Microspinosamide, a new HIV-inhibitory cyclic depsipeptide from the marine sponge Sidonops microspinosa.
Microspinosamide (1), a new cyclic depsipeptide incorporating 13 amino acid residues, was isolated from extracts of an Indonesian collection of the marine sponge Sidonops microspinosa. Its structure was elucidated by extensive NMR and mass spectral analyses, and by chemical degradation and derivatization studies. The tridecapeptide 1 incorporates numerous uncommon amino acids, and it is the first naturally occurring peptide to contain a beta-hydroxy-p-bromophenylalanine residue. Microspinosamide (1) inhibited the cytopathic effect of HIV-1 infection in an XTT-based in vitro assay with an EC(50) value of approximately 0.2 microg/mL.
Rashid
M A
MA
Division of Cancer Treatment and Diagnosis, National Cancer Institute-Frederick Cancer Research and Development Center, Building 1052, Room 121, Frederick, Maryland 21702-1201, USA.
Gustafson
K R
KR
Cartner
L K
LK
Shigematsu
N
N
Pannell
L K
LK
Boyd
M R
MR
D000818:Animals; D019380:Anti-HIV Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002853:Chromatography, Liquid; D003588:Cytopathogenic Effect, Viral / Q000187:drug effects; D047630:Depsipeptides; D015497:HIV-1 / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D009842:Oligopeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment
D019380:Anti-HIV Agents; D047630:Depsipeptides; D009842:Oligopeptides; D010456:Peptides, Cyclic; C428191:microspinosamide