Absolute configuration, stability, and interconversion of 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine valine adducts and their phenylthiohydantoin derivatives

X. Jiang
S. Wang
Y. Zhao
Q. Xia
L. Cai
X. Sun
P.P. Fu

Abstract

Pyrrolizidine alkaloid-containing plants are widespread in the world and probably the most common poisonous plants affecting livestock, wildlife, and humans. Pyrrolizidine alkaloids require metabolic activation to form dehydropyrrolizidine alkaloids that bind to cellular proteins and DNA leading to hepatotoxicity, genotoxicity, and tumorigenicity. At present, it is not clear how dehydropyrrolizidine alkaloids bind to cellular amino acids and proteins to induced toxicity. We previously reported that reaction of dehydromonocrotaline with valine generated four highly unstable 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine (DHP)-derived valine (DHP-valine) adducts that upon reaction with phenyl isothiocyanate (PITC) formed four DHP-valine-PITC adduct isomers. In this study, we report the absolute configuration and stability of DHP-valine and DHP-valine-PITC adducts, and the mechanism of interconversion between DHP-valine-PITC adducts. © 2014, Food and Drug Administration, Taiwan. Published by Elsevier Taiwan LLC. All rights reserved.

ScienceDirect Link

10.1016/j.jfda.2015.01.004

Recommended Citation

Jiang, X.; Wang, S.; Zhao, Y.; Xia, Q.; Cai, L.; Sun, X.; and Fu, P.P. (2015) "Absolute configuration, stability, and interconversion of 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine valine adducts and their phenylthiohydantoin derivatives," Journal of Food and Drug Analysis: Vol. 23 : Iss. 2 , Article 6.
Available at: https://doi.org/10.1016/j.jfda.2015.01.004