6533b872fe1ef96bd12d41d7

RESEARCH PRODUCT

10-Oximeguanacone, the First Nitrogenated Acetogenin Derivative Found To Be a Potent Inhibitor of Mitochondrial Complex I

Nestor BrunJosé R. TormoJairo SaezHillmer GranadosTeresa GallardoIván D. VélezDiego CortesBeatriz Torres

subject

Pharmacologychemistry.chemical_classificationStereochemistryOrganic ChemistryPharmaceutical ScienceBiological activityBiologyAnalytical Chemistrychemistry.chemical_compoundEnzymeComplementary and alternative medicinechemistryEnzyme inhibitorOxidoreductaseDrug DiscoveryAcetogeninbiology.proteinMolecular MedicineLactoneDerivative (chemistry)Heart metabolism

description

A new 10-keto bis-tetrahydrofuran acetogenin, guanacone (1), has been isolated from a cytotoxic extract of Annona aff. spraguei seeds. The 10-oximeguanacone derivative 1f is the first bioactive nitrogenated acetogenin found to be a very potent inhibitor of complex I. In addition, a SAR study of guanacone analogues is reported based on the titration of the NADH oxidase and NADH:ubiquinone oxidoreductase activities.

https://doi.org/10.1021/np980079+