Abstract
Chemical investigation of the Mediterranean ascidian Ciona edwardsii has been performed, leading to the isolation of two halogenated compounds: a new tyrosineiodinated derivative iodocionin (1) and the relevant brominated analogue (2), previously isolated from a Caribbean sponge. The structure of the new compound 1 has been assigned on the basis of spectroscopic analysis. Both compounds were tested for cytotoxicity in vitro against two different cancer cell lines, L5178Y (mouse lymphoma) and PC-12 (rat pheochromocytoma). Iodocionin was shown to possess significant and selective activity against lymphoma cells with an IC50 of 7.75 μg/mL.
Highlights
The sea is a large source of biogenic organohalogens, which are biosynthesized by seaweeds, sponges, corals, tunicates, bacteria, and other marine life [1]
Specimens of C. edwardsii collected in the bay of Naples were exhaustively extracted with methanol and, subsequently, with chloroform
MeOH/H2O 1:1 fraction was further separated by High-performance liquid chromatography (HPLC) on a C18 reverse phase column, yielding iodocionin (1) and compound 2 in the pure state
Summary
The sea is a large source of biogenic organohalogens, which are biosynthesized by seaweeds, sponges, corals, tunicates, bacteria, and other marine life [1]. We wish to report here the isolation from a phlebobranchiate ascidian, Ciona edwardsii (species similar but distinct from C. intestinalis) of a new tyrosine-iodinated derivative, named iodocionin (1) together with the relevant brominated analogue 2, previously isolated from the Caribbean sponge Verongula gigantea [8]. Both compounds 1 and 2 were tested for their cytotoxic activity in vitro against two different cancer cell lines, L5178Y (mouse lymphoma) and PC-12 (rat pheochromocytoma). Iodocionin (1) was shown to possess a significant and selective activity against lymphoma cells
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