Neuroprotective Glycosylated Cyclic Lipodepsipeptides, Colletotrichamides A-E, from a Halophyte-Associated Fungus, Colletotrichum gloeosporioides JS419.
Sunghee BangChangyeol LeeSoonok KimJi Hoon SongKi Sung KangStephen T DeyrupSang-Jip NamXuekui XiaSang Hee ShimPublished in: The Journal of organic chemistry (2019)
Glutamate neurotoxicity has been implicated in neuronal death in both acute CNS injury and in chronic neurodegenerative diseases. Five unique cyclic depsipeptides with neuroprotective activity, colletotrichamides A-E (1-5), were isolated from cultures of a halophyte Suaeda japonica-associated fungus, Colletotrichum gloeosporioides JS419. Spectroscopic analysis revealed that they were glycosylated cyclic lipodepsipeptides. Their relative configurations were determined by ROESY and J-based configuration analysis, and absolute configurations were established by chemical reactions including modified Mosher's method, advanced Marfey's method, and sugar derivatization. This is the first report of a glycosylated dimethyl-trioxygenated dodecanoyl moiety, and the relative as well as absolute stereochemistry was elucidated herein for the first time. Colletotrichamide C exhibited strong neuroprotective activity against glutamate in hippocampal HT22 cells.
Keyphrases
- cerebral ischemia
- blood brain barrier
- subarachnoid hemorrhage
- ms ms
- brain injury
- liver failure
- liquid chromatography tandem mass spectrometry
- molecular docking
- cell proliferation
- single cell
- cell death
- oxidative stress
- intensive care unit
- cell cycle arrest
- respiratory failure
- liquid chromatography
- endoplasmic reticulum stress