A Chemical Approach to Searching for Bioactive Ingredients in Cigarette Smoke

Abstract

Cigarette smoke, a collection of many toxic chemicals, contributes to the pathogenesis of smokingrelated 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-acetylTyr, 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.

Intracellular Metabolism of α,β-Unsaturated Carbonyl Compounds, Acrolein, Crotonaldehyde and Methyl Vinyl Ketone, Active Toxicants in Cigarette Smoke: Participation of Glutathione Conjugation Ability and Aldehyde–Ketone Sensitive Reductase Activity

“…5,6,13) Using GC/MS, we previously identified methyl vinyl ketone (MVK), an α,β-unsaturated ketone, as another active ingredient in cigarette smoke and demonstrated that MVK is abundantly present in cigarette smoke extract (CSE). 14) Furthermore, we clarified using LC/MS/MS and NMR that MVK could easily react with tyrosine at 37°C, a chemically reactive amino acid, to form N-(3-oxobutyl)-Tyr via Michael addition reaction. 14) We also found that GSH levels in mouse melanoma cells are rapidly reduced by exposure to CSE, and that MVK, ACR and CA irreversibly react with intracellular GSH to form the corresponding GSH adducts.…”

Research of indicators of the endogenous antioxidant system in rats affected with sodium nitrite on the background of tobacco intoxication

“…Активне і пасивне куріння однаково шкідливо діє на організм, підриває здоров'я людини та загрожує її життю [1][2][3]. У димі цигарок міститься біля 1900 компонентів, під впли-вом яких можлива токсична, мутагенна та канцеро-генна дії на організм людини [4,5]. До його складу входять нікотин, аміак, піримідинові основи, діоксин, оксид вуглецю, сірководень, ціаніди, оцтова й мура-шина кислоти, поліфеноли та інші токсичні речови-ни.…”

“…Його важлива роль полягає у регуляції вуглеводного обміну, оскіль-ки Cr 3+ є компонентом фактора толерантності до глю-кози [4]. Американська національна академія наук (NRS) встановила, що потреба хрому для людей скла-дає від 50 до 200 мкг/добу [5].…”

“…Американська національна академія наук (NRS) встановила, що потреба хрому для людей скла-дає від 50 до 200 мкг/добу [5]. Встановлено, що неста-ча хрому може сприяти розвитку цукрового діабету, атеросклерозу, порушенню вищої нервової діяльності, зниженню імунітету, зменшенню тривалості життя [4].…”

Cigarette Smoke Extract Disrupts Transcriptional Activities Mediated by Thyroid Hormones and Its Receptors

“…[2][3][4] In particular, MVK is abundant in the gaseous phase of cigarette smoke, is present in cigarette smoke extract (CSE), and is a major mediator of cigarette smoke. [5][6][7] Cigarette smoking may increase the risk of disease development, may reduce the effectiveness of treatment, and eventually induce recurrence. 8) Cigarette smoking has a substantial influence on human health.…”