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2013 , Vol. 33 >Issue 06: 1273 - 1278

DOI: https://doi.org/10.6023/cjoc201303055

研究论文

川桂皮中具有免疫调节活性的甾体和苯丙素类化学成分

  • 魏夏兰 ,
  • 舒朋华 ,
  • 刘婷婷 ,
  • 向明 ,
  • 张锦文 ,
  • 薛永波 ,
  • 罗增伟 ,
  • 姚广民 ,
  • 张勇慧
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  • a 华中科技大学同济医学院药学院 武汉 430030;
    b 华中科技大学同济医学院附属同济医院 武汉 430030

收稿日期: 2013-03-31

  修回日期: 2013-04-28

  网络出版日期: 2013-05-31

基金资助

教育部留学回国人员科研启动基金(No.2010-1561, 第40批);教育部新世纪优秀人才计划(No.NCET-2008-0224)资助项目.

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Steroids and Phenylpropanoids with Immunomodulatory Activities from the Stem Barks of Cinnamomum wilsonii

  • Wei Xialan ,
  • Shu Penghua ,
  • Liu Tingting ,
  • Xiang Ming ,
  • Zhang Jinwen ,
  • Xue Yongbo ,
  • Luo Zengwei ,
  • Yao Guangmin ,
  • Zhang Yonghui
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  • a School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030;
    b Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030

Received date: 2013-03-31

  Revised date: 2013-04-28

  Online published: 2013-05-31

Supported by

Project supported by the Scientific Research Foundation for the Returned Oversea Chinese Scholars, Ministry of Education (No.2010-1561, 40th) and the Program for New Century Excellent Talents in University, Ministry of Education (No.NCET-2008-0224).

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摘要

对川桂Cinnamomum wilsonii皮的化学成分进行了研究, 从中分离并鉴定出1个新的甾体类化合物, (3S,22R,24R)-stigmast-5-ene-3β,22α-diol (1), 和10个已知化合物, stigmast-5-ene-3β,7α,22α-triol (2), 24-ethylcholest-5-ene- 3β,4β,22α-triol (3), stigmast-5-ene-3β,7α-diol (4), β-谷甾醇(5), β-胡萝卜苷(6), (1R,2R)-1-(4-hydroxy-3-methoxyphenyl)- 1,2,3-propanetriol (7), (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-1,2,3-propanetriol (8), 丁子香酚(9), 甲氧基丁子香酚(10)和methyl (E)-ferulate (11).通过波谱分析和Cu靶单晶X射线衍射方法确定了新化合物1的结构及其绝对构型.测试了化合物1～11的体外免疫调节活性, 1, 5和6能显著抑制刀豆A诱导的小鼠T细胞增殖, 6和9能显著抑制脂多糖诱导的小鼠B细胞增殖.

关键词： 川桂; (3S,22R,24R)-stigmast-5-ene-3β,22α-diol; 单晶X射线衍射; 绝对构型; 免疫调节活性

本文引用格式

魏夏兰 , 舒朋华 , 刘婷婷 , 向明 , 张锦文 , 薛永波 , 罗增伟 , 姚广民 , 张勇慧 . 川桂皮中具有免疫调节活性的甾体和苯丙素类化学成分[J]. 有机化学, 2013 , 33(06) : 1273 -1278 . DOI: 10.6023/cjoc201303055

Abstract

A new steroid, (3S,22R,24R)-stigmast-5-ene-3β,22α-diol (1), together with ten known compounds, stigmast-5-ene-3β,7α,22α-triol (2), 24-ethylcholest-5-ene-3β,4β,22α-triol (3), stigmast-5-ene-3β,7α-diol (4), β-sitosterol (5), β-daucosterol (6), (1R,2R)-1-(4-hydroxy-3-methoxyphenyl)-1,2,3-propanetriol (7), (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)- 1,2,3-propanetriol (8), eugenol (9), methoxyeugenol (10), and methyl (E)-ferulate (11) were isolated from the stem barks of Cinnamomum wilsonii.The structure including the absolute configuration of 1 was determined by spectroscopic data interpretation and X-ray single-crystal diffraction analysis with Cu Kα irradiation.Compounds 1～11 were evaluated for immunomodulatory activities against murine lymphocytes.1, 5 and 6 significantly inhibited the proliferation of murine ConA-induced T cells, and 6 and 9 significantly inhibited the proliferation of LPS-induced murine B cells.

Key words： Cinnamomum wilsonii; (3S,22R,24R)-stigmast-5-ene-3β,22α-diol; X-ray single-crystal diffraction; absolute con?guration; immunomodulatory activity

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