Abstract
The first occurrence of an acetylenic 1-amino-2-alcohol, distaminolyne A (1), isolated from the New Zealand ascidian Pseudodistoma opacum, is reported. The isolation and structure elucidation of 1 and assignment of absolute configuration using the exciton coupled circular dichroism technique are described. In addition, a new N-9 hydroxy analogue (2) of the known P. opacum metabolite 7-bromohomotrypargine is also reported. Antimicrobial screening identified modest activity of 1 toward Escherichia coli, Staphylococcus aureus, and Mycobacterim tuberculosis, while 2 exhibited a moderate antimalarial activity (IC50 3.82 μM) toward a chloroquine-resistant strain (FcB1) of Plasmodium falciparum.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkynes / chemistry
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Alkynes / isolation & purification*
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Alkynes / pharmacology*
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Animals
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Antimalarials / chemistry
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Antimalarials / isolation & purification*
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Antimalarials / pharmacology*
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Carbolines / chemistry
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Carbolines / isolation & purification*
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Carbolines / pharmacology*
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Chloroquine / pharmacology
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Drug Resistance, Bacterial / drug effects
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Escherichia coli / drug effects
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Inhibitory Concentration 50
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Microbial Sensitivity Tests
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Molecular Structure
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Mycobacterium tuberculosis / drug effects
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New Zealand
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Plasmodium falciparum / drug effects
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Staphylococcus aureus / drug effects
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Urochordata / chemistry*
Substances
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Alkynes
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Antimalarials
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Carbolines
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tryptoline
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Chloroquine