title: Neamphamide A, a new HIV-inhibitory depsipeptide from the Papua New Guinea marine sponge Neamphius huxleyi.
abstract: 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.
authors.affiliation: Molecular Targets Development Program, Center for Cancer Research, National Cancer Institute, Building 1052, Room 121, Frederick, Maryland 21702-1201, USA.
authors.forename: Naoya
authors.initials: N
authors.lastname: Oku
authors.forename: Kirk R
authors.initials: KR
authors.lastname: Gustafson
authors.forename: Laura K
authors.initials: LK
authors.lastname: Cartner
authors.forename: Jennifer A
authors.initials: JA
authors.lastname: Wilson
authors.forename: Nobuharu
authors.initials: N
authors.lastname: Shigematsu
authors.forename: Sonja
authors.initials: S
authors.lastname: Hess
authors.forename: Lewis K
authors.initials: LK
authors.lastname: Pannell
authors.forename: Michael R
authors.initials: MR
authors.lastname: Boyd
authors.forename: James B
authors.initials: JB
authors.lastname: McMahon
mesh_terms: 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
chemical_list: D019380:Anti-HIV Agents; D047630:Depsipeptides; D010456:Peptides, Cyclic; C418139:callipeltin A; C492416:neamphamide A