Synthesis of clionamine B, an autophagy stimulating aminosteroid isolated from the sponge Cliona celata.

Abstract

Clionamine B (2), an aminosteroid isolated from the marine sponge Cliona celata, has been synthesized starting from the plant sapogenin tigogenin (5). A key step in the synsthesis is the stereoselective introduction of the C-20 α-hydroxyl substituent via oxidation of a γ-lactone enolate with molecular oxygen. Synthetic clionamine B (2) strongly stimulated autophagy in human breast cancer MCF-7 cells.

• Authors: Roberto Forestieri, Elizabeth Donohue, Aruna Balgi, Michel Roberge, Raymond J Andersen
• Journal: Organic letters (Org Lett) Vol. 15 Issue 15 Pg. 3918-21 (Aug 02 2013) ISSN: 1523-7052 [Electronic] United States
• PMID: 23869546 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Steroids
• clionamine B

Topics

• Animals
• Autophagy (drug effects)
• Breast Neoplasms (chemistry, metabolism, pathology)
• Humans
• MCF-7 Cells (chemistry)
• Marine Biology
• Nuclear Magnetic Resonance, Biomolecular
• Porifera (chemistry)
• Stereoisomerism
• Steroids (chemical synthesis, chemistry)