Huang Yu Wei, Guan Jing, Tang Yin, Tan Ren Xiang, Lin Li Ping
State Key Laboratory on Technologies for Chinese Medicine Pharmaceutical Process Control and Intelligent Manufacture, School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, 210023, China.
State Key Laboratory on Technologies for Chinese Medicine Pharmaceutical Process Control and Intelligent Manufacture, School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, 210023, China; State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, Nanjing University, Nanjing, 210033, China.
Phytochemistry. 2025 May;233:114407. doi: 10.1016/j.phytochem.2025.114407. Epub 2025 Jan 16.
Five previously undescribed phenylpyridones, designated as citridones H-L (1-5), along with seven known compounds, were characterized from the rice medium culture of the Cineraria repanda-derived endophytic fungus Penicillium oxalicum. Their structures were elucidated through detailed interpretation of UV, NMR, and HR-ESI-MS data. The absolute configurations of C-2 and C-3 in compounds 1-4 were determined by spectroscopic analysis and ECD calculations, while the C-5' configurations were established through computational C NMR and DP4+ analyses. These compounds represent a novel scaffold of chromone-phenylpyridone hybrids, making only the second report of such compounds from the Penicillium genus and the first to feature a unique (E)-5-methylhepta-1,3-diene group at the C-2 position. Additionally, a biosynthetic pathway for these novel chromone-phenylpyridones is proposed for the first time. Notably, compounds 3 and 4 exhibited cytotoxicity against HCT116 and H1299 cell lines when used in combination, with IC values of 4.15 ± 0.34 and 9.07 ± 1.64 μM, respectively. Furthermore, compounds 3, 4 and 5 demonstrated significant inhibitory effects against Staphylococcus aureus, with MIC values of 64, 64 and 8 μg/mL, respectively.
从来源于瓜叶菊的内生真菌草酸青霉在大米培养基中的培养物中，鉴定出了5个前所未描述的苯基吡啶酮，命名为瓜叶菊酮H-L（1-5），以及7个已知化合物。通过对紫外光谱、核磁共振光谱和高分辨电喷雾电离质谱数据的详细解析，阐明了它们的结构。通过光谱分析和电子圆二色光谱计算确定了化合物1-4中C-2和C-3的绝对构型，而C-5'构型则通过计算碳核磁共振光谱和DP4+分析确定。这些化合物代表了一种新型的色酮-苯基吡啶酮杂合物骨架，这是关于青霉属此类化合物的第二篇报道，也是第一篇在C-2位具有独特（E）-5-甲基-1,3-庚二烯基团的报道。此外，首次提出了这些新型色酮-苯基吡啶酮的生物合成途径。值得注意的是，化合物3和4联合使用时对HCT116和H1299细胞系表现出细胞毒性，IC值分别为4.15±0.34和9.07±1.64μM。此外，化合物3、4和5对金黄色葡萄球菌表现出显著的抑制作用，MIC值分别为64、64和8μg/mL。
