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- Title
Specific reaction of α,β-unsaturated carbonyl compounds such as 6-shogaol with sulfhydryl groups in tubulin leading to microtubule damage
- Authors
Ishiguro, Kazuhiro; Ando, Takafumi; Watanabe, Osamu; Goto, Hidemi
- Abstract
Abstract: 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 α,β-unsaturated carbonyl compounds. α,β-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 α,β-unsaturated carbonyl compounds. In addition, α,β-unsaturated carbonyl compounds are more reactive with sulfhydryl groups in tubulin than in 2-mercaptoethanol, dithiothreitol, glutathione and papain, a cysteine protease.
- Subjects
CARBONYL compounds; TUBULINS; POLYMERIZATION; MICROTUBULES
- Publication
FEBS Letters, 2008, Vol 582, Issue 23/24, p3531
- ISSN
0014-5793
- Publication type
Article
- DOI
10.1016/j.febslet.2008.09.027