Isolation, structure elucidation, and biological evaluation of 15-amido-3-demethoxy-2alpha,3alpha-methylenedioxyerythroculine, a new alkaloid from Hyperbaena valida.
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).
Freyer
Alan J
AJ
GlaxoSmithKline Pharmaceuticals, King of Prussia, Pennsylvania 19406, USA. Alan.J.Freyer@GSK.com
Huffman
Justin
J
Menachery
Mary D
MD
Huey
Kristina
K
Leavens
William J
WJ
Fitch
Richard W
RW
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*
C515486:15-amido-3-demethoxy-2alpha,3alpha-methylenedioxyerythroculine; D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; D018733:Nicotinic Antagonists