A Chemical Approach to Searching for Bioactive Ingredients in Cigarette Smoke
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概要
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Cigarette smoke, a collection of many toxic chemicals, contributes to the pathogenesis of smoking-related diseases such as chronic obstructive pulmonary disease and cancer. Much work has been done on the chemical analysis of ingredients in cigarette smoke, but there are few reports on the active ingredients that can modify biomolecules. We used a sensitive liquid chromatography-mass spectrometry (LC/MS) and LC/MS/MS method to show that L-tyrosine (Tyr), an amino acid with a highly reactive hydroxyl group, readily reacts with cigarette smoke extract (CSE) at body temperature (37°C) to form various Tyr derivatives. Among these derivatives were N-(3-oxobutyl)-Tyr and two acetylated compounds, N-acetyl-Tyr and O-acetyl-Tyr, which were synthesized by reaction of Tyr with methyl vinyl ketone and acetic anhydride, respectively, at 37°C. The presence of methyl vinyl ketone and acetic anhydride in CSE was confirmed by gas chromatography-mass spectrometry (GC/MS). These results indicate that Tyr can easily react with active ingredients in CSE. The present analytical methods should aid the search for active ingredients in cigarette smoke.
著者
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Suwa Kiyoko
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Womens University
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Horiyama Shizuyo
School Of Pharmacy And Pharmaceutical Sciences Mukogawa Women's University
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Honda Chie
School Of Pharmaceutical Sciences Mukogawa Women's University
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NAKAMURA Kazuki
School of Pharmaceutical Sciences, Mukogawa Women's University
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Sato Hirofumi
Osaka Municipal Technical Research Institute
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Shizuma Motohiro
Osaka Municipal Technical Research Institute
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Kunitomo Masaru
School Of Pharmaceutical Sciences Mukogawa Women's University
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Takayama Mitsuo
International Graduate School Of Arts And Sciences Yokohama City Univ.
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Takahashi Yuta
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women's University
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Shimma Shuichi
Center for Advanced Science and Innovation, Osaka University
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Toyoda Michisato
Center for Advanced Science and Innovation, Osaka University
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Suwa Kiyoko
School of Pharmacy and Pharmaceutical Sciences, Mukogawa Women's University
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