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Antiproliferative activity and absolute configuration of zonaquinone acetate from the Jamaican alga Stypopodium zonale

Penicooke, Najair, Walford, Kemil, Badal, Simone, Delgoda, Rupika, Williams, Lawrence A.D., Joseph-Nathan, Pedro, Gordillo-Román, Bárbara, Gallimore, Winklet
Phytochemistry 2013 v.87 pp. 96-101
Phaeophycophyta, acetates, antioxidant activity, breast neoplasms, colorectal neoplasms, cytotoxicity, fluorouracil, inhibitory concentration 50, liver neoplasms, metabolites, nuclear magnetic resonance spectroscopy, spectral analysis, stereochemistry, tamoxifen
The chemical investigation of specimens of the Jamaican brown alga Stypopodium zonale led to the isolation of a cytotoxic compound, zonaquinone acetate (1), along with known compounds flabellinone, not previously identified in S. zonale, stypoldione, 5′,7′-dihydroxy-2′-pentadecylchromone and sargaol. The structures of the metabolites were established by analysis of the spectral data including 1D and 2D NMR experiments while the stereochemistry of 1 was assessed by VCD measurements. Cytotoxic activity was reported in vitro for 1 against breast cancer and colon cancer cell lines at IC50 values of 19.22–21.62μM and 17.11–18.35μM respectively, comparing favorably with standard treatments tamoxifen (17.22–17.32μM) and fluorouracil (27.03–31.48μM). When tested with liver cancer cells (Hep G2), no activity was observed. Weak antioxidant activity was observed with 1 but sargaol exhibited high activity.