Phenylhydrazone Alkaloids from the Deep-Sea Cold Seep Derived Fungus Talaromyces amestolkiae HDN21-0307.
Jiajin WuWenxue WangYuhuan YangMudassir ShahJixing PengLuning ZhouGuojian ZhangQian CheJing LiTianjiao ZhuDe-Hai LiPublished in: Journal of natural products (2024)
Alkaloids with a phenylhydrazone architecture are rarely found in nature. Four unusual phenylhydrazone alkaloids named talarohydrazones A-D ( 1 - 4 ) were isolated from the deep-sea cold seep derived fungus Talaromyces amestolkiae HDN21-0307 using the one strain-many compounds (OSMAC) approach and MS/MS-based molecular networking (MN) combined with network annotation propagation (NAP) and the unsupervised substructure annotation method MS2LDA. Their structures were elucidated by spectroscopic data analysis, single-crystal X-ray diffraction, and quantum chemical calculations. Talarohydrazone A ( 1 ) possessed an unusual skeleton combining 2,4-pyridinedione and phenylhydrazone. Talarohydrazone B ( 2 ) represents the first natural phenylhydrazone-bearing azadophilone. Bioactivity evaluation revealed that compound 1 exhibited cytotoxic activity against NCI-H446 cells with an IC 50 value of 4.1 μM. In addition, compound 1 displayed weak antibacterial activity toward Staphylococcus aureus with an MIC value of 32 μg/mL.
Keyphrases
- data analysis
- ms ms
- staphylococcus aureus
- molecular dynamics
- high resolution
- induced apoptosis
- mass spectrometry
- multiple sclerosis
- rna seq
- density functional theory
- single cell
- molecular dynamics simulations
- escherichia coli
- computed tomography
- oxidative stress
- single molecule
- cell proliferation
- high performance liquid chromatography
- signaling pathway
- energy transfer
- crystal structure
- clinical evaluation
- quantum dots
- ionic liquid
- liquid chromatography
- tandem mass spectrometry