Abstract
Two novel α,β-unsaturated γ-lactono-hydrazides, geralcin A (2) and geralcin B (3), were isolated from Streptomyces sp. LMA-545. This unusual scaffold consists of the condensation of alkyl-hydrazide with an α,β-unsaturated γ-lactone, 3-(5-oxo-2H-furan-4-yl)propanoic acid (1), which was isolated from the same broth culture. Amberlite XAD-16 solid-phase extraction was used during the cultivation step, and the trapped compounds (1-3) were eluted from the resin with methanol. The structures were elucidated using (1)H, (13)C, and (15)N NMR spectroscopic analysis and high-resolution mass spectrometry. Geralcin B (3) was cytotoxic against MDA231 breast cancer cells with an IC(50) of 5 μM.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / isolation & purification*
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Anti-Bacterial Agents / pharmacology
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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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Drug Screening Assays, Antitumor
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HCT116 Cells
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HT29 Cells
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Humans
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Hydrazines / chemistry
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Hydrazines / isolation & purification*
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Hydrazines / pharmacology
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Lactones / chemistry
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Lactones / isolation & purification*
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Lactones / pharmacology
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Microbial Sensitivity Tests
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Stereoisomerism
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Streptomyces / chemistry*
Substances
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Anti-Bacterial Agents
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Antineoplastic Agents
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Hydrazines
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Lactones
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geralcin A
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geralcin B