ABSTRACT
The sesquiterpene aureol (1) was isolated by chromatographic fractionation of a non-polar extract from Smenospongia sp. Methylation of aureol yielded 5'-O-methyl-aureol (2) while the prepared acylation products of aureol were 5'-O-acetyl-aureol (3), 5'-O-benzoyl-aureol (4), 5'-O-(4-fluoro-benzoyl)-aureol (5), 5'-O-(4-chlorobenzoyl)-aureol (6), 5'-O-(4-methylbenzoyl)-aureol (7), 5'-O-nicotinoyl-aureol (8), aureol-N,N-dimethylthiocarbamate (9), 5'-O-(2-furoylcarbonyl)-aureol (10), 5'-O-(2-thienoylcarbonyl-aureol (11). The structures of aureol as well as its ten derivatives were established through spectral analysis. The in vitro cytotoxic activities of the eleven compounds were evaluated against Hepa59T/VGH, KB and Hela tumor cell lines.
Subject(s)
Porifera/chemistry , Sesquiterpenes/chemical synthesis , Animals , Drug Screening Assays, Antitumor , HeLa Cells , Humans , KB Cells , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Optical Rotation , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacology , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, InfraredABSTRACT
The marine sponge Dysidea avara contained avarol (1) and avarone (2). Avarol on acylation yielded 2',5'-O-dibenzoylavarol (3); 2,5'-O-(4-chlorobenzoyl)avarol (4); 2,5'-O-dicinnamoylavarol (5); 2,5'-O-(4-bromobenzoyl)avarol(6); 2',5'-O-dioctanoylavarol (7); 2',5'-O-(4-fluorobenzoyl)avarol (8) and diacetylavarol (9). The structural elucidation of all the compounds 1-9 have been done by spectral analysis. The cytotoxicity of these compounds were also determined and evaluated. Compounds 6 and 9 showed selective cytotoxicity against Hepa (human hepatoma) and KB cell lines respectively.
