Abstract
Six new bis(indole) alkaloids (1-6) along with eight known ones of the topsentin class were isolated from a Spongosorites sp. sponge of Korea. Based on the results of combined spectroscopic analyses, the structures of spongosoritins A-D (1-4) were determined to possess a 2-methoxy-1-imidazole-5-one core connecting the indole moieties, and these were linked by a linear urea bridge for spongocarbamides A (5) and B (6). The absolute configurations of spongosoritins were assigned by electronic circular dichroism (ECD) computation. The new compounds exhibited moderate inhibition against transpeptidase sortase A and weak inhibition against human pathogenic bacteria and A549 and K562 cancer cell lines.
Keywords:
Spongosorites sp. sponge; bis(indole) alkaloids; sortase A inhibition; spongocarbamides; spongosoritins; topsentin.
MeSH terms
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A549 Cells
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Aminoacyltransferases / antagonists & inhibitors
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Aminoacyltransferases / metabolism
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Animals
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Anti-Bacterial Agents / isolation & purification
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Anti-Bacterial Agents / pharmacology*
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Antifungal Agents / isolation & purification
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Antifungal Agents / pharmacology*
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Antineoplastic Agents / isolation & purification
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Antineoplastic Agents / pharmacology*
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Bacteria / drug effects
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Bacteria / enzymology
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Bacteria / growth & development
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Bacterial Proteins / antagonists & inhibitors
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Bacterial Proteins / metabolism
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Cell Survival / drug effects
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Cysteine Endopeptidases / metabolism
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Fungi / drug effects
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Fungi / growth & development
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Humans
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Indole Alkaloids / isolation & purification
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Indole Alkaloids / pharmacology*
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K562 Cells
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Microbial Sensitivity Tests
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Molecular Structure
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Neoplasms / drug therapy
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Neoplasms / pathology
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Porifera / metabolism*
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Structure-Activity Relationship
Substances
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Anti-Bacterial Agents
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Antifungal Agents
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Antineoplastic Agents
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Bacterial Proteins
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Indole Alkaloids
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Aminoacyltransferases
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sortase A
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Cysteine Endopeptidases