Organic Synthesis of New Putative Lycopene Metabolites and Preliminary Investigation of Their Cell-Signaling Effects

Reynaud, Eric; Aydemir, Gamze; Rühl, Ralph; Dangles, Olivier; Caris-Veyrat, Catherine

doi:10.1021/jf104092e

Cited by 37 publications

(38 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Apo‐6′‐, ‐8′‐, and ‐12′‐lycopenal standards were purchased from CaroteNature (Münsingen, Switzerland). Apo‐10′‐lycopenal, apo‐10′‐lycopenol, apo‐10′‐lycopenoic acid, apo‐14′‐lycopenal, apo‐14′‐lycopenol, apo‐14′‐lycopenoic acid, apo‐11‐lycopenal standards were synthesized previously . The glycerol phosphate oxidase assay was from Abliance (Compiegne, France).…”

Section: Methodsmentioning

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

View full text Add to dashboard Cite

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.

show abstract

Section: Methodsmentioning

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

View full text Add to dashboard Cite

show abstract

“…In particular, the recent characterization and study of carotene 99,10'-oxygenase in mammalian tissues has demonstrated that this enzyme can catalyze the cleavage of lycopene to form apo-10'-lycopenal, apo-10-lycopenol, and ALA from lycopene (14). Several reports, including our own, suggest that the biological activities of lycopene may be mediated in part by lycopene metabolites in vitro and in vivo (15)(16)(17)(18), which have displayed unique biological activities. A series of apo-lycopenals, including apo-10'-lycopenal, has recently been identified in human plasma (19).…”

Section: Introductionmentioning

confidence: 92%

Apo-10′-Lycopenoic Acid, a Lycopene Metabolite, Increases Sirtuin 1 mRNA and Protein Levels and Decreases Hepatic Fat Accumulation in ob/ob Mice3

Chung

Koo

Lian

et al. 2012

The Journal of Nutrition

View full text Add to dashboard Cite

Lycopene has been shown to be beneficial in protecting against high-fat diet-induced fatty liver. The recent demonstration that lycopene can be converted by carotene 9',10'-oxygenase into a biologically active metabolite, ALA, led us to propose that the function of lycopene can be mediated by ALA. In the present study, male ob/ob mice were fed a liquid high-fat diet (60% energy from fat) with ALA supplementation (ALA group, 240 μg · kg body weight(-1) · d(-1)) or without ALA supplementation as the control (C group) for 16 wk. Steatosis, SIRT1 expression and activity, genes involved in lipid metabolism, and ALA concentrations in the livers of mice were examined. The results showed that ALA supplementation resulted in a significant accumulation of ALA in the liver and markedly decreased the steatosis in the ALA group without altering body and liver weights compared to the C group. The mRNA and protein levels of hepatic SIRT1 were higher in the ALA group compared to the C group. SIRT1 activity also was higher in the ALA group, as indicated by the lower levels of acetylated forkhead box class O1 protein levels. In addition, the mRNA level of acetyl CoA carboxylase 1 was significantly lower in the ALA group than in the C group. Because SIRT1 plays a key role in lipid homeostasis, the present study suggests that the lycopene metabolite, ALA, protects against the development of steatosis in ob/ob mice by upregulating SIRT1 gene expression and activity.

show abstract

“…The HWE reaction has also been used to prepare putative lycopene metabolites (Scheme 33) by desymmetrization of unsaturated dialdehydes [57].…”

Section: Lipidsmentioning

confidence: 99%

Recent Applications of the Horner-Wadsworth-Emmons Reaction to the Synthesis of Natural Products

Bisceglia¹,

Orelli

2012

COC

View full text Add to dashboard Cite

The Horner-Wadsworth-Emmons reaction has evolved in the last years as one of the most powerful and reliable method for stereocontrolled olefin synthesis. The reaction has become a widespread standard tool in natural products total syntheses, providing access to relatively simple as well as highly complex synthetic targets. In this work we present the most representative applications within the field of natural product synthesis from 2000 to the present year. The examples comprise the synthesis of macrocycles, 5 to 7 membered rings, lipids and related compounds, alkaloids and cyclic ethers. They were chosen from a large amount of literature reports and illustrate the use of the HWE reaction in the synthesis and elaboration of key intermediates and in the crucial assembly of highly functionalized synthetic precursors.

show abstract

Organic Synthesis of New Putative Lycopene Metabolites and Preliminary Investigation of Their Cell-Signaling Effects

Cited by 37 publications

References 33 publications

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

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

Apo-10′-Lycopenoic Acid, a Lycopene Metabolite, Increases Sirtuin 1 mRNA and Protein Levels and Decreases Hepatic Fat Accumulation in ob/ob Mice3

Recent Applications of the Horner-Wadsworth-Emmons Reaction to the Synthesis of Natural Products

Contact Info

Product

Resources

About