4-Hydroxybenzoyl derivative from the aqueous extract of the hydroid Campanularia sp.
A new compound, N-(4-guanidinobutyl)-2-(4-hydroxyphenyl)-2-oxo-acetamide (1) was isolated from the aqueous extract of the hydroid Campanularia sp. Its structure was elucidated using NMR spectroscopic techniques and mass spectrometric analysis. The most stable conformation was determined using molecular modeling and the results of a NOESY experiment. Although compound 1 shows structural similarities to some highly potent histone deacetylase inhibitors (HDACi), e.g., suberoylanilide hydroxamic acid (SAHA) (2) and trichostatin A (TSA) (3), it does not inhibit the growth of ARP-1 cells at 100 microM concentration, a significant indication that it has no inhibitory activity to HDACs.
Houssen
Wael E
WE
Marine Natural Products Laboratory, Chemistry Department, Aberdeen University, Aberdeen AB24 3UE, Scotland, UK.
Jaspars
Marcel
M
D000818:Animals; D004354:Drug Screening Assays, Antitumor; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D056572:Histone Deacetylase Inhibitors; D006801:Humans; D006877:Hydroxamic Acids / Q000737:chemistry / Q000494:pharmacology; D062385:Hydroxybenzoates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D037402:Hydrozoa / Q000737:chemistry*; D015394:Molecular Structure; D009520:New Zealand; D019906:Nuclear Magnetic Resonance, Biomolecular; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured; D000077337:Vorinostat
D004791:Enzyme Inhibitors; D056572:Histone Deacetylase Inhibitors; D006877:Hydroxamic Acids; D062385:Hydroxybenzoates; C499915:N-(4-guanidinobutyl)-2-(4-hydroxyphenyl)-2-oxo-acetamide; D000077337:Vorinostat