Cytotoxic metabolites from the Okinawan ascidian Diplosoma virens.
The unstable isomeric compounds 5-hydroxy-7-prop-2-en-(E)-ylidene-7,7adihydro-2H-cyclopenta[b]pyran-6-one (1) and 5-hydroxy-7-prop-2-en-(Z)-ylidene-7,7adihydro-2H-cyclopenta[b]pyran-6-one (2), previously described as antimicrobial metabolites from the sponge Ulosa sp., were isolated and identified as major components of the ascidian Diplosoma virens. In this paper, full spectral data for 2 and complete 13CNMR data for 1, based on 2D NMR measurements, are provided for the first time. Compounds 1 and 2 showed cytotoxity against HCT116 cells (human colorectal cancer cells) by triggering apoptotic cell death.
Ogi
Takayuki
T
Department of Chemistry, Biology and Marine Science, University of the Ryukyus, Nishihara-cho Okinawa 903-0123, Japan.
Taira
Junsei
J
Margiastuti
Palupi
P
Ueda
Katsuhiro
K
D000818:Animals; D053148:Caspase 3 / Q000378:metabolism; D053179:Caspase 7 / Q000378:metabolism; D016923:Cell Death / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D045325:HCT116 Cells; D006801:Humans; D007564:Japan; D009682:Magnetic Resonance Spectroscopy; D011714:Pyrans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014561:Urochordata / Q000737:chemistry*
D011714:Pyrans; D053148:Caspase 3; D053179:Caspase 7