Identification of an Epoxide Metabolite of Lycopene in Human Plasma Using 13C-Labeling and QTOF-MS

Cichon, Morgan J.; Moran, Nancy E.; Riedl, Ken M.; Schwartz, Steven J.; Clinton, Steven K.

doi:10.3390/metabo8010024

Cited by 9 publications

(7 citation statements)

References 43 publications

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“…As reviewed above, Moran found a higher turnover rate of absorbed all-trans lycopene compared to cislycopene, suggesting that there may be differential degradation or metabolism of the different isomers within body tissues and that trans-to-cis isomerization may occur. Further analyses of serum samples from Moran et al were performed by Cichon et al and a 1,2 lycopene epoxide was found in plasma beginning 2-4 h post-dosing and represented 1.7% of the dose [97]. This work supports previous work by Khachik et al, who enrolled three lactating women one month postpartum and analyzed breastmilk and serum for carotenoids [98].…”

Section: Excretionsupporting

confidence: 73%

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Lycopene: A Critical Review of Digestion, Absorption, Metabolism, and Excretion

2021

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Lycopene is a non-provitamin A carotenoid that exhibits several health benefits. Epidemiological data support a correlation between lycopene intake and the attenuation of several chronic diseases, including certain types of cancers and cardiovascular diseases. It is currently unknown whether the beneficial effects are from the native structure of lycopene or its metabolic derivatives: lycopenals, lycopenols, and lycopenoic acids. This literature review focuses on the current research on lycopene digestion, absorption, metabolism, and excretion. This review primarily focuses on in vivo studies because of the labile nature and difficulty of studying carotenoids within in vitro experimental models. The studies presented address tissue accumulation of lycopene, the modification of bioavailability due to genetic and dietary factors, and lycopene cleavage by the enzymes ß-carotene oxygenase 1 (BCO1) and ß-carotene oxygenase 2 (BCO2). The current literature suggests that the majority of lycopene is cleaved eccentrically by BCO2, yet further research is needed to probe the enzymatic cleavage activity at the tissue level. Additionally, results indicate that single nucleotide polymorphisms and dietary fat influence lycopene absorption and thus modify its health effects. Further research exploring the metabolism of lycopene, the mechanisms related to its health benefits, and optimal diet composition to increase the bioavailability is required.

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Section: Excretionsupporting

confidence: 73%

“…Isotopically labeled carotenoids are an effective way of investigating lycopene excretion in vivo. Such studies have been carried out using lycopene with rats, gerbils, and humans [92,[95][96][97]. One study used F344 male rats that were fed an AIN-93G diet enriched with lycopene (25 mg per kg diet) [95].…”

Section: Excretionmentioning

confidence: 99%

Lycopene: A Critical Review of Digestion, Absorption, Metabolism, and Excretion

2021

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“…Its expression by human intestinal cells further supports the hypothesis that it may act during digestion . Indeed, LYC metabolites have been found circulating in human plasma, although the origin of these metabolites has not been established.…”

Section: Introductionsupporting

confidence: 53%

“…Also, this study was conducted in healthy male subjects, and differences could be observed in other demographic groups. Finally, only apo‐lycopenoids (i.e., <40 carbon metabolites) were studied in this work, to the exclusion of other reported LYC epoxides and diols, which have been previously examined …”

Section: Discussionmentioning

confidence: 99%

The Effect of an Iron Supplement on Lycopene Metabolism and Absorption During Digestion in Healthy Humans

Kopec

Caris-Veyrat

Nowicki

et al. 2019

Molecular Nutrition Food Res

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Scope To investigate the formation and absorption of lycopene (LYC) metabolites in the human upper gastrointestinal lumen, in the absence and presence of iron. Methods Healthy males (n = 7) consumed test meals that deliver ≈22 mg LYC + ≈0.3 mg apo‐lycopenals from oleoresin without (‐FeSO4) and with ferrous sulfate (160 mg, +FeSO4). Subjects were intubated with a naso‐gastric/naso‐duodenal tube. Digesta, blood plasma, and the triglyceride‐rich lipoprotein (TRL) fractions of plasma were analyzed using LC–MS/MS, to measure LYC and apo‐lycopenoids. Results Digesta LYC concentrations increased with time (p = 1.2 × 10−7), decrease with time × iron (p = 1.1 × 10−5), and remain ≈200× higher than apo‐lycopenals/lycopenone. Digesta apo‐8′‐, ‐10′‐, ‐12′‐, ‐14′‐, ‐15‐lycopenal, and apo‐13‐lycopenone concentrations increased with time (p < 0.01), apo‐12′‐, ‐14′‐, ‐15‐lycopenal, apo‐13‐lycopenone increase with iron (p < 0.05), and time × iron decrease apo‐8′‐, ‐10′‐, ‐12′‐, ‐14′‐, ‐15‐lycopenal, apo‐13‐lycopenone concentrations (p < 0.01). A 1.9‐fold decrease in LYC TRL area‐under‐the‐time‐concentration‐curve is observed after the test meal +FeSO4 versus the test meal –FeSO4 (p = 0.02). Apo‐lycopenals were detected in later TRL fractions, and no apo‐lycopenols or apo‐lycopenoic acids were observed in any samples. Conclusions FeSO4 reduces LYC absorption. Apo‐lycopenals appear to be absorbed from foods, and not made in significant quantities during digestion.

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“…Some studies suggest that metabolites of lycopene may play a role in the biological activities of lycopene. However, only a limited number of studies have investigated the role of lycopene metabolites in vivo [ 128 , 129 , 130 , 131 , 132 ].…”

Section: Carotenoid Lycopene: Chemistry and Its Isomersmentioning

confidence: 99%

Potential Role of Lycopene in the Prevention of Postmenopausal Bone Loss: Evidence from Molecular to Clinical Studies

Walallawita

Wolber

Ziv‐Gal

et al. 2020

IJMS

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Osteoporosis is a metabolic bone disease characterized by reduced bone mineral density, which affects the quality of life of the aging population. Furthermore, disruption of bone microarchitecture and the alteration of non-collagenous protein in bones lead to higher fracture risk. This is most common in postmenopausal women. Certain medications are being used for the treatment of osteoporosis; however, these may be accompanied by undesirable side effects. Phytochemicals from fruits and vegetables are a source of micronutrients for the maintenance of bone health. Among them, lycopene has recently been shown to have a potential protective effect against bone loss. Lycopene is a lipid-soluble carotenoid that exists in both all-trans and cis-configurations in nature. Tomato and tomato products are rich sources of lycopene. Several human epidemiological studies, supplemented by in vivo and in vitro studies, have shown decreased bone loss following the consumption of lycopene/tomato. However, there are still limited studies that have evaluated the effect of lycopene on the prevention of bone loss in postmenopausal women. Therefore, the aim of this review is to summarize the relevant literature on the potential impact of lycopene on postmenopausal bone loss with molecular and clinical evidence, including an overview of bone biology and the pathophysiology of osteoporosis.

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Identification of an Epoxide Metabolite of Lycopene in Human Plasma Using 13C-Labeling and QTOF-MS

Cited by 9 publications

References 43 publications

Lycopene: A Critical Review of Digestion, Absorption, Metabolism, and Excretion

Lycopene: A Critical Review of Digestion, Absorption, Metabolism, and Excretion

The Effect of an Iron Supplement on Lycopene Metabolism and Absorption During Digestion in Healthy Humans

Potential Role of Lycopene in the Prevention of Postmenopausal Bone Loss: Evidence from Molecular to Clinical Studies

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