Reactions of β-Carotene with Cigarette Smoke Oxidants. Identification of Carotenoid Oxidation Products and Evaluation of the Prooxidant/Antioxidant Effect

The influence of 11 kinds of oxygen-containing sulfur flavor molecules was examined on β-carotene stability under UVA irradiation in ethanol system. Both the effects of sulfides on dynamic degradation of β-carotene and the relation between structure and effect were investigated. The oxidation products of β-carotene accelerated by sulfides under UVA irradiation were also identified. The results indicated that the disulfides had more obvious accelerative effects on the photodegradation of β-carotene than mono sulfides. The degradation of β-carotene after methyl (2-methyl-3-furyl) disulfide (MMFDS), methyl furfuryl disulfide (MFDS) and bis(2-methyl-3-furyl) disulfide (BMFDS) exposure followed first-order kinetics. Furan-containing sulfides such as MMFDS and BMFDS showed more pronounced accelerative effects than their corresponding isomers. The oxidation products were identified as 13-cis-β-carotene, 9,13-di-cis-β-carotene and all-trans-5,6-epoxy-β-carotene. These results suggest that both the sulfur atom numbers and the furan group in oxygen-containing sulfides play a critical role in the photooxidation of β-carotene.

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Qualitative and quantitative comparison of the cytotoxic and apoptotic potential of phytosterol oxidation products with their corresponding cholesterol oxidation products

British Journal Of Nutrition ◽

10.1079/bjn20051500 ◽

2005 ◽

Vol 94 (3) ◽

pp. 443-451 ◽

Cited By ~ 79

Author(s):

Eileen Ryan ◽

Jay Chopra ◽

Florence McCarthy ◽

Anita R. Maguire ◽

Nora M. O'Brien

Keyword(s):

Cell Line ◽

Biological Effects ◽

Oxidation Products ◽

Cholesterol Oxidation ◽

Monocytic Cell ◽

Monocytic Cell Line ◽

Cholesterol Oxidation Products ◽

Phytosterol Oxidation Products ◽

Induced Apoptosis ◽

Β Carotene

Phytosterols contain an unsaturated ring structure and therefore are susceptible to oxidation under certain conditions. Whilst the cytotoxicity of the analogous cholesterol oxidation products (COP) has been well documented, the biological effects of phytosterol oxidation products (POP)have not yet been fully ascertained. The objective of the present study was to examine the cytotoxicity of β-sitosterol oxides and their corresponding COP in a human monocytic cell line (U937), a colonic adenocarcinoma cell line (CaCo-2) and a hepatoma liver cell line (HepG2). 7β-Hydroxysitosterol, 7-ketositosterol, sitosterol-3β,5α,6β-triol and a sitosterol-5α,6α-epoxide–sitosterol-5β,6β-epoxide (6:1) mixture were found to be cytotoxic to all three cell lines employed; the mode of cell death was by apoptosis in the U937 cell line and necrosis in the CaCo-2 and HepG2 cells. 7β-Hydroxysitosterol was the only β-sitosterol oxide to cause depletion in glutathione, indicating that POP-induced apoptosis may not be dependent on the generation of an oxidative stress. A further objective of this study was to assess the ability of the antioxidants α-tocopherol, γ-tocopherol and β-carotene to modulate POP-induced cytotoxicity in U937 cells. Whilst α/γ-tocopherol protected against 7β-hydroxycholesterol-induced apoptosis, they did not confer protection against 7β-hydroxysitosterol-or 7-ketositosterol-induced toxicity, indicating that perhaps COP provoke different apoptotic pathways than POP. β-Carotene did not protect against COP- or POP-induced toxicity. In general, results indicate that POP have qualitatively similar toxic effects to COP. However, higher concentrations of POP are required to elicit comparable levels of toxicity.

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Oxidation Products of β-Carotene during the Peroxidation of Methyl Linoleate in the Bulk Phase

Bioscience Biotechnology and Biochemistry ◽

10.1271/bbb.62.1301 ◽

1998 ◽

Vol 62 (7) ◽

pp. 1301-1306 ◽

Cited By ~ 24

Author(s):

Ryo YAMAUCHI ◽

Kakue TSUCHIHASHI ◽

Koji KATO

Keyword(s):

Methyl Linoleate ◽

Bulk Phase ◽

Oxidation Products ◽

Β Carotene

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Inhibition by β-Carotene of Upper Respiratory Tumorigenesis in Hamsters Receiving Diethylnitrosamine Followed by Cigarette Smoke Exposure

Japanese Journal of Cancer Research ◽

10.1111/j.1349-7006.1999.tb00728.x ◽

1999 ◽

Vol 90 (2) ◽

pp. 154-161 ◽

Cited By ~ 10

Author(s):

Fumio Furukawa ◽

Akiyoshi Nishikawa ◽

Ken-ichiro Kasahara ◽

In-Seon Lee ◽

Keiji Wakabayashi ◽

...

Keyword(s):

Cigarette Smoke ◽

Smoke Exposure ◽

Cigarette Smoke Exposure ◽

Upper Respiratory ◽

Β Carotene

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β-Carotene and Cigarette Smoke Condensate Regulate Heme Oxygenase-1 and Its Repressor Factor Bach1: Relationship with Cell Growth

Antioxidants and Redox Signaling ◽

10.1089/ars.2006.8.1069 ◽

2006 ◽

Vol 8 (5-6) ◽

pp. 1069-1080 ◽

Cited By ~ 24

Author(s):

Paola Palozza ◽

Simona Serini ◽

Diego Currò ◽

Gabriella Calviello ◽

Kazuhiko Igarashi ◽

...

Keyword(s):

Cell Growth ◽

Cigarette Smoke ◽

Heme Oxygenase ◽

Heme Oxygenase 1 ◽

Cigarette Smoke Condensate ◽

Β Carotene

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β-carotene oxidation products modify cholesterol biosynthesis and growth of cultured human epidermoid carcinoma cell

Bulletin of Experimental Biology and Medicine ◽

10.1007/bf02447377 ◽

1998 ◽

Vol 126 (3) ◽

pp. 928-931 ◽

Cited By ~ 1

Author(s):

M. V. Malakhova ◽

V. F. Orlova ◽

V. A. Karpov ◽

V. M. Govorun ◽

E. M. Khalilov

Keyword(s):

Carcinoma Cell ◽

Cholesterol Biosynthesis ◽

Epidermoid Carcinoma ◽

Oxidation Products ◽

Β Carotene ◽

Human Epidermoid Carcinoma

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Effects of Different Phases of Cigarette Smoke on Lipid Peroxidation and Membrane Structure in Liposomes

Australian Journal of Chemistry ◽

10.1071/ch13663 ◽

2014 ◽

Vol 67 (6) ◽

pp. 858 ◽

Cited By ~ 4

Author(s):

Nadezhda P. Palmina ◽

Elena L. Maltseva ◽

Tatyana E. Chasovskaya ◽

Valery V. Kasparov ◽

Nataliya G. Bogdanova ◽

...

Keyword(s):

Lipid Peroxidation ◽

Double Bond ◽

Gas Phase ◽

Lipid Bilayer ◽

Cigarette Smoke ◽

Membrane Structure ◽

Malonic Dialdehyde ◽

Oxidation Products ◽

Liposomal Membranes ◽

First Time

This paper discloses for the first time the effects of the gas phase (GP) and the tar of cigarette smoke on lipid peroxidation (LPO) and on the structure of different lipid regions in liposomes. The LPO development was analysed in terms of the total unsaturation of lipids (double-bond, DB, content) and the formation of dienic conjugates (DC), ketodienes (KD), and malonic dialdehyde (MDA). As expected, the exposure of liposomes to either the GP or the tar led to a significant decrease in the DB content. However, the formation of oxidation products revealed different dynamics: MDA generation was inhibited, while the formation of DC and KD increased during the first few hours of the LPO development followed by its inhibition. The smoke constituents exhibited opposite effects on the structure of the lipid bilayer of liposomes: the GP markedly enhanced the microviscosity of liposomal membranes, whereas the tar caused a drastic lowering of microviscosity.

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