| RRC ID |
70461
|
| Author |
Sugawara K, Watarai H, Ise Y, Yokose H, Morii Y, Yamawaki N, Okada S, Matsunaga S.
|
| Title |
Structure Elucidation of Calyxoside B, a Bipolar Sphingolipid from a Marine Sponge Cladocroce sp. through the Use of Beckmann Rearrangement.
|
| Journal |
Mar Drugs
|
| Abstract |
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.
|
| Volume |
19(6)
|
| Published |
2021-5-21
|
| DOI |
10.3390/md19060287
|
| PII |
md19060287
|
| PMID |
34063932
|
| PMC |
PMC8224005
|
| MeSH |
Amides / chemistry
Animals
Cytokines / metabolism
Cytotoxins / chemistry*
Cytotoxins / isolation & purification
Cytotoxins / pharmacology
Glycosphingolipids / chemistry*
Glycosphingolipids / isolation & purification
Glycosphingolipids / pharmacology
HeLa Cells
Humans
Mice, Inbred C57BL
Mice, Knockout
Molecular Structure
Porifera / chemistry*
Stereoisomerism
|
| IF |
4.073
|
| Resource |
| Human and Animal Cells |
HeLa(RCB0007) |
