Neuroprotective Glycosylated Cyclic Lipodepsipeptides, Colletotrichamides A-E, from a Halophyte-Associated Fungus, Colletotrichum gloeosporioides JS419
- Authors
- Bang, Sunghee; Lee, Changyeol; Kim, Soonok; Song, Ji Hoon; Kang, Ki Sung; Deyrup, Stephen T.; Nam, Sang-Jip; Xia, Xuekui; Shim, Sang Hee
- Issue Date
- 6-Sep-2019
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.84, no.17, pp.10999 - 11006
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 84
- Number
- 17
- Start Page
- 10999
- End Page
- 11006
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/996
- DOI
- 10.1021/acs.joc.9b01511
- ISSN
- 0022-3263
- Abstract
- 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.
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