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阿扎 coccones F-H,一种来自内生真菌棘孢木层孔菌(MK214079)的新型黄皮酰胺衍生生物碱。

Azacoccones F-H, new flavipin-derived alkaloids from an endophytic fungus Epicoccum nigrum MK214079.

机构信息

Institute of Pharmaceutical Biology and Biotechnology, Heinrich Heine University, Universitaetsstrasse 1, Geb. 26.23, 40225 Duesseldorf, Germany; Department of Pharmacy, Faculty of Health Sciences, Universitas Jenderal Soedirman, Jalan dr. Soeparno, Karangwangkal, 53123 Purwokerto, Indonesia.

Institute for Microbiology, Cluster of Excellence on Plant Sciences (CEPLAS), Heinrich Heine University, 40204 Duesseldorf, Germany; Bioeconomy Science Center (BioSC), c/o Forschungszentrum Jülich, 52425 Juelich, Germany.

出版信息

Fitoterapia. 2020 Oct;146:104698. doi: 10.1016/j.fitote.2020.104698. Epub 2020 Jul 31.

Abstract

Three new flavipin-derived alkaloids, azacoccones F-H (1-3), along with six known compounds (4-9) were isolated from the endophytic fungus Epicoccum nigrum MK214079 associated with leaves of Salix sp. The structures of the new compounds were established by analysis of their 1D/2D nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectroscopy (HRESIMS) data. The absolute configuration of azacoccones F-H (1-3) was determined by comparison of experimental electronic circular dichroism (ECD) data with reported ones and biogenetic considerations. Epicocconigrone A (4), epipyrone A (5), and epicoccolide B (6) exhibited moderate antibacterial activity against Staphylococcus aureus ATCC 29213 with minimal inhibitory concentration (MIC) values ranging from 25 to 50 μM. Furthermore, epipyrone A (5) and epicoccamide A (7) displayed mild antifungal activity against Ustilago maydis AB33 with MIC values of 1.6 and 1.8 mM, respectively. Epicorazine A (8) showed pronounced cytotoxicity against the L5178Y mouse lymphoma cell line with an IC value of 1.3 μM.

摘要

从与柳属植物叶片共生的内生真菌棘孢木霉 MK214079 中分离得到三个新的黄皮酰胺衍生生物碱(1-3),以及六个已知化合物(4-9)。通过分析它们的 1D/2D 核磁共振(NMR)和高分辨电喷雾电离质谱(HRESIMS)数据,确定了新化合物的结构。通过比较实验电子圆二色性(ECD)数据与文献报道的数据以及生物发生考虑,确定了 azacoccones F-H(1-3)的绝对构型。Epicocconigrone A(4)、epipyrone A(5)和 epicoccolide B(6)对金黄色葡萄球菌 ATCC 29213 表现出中等的抗菌活性,最小抑菌浓度(MIC)值范围为 25-50 μM。此外,epipyrone A(5)和 epicoccamide A(7)对玉米黑粉菌 AB33 表现出轻微的抗真菌活性,MIC 值分别为 1.6 和 1.8 mM。Epicorazine A(8)对 L5178Y 小鼠淋巴瘤细胞系表现出显著的细胞毒性,IC 值为 1.3 μM。

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