Formation of cleavage products by autoxidation of lycopene

Kim, Seon-Jae; Nara, Eiichi; Kobayashi, Hidetaka; Terao, Junji; Nagao, Akihiko

doi:10.1007/s11745-001-0706-8

Cited by 77 publications

(50 citation statements)

References 46 publications

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“…Bixin aldehyde (C 24 -dialdehyde), the intermediate in the biosynthesis of the plant pigment annatto, is formed by enzymatic cleavage of lycopene by a lycopene dioxygenase (2). Autooxidation of lycopene can also produce aldehyde products of different chain lengths by oxdative cleavage of lycopene (8). Here, we report the biosynthesis of carotenoid aldehydes by enzymatic oxidation of the linear end(s) of the carotenoid backbone.…”

Section: Discussionmentioning

confidence: 98%

Novel Carotenoid Oxidase Involved in Biosynthesis of 4,4′-Diapolycopene Dialdehyde

Luan

Schenzle

Odom

et al. 2005

Appl Environ Microbiol

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Biosynthesis of C 30 carotenoids is relatively restricted in nature but has been described in Staphylococcus and in methylotrophic bacteria. We report here identification of a novel gene (crtNb) involved in conversion of 4,4-diapolycopene to 4,4-diapolycopene aldehyde. An aldehyde dehydrogenase gene (ald) responsible for the subsequent oxidation of 4,4-diapolycopene aldehyde to 4,4-diapolycopene acid was also identified in Methylomonas. CrtNb has significant sequence homology with diapophytoene desaturases (CrtN). However, data from knockout of crtNb and expression of crtNb in Escherichia coli indicated that CrtNb is not a desaturase but rather a novel carotenoid oxidase catalyzing oxidation of the terminal methyl group(s) of 4,4-diaponeurosporene and 4,4-diapolycopene to the corresponding terminal aldehyde. It has moderate to low activity on neurosporene and lycopene and no activity on ␤-carotene or -carotene. Using a combination of C 30 carotenoid synthesis genes from Staphylococcus and Methylomonas, 4,4-diapolycopene dialdehyde was produced in E. coli as the predominant carotenoid. This C 30 dialdehyde is a dark-reddish purple pigment that may have potential uses in foods and cosmetics.

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Section: Discussionmentioning

confidence: 98%

Novel Carotenoid Oxidase Involved in Biosynthesis of 4,4′-Diapolycopene Dialdehyde

Luan

Schenzle

Odom

et al. 2005

Appl Environ Microbiol

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“…Utilizing various oxidizing systems and in vitro experiments, scientists have demonstrated lycopene’s susceptibility to cleavage, and identified unique oxidative products of lycopene. After incubating lycopene under atmospheric oxygen at 37 °C for 72 h, Kim et al identified eight oxidative products (3,7,11-trimethyl-2,4,6,10-dodecatetraen-1-al,6,10,14-trimethyl-3,5,7,9,13-pentadecapentaen-2-one, acyclo-retinal, apo-14′-lycopenal, apo-12′-lycopenal, apo-10′-lycopenal, apo-8′-lycopenal, and apo-6′-lycopenal) [157]. Utilizing another oxidizing system, Caris-Veyrat et al identified eight apolycopenals and three apolycopenones generated from oxidation of lycopene [158].…”

Section: Effects Of Tomato and Lycopene Consumption Against Nash Amentioning

confidence: 99%

Non-Alcoholic Steatohepatitis and Hepatocellular Carcinoma: Implications for Lycopene Intervention

Wang

2013

Nutrients

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Increased prevalence of non-alcoholic fatty liver disease (NAFLD) is one of the consequences of the current obesity epidemic. NAFLD is a major form of chronic liver disease that is highly prevalent in obese and overweight adults and children. Nonalcoholic steatohepatitis (NASH) is the severe form of NAFLD, and uncontrolled inflammation as displayed in NASH has been identified as one of the key events in enhancing hepatic carcinogenesis. Lycopene is a non-provitamin A carotenoid and the pigment principally responsible for the characteristic deep-red color of ripe tomato and tomato products, as well as some fruits and vegetables. Lycopene’s innate antioxidant and anti-inflammatory properties have generated research interests on its capacity to protect against human diseases that are associated with oxidative stress and inflammation. In addition, differential mechanisms of lycopene metabolism including endogenous cleavage by carotenoid cleavage oxygenases (BCOs), generate lycopene metabolites that may also have significant impact on human disease development. However, it remains to be elucidated as to whether lycopene or its metabolites apolycopenoids have protective effects against obesity-related complications including inflammation and tumorigenesis. This article summarizes the in vivo experiments that elucidated molecular mechanisms associated with obesity-related hepatic inflammation and carcinogenesis. This review also provides an overview of lycopene metabolism, and the molecular pathways involved in the potential beneficial properties of lycopene and apolycopenoids. More research is clearly needed to fully unravel the importance of BCOs in tomato carotenoid metabolism and the consequence on human health and diseases.

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“…Nonetheless, the challenge is that numerous tomato carotenoids such as β-carotene and lycopene are particularly sensitive to degradation in cell culture systems [63-67]. Thus, it is a challenge to elucidate the roles of the carotenoids in vitro although the polyphenols are comparatively easy to examine in cell culture.…”

Section: Tomatoes and Prostate Cancermentioning

confidence: 99%

Tomato-based food products for prostate cancer prevention: what have we learned?

Tan

Thomas‐Ahner

Grainger

et al. 2010

Cancer Metastasis Rev

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Evidence derived from a vast array of laboratory studies and epidemiological investigations have implicated diets rich in fruits and vegetables with a reduced risk of certain cancers. However, these approaches cannot demonstrate causal relationships and there is a paucity of randomized, controlled trials due to the difficulties involved with executing studies of food and behavioral change. Rather than pursuing the definitive intervention trials that are necessary, the thrust of research in recent decades has been driven by a reductionist approach focusing upon the identification of bioactive components in fruits and vegetables with the subsequent development of single agents using a pharmacologic approach. At this point in time, there are no chemopreventive strategies that are standard of care in medical practice that have resulted from this approach. This review describes an alternative approach focusing upon development of tomato-based food products for human clinical trials targeting cancer prevention and as an adjunct to therapy. Tomatoes are a source of bioactive phytochemicals and are widely consumed. The phytochemical pattern of tomato products can be manipulated to optimize anticancer activity through genetics, horticultural techniques, and food processing. The opportunity to develop a highly consistent tomato-based food product rich in anticancer phytochemicals for clinical trials targeting specific cancers, particularly the prostate, necessitates the interactive transdisciplinary research efforts of horticulturalists, food technologists, cancer biologists, and clinical translational investigators.

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Formation of cleavage products by autoxidation of lycopene

Cited by 77 publications

References 46 publications

Novel Carotenoid Oxidase Involved in Biosynthesis of 4,4′-Diapolycopene Dialdehyde

Novel Carotenoid Oxidase Involved in Biosynthesis of 4,4′-Diapolycopene Dialdehyde

Non-Alcoholic Steatohepatitis and Hepatocellular Carcinoma: Implications for Lycopene Intervention

Tomato-based food products for prostate cancer prevention: what have we learned?

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