An Alkaloid from Scorpion Venom: Chemical Structure and Synthesis

While most scorpion venom components identified in the past are peptidic or proteinic in nature, we report here a new alkaloid isolated from the venom of the Mexican scorpion Megacormus gertschi. Nuclear magnetic resonance and mass spectrometric investigations elucidate the structure of the alkaloid...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2018-08, Vol.81 (8), p.1899-1904
Main Authors: Banerjee, Shibdas, Gnanamani, Elumalai, Lynch, Stephen R, Zuñiga, Fernando Zamudio, Jiménez-Vargas, Juana María, Possani, Lourival Domingos, Zare, Richard N
Format: Article
Language:English
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Summary:While most scorpion venom components identified in the past are peptidic or proteinic in nature, we report here a new alkaloid isolated from the venom of the Mexican scorpion Megacormus gertschi. Nuclear magnetic resonance and mass spectrometric investigations elucidate the structure of the alkaloid as (Z)-N-(2-(1H-imidazol-4-yl)­ethyl)-3-(4-hydroxy-3-methoxyphenyl)-2-methoxyacrylamide (1). A chemical method of synthesizing this alkaloid is also described. Although abundant in venom, the above alkaloid was not found to have insecticidal activity. Structural analysis suggests that this venom alkaloid might be of potential interest for evaluating its medicinal effect.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.8b00527