Isolation, Structure Elucidation, and Biological Evaluation of 15-Amido-3-demethoxy-2α,3α-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-2α,3α-methylenedioxyerythroculi...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2006-10, Vol.69 (10), p.1514-1516
Main Authors: Freyer, Alan J, Huffman, Justin, Menachery, Mary D, Huey, Kristina, Leavens, William J, Fitch, Richard W
Format: Article
Language:English
Subjects:
alkaloids
Biological and medical sciences
chemical structure
General pharmacology
Hyperbaena valida
Medical sciences
Menispermaceae
methylenedioxyerythroculine
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
stereochemistry
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Summary: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-2α,3α-methylenedioxyerythroculine and compound 2 as the known 3-demethoxy-2α,3α-methylenedioxyerythroculine. Antagonism of a 100 μM nicotine response was observed for alkaloid 1 (IC50 value of 94 ± 8 μM) and alkaloid 2 (IC50 value of 77 ± 19 μM).
ISSN:0163-3864
1520-6025
DOI:10.1021/np060291a