2-(1H-pyrrolyl)carboxylic acids as pigment precursors in garlic greening

Journal of Agricultural and Food Chemistry
Dan WangGuanghua Zhao

Abstract

Six model compounds having a 2-(1 H-pyrrolyl)carboxylic acid moiety and a hydrophobic R group were synthesized to study their effects on garlic greening, the structures of which are similar to that of 2-(3,4-dimethyl-1 H-pyrrolyl)-3-methylbutanoic acid (PP-Val) (a possible pigment precursor for garlic greening). The puree of freshly harvested garlic bulbs turned green after being soaked in solutions of all these compounds, and with both increasing concentrations and incubation time the green color of the puree became deeper. In contrast, neither pyrrole alone nor pyrrole combined with free amino acids had the ability to discolor the puree. The compounds exhibited a good relationship between structure and activity of garlic greening, namely, the smaller the size of the R group, the larger the contribution. Also, it was found that the unidentified yellow species can be produced by reacting the model compounds with pyruvic acid at room temperature (23-25 degrees C). Moreover, blue species were formed by incubation of the model compounds with di(2-propenyl) thiosulfinate at room temperature. On the basis of these observations, a pathway for garlic greening was proposed.

References

Apr 21, 2001·Journal of Agricultural and Food Chemistry·C Shen, K L Parkin
Aug 5, 2004·Journal of Agricultural and Food Chemistry·Roman KubecJan Velísek
Sep 1, 2005·Journal of Agricultural and Food Chemistry·Bing BaiXiaosong Hu
Feb 2, 2006·Journal of Agricultural and Food Chemistry·Shinsuke ImaiHiroshi Sawada
Jun 22, 2006·Journal of Agricultural and Food Chemistry·Makoto IchikawaKazuhisa Ono
Oct 13, 2006·Journal of Agricultural and Food Chemistry·Bing BaiGuanghua Zhao
Apr 25, 2007·Critical Reviews in Food Science and Nutrition·J B Adams, H M Brown

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Citations

Feb 26, 2013·Journal of the Science of Food and Agriculture·Conghua MouXuguang Qiao
Mar 3, 2021·Food Research International·Ruixuan ZhaoXuguang Qiao
Dec 31, 2010·Organic Letters·Mohammad Reza IslamiThomas T Tidwell

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