Structure Elucidation of Calyxoside B, a Bipolar Sphingolipid from a Marine Sponge Cladocroce sp. through the Use of Beckmann Rearrangement
| Autor: | Nobuhiro Yamawaki, Yasuhiro Morii, Hiroshi Watarai, Shigeki Matsunaga, Kenji Sugawara, Yuji Ise, Shigeru Okada, Hisayoshi Yokose |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Ketone
QH301-705.5 Stereochemistry Pharmaceutical Science 01 natural sciences 03 medical and health sciences chemistry.chemical_compound Drug Discovery Beckmann rearrangement Structural isomer Biology (General) Derivatization Pharmacology Toxicology and Pharmaceutics (miscellaneous) 030304 developmental biology chemistry.chemical_classification 0303 health sciences biology glycosphingolipid 010405 organic chemistry Chemistry structure elucidation marine natural products Biological activity Glycosphingolipid Oxime biology.organism_classification 0104 chemical sciences Sponge marine sponge |
| Zdroj: | Marine Drugs Volume 19 Issue 6 Marine Drugs, Vol 19, Iss 287, p 287 (2021) |
| ISSN: | 1660-3397 |
| DOI: | 10.3390/md19060287 |
| Popis: | Marine sponges are an excellent source of biologically active secondary metabolites. We focus on deep-sea sponges for our discovery study. A marine sponge Cladocroce sp. exhibited cytotoxic activity in the bioactivity screening. From this sponge a previously unreported cytotoxic glycosphingolipid, calyxoside B, was isolated and the structure of this compound was elucidated by analyses of MS and NMR spectra and chemical derivatization. We converted the ketone in the middle of a long aliphatic chain into an oxime to which was applied Beckmann rearrangement to afford two positional isomers of amides. The products were subjected to acidic hydrolysis followed by LC-MS analysis, permitting us to assign unequivocally the position of the ketone. Calyxoside B shows cytotoxicity against HeLa cells with an IC50 value of 31 µM and also weakly stimulated the production of cytokines in mice. |
| Databáze: | OpenAIRE |
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