title: On the antibiotic and antifungal activity of pestalone, pestalachloride A, and structurally related compounds.
abstract: Pestalone (1) is a prominent marine natural product first isolated by M. Cueto et al. in 2001 from a co-fermentation of a marine fungus with a marine bacterium. For more than 10 years, 1 had been considered as a promising new antibiotic compound, the reported MIC against methicillin-resistant Staphylococcus aureus (MRSA) being 37 ng/mL. After overcoming the limited availability of 1 by total synthesis (N. Slavov et al., 2010) we performed new biological tests, which did not confirm the expected degree of antibiotic activity. The observed activity of pestalone against different MRSA strains was 3-10 μg/mL, as determined independently in two laboratories. A number of synthetic derivatives of 1 including pestalachloride A and other isoindolinones (formed from 1 by reaction with amines) did not exhibit higher activities as compared to 1 against MRSA and a series of plant pathogens.
authors.affiliation: Department of Chemistry, University of Cologne , Greinstrasse 4, 50939 Köln, Germany.
authors.forename: Daniel
authors.initials: D
authors.lastname: Augner
authors.forename: Oleg
authors.initials: O
authors.lastname: Krut
authors.forename: Nikolay
authors.initials: N
authors.lastname: Slavov
authors.forename: Dario C
authors.initials: DC
authors.lastname: Gerbino
authors.forename: Hans-Georg
authors.initials: HG
authors.lastname: Sahl
authors.forename: Jürgen
authors.initials: J
authors.lastname: Benting
authors.forename: Carl F
authors.initials: CF
authors.lastname: Nising
authors.forename: Stefan
authors.initials: S
authors.lastname: Hillebrand
authors.forename: Martin
authors.initials: M
authors.lastname: Krönke
authors.forename: Hans-Günther
authors.initials: HG
authors.lastname: Schmalz
mesh_terms: D000840:Anisoles / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001577:Benzophenones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D060467:Disease Resistance; D054833:Isoindoles / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure
chemical_list: D000840:Anisoles; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001577:Benzophenones; D054833:Isoindoles; C532658:pestalachloride A; C442628:pestalone