Department of Microbial Drugs, Helmholtz Centre for Infection Research, German Centre for Infection Research (DZIF), Partner Site Hannover/Braunschweig, Inhoffenstrasse 7, 38124 Braunschweig, Germany; Department of Plant Protection, Faculty of Agriculture, University of Tabriz, Tabriz, Iran.
Department of Microbial Drugs, Helmholtz Centre for Infection Research, German Centre for Infection Research (DZIF), Partner Site Hannover/Braunschweig, Inhoffenstrasse 7, 38124 Braunschweig, Germany; Department of Chemistry, Faculty of Science, University of Dschang, P.O. Box 67, Dschang, Cameroon.
Fitoterapia. 2019 Apr;134:314-322. doi: 10.1016/j.fitote.2019.02.015. Epub 2019 Feb 23.
Chemical analysis of extracts from cultures of the plant pathogenic fungus Cytospora sp. strain CCTU A309 collected in Iran led to the isolation of two previously unreported heptanedioic acid derivatives namely (2R,3S) 2-hydroxy-3-phenyl-4-oxoheptanedioic acid (1) and (2S,3S) 2-hydroxy-3-phenyl-4-oxoheptanedioic acid (2) as diastereomers, four previously undescribed prenylated p-terphenyl quinones 3-6 in addition to five known metabolites. Their structures were elucidated on the basis of extensive spectroscopic analysis and high-resolution mass spectrometry. For metabolites 1 and 2, the absolute configurations at C-2 were deduced from comparison of the H NMR difference of their (S)- and (R)-phenylglycine methyl ester derivatives while the relative configurations were tentatively assigned by a J-based analysis and confirmed by comparison of C chemical shifts to literature data. The isolated compounds were tested for their cytotoxic, antimicrobial (including biofilm inhibition), antiviral, and nematicidal activities. While only moderate antimicrobial effects were observed, the terphenyl quinone derivatives 3-6 and leucomelone (10) exhibited significant cytotoxicity against the mouse fibroblast L929 and cervix carcinoma KB-3-1 cell lines with IC values ranging from 2.4 to 26 μg/mL. Furthermore, metabolites 4-6 showed interesting antiviral activity against hepatitis C virus (HCV).
从伊朗采集的植物病原真菌 Cytospora sp. 菌株 CCTU A309 的培养物提取物的化学分析导致分离出两种以前未报道的庚二酸衍生物，即（2R，3S）2-羟基-3-苯基-4-氧代庚二酸（1）和（2S，3S）2-羟基-3-苯基-4-氧代庚二酸（2）作为非对映异构体，此外还有四种以前未描述的prenylated p-terphenyl quinones 3-6，以及五种已知代谢物。它们的结构是根据广泛的光谱分析和高分辨率质谱确定的。对于代谢物 1 和 2，C-2 的绝对构型是通过比较其（S）-和（R）-苯甘氨酸甲酯衍生物的 H NMR 差来推断的，而相对构型则通过基于 J 的分析和与文献数据的 C 化学位移比较来初步确定。对分离得到的化合物进行了细胞毒性、抗菌（包括生物膜抑制）、抗病毒和杀线虫活性测试。虽然只观察到中等的抗菌作用，但 terphenyl quinone 衍生物 3-6 和 leucomelone（10）对小鼠成纤维细胞 L929 和宫颈癌细胞 KB-3-1 表现出显著的细胞毒性，IC 值范围为 2.4 至 26μg/mL。此外，代谢物 4-6 对丙型肝炎病毒（HCV）表现出有趣的抗病毒活性。
