Tedanolide C: a potent new 18-membered-ring cytotoxic macrolide isolated from the Papua New Guinea marine sponge Ircinia sp.
Cytotoxicity-guided fractionation of the crude methanol extract of a marine sponge, Ircinia sp., yielded tedanolide C (1), a new 18-membered macrolide. The structure was solved by interpreting NMR and MS data, and the relative stereochemistry was determined from a combination of homo- and heteronuclear coupling constants in conjunction with molecular modeling. Compound 1 exhibited potent cytotoxicity against HCT-116 cells in vitro. Cell cycle analysis showed that treatment of cells with compound 1 arrested cells in the S-phase.
Chevallier
Camille
C
Department of Medicinal Chemistry, University of Utah, Salt Lake City, Utah 84112, USA.
Bugni
Tim S
TS
Feng
Xidong
X
Harper
Mary Kay
MK
Orendt
Anita M
AM
Ireland
Chris M
CM
D000818:Animals; D002453:Cell Cycle / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D045325:HCT116 Cells; D006801:Humans; D018942:Macrolides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008968:Molecular Conformation; D011161:Porifera / Q000737:chemistry*; D012015:Reference Standards; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D018942:Macrolides; C516408:tedanolide C