School of Chemical Engineering, Guizhou Institute of Technology, Guiyang, 550025, PR China.
Department of Nephrology, Zhongnan Hospital of Wuhan University, School of Pharmaceutical Sciences, Wuhan University, Wuhan, 430071, PR China; Key Laboratory of Combinatorial Biosynthesis and Drug Discovery, Ministry of Education and School of Pharmaceutical Sciences, Wuhan University, Wuhan, 430071, PR China.
Phytochemistry. 2025 Jan;229:114273. doi: 10.1016/j.phytochem.2024.114273. Epub 2024 Sep 6.
Three previously undescribed pyrrolizidinone alkaloids, penicipyrrolizidinones A and B (1 and 2), possessing an unprecedented 2-methyl-2-(oct-6-enoyl)pyrrolizidin-3-one skeleton, and penicipyrrolizidinone C (3), featuring a rare 1-alkenyl-2-methyl-pyrrolizidin-3,7-dione skeleton, together with four known pyrrolidine derivatives (4-7) were isolated from the mangrove-derived fungus Penicillium sp. DM27. Their structures were elucidated through comprehensive spectroscopic analysis, theoretical calculations of ECD spectra, and the modified Mosher's method. A plausible biosynthetic pathway for penicipyrrolizidinones A-C (1-3) was proposed. Compounds 4 and 5 exhibited moderate cytotoxicity against B16-F10 melanoma cells with IC values of 10.5 μM and 15.5 μM, respectively.
从红树林来源的真菌青霉 DM27 中分离得到三个以前未描述的吡咯里西啶酮生物碱，分别为 penicipyrrolizidinones A 和 B（1 和 2），具有前所未有的 2-甲基-2-（辛-6-烯酰基）吡咯里西啶-3-酮骨架，以及 penicipyrrolizidinone C（3），具有罕见的 1-烯基-2-甲基-吡咯里西啶-3,7-二酮骨架，以及四个已知的吡咯烷衍生物（4-7）。通过综合光谱分析、ECD 光谱的理论计算和改良的 Mosher 法确定了它们的结构。提出了 penicipyrrolizidinones A-C（1-3）的可能生物合成途径。化合物 4 和 5 对 B16-F10 黑色素瘤细胞表现出中等的细胞毒性，IC 值分别为 10.5 μM 和 15.5 μM。
