Journal
FEBS LETTERS
Volume 582, Issue 23-24, Pages 3531-3536Publisher
WILEY
DOI: 10.1016/j.febslet.2008.09.027
Keywords
Cancer; Ginger; Microtubule; Tubulin; alpha, beta-Unsaturated carbonyl compound
Funding
- Japan Foundation for Applied Enzymology
- Japanese Society for the Promotion of Science
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6-Shogaol and 6-gingerol are ginger components with similar chemical structures. However, while 6-shogaol damages microtubules, 6-gingerol does not. We have investigated the molecular mechanism of 6-shogaol-induced microtubule damage and found that the action of 6-shogaol results from the structure of alpha, beta-unsaturated carbonyl compounds. alpha, beta-Unsaturated carbonyl compounds such as 6-shogaol react with sulfhydryl groups of cysteine residues in tubulin, and impair tubulin polymerization. The reaction with sulfhydryl groups depends on the chain length of a, b-unsaturated carbonyl compounds. In addition, alpha, beta-unsaturated carbonyl compounds are more reactive with sulfhydryl groups in tubulin than in 2-mercaptoethanol, dithiothreitol, glutathione and papain, a cysteine protease.
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