A New Iodinated Metabolite and a New Alkyl Sulfate from the Senegalese Sponge Ptilocaulis spiculifer

Journal of Natural Products
1996.0

Abstract

The hydrophilic extract of the Senegalese sponge Ptilocaulis spiculifer was analyzed. A new iodinated tyrosine derivative, dakaramine (1), a new alkyl sulfate (2, as the counterion of 1), and the known ecdysonic sterol meristerone A (3) were isolated. The structure of 1 (molecular formula C₁₅H₂₄I₂N₂O) was determined via combined HRFABMS and NMR (¹H, ¹³C, COSY, ROESY, HMQC, HMBC) analyses, featuring a symmetrically tetrasubstituted benzene ring with iodine atoms at positions 5 and 5′, and oxypropylidene/ethylidene chains terminated by dimethylammonium groups. For compound 2, its molecular formula (C₈H₁₇O₄S) was established by negative ion HRFABMS, and the structure (including R configuration at C-3) was confirmed by solvolysis to (R)-3-ethyl-4-methylpentan-1-ol (4). Compound 3 was identified by comparison with literature spectral data. Both 1 and 2 are new compounds; the parent alcohol of 2 has been synthesized but not reported as a natural product.

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