苍白菌素类化合物：来源于海藻内生真菌拟青霉 Maire KMM 4675 的聚酮化合物。

Pallidopenillines: Polyketides from the Alga-Derived Fungus Penicillium thomii Maire KMM 4675.

机构信息

Far Eastern Federal University , Suhanova 8, Vladivostok 690950, Russian Federation.

Nha Trang Institute of Technology Research and Application, Vietnam Academy of Science and Technology , Hanoi, Vietnam.

出版信息

J Nat Prod. 2016 Dec 23;79(12):3031-3038. doi: 10.1021/acs.jnatprod.6b00624. Epub 2016 Nov 29.

DOI:10.1021/acs.jnatprod.6b00624

PMID:28006908

Abstract

Eleven new polyketides, pallidopenillines 1-11, were isolated from the alga-derived fungus Penicillium thomii. The structures of these compounds were established based on spectroscopic methods. The absolute configuration of pallidopenilline A (1) as 4R, 5S, 8S, 9R, 10R, 13R was established using a combination of the modified Mosher's method, X-ray analysis, and NOESY data. The absolute configurations of 2-5 were determined by time-dependent density functional theory calculations of the ECD spectra and ECD and NOESY data. It was shown that 1-acetylpallidopenilline A (2) and pallidopenilline G (10) inhibit the growth of colonies of 22Rv1 cells by 40% at 2 and 1 μM, respectively.

摘要

从藻类来源的真菌拟青霉（Penicillium thomii）中分离得到了 11 个新的聚酮化合物，即苍白霉素 1-11。基于光谱方法确定了这些化合物的结构。通过改进的 Mosher 法、X 射线分析和 NOESY 数据的组合，确定了苍白霉素 A（1）的绝对构型为 4R,5S,8S,9R,10R,13R。通过对 ECD 光谱和 ECD 和 NOESY 数据的时间依赖密度泛函理论计算，确定了 2-5 的绝对构型。结果表明，1-乙酰苍白霉素 A（2）和苍白霉素 G（10）在 2 μM 和 1 μM 时分别抑制 22Rv1 细胞菌落生长 40%。