Homophymine A, an Anti-HIV Cyclodepsipeptide from the Sponge Homophymia sp.
The Journal of Organic Chemistry2008Vol. 73(14), pp. 5319–5327
Citations Over TimeTop 10% of 2008 papers
Angela Zampella, Valentina Sepe, Paolo Luciano, Filomena Bellotta, Maria Chiara Monti, Maria Valeria D’Auria, Trine Jepsen, Sylvain Petek, Marie‐Thérèse Adeline, Olivier Laprévôte, Anné-Marie Aubertin, Cécile Debitus, Christiane Poupat, A. Ahond
Abstract
A new anti-HIV cyclodepsipeptide, homophymine A, was isolated from a New Caledonian collection of the marine sponge Homophymia sp. The structure of homophymine A was determined by interpretation of spectroscopic data, acid hydrolysis, and LC-MS analysis. Homophymine A contains 11 amino acid residues and an amide-linked 3-hydroxy-2,4,6-trimethyloctanoic acid moiety. Along with four D-, two L-, and one N-methyl amino acids, it also contains four unusual amino acid residues: (2S,3S,4R)-3,4-diMe-Gln, (2R,3R,4S)-4-amino-2,3-dihydroxy-1,7-heptandioic acid, L-ThrOMe, and (2R,3R,4R)-2-amino-3-hydroxy-4,5-dimethylhexanoic acid. In a cell-based XTT assay, homophymine A exhibited cytoprotective activity against HIV-1 infection with a IC50 of 75 nM.
Related Papers
- → Total Synthesis and Cytotoxicity Studies of a Cyclic Depsipeptide with Proposed Structure of Palau'amide(2005)53 cited
- → Crystal structure of a depsipeptide, Boc-(Leu-Leu-Lac)3-Leu-Leu-OEt(2001)20 cited
- → Ab initio studies on the binding of Na+ and K+ to the fundamental components of depsipeptides(2009)2 cited
- → Crystal structure of a depsipeptide, Boc–(Leu–Leu–Lac)3–Leu–Leu–OEt(2001)1 cited
- Total synthesis and cytotoxicity studies of a cyclic depsipeptide with proposed structure of palau'amide(2005)