Cytotoxic Polyketides Isolated from the Deep-Sea-Derived Fungus Penicillium chrysogenum MCCC 3A00292
Cytotoxic Polyketides Isolated from the Deep-Sea-Derived Fungus Penicillium chrysogenum MCCC 3A00292
复制标题
从深海来源的真菌 Penicillium chrysogenum MCCC 3A00292 中分离出细胞毒性聚酮化合物
DOI：
10.3390/md17120686
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发表时间：
2019-12-01
期刊：
影响因子：
5.4
通讯作者：
Zhang, Gaiyun
中科院分区：
文献类型：
--
作者：
Niu, Siwen;Xia, Manli;Zhang, Gaiyun
对深海来源的真菌产黄青霉菌MCCC 3A 00292的固体培养物进行的化学检查导致分离出三种新的版本醇型类似物，即青霉醇A-C（1-3），和两种新的内酯衍生物，即青霉内酯A和B（6和7），以及沿着11种已知的聚酮化合物。通过高分辨电喷雾质谱（HRESIMS）和核磁共振（NMR）数据的综合分析，确定了新化合物的平面结构，并通过电子圆二色性（ECD）光谱的实验数据与计算数据的比较，解析了它们的绝对构型.化合物1是以2，3-二氢吡喃-4-酮环为特征的第二种化合物。另外，化合物6和7是由1，3-二羟基-5-甲苯单元分别与α-甲基-γ-羟基-γ-乙酸α，β-不饱和-γ-内酯部分和α-羟基-γ-甲基-γ-乙酸α，β-不饱和-γ-内酯单元缩合而构建的γ-内酯衍生物的第一代表。评价了所有分离的化合物对BIU-87、ECA 109、BEL-7402、PANC-1和Hela-S3五种人癌细胞系的细胞毒活性。化合物1显示出对BIU-87细胞系的选择性抑制作用（IC 50 = 10.21 μ M），而化合物4、5、8和12-16显示出对ECA 109、BIU-87和BEL-7402细胞系的抑制活性，IC 50值在7.70至> 20 μ M的范围内。
The chemical examination of the solid cultures of the deep-sea-derived fungus Penicillium chrysogenum MCCC 3A00292 resulted in the isolation of three new versiol-type analogues, namely peniciversiols A-C (1-3), and two novel lactone derivatives, namely penicilactones A and B (6 and 7), along with 11 known polyketides. The planar structures of the new compounds were determined by the comprehensive analyses of the high-resolution electrospray ionization mass spectroscopy (HRESIMS) and nuclear magnetic resonance (NMR) data, while their absolute configurations were resolved on the basis of comparisons of the experimental electronic circular dichroism (ECD) spectra with the calculated ECD data. Compound 1 is the second example of versiols featuring a 2,3-dihydropyran-4-one ring. Additionally, compounds 6 and 7 are the first representatives of gamma-lactone derivatives constructed by a 1,3-dihydroxy-5-methylbenzene unit esterifying with the alpha-methyl-gamma-hydroxy-gamma-acetic acid alpha,beta-unsaturated-gamma-lactone moiety and alpha-hydroxy-gamma-methyl-gamma-acetic acid alpha,beta-unsaturated-gamma-lactone unit, respectively. All of the isolated compounds were evaluated for their cytotoxic activities against five human cancer cell lines of BIU-87, ECA109, BEL-7402, PANC-1, and Hela-S3. Compound 1 exhibited a selective inhibitory effect against the BIU-87 cell line (IC50 = 10.21 mu M), while compounds 4, 5, 8, and 12-16 showed inhibitory activities against the ECA109, BIU-87, and BEL-7402 cell lines with the IC50 values ranging from 7.70 to > 20 mu M.