Abstract
Two new indole spermidine alkaloids, didemnidines A (1) and B (2), have been isolated from the New Zealand ascidian Didemnum sp. The structures of the metabolites, determined by analysis of 2D NMR spectra and confirmed via synthesis, embody an indole-3-glyoxylamide moiety linked to the N(1) position of spermidine, the latter motif being particularly rare among marine natural products. Didemnidine B and a synthetic precursor exhibited mild in vitro growth inhibition of Plasmodium falciparum with IC(50)'s of 15 and 8.4 μM, respectively.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antiprotozoal Agents* / chemistry
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Antiprotozoal Agents* / isolation & purification
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Antiprotozoal Agents* / pharmacology
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Indole Alkaloids* / chemistry
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Indole Alkaloids* / isolation & purification
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Indole Alkaloids* / pharmacology
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Leishmania donovani / drug effects
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Molecular Structure
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New Zealand
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Nuclear Magnetic Resonance, Biomolecular
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Plasmodium falciparum / drug effects
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Spermidine* / analogs & derivatives
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Spermidine* / chemistry
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Spermidine* / isolation & purification
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Spermidine* / pharmacology
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Structure-Activity Relationship
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Trypanosoma / drug effects
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Urochordata / chemistry*
Substances
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Antiprotozoal Agents
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Indole Alkaloids
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didemnidine A
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didemnidine B
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Spermidine