Two Gracilioethers Containing a [2(5H)-Furanylidene]ethanoate Moiety and 9,10-Dihydroplakortone G: New Polyketides from the Caribbean Marine Sponge Plakortis halichondrioides

Abstract

Gracilioether M (6) and 11,12-dihydrogracilioether M (7), two polyketides with a [2(5H)-furanylidene]ethanoate moiety, along with known plakortone G (9) and its new naturally occurring derivative 9,10-dihydroplakortone G (8), were isolated from the Caribbean marine sponge Plakortis halichondrioides. The structures and absolute configuration of 6, 7, and 8 were characterized by analysis of HRESIMS and NMR spectroscopic data, chemical derivatization, and side-by-side comparisons with published NMR data of related analogs. Compounds 6 and 7 and a mixture of 8 and 9 were evaluated for cytotoxicity against MCF-7 human breast cancer cells. In addition, the in vitro antiplasmodial activity against Plasmodium berghei of these compounds was scrutinized using a drug luminescence assay.

Probing the Antiplasmodial Properties of Plakortinic Acids C and D: An Uncommon Pair of Marine Peroxide-Polyketides Isolated from a Two-Sponge Association of Plakortis symbiotica and Xetospongia deweerdtae Collected near Puerto Rico

“…Likewise, the observed antiplasmodial activity demonstrated by these compounds can be attributed to their unique chemical structure, which includes two endoperoxide ring systems (see Figure 1 ). Such structural features have consistently been highlighted for their fundamental role in conferring antiplasmodial activity [ 26 , 71 , 72 ]. This aspect adds significant value to the ongoing investigation of plakortinic acids C ( 1 ) and D ( 2 ), not only due to their uncommon and extraordinary molecular structures, but also due to the mixture’s notable efficacy as an antiplasmodial agent, as supported by the results presented here.…”