Stereocalpin B, a New Cyclic Depsipeptide from the Antarctic Lichen Ramalina terebrata
| Autor: | Seulah Lee, Se Yun Jeong, Dieu Linh Nguyen, Jae Eun So, Ki Hyun Kim, Ji Hee Kim, Se Jong Han, Sung-Suk Suh, Jun Hyuck Lee, Ui Joung Youn |
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| Jazyk: | angličtina |
| Rok vydání: | 2022 |
| Předmět: | |
| Zdroj: | Metabolites, Vol 12, Iss 2, p 141 (2022) |
| Druh dokumentu: | article |
| ISSN: | 12020141 2218-1989 |
| DOI: | 10.3390/metabo12020141 |
| Popis: | 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 μg/mL. Compound 2 exhibited cell growth inhibition against HCT116 cell lines, with the IC50 value of 20 ± 1.20 μM, 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 μM. |
| Databáze: | Directory of Open Access Journals |
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