TY - JOUR
T1 - Roles of Tobacco Cellulose, Sugars, and Chlorogenic Acid as Precursors to Catechol in Cigarette Smoke
AU - Carmella, Steven G.
AU - Hecht, Stephen S.
AU - Tso, T. C.
AU - Hoffmann, Dietrich
PY - 1984/1
Y1 - 1984/1
N2 - Tobacco was extracted sequentially with hexane and methanol-H2O, and the extracts were pyrolyzed at 650 °C in order to identify likely leaf precursors to the tobacco smoke cocarcinogen catechol. The results demonstrated that the methanol-H2O extract and the extracted tobacco residue were good pyrolytic precursors to catechol. Subfractions of the methanol-H2O extract were isolated by HPLC and pyrolyzed. Fructose, glucose, sucrose, and chlorogenic acid were thus identified as important pyrolytic precursors to catechol. Cellulose, a component of the extracted tobacco residue, was also found to be a good precursor to catechol in pyrolysis experiments. To determine the role of these substances as precursors to catechol under the conditions prevailing in a burning cigarette, either [14C(U)]cellulose, [14C(U)] fructose, or various levels of the unlabeled polyphenols chlorogenic acid or rutin were added to cigarettes and the mainstream smoke was analyzed for [14C] catechol and catechol. On the basis of these experiments, we estimated the minimum contributions of these compounds to mainstream smoke catechol levels as follows: cellulose, 7-12%; total of fructose, glucose, and sucrose, 4%; chlorogenic acid, 13%; rutin, 1%. It is suggested that a significant portion of the remaining catechol in mainstream cigarette smoke is formed from pectin, starch, and hemicellulose.
AB - Tobacco was extracted sequentially with hexane and methanol-H2O, and the extracts were pyrolyzed at 650 °C in order to identify likely leaf precursors to the tobacco smoke cocarcinogen catechol. The results demonstrated that the methanol-H2O extract and the extracted tobacco residue were good pyrolytic precursors to catechol. Subfractions of the methanol-H2O extract were isolated by HPLC and pyrolyzed. Fructose, glucose, sucrose, and chlorogenic acid were thus identified as important pyrolytic precursors to catechol. Cellulose, a component of the extracted tobacco residue, was also found to be a good precursor to catechol in pyrolysis experiments. To determine the role of these substances as precursors to catechol under the conditions prevailing in a burning cigarette, either [14C(U)]cellulose, [14C(U)] fructose, or various levels of the unlabeled polyphenols chlorogenic acid or rutin were added to cigarettes and the mainstream smoke was analyzed for [14C] catechol and catechol. On the basis of these experiments, we estimated the minimum contributions of these compounds to mainstream smoke catechol levels as follows: cellulose, 7-12%; total of fructose, glucose, and sucrose, 4%; chlorogenic acid, 13%; rutin, 1%. It is suggested that a significant portion of the remaining catechol in mainstream cigarette smoke is formed from pectin, starch, and hemicellulose.
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U2 - 10.1021/jf00122a023
DO - 10.1021/jf00122a023
M3 - Article
AN - SCOPUS:0008492480
SN - 0021-8561
VL - 32
SP - 267
EP - 273
JO - Journal of agricultural and food chemistry
JF - Journal of agricultural and food chemistry
IS - 2
ER -