Isolation of aureol from Smenospongia sp. and cytotoxic activity of some aureol derivatives.
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.
Shen
Ya-Ching
YC
Institute of Marine Resources, National Sun Yat-Sen University, 70-Lien Hai Road, Kaohsiung, Taiwan, Republic of China. ycshen@mail.nsysu.edu.tw
Liaw
Chia-Ching
CC
Ho
Jing-Ren
JR
Khalil
Ashraf Taha
AT
Kuo
Yau-Haur
YH
D000818:Animals; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D007624:KB Cells; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009904:Optical Rotation; D011161:Porifera / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
D012717:Sesquiterpenes; C455540:aureol