Isolation and structures of pipecolidepsins A and B, cytotoxic cyclic depsipeptides from the Madagascan sponge Homophymia lamellosa.
Two new cyclic depsipeptides, pipecolidepsins A and B (1 and 2), have been isolated from the sponge Homophymia lamellosa collected off the coast of Madagascar. Their structures were determined by a combination of NMR experiments and by LC-MS analysis of the amino acid fragments obtained by hydrolysis and derivatization using Marfey's reagent. In addition to several common amino acids, these peptides contain unusual residues, including 2-amino-3-hydroxy-4,5-dimethylhexanoic acid, 3-ethoxyasparagine, 3,4-dimethylglutamine, 4,7-diamino-2,3-dihydroxy-7-oxoheptanoic acid, and 3-hydroxyaspartic acid as well as a terminal 3-hydroxy-2,4,6-trimethylheptanoic acid residue. Pipecolidepsins A and B displayed cytotoxic activity against a panel of different human tumor cell lines.
Medicinal Chemistry Department, PharmaMar S. A., Pol. Ind. La Mina Norte , Avenida de los Reyes 1, 28770, Colmenar Viejo (Madrid), Spain.
Laura
L
Coello
Fernando
F
Reyes
María Jesús
MJ
Martín
Carmen
C
Cuevas
Rogelio
R
Fernández
D000818:Animals; D001224:Aspartic Acid / Q000031:analogs & derivatives; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification*; D004354:Drug Screening Assays, Antitumor; D005973:Glutamine / Q000031:analogs & derivatives; D006801:Humans; D008270:Madagascar; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*
C419323:3,4-dimethylglutamine; D047630:Depsipeptides; C587510:pipecolidepsin A; C000590244:pipecolidepsin B; D005973:Glutamine; C011274:3-hydroxyaspartic acid; D001224:Aspartic Acid