Two cell differentiation inducing pyridoacridines from a marine sponge Biemna sp. and their chemical conversions - Archive ouverte HAL Access content directly
Journal Articles Tetrahedron Year : 2015

Two cell differentiation inducing pyridoacridines from a marine sponge Biemna sp. and their chemical conversions

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Abstract

Two pyridoacridines, N-hydroxymethylisocystodamine (1) and neolabuanine A (2), together with the known ecionine A (3), ecionine B (4), isocystodamine (5), N-methylisocystodamine (6), 9-hydroxyisoascididemin (7), and biemnadin (8), were isolated from a marine sponge Biemna sp. Several of these compounds were shown to induce cell differentiation of K562 leukemia cells into erythrocytes. Following inspection of the NMR data, and comparison of these data with literature values, we demonstrated that neolabuanine A (2) had the structure previously reported as labuanine A (2), and that the compound initially reported under the name of labuanine A possessed the structure assigned to ecionine A (3). We found that both neolabuanine A (2) and ecionine A (3) were gradually converted to 9-hydroxyisoascididemin (7), indicating that 2 and 3 can be considered both as precursors of 7.

Dates and versions

hal-01174228 , version 1 (08-07-2015)

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Daniel A. Pedrazzoli Moran, Kentaro Takada, Yuji Ise, Nataly Bontemps, Rohan A. Davis, et al.. Two cell differentiation inducing pyridoacridines from a marine sponge Biemna sp. and their chemical conversions. Tetrahedron, 2015, 71 (30), pp.5013-5018. ⟨10.1016/j.tet.2015.05.070⟩. ⟨hal-01174228⟩
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