Isolation and Characterization of α,β-Unsaturated γ-Lactono-Hydrazides from Streptomyces sp. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Natural Products Année : 2012

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

Résumé

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.

Domaines

Chimie organique
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Dates et versions

hal-00710824 , version 1 (21-06-2012)

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Citer

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, 2012, 75 (5), pp.915-9. ⟨10.1021/np300026p⟩. ⟨hal-00710824⟩
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