title: Isolation, structure elucidation, and biological evaluation of 15-amido-3-demethoxy-2alpha,3alpha-methylenedioxyerythroculine, a new alkaloid from Hyperbaena valida.
abstract: A phytochemical investigation of the leaves of Hyperbaena valida resulted in the isolation and characterization of two erythrina-type alkaloids, 1 and 2, which were found to be antagonists at nicotinic receptors. Compound 1 was assigned as the new 15-amido-3-demethoxy-2alpha,3alpha-methylenedioxyerythroculine and compound 2 as the known 3-demethoxy-2alpha,3alpha-methylenedioxyerythroculine. Antagonism of a 100 microM nicotine response was observed for alkaloid 1 (IC50 value of 94 +/- 8 microM) and alkaloid 2 (IC50 value of 77 +/- 19 microM).
authors.affiliation: GlaxoSmithKline Pharmaceuticals, King of Prussia, Pennsylvania 19406, USA. Alan.J.Freyer@GSK.com
authors.forename: Alan J
authors.initials: AJ
authors.lastname: Freyer
authors.forename: Justin
authors.initials: J
authors.lastname: Huffman
authors.forename: Mary D
authors.initials: MD
authors.lastname: Menachery
authors.forename: Kristina
authors.initials: K
authors.lastname: Huey
authors.forename: William J
authors.initials: WJ
authors.lastname: Leavens
authors.forename: Richard W
authors.initials: RW
authors.lastname: Fitch
mesh_terms: D000465:Algorithms; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D007563:Jamaica; D029583:Menispermaceae / Q000737:chemistry*; D015394:Molecular Structure; D018733:Nicotinic Antagonists / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*
chemical_list: C515486:15-amido-3-demethoxy-2alpha,3alpha-methylenedioxyerythroculine; D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; D018733:Nicotinic Antagonists