A Possible Indicator of Oxidative Damage in Smokers: (13Z)-Lycopene?

In vitro, the gaseous phase of cigarette smoke is known to induce both isomerization and degradation of dietary carotenoids, such as β-carotene and lycopene. However, the effects of cigarette smoke on the composition of circulating lycopene in vivo are not well understood. In this study, we examined...

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Main Authors: Daniel L. Graham, Mario Lorenz, Andrew J. Young, Gordon M. Lowe
Format: Article
Language:English
Published: MDPI AG 2017-09-01
Series:Antioxidants
Subjects:
Online Access:https://www.mdpi.com/2076-3921/6/3/69
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spelling doaj-1f28bc731ccb433f867d45146cc7e1e02020-11-25T00:29:48ZengMDPI AGAntioxidants2076-39212017-09-01636910.3390/antiox6030069antiox6030069A Possible Indicator of Oxidative Damage in Smokers: (13Z)-Lycopene?Daniel L. Graham0Mario Lorenz1Andrew J. Young2Gordon M. Lowe3Faculty of Science, Liverpool John Moores University, Byrom Street, Liverpool L3 3AF, UKCharité—Universitätsmedizin Berlin, corporate member of Freie Universität Berlin, Humboldt-Universität zu Berlin, and Berlin Institute of Health, Department of Cardiology and Angiology, CCM, Charitéplatz 1, 10117 Berlin, GermanySchool of Natural Sciences and Psychology, Liverpool John Moores University, Byrom Street, Liverpool L3 3AF, UKSchool of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, Byrom Street, Liverpool L3 3AF, UKIn vitro, the gaseous phase of cigarette smoke is known to induce both isomerization and degradation of dietary carotenoids, such as β-carotene and lycopene. However, the effects of cigarette smoke on the composition of circulating lycopene in vivo are not well understood. In this study, we examined the lycopene profiles of plasma from non-smokers and smokers. No oxidative intermediates of lycopene that have been observed previously in vitro were detected in the plasma, but evidence of isomerization of the carotenoid was seen. Four geometric forms of lycopene were detected in the plasma of both smokers and non-smokers, namely the (5Z), (9Z), (13Z) and (all-E) forms. The relative amounts of these isomers differed between the two cohorts and there was a significant difference (p < 0.05) between smokers and non-smokers for the ratio of total-Z:all-E lycopene, and in the relative amounts of (13Z) and (all-E)-lycopene. The ratio of (all-E):(13Z)-lycopene was 0.84:1.00 in smokers compared to 1.04:1.00 in non-smokers. In smokers, the (13Z)-isomer was generated in preference to the more thermodynamically stable (5Z) and (9Z)-isomers. This mirrors the scenario seen in vitro, in which the formation of (13Z)-lycopene was the main isomer that accompanied the depletion of (all-E) lycopene, when exposed to cigarette smoke. The results suggest that the relative amount of (13Z)-lycopene could be used as an indicator of oxidative damage to lycopene in vivo.https://www.mdpi.com/2076-3921/6/3/69carotenoidisomerizationlycopenesmokingtomato
collection DOAJ
language English
format Article
sources DOAJ
author Daniel L. Graham
Mario Lorenz
Andrew J. Young
Gordon M. Lowe
spellingShingle Daniel L. Graham
Mario Lorenz
Andrew J. Young
Gordon M. Lowe
A Possible Indicator of Oxidative Damage in Smokers: (13Z)-Lycopene?
Antioxidants
carotenoid
isomerization
lycopene
smoking
tomato
author_facet Daniel L. Graham
Mario Lorenz
Andrew J. Young
Gordon M. Lowe
author_sort Daniel L. Graham
title A Possible Indicator of Oxidative Damage in Smokers: (13Z)-Lycopene?
title_short A Possible Indicator of Oxidative Damage in Smokers: (13Z)-Lycopene?
title_full A Possible Indicator of Oxidative Damage in Smokers: (13Z)-Lycopene?
title_fullStr A Possible Indicator of Oxidative Damage in Smokers: (13Z)-Lycopene?
title_full_unstemmed A Possible Indicator of Oxidative Damage in Smokers: (13Z)-Lycopene?
title_sort possible indicator of oxidative damage in smokers: (13z)-lycopene?
publisher MDPI AG
series Antioxidants
issn 2076-3921
publishDate 2017-09-01
description In vitro, the gaseous phase of cigarette smoke is known to induce both isomerization and degradation of dietary carotenoids, such as β-carotene and lycopene. However, the effects of cigarette smoke on the composition of circulating lycopene in vivo are not well understood. In this study, we examined the lycopene profiles of plasma from non-smokers and smokers. No oxidative intermediates of lycopene that have been observed previously in vitro were detected in the plasma, but evidence of isomerization of the carotenoid was seen. Four geometric forms of lycopene were detected in the plasma of both smokers and non-smokers, namely the (5Z), (9Z), (13Z) and (all-E) forms. The relative amounts of these isomers differed between the two cohorts and there was a significant difference (p < 0.05) between smokers and non-smokers for the ratio of total-Z:all-E lycopene, and in the relative amounts of (13Z) and (all-E)-lycopene. The ratio of (all-E):(13Z)-lycopene was 0.84:1.00 in smokers compared to 1.04:1.00 in non-smokers. In smokers, the (13Z)-isomer was generated in preference to the more thermodynamically stable (5Z) and (9Z)-isomers. This mirrors the scenario seen in vitro, in which the formation of (13Z)-lycopene was the main isomer that accompanied the depletion of (all-E) lycopene, when exposed to cigarette smoke. The results suggest that the relative amount of (13Z)-lycopene could be used as an indicator of oxidative damage to lycopene in vivo.
topic carotenoid
isomerization
lycopene
smoking
tomato
url https://www.mdpi.com/2076-3921/6/3/69
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