Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (2): 507-514.DOI: 10.6023/cjoc201806045 Previous Articles     Next Articles

ARTICLE

海绵放线菌Nocardiopsis dassonvillei OUCMDZ-4534的活性天然产物

刘海珊, 朱国良, 赵水鸽, 付鹏, 朱伟明   

  1. 中国海洋大学医药学院 海洋药物教育部重点实验室 青岛 266003
  • 收稿日期:2018-06-29 修回日期:2018-08-08 出版日期:2019-02-25 发布日期:2018-09-05
  • 通讯作者: 朱伟明 E-mail:weimingzhu@ouc.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.81561148012,U1501221,U1606403)资助项目.

Bioactive Natural Products from the Marine Sponge-Derived Nocardiopsis dassonvillei OUCMDZ-4534

Liu Haishan, Zhu Guoliang, Zhao Shuige, Fu Peng, Zhu Weiming   

  1. Key Laboratory of Marine Drugs, Ministry Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003
  • Received:2018-06-29 Revised:2018-08-08 Online:2019-02-25 Published:2018-09-05
  • Contact: 10.6023/cjoc201806045 E-mail:weimingzhu@ouc.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 81561148012, U1501221, U1606403).

Nocardiopsis dassonvillei OUCMDZ-4534 was isolated and identified from the sponge, Dysidea avara, from Xisha Islands of China. Compounds 1~12 were isolated from the fermenation broth of N. dassonvillei OUCMDZ-4534. By means of spectroscopic analysis, electronic circular dichroism (ECD) and 13C NMR calculations, their structures were identified as (3aS,7aS)-3a-hydroxy-3a,7a-dihydrobenzofuran-2(3H)-one (1a), (3aR,7aR)-3a-hydroxy-3a,7a-dihydrobenzofuran-2(3H)-one (1b), phenazine (2), 1-hydroxyphenazine (3), 1-methoxyphenazine (4), 1,6-dihydroxyphenazine (5), 1-hydroxy-6-methoxy-phenazine (6), 1,6-dihydroxy phenazin-5-oxide (7), dihydrogeodin (8), 2-acetamidophenol (9), 2-benzamidophenol (10), (E)-7-hydroxy cinnamic acid (11), and (E)-7-hydroxy-6-methoxycinnamic acid (12), respectively. This is the first time to resolve racemic-1 and identify the absolute structures of 1a and 1b. Compounds 1 and 9 displayed selective inhibition on A549 and K562 cell lines with the half maximal inhibitory concentration (IC50) of 0.47 and 0.46 μmol·L-1, respectively. Compounds 4~8 showed inhibitory activities against K562, A549 and MCF-7 cell lines with IC50 values ranging from 0.02 to 1.48 μmol·L-1. Compound 11 was cytotoxic to K562 while compound 12 was active against K562 and MCF-7 cell lines with the IC50 values of 1.14, 0.88 and 0.65 μmol·L-1, respectively. Compounds 7 and 8 showed antimicrobial activities against Aspergillus fumigatus and Pseudoalteromonas nigrifaciens with the minimum inhibitory concentration (MIC) of 25.00 and 2.00 μg·mL-1, respectively. Compounds 4~6 and 9 also exhibited inhibitions against the H1N1 virus with the IC50 values of 0.04, 0.16, 0.06 and 0.30 mmol·L-1, respectively.

Key words: marine actinobacterium, Nocardiopsis dassonvillei, phenazine analogues, cytotoxicity, antibacterial activity, anti-H1N1 virus activity