The sea star Oreaster reticulatus contains, along with the known ophidiacerebrosides C–E, nine new glycosphingolipids named oreacerebrosides A–I. Their structures were elucidated by a combination of spectroscopic methods and chemical degradation. All compounds contain a 4,8,10-triunsaturated sphingoid base. Oreacerebrosides A–C have a β-glucopyranoside as the sugar residue, as found in ophidiacerebrosides C–E and in all known compounds of this type; in contrast, oreacerebrosides D–I are the first examples of β-galactosylceramides containing this unusual sphingoid base. Four representative glycosphingolipids were tested for cytotoxic activity on rat glioma C6 cells and were shown to be mildly cytotoxic; the glucosylceramides were more active than the galactosylceramides. In addition, oreacerebroside I, but not ophidiacerebroside E, was shown to exert proangiogenic activity and was able to increase VEGF-induced human endothelial cell proliferation.

Oreacerebrosides: Bioactive Cerebrosides with a Triunsaturated Sphingoid Base from the Sea Star Oreaster reticulatus / Costantino, Valeria; DE ROSA, Caterina; Fattorusso, Ernesto; Imperatore, Concetta; Mangoni, Alfonso; Irace, Carlo; Maffettone, Carmen; Capasso, Domenica; L., Malorni; R., Palumbo; Pedone, Carlo. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - (2007), pp. 5277-5283. [10.1002/ejoc.200700390]

Oreacerebrosides: Bioactive Cerebrosides with a Triunsaturated Sphingoid Base from the Sea Star Oreaster reticulatus

COSTANTINO, VALERIA;DE ROSA, CATERINA;FATTORUSSO, ERNESTO;IMPERATORE, CONCETTA;MANGONI, ALFONSO;IRACE, CARLO;MAFFETTONE, CARMEN;CAPASSO, DOMENICA;PEDONE, CARLO
2007

Abstract

The sea star Oreaster reticulatus contains, along with the known ophidiacerebrosides C–E, nine new glycosphingolipids named oreacerebrosides A–I. Their structures were elucidated by a combination of spectroscopic methods and chemical degradation. All compounds contain a 4,8,10-triunsaturated sphingoid base. Oreacerebrosides A–C have a β-glucopyranoside as the sugar residue, as found in ophidiacerebrosides C–E and in all known compounds of this type; in contrast, oreacerebrosides D–I are the first examples of β-galactosylceramides containing this unusual sphingoid base. Four representative glycosphingolipids were tested for cytotoxic activity on rat glioma C6 cells and were shown to be mildly cytotoxic; the glucosylceramides were more active than the galactosylceramides. In addition, oreacerebroside I, but not ophidiacerebroside E, was shown to exert proangiogenic activity and was able to increase VEGF-induced human endothelial cell proliferation.
2007
Oreacerebrosides: Bioactive Cerebrosides with a Triunsaturated Sphingoid Base from the Sea Star Oreaster reticulatus / Costantino, Valeria; DE ROSA, Caterina; Fattorusso, Ernesto; Imperatore, Concetta; Mangoni, Alfonso; Irace, Carlo; Maffettone, Carmen; Capasso, Domenica; L., Malorni; R., Palumbo; Pedone, Carlo. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - (2007), pp. 5277-5283. [10.1002/ejoc.200700390]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/200902
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