Abstract
Waikikiamides A-C (1-3), structurally complex diketopiperazine derivatives, and putative biogenic precursors, (+)-semivioxanthin (4), notoamide F (5), and (-)-notoamide A (6), were isolated from Aspergillus sp. FM242. 1 and 2, bearing a hendecacyclic ring system, represent a novel skeleton. 3 features the first unique heterodimer of two notoamide analogs with an N-O-C bridge. Compounds 1 and 3 exhibit antiproliferative activity with IC50 values in the range of 0.56 to 1.86 μM. The gene clusters mined from the sequenced genome support their putative biosynthetic pathways.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / isolation & purification
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Antineoplastic Agents / pharmacology*
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Aspergillus / chemistry*
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Cell Proliferation / drug effects
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Crystallography, X-Ray
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Diketopiperazines / chemistry
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Diketopiperazines / isolation & purification
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Diketopiperazines / pharmacology
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Dimerization
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Drug Screening Assays, Antitumor
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Models, Molecular
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Molecular Conformation
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Polyketides / chemistry
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Polyketides / isolation & purification
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Polyketides / pharmacology
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Stereoisomerism
Substances
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Antineoplastic Agents
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Diketopiperazines
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Polyketides