title: 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.
authors.affiliation: Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles ICSN, Gif-sur-Yvette, France.
authors.forename: Géraldine
authors.initials: G
authors.lastname: Le Goff
authors.forename: Marie-Thérèse
authors.initials: MT
authors.lastname: Martin
authors.forename: Claudine
authors.initials: C
authors.lastname: Servy
authors.forename: Sylvie
authors.initials: S
authors.lastname: Cortial
authors.forename: Philippe
authors.initials: P
authors.lastname: Lopes
authors.forename: Anne
authors.initials: A
authors.lastname: Bialecki
authors.forename: Jacqueline
authors.initials: J
authors.lastname: Smadja
authors.forename: Jamal
authors.initials: J
authors.lastname: Ouazzani
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D045325:HCT116 Cells; D019073:HT29 Cells; D006801:Humans; D006834:Hydrazines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D006834:Hydrazines; D007783:Lactones; C574261:geralcin A; C574262:geralcin B