有机化学 ›› 2013, Vol. 33 ›› Issue (06): 1273-1278.DOI: 10.6023/cjoc201303055 上一篇    下一篇

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a, 舒朋华a, 刘婷婷a, 向明a, 张锦文b, 薛永波a, 罗增伟a, 姚广民a, 张勇慧a   

  1. 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 发布日期:2013-05-31
  • 通讯作者: 姚广民, 张勇慧 E-mail:gyap@hust.edu.cn;zhangyh@mails.tjmu.edu.cn
  • 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.

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

Wei Xialana, Shu Penghuaa, Liu Tingtinga, Xiang Minga, Zhang Jinwenb, Xue Yongboa, Luo Zengweia, Yao Guangmina, Zhang Yonghuia   

  1. 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:2013-03-31 Revised:2013-04-28 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).

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111的体外免疫调节活性, 1, 56能显著抑制刀豆A诱导的小鼠T细胞增殖, 69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

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 111 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