title: Inhibition of nonenzymic lipid peroxidation by benzylisoquinoline alkaloids.
abstract: A group of benzylisoquinoline alkaloids, including five simple benzylisoquinolines, three phtalideisoquinolines, six aporphines, three protoberberines, and two benzophenanthridines, have been studied as inhibitors of lipid peroxidation stimulated by Fe2+/cysteine in rat liver microsomal fractions. Protopapaverine, apomorphine, laudanosoline, tetrahydroberberine, isoboldine, bulbocapnine, boldine, anonaine, glaucine, and stepholidine showed antiperoxidative effects, and structure-activity relationships were established. In simple benzylisoquinolines, the presence of phenolic hydroxyls or similar reactive groups is necessary for inhibition of peroxidation, while in aporphines and protoberberines nonhydroxylated compounds can exert antiperoxidative effects. The phtalideisoquinolines and benzophenanthridines tested were inactive.
authors.affiliation: Departamento de Farmacología, Facultad de Farmacia, Valencia, Spain.
authors.forename: L A
authors.initials: LA
authors.lastname: Martínez
authors.forename: J L
authors.initials: JL
authors.lastname: Ríos
authors.forename: M
authors.initials: M
authors.lastname: Payá
authors.forename: M J
authors.initials: MJ
authors.lastname: Alcaraz
mesh_terms: D000470:Alkaloids / Q000494:pharmacology*; D000818:Animals; D001060:Aporphines / Q000737:chemistry / Q000494:pharmacology; D001600:Berberine Alkaloids / Q000737:chemistry / Q000494:pharmacology; D003545:Cysteine / Q000378:metabolism; D005296:Ferrous Compounds / Q000378:metabolism; D015227:Lipid Peroxidation / Q000187:drug effects*; D008862:Microsomes, Liver / Q000378:metabolism; D015394:Molecular Structure; D011804:Quinolines / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D013329:Structure-Activity Relationship
chemical_list: D000470:Alkaloids; D001060:Aporphines; D001600:Berberine Alkaloids; D005296:Ferrous Compounds; D011804:Quinolines; C009090:protoberberine; D003545:Cysteine