Neuroprotective Glycosylated Cyclic Lipodepsipeptides, Colletotrichamides A-E, from a Halophyte-Associated Fungus, Colletotrichum gloeosporioides JS']JS419

被引：24

作者：

Bang, Sunghee ^{[1
]}

Lee, Changyeol ^{[1
]}

Kim, Soonok ^{[2
]}

Song, Ji Hoon ^{[3
]}

Kang, Ki Sung ^{[3
]}

Deyrup, Stephen T. ^{[4
]}

Nam, Sang-Jip ^{[5
]}

Xia, Xuekui ^{[6
]}

Shim, Sang Hee ^{[1
]}

机构：

[1] Duksung Womens Univ, Coll Pharm, Seoul 01369, South Korea

[2] Natl Inst Biol Resources, Biol Resources Assessment Div, Incheon 22689, South Korea

[3] Gachon Univ, Coll Korean Med, Seongnam 13120, South Korea

[4] Siena Coll, Dept Chem & Biochem, Loudonville, NY 12211 USA

[5] Ewha Womans Univ, Dept Chem & Nano Sci, Seoul 03760, South Korea

[6] Qllu Univ Technol, Shandong Acad Sci, Biol Inst, Jinan 250103, Shandong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 17期

基金：

新加坡国家研究基金会;

关键词：

CONFIGURATION; METABOLITES; DISEASES;

D O I：

10.1021/acs.joc.9b01511

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：10999 / 11006

页数：8

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