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顺式-5’-(2-氧代丙基)-烟碱的化学结构和生物活性

Chemical structure and bioactivity of cis-5’-oxopropylnicotine

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【作者】 杨彩艳黄晓燕马云保耿长安张雪梅陈纪军

【Author】 YANG Cai-yan;HUANG Xiao-yan;MA Yun-bao;GENG Chang-an;ZHANG Xue-mei;CHEN Ji-jun;State Key Laboratory of Phytochemistry and Plant Resources in West China,Kunming Institute of Botany,Chinese Academy of Sciences;

【机构】 中国科学院昆明植物研究所植物化学与西部植物资源持续利用国家重点实验室

【摘要】 该文对烟叶的化学成分及其生物活性进行研究,采用硅胶,Sephadex LH-20,MCI GEL CHP 20P,HPLC等色谱技术分离纯化,根据波谱学数据(UV,IR,MS,1D和2D NMR)进行结构鉴定。从烟叶中分离鉴定了6个化合物,结构分别鉴定为顺式-5’-(2-氧代丙基)-烟碱(1),3-O-(9,12,15-octadecatrienoyl)-glyceryl-β-D-galactppyranoside(2),(l’R,2R,5S,10R)-2-(1’,2’-dihydroxy-l’-methylethyl)-6,10-dimethylspiro[4,5]dec-6-en-8-one(3),(l’S,2R,5S,10R)-2-(1’,2’-dihydroxy-l’-methylethyl)-6,10-dimethylspiro[4,5]dec-6-en-8-one(4),2,3-二羟基丙基-β-D-吡喃半乳糖苷(5),苯乙醇β-D-葡萄糖苷(6)。其中化合物1为新的生物碱,化合物2~5为首次从烟草中分离得到。对化合物1和2进行辣椒素受体(TRPV1)、褪黑素受体(MT1,MT2)的激动活性筛选,结果表明化合物1在1.53 mmol·L-1时对MT2的激动率为55.41%;化合物2在0.59 mmol·L-1时对TRPV1的激动率为128.11%,在0.73 mmol·L-1时对MT1的激动率为52.00%。

【Abstract】 In this paper,the chemical constituents and bioactivities of leaves of Nicotiana tabacum were investigated. Six compounds were isolated by means of various chromatographic techniques( silica gel,Sephadex LH-20,MCI GEL CHP-20 P and HPLC),and their structures were elucidated as cis-5’-( 2-oxopropyl)-nicotine( 1),3-O-( 9,12,15-octadecatrienoyl)-glyceryl-β-D-galactppyranoside( 2),( l’R,2R,5S,10R)-2-( 1’,2’-dihydroxy-l’-methylethyl)-6,10-dimethylspiro [4,5]dec-6-en-8-one( 3),( l’S,2R,5S,l0R)-2-( 1’,2’-dihydroxy-l’-methylethyl)-6,10-dimethylspiro [4,5] dec-6-en-8-one( 4),2,3-dihydroxypropyl-β-D-galactoside( 5) and phenylethyl β-D-glucopyranoside( 6) by extensive spectroscopic analyses( UV,IR,MS,1D-and 2D-NMR). Among them,compound 1 is a new alkaloid,and compounds 2-6 are isolated for the first time from N. tabacum. Compounds 1 and 2 were assayed for agitating activities on transient receptor potential vanilloid 1( TRPV1),melatonin receptor 1 and 2( MT1 and MT2),1 showed agitating rate of 55. 41%( 1. 53 mmol · L- 1) on MT2 and 2 possessed agitating rate of 128. 11%( 0. 59 mmol · L- 1) and 52. 00%( 0. 73mmol·L- 1) on TRPV1 and MT1,respectively.

【基金】 国家杰出青年科学基金项目(81025023)
  • 【文献出处】 中国中药杂志 ,China Journal of Chinese Materia Medica , 编辑部邮箱 ,2016年04期
  • 【分类号】R284.1
  • 【被引频次】5
  • 【下载频次】142
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