Isolation and Characterization of α,β-Unsaturated γ-Lactono-Hydrazides from Streptomyces sp.

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.
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https://hal.archives-ouvertes.fr/hal-00710824
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Submitted on : Thursday, June 21, 2012 - 4:25:37 PM
Last modification on : Monday, September 2, 2019 - 9:42:59 AM

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Géraldine Le Goff, Marie-Thérèse Martin, Claudine Servy, Sylvie Cortial, Philippe Lopes, et al.. Isolation and Characterization of α,β-Unsaturated γ-Lactono-Hydrazides from Streptomyces sp.. Journal of Natural Products, American Chemical Society, 2012, 75 (5), pp.915-9. ⟨10.1021/np300026p⟩. ⟨hal-00710824⟩

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