Citation: Liu Haishan, Zhu Guoliang, Zhao Shuige, Fu Peng, Zhu Weiming. Bioactive Natural Products from the Marine Sponge-Derived Nocardiopsis dassonvillei OUCMDZ-4534[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 507-514. doi: 10.6023/cjoc201806045 shu

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

Key Laboratory of Marine Drugs, Ministry Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003

Corresponding author: Zhu Weiming, weimingzhu@ouc.edu.cn
Received Date: 29 June 2018
Revised Date: 8 August 2018
Available Online: 5 February 2018
Fund Project: the National Natural Science Foundation of China 81561148012Project supported by the National Natural Science Foundation of China (Nos. 81561148012, U1501221, U1606403)the National Natural Science Foundation of China U1606403the National Natural Science Foundation of China U1501221

Figures(4)

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.
- marine actinobacterium,
- Nocardiopsis dassonvillei,
- phenazine analogues,
- cytotoxicity,
- antibacterial activity,
- anti-H1N1 virus activity
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