New Isocoumarin and Pyrone Derivatives from the Chinese Mangrove Plant Rhizophora mangle -Associated Fungus Phomopsis sp. DHS-11.
Zhikai GuoBiting ChenDandan ChenXiaoling DengJingzhe YuanShiqing ZhangZijun XiongJing XuPublished in: Molecules (Basel, Switzerland) (2023)
Mangrove-associated fungi are important sources for the discovery of new bioactive natural products. Three new isocoumarins ( 1 - 3 ) and one new pyrone derivative ( 4 ) were isolated from the ethyl acetate extract of the fermentation broth of the mangrove endophytic fungus Phomopsis sp. DHS-11. Nuclear magnetic resonance (NMR) spectroscopy (one-dimensional and two-dimensional) and mass spectrometry were used to determine the structures of these new compounds. The absolute configurations for the new isocoumarins 1 - 3 were determined by comparing their experimental and calculated electronic circular dichroism (ECD) spectra, while the configuration for the new pyrone-derivative 4 was tentatively solved by comparison of its 13 C NMR data with reported data. In the biological activity test, compounds 1 and 3 showed cytotoxic activity against HeLa cells with IC 50 values of 11.49 ± 1.64 µM and 8.70 ± 0.94 µM, respectively. The initial structure and activity relationship (SAR) analysis revealed that the length of the side chain at C-3 for isocoumarin-type compounds 1 - 3 could affect the cytotoxicity against HeLa cells. Compound 4 exhibited cytotoxic activities against human hepatoma cells HepG2 with an IC 50 value of 34.10 ± 2.92 µM. All compounds have no immunosuppressive activity.
Keyphrases
- cell cycle arrest
- induced apoptosis
- magnetic resonance
- mass spectrometry
- cell death
- high resolution
- oxidative stress
- endoplasmic reticulum stress
- electronic health record
- cell proliferation
- single cell
- liquid chromatography
- ms ms
- contrast enhanced
- ionic liquid
- data analysis
- high performance liquid chromatography
- deep learning
- high throughput
- capillary electrophoresis
- tandem mass spectrometry
- water soluble