Two new bicyclic cembranolides from a new Sarcophyton species and determination of the absolute configuration of sarcoglaucol-16-one.
During the chemical investigation of a new species of soft coral belonging to the genus Sarcophyton, two novel cembranoid compounds with a 12Z double bond (1 and 2) were obtained. Determination of the double bond configurations was done using NMR spectroscopic data and the results of molecular modeling studies. Compound 3, one of several known compounds (3-5), was found to be cytotoxic toward an MCF7 tumor cell line.Additionally, we report the absolute stereochemistry of the cembrane sarcoglaucol-16-one (6), which was determined using the modified Mosher[prime or minute]s method.
Gross
Harald
H
Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, D-53115 Bonn, Germany.
Wright
Anthony D
AD
Beil
Winfried
W
König
Gabriele M
GM
D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D045744:Cell Line, Tumor; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D001643:Bridged Bicyclo Compounds; D004224:Diterpenes; C498027:sarcoglaucol-16-one; C037071:cembrane