来自红树林来源真菌青霉 DM27 的三个具有前所未有的骨架的吡咯里西啶酮生物碱：蓬皮蝇菌素 A-C。
Penicipyrrolizidinones A-C, three pyrrolizidinone alkaloids with unprecedented skeletons from the mangrove-derived fungus Penicillium sp. DM27.
机构信息
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.
出版信息
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。
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