A review about lycopene-induced nuclear hormone receptor signalling in inflammation and lipid metabolism via still unknown endogenous apo-10´-lycopenoids

Lycopene is the red pigment in tomatoes and tomato products and is an important dietary carotenoid found in the human organism. Lycopene-isomers, oxidative lycopene metabolites and apo-lycopenoids are found in the food matrix. Lycopene intake derived from tomato consumption is associated with alteration of lipid metabolism and a lower incidence of cardiovascular diseases (CVD). Lycopene is mainly described as a potent antioxidant but novel studies are shifting towards its metabolites and their capacity to mediate nuclear receptor signalling. Di-/tetra-hydro-derivatives of apo-10´-lycopenoic acid and apo-15´-lycopenoic acids are potential novel endogenous mammalian lycopene metabolites which may act as ligands for nuclear hormone mediated activation and signalling. In this review, we postulate that complex lycopene metabolism results in various lycopene metabolites which have the ability to mediate transactivation of various nuclear hormone receptors like RARs, RXRs and PPARs. A new mechanistic explanation of how tomato consumption could positively modulate inflammation and lipid metabolism is discussed

Effect of a carotenoid-producing Bacillus strain on intestinal barrier integrity and systemic delivery of carotenoids : a randomised trial in animals and humans

The aim of the present study was to investigate effects of the carotenoid-producing Bacillus indicus strain PD01 on intestinal barrier function and its ability to survive passage through the gastrointestinal tract and to assess systemic bioavailability of these carotenoids in vivo. As model for impaired barrier function, 16 early weaned piglets were randomly assigned to a control diet or control diet with PD01 for 23 days. In addition, 67 overweight/obese, otherwise healthy individuals were randomly assigned to groups receiving PD01 or placebo for 6 weeks. PD01 survived passage through the gastrointestinal tract in piglets and human subjects and resulted in significant accumulation of PD01 derived carotenoids (methyl-glycosyl-apo-8'-lycopenoate and glycosyl-apo-8'- lycopene) in human plasma after 3- and 6-weeks supplementation versus baseline (0.044 and 0.076 vs 0 mu M, respectively; p = 0.104). In summary, PD01 survived transit through the gastrointestinal tract, resulted in systemic carotenoid accumulation and improved compromised barrier function outcomes

Synthèse organique d'apo-lycopénoïdes, étude des propriétés antioxydantes et de complexation avec l'albumine de sérum humain

Les études épidémiologiques ont montré qu'une consommation régulière en tomate et ses produits dérivés de tomate permet de lutter contre diverses pathologies dégénératives associées notamment au stress oxydant (maladies cardiovasculaires, cancers etc..). Les effets bénéfiques pourraient être dus au lycopène pigment rouge de la tomate et/ou à ses métabolites qui interviendraient dans ce processus soit de part leurs capacités antioxydantes, soit au travers de la régulation de l expression de gènes. Dans ce contexte, quatre familles de molécules dérivées du lycopène, pouvant être des métabolites potentiels, ont été ciblées pour la synthèse organique : les apo-11-lycopénoïdes, les apo- 14 -lycopénoïdes, les apo-12 -lycopénoïdes et les apo-10 -lycopénoïdes. Chacune des familles a été synthétisée, via des réactions de couplages tels que Wittig et Horner-Wadsworth-Emmons, avec quatre fonctions chimiques terminales : ester, acide carboxylique, alcool et aldéhyde. Par la suite deux types de propriétés physico-chimiques des composés synthétisés ont été étudiés : mesure du pouvoir antioxydant dans des conditions expérimentales mimant un stress oxydant dans le compartiment gastro-intestinal (inhibition de la peroxydation lipidique initiée par la metmyoglobine en milieu micellaire) et une étude d interaction avec l'albumine de sérum humain, protéine impliquée dans le transport des acides gras dans le plasma.Epidemiological studies have shown that regular consumption of tomatoes and its derived products participate to the prevention of degenerative pathologies associated with oxidative stress (cardiovascular disease, cancers). The beneficial effects could come from lycopene and/or its metabolites. In this context four families of lycopene derived compounds, mimicking possible metabolites, were targeted to be synthesized: the apo-11- lycopenoids, the apo-14 - lycopenoids, the apo-12 - lycopenoids and the apo-10 -lycopenoids. For each family, Wittig and Horner- Wadsworth-Emmons coupling reaction were used and four different ending functions were obtained: ester, carboxylic acid, alcohol and aldehyde. Then two physico-chemical properties were studied: antioxidant effect mimicking oxidative stress in the gastro-intestinal tract (inhibition of lipidic peroxidation initiated by metmyoglobin protein in micellar medium) and study of the interaction with human serum albumin, a protein involved in the transport of fatty acid in the plasma.AVIGNON-Bib. numérique (840079901) / SudocSudocFranceF

Stabilité de microconstituants de la tomate (composés phénoliques, caroténoïdes, vitamines C et E) au cours des procédés de transformation (études en systèmes modèles, mise au point d'un modèle stoechio-cinétique et validation pour l'étape unitaire de préparation de sauce tomate)

La tomate, fruit largement consommé frais mais aussi sous forme transformée, est reconnue pour ses qualités nutritionnelles. Riche en microconstituants, tels les caroténoïdes (le lycopène en particulier), les composés phénoliques et la vitamine C, sa consommation régulière permettrait de réduire les risques de maladies cardiovasculaires et de certains cancers. Cependant, les traitements thermiques appliqués lors de la préparation industrielle de produits à base de tomate peuvent être à l'origine de réactions chimiques entraînant la dégradation de ces antioxydants. D'autre part, l'ajout d'huile végétale, pour la préparation de la sauce tomate notamment, met en jeu des réactions d'oxydation des lipides pouvant contribuer à l'instabilité de ces microconstituants. L objectif principal de cette thèse est la détermination des cinétiques réactionnelles impliquées dans l évolution des microconstituants de la tomate lors des procédés industriels de transformation.Dans un premier temps, une étude qualitative et quantitative sur plusieurs produits industriels (concentrés, pulpe, sauces) à base de tomate a été menée afin de déterminer les microconstituants marqueurs de la qualité nutritionnelle : (E)-lycopène et (E)-b-carotène pour les caroténoïdes, rutine, 7-O-glucosyl-naringénine et acide chlorogénique pour les composés phénoliques ainsi que les vitamines C et E ont été retenus. Cette première étude a permis de déterminer l impact de procédés industriels sur les teneurs en microconstituants pour des produits collectés en entrée et en sortie de process pour deux usines de la région PACA.Par la suite, la stabilité des 7 marqueurs sélectionnés a été étudiée dans trois systèmes modèles modélisant la sauce tomate à des températures simulant des conditions de cold et hot breaks. Ces systèmes modèles comprennent un milieu aqueux acide (pH 3,8) contenant de l amidon, un milieu lipidique constitué d'huile et de phospholipides végétaux et une émulsion H/E (huile dans eau) intégrant ces divers constituants. L oxydation des lipides et son éventuelle protection par les microconstituants ont été évaluées par détermination de l'évolution des teneurs en diènes conjugués et trilinoléine. Parmi tous les antioxydants, la vitamine C s'est avérée être le moins stable en émulsion comme en milieu aqueux; sa vitesse d'oxydation est influencée par la teneur en oxygène dans le milieu. Les teneurs en composés phénoliques sont peu affectées, même à haute température (95 C) tandis que les caroténoïdes s'isomérisent rapidement quelles que soient les conditions appliquées. Dans l'émulsion modèle, l'oxydation lipidique est nettement accélérée quand la température s'élève et tous les marqueurs se dégradent plus rapidement qu'en milieu aqueux ou lipidique.La détermination des constantes de vitesses a été réalisée, soit individuellement pour chaque cinétique, soit par desapproches globales (modèle oxydation lipidique et modèle stoechio-cinétique). Ce dernier modèle a pour but de proposer des conditions limitant l oxydation lipidique et la dégradation des microconstituants de la tomate au cours des procédésTomato is a fruit widely consumed either fresh or processed possessing recognized nutritional qualities. Rich in microconstituents like carotenoids (such as lycopene), phenolic compounds and vitamin C, its regular consumption could reduce risks of cardio-vascular diseases and cancers. However, thermal treatments applied during industrial preparation of tomato products may involve various chemical reactions leading to the degradation of these antioxidants. Besides, addition of vegetable oil for the preparation of tomato sauce may lead to lipid oxidation contributing to the microconstituent instability.The main objective of this thesis is the determination of reaction kinetics for tomato microconstituents during industrial processing.First, a qualitative and quantitative study on several industrial tomato products (pastes, pulp, sauces) was carried out in order to select markers of the nutritional quality: (E)-lycopene and (E)-b-carotene for carotenoids, rutin, naringenin 7-O-glucoside and chlorogenic acid for phenolics as well as vitamins C and E. Additionally, an impact of processing was determined for industrial products collected before and after processing in two different plants in the PACA Region. Then, the stability of the selected markers was studied in model systems mimicking tomato sauce at hot and cold break temperatures. For this purpose, three model systems were developed: an aqueous model containing starch, a lipidic model consisting of vegetable oil and phospholipids and an O/W (oil-in-water) emulsion integrating all these constituents. Lipid oxidation and its possible protection by antioxidants were evaluated by the follow-up of conjugated dienes and trilinolein. Among all the antioxidants, vitamin C proved to be the least stable in both the emulsion and aqueous models. Its oxidation rate was found to be oxygen dependent. Phenolic compounds were little affected, even at high temperature (95 C) whereas carotenoids rapidly isomerised whatever the conditions applied. In the emulsion model, lipid oxidation is clearly accelerated when the temperature increases and all markers are more rapidly degraded than in the aqueous or lipidic model. Rate constants were determined, either individually for each kinetics, either using global approaches (lipid oxidationmodel and stoichio-kinetic model). This last model aims at giving process conditions limiting lipid oxidation and microconstituent degradationAVIGNON-Bib. numérique (840079901) / SudocSudocFranceF

Lycopene and Its Antioxidant Role in the Prevention of Cardiovascular Diseases—A Critical Review

The present review is based mainly on papers published between 2000 and 2011 and gives information about the properties of the carotenoid lycopene in chemical and biological systems and its possible role in preventing cardiovascular diseases (CVD). The main aim of this report is to highlight its role as an antioxidant, also reported are bioactive properties that may influence the development of foam cells and protection against endothelial cell damage. The paper will also examine recent observations that lycopene may improve blood flow and reduce inflammatory responses. Lycopene possesses antioxidant properties in vitro, and some epidemiological studies have reported protective effects against the progression of CVD. The oxidation of human low density lipoproteins (LDL) is a fundamental mechanism in the initiation of atherosclerosis. A beneficial role of lycopene as antioxidant in the prevention of CVD is suggested but the data are still controversial. Lycopene is believed to be the most potent carotenoid antioxidant in vitro. Tissue culture experiments and animal studies support potential cardioprotective effects for lycopene and other carotenoids in the blood. Most studies showed beneficial effects of lycopene to individuals who are antioxidant-deficient like elderly patients, or humans exposed to higher levels of oxidative stress like smokers, diabetics, hemodialysis patients and acute myocardial infarction patients. By defining the right population and combining antioxidant potentials of lycopene with vitamins and other bioactive plant compounds, the beneficial role of lycopene in CVD can be clarified in future studies

Tomato carotenoids processing during simulated digestion: stability and transfer between tomato particles from Hot Break and Cold Break tomato purée, emulsion and mixed micelles

National audienceIntroduction. The process of digestion of plant food matrix could modulate the bioaccessibility of nutritionally relevant lipophilic micronutrients like carotenoids. Different steps are: diffusion of carotenoids into an oil phase, which also depends on food processing, transfer of carotenoids either into emulsion (gastric digestion) or inside micelles (intestinal digestion), possible degradation through oxidation. To better understand the factors limiting the bioaccessibility of carotenoids, we investigated their stability and their kinetics of transfer in experimental models mimicking digestion, i.e. from tomato particles to emulsions and mixed micelles and from emulsions to mixed micelles. Materials and Methods. Oil-in-water emulsions, mimicking those in the gastric compartment, were elaborated and characterized. Main carotenoids present in food (i.e. β-carotene, lycopene and lutein) were incorporated into these emulsions and we measured the emulsion droplet size and their stability as well as the stability of carotenoids during 4 hours at 37°C in the dark and room pressure. Transfer of carotenoids to mixed micelles was studied for carotenoid-enriched emulsions and also for tomato particles, prepared from tomato purée produced either by cold break (CB) or hot break (HB) tomato processing. Results and Discusson. Carotenoids did not modify neither mode nor size distribution of emulsion lipid droplets. No significant change in the total carotenoid concentration was observed during the transfers but a 3–8% isomerization of the carotenoids. 吀e transfer of carotenoids from emulsion to mixed micelles was time and carotenoid dependent: lutein was significantly more efficiently transferred (23%) than β-carotene (9%) and lycopene (7%). A larger proportion of lycopene was transferred to the oil phase for HB particles (6%), compared to CB particles (3%); the opposite was observed for the β-carotene (29% CB and 21% HB). A very small but significant transfer of carotenoids was observed directly from tomato particles to mixed micelles: 0.09–1.6% for β-carotene and 0.05–0.09% for lycopene. Carotenoids from tomato particles were better transferred to mixed micelles from HB than from CB tomato particles. Conclusions. Carotenoids are stable during digestion but their transfer efficiency is a limiting factor for their bioaccessibility. More interestingly, we showed for the first time that processing type of tomato (HB or CB) influences the diffusion of carotenoids into emulsion and mixed micelles. Thus type of tomato processing impact carotenoid bioaccessibility and nutritional value of tomato products. Several hypotheses are under study to explain these results: modification of the structure of tomato particles and/or differences in their biochemical composition

Microwave heating of tomato puree in the presence of onion and EVOO: The effect on lycopene isomerization and transfer into oil

Tomatoes, the major sources of lycopene in human diet, are often processed into multi-ingredient products that contain vegetable oil and onion. Microwave heating (250W for 20 min) tomato-based purees in the presence ofboth onion and extra virgin olive oil (EVOO) clearly promoted Z-isomerization of lycopene and increased transfer of lycopene into oil (expressed as partition factor (PF) between tomato-based puree and oil), while only PF increased with either one of both ingredients. The proportion of Z-lycopene and PF increased with the additionof onion (10–50%) and EVOO (1–10%). This increase could be fitted with a linear equation, with R2 over 0.807. Microwave heating time (0–30 min at 250 W) also promoted Z-isomerization of lycopene and PF (R2 over 0.910), and among different microwave heating combinations (power, time), the combinations of high power and short time had greater effects. The PF of total-Z-lycopene was higher than that of all-E-lycopene. Theproportion of total-Z-lycopene and 5-Z-lycopene present in the tomato-based purees after the same microwave treatment was positively correlated with the PF of total lycopene, with R2 higher than 0.690 (p=0.0008), which illustrated that the increased proportion of Z-lycopene with onion and EVOO could contribute to enhancedtransfer of lycopene

Interactions between Carotenoids from Marine Bacteria and Other Micronutrients: Impact on Stability and Antioxidant Activity

Recently isolated spore-forming pigmented marine bacteria Bacillus indicus HU36 are sources of oxygenated carotenoids with original structures (about fifteen distinct yellow and orange pigments with acylated d-glucosyl groups). In this study, we evaluated the stability (sensitivity to iron-induced autoxidation) and antioxidant activity (inhibition of iron-induced lipid peroxidation) of combinations of bacterial HU36 carotenoids with the bacterial vitamin menaquinone MQ-7 and with phenolic antioxidants (vitamin E, chlorogenic acid, rutin). Unexpectedly, MQ-7 strongly improves the ability of HU36 carotenoids to inhibit FeII-induced lipid peroxidation, although MQ-7 was not consumed in the medium. We propose that their interaction modifies the carotenoid antioxidant mechanism(s), possibly by allowing carotenoids to scavenge the initiating radicals. For comparison, β-carotene and lycopene in combination were shown to exhibit a slightly higher stability toward iron-induced autoxidation, as well as an additive antioxidant activity as compared to the carotenoids, individually. HU36 carotenoids and phenolic antioxidants displayed synergistic activities in the inhibition of linoleic acid peroxidation induced by heme iron, but not by free iron. Synergism could arise from antioxidants interacting via electron transfer through the porphyrin nucleus of heme iron. Overall, combining antioxidants acting via complementary mechanisms could be the key for optimizing the activity of this bacterial carotenoid cocktail