,2016,41(10):1870-1875.
[16]秦语欣,张先灵,王蕾,等.HPLC-MS法研究川乌炮制前后化学成分的变化[J].北京中医药大学学报,2016,39(4):298-303.
[17]毛叶勤,姚鑫,陈琳.HILIC-HPLC-MS/MS测定酸枣仁内氨基酸类成分的含量[J].中国实验方剂学杂志,2016,22(21):67-72.
[18]张巧月,刘艳艳,万昶宸,等.HPLC-ESI-MS/MS法测定连翘心中的8种化学成分[J].中草药,2017,48(1):192-196.
[19]南泽东,任华忠,赵明波,等.HPLC-MS鉴定塔中栽培肉苁蓉药材的17个成分[J].中国实验方剂学杂志,2018,24(20):62-67.
[20]董捷鸣,崔健,赵小梅,等.2种颜色拳参饮片HPLCMS指纹图谱比较研究[J].药物分析杂志,2017,37(8):1503-1508.
[21]毛思浩,陈碧莲,唐登峰.毛叶香茶菜HPLC指纹图谱的建立及其液-质联用分析[J].中国现代应用药学,2018,35(4):556-560.
[22]秦建平,吴建雄,郎悦,等.痛宁凝胶的HPLC-MS指纹图谱研究[J].现代药物与临床,2016,31(4):427-430.
[23]艾鑫卫,胡思平,龚姮姮,等.高效液相色谱-串联质谱法测定各生长期紫苏中酚类物质的含量[J].食品科学,2016,37(18):126-131.
[24]陈伟,刘玉玲,贺玖明,等.液相色谱-串联质谱法测定兔血浆中α-细辛脑的浓度[J].药物分析杂志,2006,26(10):1364-1368.
[25]ZHOU L,QI W,XU C,et al.A rapid method for simultaneous determination of 52 marker compounds in Xiao-Qing-Long-Tang by ultra high performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry[J].J Sep Sci,2014,37(22):3260-3267.
[26]GUO T,LI Y H.Determination of four lignanoids in roots,stems and leaves of Zanthoxylum armatum DC by HPLC-DAD with HPLC-ESI-QTOF-MS confirmation[J].J Anal Chem,2016,71(5):527-533.
[27]ZHANG S X,Tani T,Yamaji S,et al.Glycosyl flavonoids from the roots and rhizomes of Asarum longerhizomatosum[J].J Asian Nat Prod Res,2003,5(1):25-30.
[28]Ishikura N.Anthocyanins of Asarum asaroides[J].Phytochemistry,1971,10(12):3297-3298.
[29]于营,朴向民,欧阳艳飞,等.北细辛种苗分级标准研究[J].特产研究,2017,40(4):1-5.
[30]国家药典委员会.中华人民共和国药典.一部[M].北京:化学工业出版社,2005:159.