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Indole Diketopiperazine Alkaloids from the Marine Sediment-Derived Fungus Aspergillus chevalieri against Pancreatic Ductal Adenocarcinoma

文献类型： 外文期刊

作者： El-Kashef, Dina H. 1 ; Obidake, Deborah D. 1 ; Schiedlauske, Katja 1 ; Deipenbrock, Alina 1 ; Scharf, Sebastian 3 ; Wang, Hao 5 ; Naumann, Daniela 6 ; Friedrich, Daniel 6 ; Miljanovic, Simone 1 ; Haj Hassani Sohi, Takin 7 ; Janiak, Christoph 7 ; Pfeffer, Klaus 3 ; Teusch, Nicole 1 ; Wang, Bin-Gui 1 ; Dai, Haofu 1 ;

作者机构： 1.Heinrich Heine Univ Dusseldorf, Inst Pharmaceut Biol & Biotechnol, D-40225 Dusseldorf, Germany

2.Minia Univ, Fac Pharm, Dept Pharmacognosy, Al Minya 61519, Egypt

3.Heinrich Heine Univ, Hosp Hyg, Med Fac, D-40225 Dusseldorf, Germany

4.Heinrich Heine Univ, Inst Med Microbiol, D-40225 Dusseldorf, Germany

5.Chinese Acad Trop Agr Sci, Inst Trop Biosci & Biotechnol, Hainan Key Lab Res & Dev Nat Prod Li Folk Med, Haikou 571101, Peoples R China

6.Univ Cologne, Dept Chem & Biochem, D-50939 Cologne, Germany

7.Heinrich Heine Univ Dusseldorf, Inst Inorgan Chem & Struct Chem, D-40225 Dusseldorf, Germany

关键词： Aspergillus chevalieri; indole diketopiperazine alkaloids; prenylation; genome sequencing; X-ray diffraction; pancreatic cancer; pancreatic ductal adenocarcinoma

期刊名称：MARINE DRUGS （ 影响因子：5.4； 五年影响因子：5.5 ）

ISSN：

年卷期： 2024 年 22 卷 1 期

页码：

收录情况： SCI

摘要： A new prenylated indole diketopiperazine alkaloid, rubrumline P (1), was isolated along with six more analogues and characterized from the fermentation culture of a marine sediment-derived fungus, Aspergillus chevalieri, collected at a depth of 15 m near the lighthouse in Dahab, Red Sea, Egypt. In the current study, a bioassay-guided fractionation allowed for the identification of an active fraction displaying significant cytotoxic activity against the human pancreatic adenocarcinoma cell line PANC-1 from the EtOAc extract of the investigated fungus compared to the standard paclitaxel. The structures of the isolated compounds from the active fraction were established using 1D/2D NMR spectroscopy and mass spectrometry, together with comparisons with the literature. The absolute configuration of the obtained indole diketopiperazines was established based on single-crystal X-ray diffraction analyses of rubrumline I (2) and comparisons of optical rotations and NMR data, as well as on biogenetic considerations. Genome sequencing indicated the formation of prenyltransferases, which was subsequently confirmed by the isolation of mono-, di-, tri-, and tetraprenylated compounds. Compounds rubrumline P (1) and neoechinulin D (4) confirmed preferential cytotoxic activity against PANC-1 cancer cells with IC50 values of 25.8 and 23.4 mu M, respectively. Although the underlying mechanism-of-action remains elusive in this study, cell cycle analysis indicated a slight increase in the sub-G1 peak after treatment with compounds 1 and 4.

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