Homophymine A, an anti-HIV cyclodepsipeptide from the sponge Homophymia sp.
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.
Zampella
Angela
A
Dipartimento di Chimica delle Sostanze Naturali, Universita di Napoli Federico II, via D. Montesano 49, 80131, Napoli, Italy.
Sepe
Valentina
V
Luciano
Paolo
P
Bellotta
Filomena
F
Monti
Maria Chiara
MC
D'Auria
Maria Valeria
MV
Jepsen
Trine
T
Petek
Sylvain
S
Adeline
Marie-Thérèse
MT
Laprévôte
Olivier
O
Aubertin
Anne-Marie
AM
Debitus
Cécile
C
Poupat
Christiane
C
Ahond
Alain
A
D000818:Animals; D019380:Anti-HIV Agents / Q000737:chemistry*; D047630:Depsipeptides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D019380:Anti-HIV Agents; D047630:Depsipeptides; C531861:homophymine A