海绵放线菌Nocardiopsis dassonvillei OUCMDZ-4534的活性天然产物
收稿日期: 2018-06-29
修回日期: 2018-08-08
网络出版日期: 2018-09-05
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
Received date: 2018-06-29
Revised date: 2018-08-08
Online published: 2018-09-05
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 81561148012, U1501221, U1606403).
拟诺卡氏菌（Nocardiopsis dassonvillei）OUCMDZ-4534分离自西沙贪婪倔海绵（Dysidea avara），其发酵提取物表现出生物碱显色、系列紫外吸收及抑菌和肿瘤细胞毒活性.从其发酵产物中分离到12个化合物.通过质谱（MS）、紫外（UV）、红外光谱（IR）、电子圆二色谱（ECD）、核磁共振（NMR）和化学计算等方法，首次确定了外消旋体1中对映体的绝对构型分别为（3aS，7aS）-3a-羟基-3a，7a-二氢苯并呋喃-2（3H）-酮（1a）和（3aR，7aR）-3a-羟基-3a，7a-二氢苯并呋喃-2（3H）-酮（1b），其它化合物依次被确定为吩嗪（2）、1-羟基吩嗪（3）、1-甲氧基吩嗪（4）、1，6-二羟基吩嗪（5）、1-羟基-6-甲氧基吩嗪（6）、1，6-二羟基吩嗪-5-氧化物（7）、2-（4-甲基-2，6-二羟基-3，5-二氯）苯甲酰基-3-甲氧基-5-羟基苯甲酸甲酯（8）、N-（2-羟基苯基）乙酰胺（9）、N-（2-羟基苯基）苯甲酰胺（10）、（E）-3-（4-羟基）苯丙烯酸（11）和（E）-3-（4-羟基-3-甲氧基）苯丙烯酸（12）.化合物1和9分别对A549和K562细胞有选择性抑制作用，半数抑制浓度（IC50）分别为0.47和0.46 μmol·L-1；化合物4~8对K562、A549和MCF-7细胞表现出不同程度抑制作用，IC50值在0.02~1.48 μmol·L-1之间；化合物11对K562细胞以及化合物12对K562和MCF-7细胞有较强抑制活性，IC50分别为1.14、0.88和0.62 μmol·L-1.化合物7和8分别对烟曲霉（Aspergillus fumigates）和交替假单胞菌（Pseudoalteromonas nigrifaciens）有抑制活性，其最小抑菌浓度（MIC）分别为25.00和2.00 μg·mL-1.化合物4~6和9还表现出对甲型流感H1N1病毒的抑制活性，IC50分别为0.04、0.15、0.06和0.30 mmol·L-1.
刘海珊 , 朱国良 , 赵水鸽 , 付鹏 , 朱伟明 . 海绵放线菌Nocardiopsis dassonvillei OUCMDZ-4534的活性天然产物[J]. 有机化学, 2019 , 39(2) : 507 -514 . DOI: 10.6023/cjoc201806045
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.
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