高等学校化学学报 ›› 2014, Vol. 35 ›› Issue (8): 1665-1669.doi: 10.7503/cjcu20140080

• 有机化学 • 上一篇    下一篇

从细脚拟青霉分离的新环二肽与新十元环内酯

郑永标1(), 庞海月1, 王继峰2, 陈丹霞1, 施国伟2, 黄建忠1   

  1. 1. 福建师范大学生命科学学院, 工业微生物教育部工程研究中心, 福州 350117
    2. 复旦大学附属上海市第五人民医院, 上海 200240
  • 收稿日期:2014-01-23 出版日期:2014-08-10 发布日期:2019-08-01
  • 作者简介:联系人简介:郑永标, 男, 博士, 副教授, 主要从事微生物天然产物研究. E-mail: yongbiaozheng@fjnu.edu.cn
  • 基金资助:
    基金项目:福建省科技计划重点项目(批准号: 2011N0013)和福建省自然科学基金(批准号: 2013J01122)资助.

Novel Diketopiperazine and Ten-membered Macrolides from the Entomogenous Fungus Paecilomyces tenuipes

ZHENG Yongbiao1,*(), PANG Haiyue1, WANG Jifeng2, CHEN Danxia1, SHI Guowei2, HUANG Jianzhong1   

  1. 1. Engineering Research Centre of Industrial Microbiology, Ministry of Education, College of Life Sciences, Fujian Normal University, Fuzhou 350117, China
    2. Fudan Institute of Urology, The Fifth People’s Hospital of Shanghai, Fudan University, Shanghai 200240, China
  • Received:2014-01-23 Online:2014-08-10 Published:2019-08-01
  • Contact: ZHENG Yongbiao E-mail:yongbiaozheng@fjnu.edu.cn
  • Supported by:
    Supported by the Science Foundation of Fujian Province, China(No. 2011N0013) and the Natural Science Foundation of Fujian Province,China(No. 2013J01122).

摘要:

利用反相色谱、 凝胶色谱和硅胶色谱从细脚拟青霉发酵液中分离得到4个活性化合物. 通过核磁共振波谱、 质谱、 X射线晶体衍射分析和理化数据鉴定化合物1为新环二肽[(3S)-6-苯乙基-3-异丙基-1-甲基-2,5-二酮哌嗪], 化合物2为新十元环内酯[(4S,10R)-4-羟基-8-氧代-10-甲基癸内酯], 化合物3为Cepharosporolide C, 化合物4为Cepharosporolide E. 细胞毒性实验结果表明, 5 μmol/L的化合物1对前列腺癌细胞22RV1和DU-145的抑制率分别为37.8%和38.6%, 5 μmol/L的化合物2对前列腺癌细胞22RV1和DU-145的抑制率分别为32.5%和40.6%, 具有一定抗肿瘤活性.

关键词: 细脚拟青霉, (3S)-6-苯乙基-3-异丙基-1-甲基-2, 5-二酮哌嗪, (4S, 10R)-4-羟基-8-氧代-10-甲基癸内酯, 细胞毒性

Abstract:

Paecilomyces tenuipes with high edible and medicinal value was the anamorph of Cordyceps takaomontana. Four compounds were isolated from the cultured broth of Paecilomyces tenuipes by repeated column chromatography over RP-18, sephadex LH-20 and silica gel. Their structures were determined on the basis of NMR data, HRMS-EI technique and X-ray single crystal diffraction. One novel diketopiperazine (3S)-6-benzyl-3-isopropyl-1-methylpiperazine-2,5-dione(1) and one novel ten-membered macrolide(4S,10R)-4-hydroxy-10-methyloxecane-2,8-dione(2), together with two known ten-membered macrolides Cepharosporolide C(3) and Cepharosporolide E(4) were obtained. Compound 1 showed the moderate cytoto-xicity in the MTT assay against prostate cancer cells 22RV1 and DU-145 with inhibition rate of 37.8% and 38.6%, and those of compound 2 were 32.5% and 40.6%, respectively.

Key words: Paecilomyces tenuipes, (3S)-6-Benzyl-3-isopropyl-1-methylpiperazine-2, 5-dione, (4S, 10R)-4-Hydroxy-10-methyloxecane-2, 8-dione, Cytotoxicity

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