2006•Journal of Natural ProductsOpen access

Isolation, Structure Elucidation, and Biological Evaluation of 15-Amido-3-demethoxy-2α,3α-methylenedioxyerythroculine, a New Alkaloid from Hyperbaena valida

Alan J. Freyer, Justin M. Huffman, Mary D. Menachery, Kristina Huey, William J. Leavens, Richard W. Fitch

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).

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Key concepts: Alkaloid, Stereochemistry, Chemistry, Isolation (microbiology), Organic chemistry, Biology, Bioinformatics