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Ginger and Its Bioactive Component Inhibit Enterotoxigenic Escherichia coli Heat-Labile Enterotoxin-Induced Diarrhea in Mice

Jaw-Chyun Chen^†, Li-Jiau Huang^‡, Shih-Lu Wu^§, Sheng-Chu Kuo^‡, Tin-Yun Ho* and Chien-Yun Hsiang*

Graduate Institute of Chinese Pharmaceutical Sciences, Graduate Institute of Pharmaceutical Chemistry, Department of Biochemistry, Graduate Institute of Chinese Medical Science, Department of Microbiology, China Medical University, Taichung 40402, Taiwan

J. Agric. Food Chem., 2007, 55 (21), pp 8390–8397

DOI: 10.1021/jf071460f

Publication Date (Web): September 20, 2007

* To whom correspondence should be addressed. Tel.: +886 4 22053366 ext. 2163 (C.-Y.H.); +886 4 22053366 ext. 3302 (T.-Y.H.). Fax: +886 4 22053764 (C.-Y.H.); +886 4 22032295 (T.-Y.H.). E-mail: cyhsiang@mail.cmu.edu.tw (C.-Y.H.); tyh@mail.cmu.edu.tw (T.-Y.H.)., †

Graduate Institute of Chinese Pharmaceutical Sciences.

, ‡

Graduate Institute of Pharmaceutical Chemistry.

, §

Department of Biochemistry.

Graduate Institute of Chinese Medical Science.

Department of Microbiology.

Abstract

Ginger is one of the most commonly used fresh herbs and spices. Enterotoxigenic Escherichia coli heat-labile enterotoxin (LT)-induced diarrhea is the leading cause of infant death in developing countries. In this study, we demonstrated that ginger significantly blocked the binding of LT to cell-surface receptor G_M1, resulting in the inhibition of fluid accumulation in the closed ileal loops of mice. Biological-activity-guided searching for active components showed that zingerone (vanillylacetone) was the likely active constituent responsible for the antidiarrheal efficacy of ginger. Further analysis of chemically synthesized zingerone derivatives revealed that compound 31 (2-[(4-methoxybenzyl)oxy]benzoic acid) significantly suppressed LT-induced diarrhea in mice via an excellent surface complementarity with the B subunits of LT. In conclusion, our findings provide evidence that ginger and its derivatives may be effective herbal supplements for the clinical treatment of enterotoxigenic Escherichia coli diarrhea.

Keywords:

Ginger; zingerone; enterotoxigenic Escherichia coli; heat-labile enterotoxin; diarrhea

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