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Stereocalpin B, a New Cyclic Depsipeptide from the Antarctic Lichen Ramalina terebrata

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Title
Stereocalpin B, a New Cyclic Depsipeptide from the Antarctic Lichen Ramalina terebrata
Other Titles
남극 지의류 Ramalina terebrata로부터 분리된 신규 cyclic depsipeptide, Stereocalpin B
Authors
Lee, Seulah
Jeong, Se Yun
NGUYEN, Dieu Linh
So, Jae Eun
Kim, Ki Hyun
Kim, Ji Hee
Han, Se Jong
Suh, Sung-Suk
Lee, Jun Hyuck
Youn, Ui Joung
Subject
Biochemistry & Molecular Biology
Keywords
Ramalina terebratadibenzofurancyclic depsipeptidesantimicrobialcytotoxicityanti-inflammation
Issue Date
2022-02
Citation
Lee, Seulah, et al. 2022. "Stereocalpin B, a New Cyclic Depsipeptide from the Antarctic Lichen Ramalina terebrata". METABOLITES, 12(2): 141-150.
Abstract
Stereocalpin B, a new cyclic depsipeptide (1), and a new dibenzofuran derivative (3), were isolated from the Antarctic lichen, Ramalina terebrata (Ramalinaceae), along with a known cyclic depsipeptide (2). The structures of new compounds were characterized by comprehensive spectrometric analyses; high-resolution fast atom bombardment mass spectrometry (HR-FABMS) and liquid chromatography-tandem mass spectrometry (LC-MS/MS). Stereocalpin B (1) existed in a rotameric equilibrium, which was confirmed using nuclear Overhauser effect spectroscopy (NOESY)/exchange spectroscopy (EXSY) spectrum. Absolute configurations of the amino acid units in 1 were assigned using the advanced Marfey's method and subsequent NOESY analysis of the 5-hydroxy-2,4-dimethyl-3-oxo-decanoic acid residue confirmed the complete stereochemistry of 1. Compounds 1-3 exhibited moderate antimicrobial activities against E. coli, with the IC50 values ranging from 18-30 mu g/mL. Compound 2 exhibited cell growth inhibition against HCT116 cell lines, with the IC50 value of 20 +/- 1.20 mu M, and compounds 1 and 2 also showed potent anti-inflammatory activities against lipopolysaccharide (LPS)-induced RAW264.7 macrophages with the IC50 values ranging from 5-7 mu M.
URI
https://repository.kopri.re.kr/handle/201206/13301
DOI
http://dx.doi.org/10.3390/metabo12020141
Type
Article
Station
King Sejong Station
Indexed
SCIE
Appears in Collections  
2021-2021, Development of potential candidates as antibiotics based on polar genetic resources (21-21) / Lee, Jun Hyuck (PM21030)
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