title: Biochemical activities of berberine, palmatine and sanguinarine mediating chemical defence against microorganisms and herbivores.
abstract: The alkaloids berberine, palmatine and sanguinarine are toxic to insects and vertebrates and inhibit the multiplication of bacteria, fungi and viruses. Biochemical properties which may contribute to these allelochemical activities were analysed. Acetylcholine esterase, butyrylcholinesterase, choline acetyl transferase, alpha 1- and alpha 2-adrenergic, nicotinergic, muscarinergic and serotonin2 receptors were substantially affected. Sanguinarine appears to be the most effective inhibitor of choline acetyl-transferase (IC50 284 nM), while the protoberberines were inactive at this target. Berberine and palmatine were most active at the alpha 2-receptor (binding with IC50 476 and 956 nM, respectively). Furthermore, berberine and sanguinarine intercalate DNA, inhibit DNA synthesis and reverse transcriptase. In addition, sanguinarine (but not berberine) affects membrane permeability and berberine protein biosynthesis. In consequence, these biochemical activities may mediate chemical defence against microorganisms, viruses and herbivores in the plants producing these alkaloids.
authors.affiliation: Institut für Pharmazeutische Biologie, Universität Heidelberg, Germany.
authors.forename: T
authors.initials: T
authors.lastname: Schmeller
authors.forename: B
authors.initials: B
authors.lastname: Latz-Brüning
authors.forename: M
authors.initials: M
authors.lastname: Wink
mesh_terms: D000110:Acetylcholinesterase / Q000378:metabolism; D000470:Alkaloids / Q000494:pharmacology*; D000818:Animals; D000900:Anti-Bacterial Agents / Q000494:pharmacology; D053119:Benzophenanthridines; D001599:Berberine / Q000494:pharmacology*; D001600:Berberine Alkaloids / Q000494:pharmacology*; D001921:Brain / Q000378:metabolism*; D002091:Butyrylcholinesterase / Q000378:metabolism; D002462:Cell Membrane / Q000378:metabolism; D002795:Choline O-Acetyltransferase / Q000037:antagonists & inhibitors; D002800:Cholinesterase Inhibitors / Q000494:pharmacology; D004256:DNA Polymerase I / Q000037:antagonists & inhibitors; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D004912:Erythrocytes / Q000187:drug effects / Q000502:physiology*; D006461:Hemolysis; D007546:Isoquinolines; D007700:Kinetics; D011869:Radioligand Assay; D011941:Receptors, Adrenergic / Q000378:metabolism; D011976:Receptors, Muscarinic / Q000378:metabolism; D017981:Receptors, Neurotransmitter / Q000378:metabolism*; D011985:Receptors, Serotonin / Q000378:metabolism; D018894:Reverse Transcriptase Inhibitors / Q000494:pharmacology; D013552:Swine
chemical_list: D000470:Alkaloids; D000900:Anti-Bacterial Agents; D053119:Benzophenanthridines; D001600:Berberine Alkaloids; D002800:Cholinesterase Inhibitors; D004791:Enzyme Inhibitors; D007546:Isoquinolines; D011941:Receptors, Adrenergic; D011976:Receptors, Muscarinic; D017981:Receptors, Neurotransmitter; D011985:Receptors, Serotonin; D018894:Reverse Transcriptase Inhibitors; D001599:Berberine; C005705:sanguinarine; D002795:Choline O-Acetyltransferase; D004256:DNA Polymerase I; D000110:Acetylcholinesterase; D002091:Butyrylcholinesterase; C005413:palmatine