Abstract
Microcionamides A (1) and B (2) have been isolated from the Philippine marine sponge Clathria (Thalysias) abietina. These new linear peptides are cyclized via a cystine moiety and have their C-terminus blocked by a 2-phenylethylenamine group. Their total structures, including absolute stereochemistry, were determined by a combination of spectral and chemical methods. Compound 1 was shown to slowly isomerize about the C-36/C-37 double bond when stored in DMSO. Microcionamides A (1) and B (2) exhibited significant cytotoxicity against the human breast tumor cells lines MCF-7 and SKBR-3 and displayed inhibitory activity against Mycobacterium tuberculosis H(37)Ra.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Animals
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Anti-Bacterial Agents / chemistry*
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Anti-Bacterial Agents / isolation & purification
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Anti-Bacterial Agents / toxicity
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Antineoplastic Agents / chemistry*
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Antineoplastic Agents / isolation & purification
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Antineoplastic Agents / toxicity
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Apoptosis
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Cell Line, Tumor
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Female
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Humans
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Mycobacterium tuberculosis / drug effects
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Peptides / chemistry
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Peptides, Cyclic / chemistry*
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Peptides, Cyclic / isolation & purification
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Peptides, Cyclic / toxicity*
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Philippines
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Porifera / chemistry*
Substances
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Anti-Bacterial Agents
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Antineoplastic Agents
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Peptides
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Peptides, Cyclic
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microcionamide A
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microcionamide B