Neamphamide A, a new HIV-inhibitory depsipeptide from the Papua New Guinea marine sponge Neamphius huxleyi.
A new HIV-inhibitory cyclic depsipeptide, neamphamide A (2), was isolated from a Papua New Guinea collection of the marine sponge Neamphius huxleyi. Its structure was established through interpretation of spectroscopic data and by acid hydrolysis, derivatization of the free amino acids, and LC-MS analysis of the derivatives. Neamphamide A (2) contains 11 amino acid residues and an amide-linked 3-hydroxy-2,4,6-trimethylheptanoic acid moiety. The amino acid constituents were identified as L-Leu, L-NMeGln, D-Arg, D- and L-Asn, two residues of D-allo-Thr, L-homoproline, (3S,4R)-3,4-dimethyl-L-glutamine, beta-methoxytyrosine, and 4-amino-7-guanidino-2,3-dihydroxyheptanoic acid. In a cell-based XTT assay, 2 exhibited potent cytoprotective activity against HIV-1 infection with an EC50 of approximately 28 nM.
Oku
Naoya
N
Molecular Targets Development Program, Center for Cancer Research, National Cancer Institute, Building 1052, Room 121, Frederick, Maryland 21702-1201, USA.
Gustafson
Kirk R
KR
Cartner
Laura K
LK
Wilson
Jennifer A
JA
Shigematsu
Nobuharu
N
Hess
Sonja
S
Pannell
Lewis K
LK
Boyd
Michael R
MR
McMahon
James B
JB
D000818:Animals; D019380:Anti-HIV Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D047630:Depsipeptides; D015497:HIV-1 / Q000187:drug effects*; D015394:Molecular Structure; D010219:Papua New Guinea; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism
D019380:Anti-HIV Agents; D047630:Depsipeptides; D010456:Peptides, Cyclic; C418139:callipeltin A; C492416:neamphamide A