LYCOPENE - chemical information, properties, structures, articles, patents and more chemical data. Lycopene is an isomer of the carotenes, the yellow colouring matter, both having the same molecular formula, C40H56, but differing in structure. [28] reported a reduction of nearly 30% over 16 weeks in patients consuming Olestra together with lycopene, and the presence of very high levels of phytosterols in some functional foods, which have been demonstrated to reduce carotenoid absorption. Fig. Be on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox. Hence, a double blind phase I/II pilot study assessing the effectiveness of lycopene with panitumumab-treated colorectal patients is underway [126]. Isolation procedures for lycopene were first reported in 1910, and the structure of the molecule was determined by 1931. Since ascorbic acid that acts as vitamin C is not recognized as a vitamin, but rather as a functional ingredient having antioxidant activity, it will be explained as a functional ingredient in this article as well. Natalie J Oswell, ... Ronald B Pegg, in Encyclopedia of Analytical Science (Third Edition), 2019. Metabolic pathway of carotenoids. Various in vitro studies have demonstrated that it possesses antiinflammatory, antiangiogenic, antiinvasive, and antimetastatic properties which assure its promising role in the prevention of colon cancer. Omissions? Lycopene is the most predominant carotenoid in human plasma, present naturally in greater amounts than beta-carotene and other dietary carotenoids. 1.2.5. Our body organs store varying amount of lycopene. Lycopene is a phytonutrient. Variations may be influenced by factors such as ingestion of alcohol or smoking [29,31,32]. By signing up for this email, you are agreeing to news, offers, and information from Encyclopaedia Britannica. More than 72 lycopene isomers have been identified, the most important being all-trans-lycopene, neolycopene A (6-cis-lycopene), 5-cis-lycopene, prolycopene (1-, 3-, 5-, 7-, 9-, 11-cis-lycopene), and cis-lycopene (1-, 3-, 5-, 6-, 7-, 9-, 11-cis-lycopene) [13]. It is liquid at 0°C. In general, lycopene is found in human milk at approximately 3.8 μg/100 g, or 10% of the serum concentrations [29,36], although a low correlation has been found between the amount of lycopene in the diet of tested mothers and concentrations in breast milk. Lycopene is lipophilic and insoluble in water. Epidemiological studies support the possibility that lycopene can reduce cancer risk. Lists the various brand names available for medicines containing lycopene. What is Lycopene. Figure 15.6. Relatively low concentrations of β-carotene are effective in preventing lipid peroxidation by singlet oxygen. A plant-bore compound that, while not necessary for normal metabolic function, enhances the overall health of an organism. Carotenoids such as lycopene and β-carotene from fruits and vegetables protect lipids and other biological systems by interfering with the activation of oxygen. Fig. Fig. It is reported that lycopene can alter the functionality of different inflammatory pathways in vitro. Significant amounts have also been found in other tissues, especially those rich in lipids, such as adipose tissue, adrenal glands, prostate, kidney, and ovaries [14,30,34]. It is a member of the carotenoid family of compounds, and because it consists entirely of carbon and hydrogen, is also a carotene. In gastric and pancreatic malignancies, lycopene was shown to down-regulate Bcl-2 and Erk proteins, emerging as an important natural product that can target and interact with the PI3K/Akt signaling pathway [135]. Metabolic pathway of Anthocyanin. Structural chemical formula object and model of 3d molecule consisting of blue and white atoms joined by the small elements isolated vector illustration Lycopene is a chemical molecular formula. With respect to the known commercial food supplement, based on lycopene, cuch biological lycopenehas unique quality features: the total extract is 100% natural, absense of chemical solvents, lycopene concentration in the final natural formula (not artificial); absence dosing problems and contraindications. 502-65-8 Lycopene is an open chain unsaturated carotenoid that gives tomatoes, guava, rose hip, watermelon and pink grapefruit its red color. It has therapeutic promises in the therapy of colon, lung, breast, liver and prostate cancer [133]. On the other hand, any factor that decreases fat absorption will also decrease lycopene absorption, as is the case with the synthetic oil Olestra in food or drug formulations. 1.2.5 shows the active oxygen scavenging system of plants. All of α-carotene β-carotene, lycopene, and β-cryptoxanthin have antioxidant activity. Fig. On the other hand, the physical and chemical properties of seed's lipids indicated that the refractive index was 1.518, melting point 13.0°C, iodine value 74.2, acid number 1.1, unsaponifiable matters 0.7%, saponification value 188.9, ester value 187.8 and glycerol content 10.3%. During its metabolism, the oxidation of lycopene first produces lycopene 1,2-epoxide and then lycopene 5,6-epoxide as the main metabolites (Fig. The absorbance measured at 450 nm for the separated carotenoids can be compared against calibration curves and used to calculate analyte concentrations in the extract. Empirical … [124] reported that lycopene and fish oil combined at physiological concentration induced a synergistic inhibitory effect on tumor growth in a mouse xenograft model of colon cancer due to enhanced expression of cell-cycle inhibitors such as p21CIP1/WAF1 and p27Kip1 and suppression of PCNA, β-catenin, cyclin D1, and c-Myc proteins. acidophila) yet is less susceptible to degradation. Lycopene is an isomer of the carotenes, the yellow colouring matter, both having the same molecular formula, C40H56, but Lycopene, an organic compound belonging to the isoprenoid series and responsible for the red colour of the tomato, the hips and haws of the wild rose, and many other fruits. Lycopene is a highly unsaturated hydrocarbon, containing 11 conjugated and 2 unconjugated double bonds. Natural sources of lycopene: tomato, grapefruit, pomegranate, red bell pepper, beetroot, mango and carrot. Anticarcinogenic activity of tomato was studied in mice in which carcinoma was induced by croton oil (carcinogen). Besides that, basil produced at the center received a rating from the processor as being more fragrant than ordinary cultivated. Relative to β-carotene, lycopene has the same molecular mass and chemical formula, yet lycopene is an open-polyene chain lacking the β-ionone ring structure. However, processed tomato products contain higher amounts of lycopene as processing steps often involve water loss [115]. Fig. 1.2.3. Compounds called lycopenes, which are present in grapefruit, tomatoes, and watermelon, have been linked to reduced risk, as has the nutrient selenium, which is found in nuts, oranges, and wheat germ.…. Because of the lack of adverse-effect data for lycopene in animals or healthy humans, the Institute of Medicine has not set a tolerable upper intake level for lycopene. [35]. Apart from its antioxidant properties, it also plays a role in regulating hormone action, cell cycle progression, cell death and survival mechanisms, gap junction communication, and epigenetics which complement together to generate its anticancerous effect [112]. It suppresses the nuclear translocation of NF-κBp65 subunit and inhibits the phosphorylation of IKKα and IKBα resulting in overall inactivation of NF-κB. For example, it is found in higher concentration in adipose tissues, adrenal glands, testes, and liver while in lower concentration in kidney, prostate, lungs, and ovary [111]. It is one of a number of pigments called carotenoids. Chemical structure of lycopene. Edwin N. Frankel, in Lipid Oxidation (Second Edition), 2012. Furthermore, this chemopreventive combination inhibited tumor progression and inflammation through suppression of MMP-7, MMP-9, COX-2, and PGE2. The experimental group that was treated with S. lycopersicum had a prolonged time for the appearance of papillomas compared to the animals that were administrated with carcinogen only. The total polyphenol content of basil produced at the plant factory research center was 117 ± 12 mg × 100 g− 1 (± SE), which was larger than that of anthocyanin rich grape “Kyoho.” And the total polyphenol content of the leaf lettuce produced at the center was 117 ± 12 mg × 100 g− 1, which was comparable to that of mizuna rich in anthocyanin. An epidemiological study in elderly Americans indicated that high tomato intake was associated with a 50% reduction in mortality from cancers at all sites, and a case–control study in Italy showed potential protection from high consumption of lycopene from tomatoes against cancers of the digestive tract [116]. Lycopene, chlorogenic acid, and p-coumaric acids are present in tomato, which is helpful in reducing the chances of cancer. In an intervention study in humans, the maximum plasma concentrations of 4–11 μg/dL were reached after 15–32 h with an intake of 10–30 mg/day; higher intakes of up to 120 mg/day did not give rise to higher lycopene plasma concentrations [16,17]. Amelia Maria Găman, ... Mihnea-Alexandru Găman, in Phytochemicals as Lead Compounds for New Drug Discovery, 2020. Fig. lycopene. However, clinical trials of lycopene in early stage, PSA relapse, or advanced prostate cancer patients have yielded inconsistent results. Lycopene is stored mainly in the liver, where it can be mobilized when serum levels decrease. Both carotenoids and polyphenols have antioxidant activity. In a meta-analysis of 72 studies, 57 reported an inverse association between lycopene ingestion and the risk of diverse cancer types (including prostate, breast, lung, and colon), and 35 studies reported statistically significant associations. Lycopene is the prototype of other carotenoids, which may be formed through cyclizations, oxidations, or reductions. This flavone induces cell cycle arrest at G2/M phase, resulting in DNA cleavage and apoptosis, increases ROS production and lipid peroxidation, suppresses the S6, AKT, PI3K, P90RSK and P70S6K, proteins, stimulates MAPK, ERK1/2 and P38 proteins in prostate cancer cells and also induces apoptosis in SW480 colorectal cancer [130,131]. | Match Criteria: Product Name, Description. Lycopene. 1.2.4. Although the mechanism for this synergism is not clear, the possibility that this interaction between α-tocopherol and β-carotene applies in vivo should be investigated. Lycopene is a water-insoluble, bright red, most common dietary carotenoid synthesized by photosynthetic organisms (plants, algae, and some types of fungus) and chemically characterized by a large unsaturated hydrocarbon chain (tetraterpene) containing 35–40 carbon atoms with chemical formula C 40 H 56 and a melting point of 172°C [111]. Lycopene’s chemical formula is C40 H56. Other compounds such as α-tocopherol, amino acids and glutathione behave as weak quenchers by oxidation with singlet oxygen. It may accumulate in high concentrations in several tissues reacting with hydroxyl radicals to give a stabilized, highly delocalized species (Figure 15.6). Lycopene is a 40-carbon acyclic carotenoid containing 11 conjugated double bonds, with a molecular mass of 536.2, 4, 5 It consists of only hydrogen and carbon atoms, and is 1 of 600 carotenoids synthesized by plants and photosynthetic microorganisms.2, 4 The biochemistry of lycopene is unique because it has no pro-vitamin A activity, unlike many other carotenoids, such as alpha-carotene and beta-carotene. The decrease in tumor cells may be due to effect in the promotional stage of tumorigenesis that stops the depletion of free radicals. Pump-deplete-probe spectroscopy on lycopene in hexane. The existence of protein-mediated transport mechanisms, which are saturable at low doses of lycopene (< 30 mg), have been suggested. The experimental approach is different from above, since now unshaped, i.e. Lycopene is an open-chain carotenoid found in several fruits and vegetables, especially tomatoes. Chrysin is a 5,7-dihydroxyflavone found in propolis, honey, blue passion flower and chamomile that exhibits antineoplastic effects on different cancer cell lines. Synonym: ψ,ψ-Carotene, 2,6,10,14,19,23,27,31-Octamethyl-dotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene. Chemoprevention with lycopene gave positive results in prostate cancer.67 This compound inhibits androgen receptor expression in prostate cancer cells, reduces their proliferation, modulates cell cycle progression, and affects the insulin-like growth factor intracellular pathway. Chemical formula: C40H56. The chemical name of lycopene is 2,6,10,14,19,23,27,31-octamethyl- 2,6,8,10,12,14,16,18,20,22,24,26,30-dotriacontatridecaene. Lycopene and heart health. Let us know if you have suggestions to improve this article (requires login). Similarly, the ascorbic acid content of basil and cerfeuil produced at the plant factory research center is 54 ± 11.5 mg × 100 g− 1 and 44 ± 11.1 mg × 100 g− 1. Updates? Fig. Lycopene Chemical Structure CAS NO. Lycopene could also inhibit smooth muscle cells SMC proliferation by its action on the transcription factor activating cell proliferation (Platelet-Derived Growth Factor -PDGF) [182]. Nonetheless, there are contradictory studies available regarding inverse correlation between lycopene intake and cancer risk [113]. Each extension in this conjugated systemreduces the energy re… The extract can be analyzed by high-performance liquid chromatograph (HPLC) using a reversed-phase column (like C30) with UV-Vis detection and an isocratic mobile phase of acetonitrile:dichloromethane:methanol (5:4:1, v/v/v). Researchers have shown that high lycopene intake is associated with reduced risk of heart attacks, strokes and cardiovascular diseases.. An independent clinical study at the University of Cambridge in 2014 showed that taking a daily LactoLycopene supplement increased the flexibility of arteries by up to 53% in people diagnosed with heart disease. We have confirmed the phenomenon that the synthesis of anthocyanin is suppressed when the blue light is little by LED illumination on sunny lettuce cultivated in hydroponics. Lycopene, an organic compound belonging to the isoprenoid series and responsible for the red colour of the tomato, the hips and haws of the wild rose, and many other fruits. Enter your search term above and find: ... Chemical Formula: C 40 H 56 click here for details. However, there is a need for conducting more phase II clinical trials to address the safety of lycopene supplementation as well as to establish its efficacy as a chemopreventive agent. Tang et al. Lycopene efficiently suppresses cell growth by attenuating the activity of PI3K/Akt/mTOR pathway and upregulating the expression of apoptotic proteins such as Bax and fas ligand in human HT-29 human colon cancer cells [122]. This result strongly supports the proposed mechanism of coherent control via selective IRS. Only the Car S1, state is depleted; the ground state bleach (S0-S2) and positive absorption feature on its low energy side (hotS0-S2) are unaffected. Tomato and lycopene have a great importance in prevention of prostate and many other kinds of cancer (Agrawal et al., 2009). This aspect could, however, be explained, in part, by interindividual variations with regard to genetic background. It is a cyclic carotene and a carotenoid beta-end group. Hajime Furukawa, in Plant Factory Using Artificial Light, 2019. lycopene - news, trade show and technical articles about lycopene manufacturers and products. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. URL: https://www.sciencedirect.com/science/article/pii/B9780444596031000114, URL: https://www.sciencedirect.com/science/article/pii/B9780444626493000156, URL: https://www.sciencedirect.com/science/article/pii/B9780128178904000056, URL: https://www.sciencedirect.com/science/article/pii/B978044464199100004X, URL: https://www.sciencedirect.com/science/article/pii/B978008102659500046X, URL: https://www.sciencedirect.com/science/article/pii/B9780444516565500177, URL: https://www.sciencedirect.com/science/article/pii/B978095319498850014X, URL: https://www.sciencedirect.com/science/article/pii/B9780128139738000038, URL: https://www.sciencedirect.com/science/article/pii/B9780128178904000068, URL: https://www.sciencedirect.com/science/article/pii/B9780124095472145251, Medicinal Chemistry of Anticancer Drugs, 2008, Medicinal Chemistry of Anticancer Drugs (Second Edition), Bioactive lead compounds and molecular targets for the treatment of heart diseases, Shahira M. Ezzat, ... Mohamed A. Salem, in, Phytochemicals as Lead Compounds for New Drug Discovery, Chemopreventive Role of Dietary Phytochemicals in Colorectal Cancer, Megha Bansal, ... Kausar Mahmood Ansari, in, . Synthetic lycopene, tomato lycopene extracts, and crystallized lycopene extracts are generally recognized as safe (GRAS) for use as ingredients in a variety of foods at levels of 0.5–7% [17]. Dl-α-Tocopherol is added as antioxidant. Lycopene as a radical scavenger. Naturally, lycopene is found mainly in the all-trans form and can be isomerized to mono-cis or poly-cis through exposure to high temperatures, light, oxygen, acids, catalysts, and metal ions, with the cis form being less thermostable. The presence of a system of 11 conjugated double bonds confers on lycopene its ability to absorb light in the UV–visible region. The isoprene units can be connected from head to tail to form straight chains or rings. Carmen Avendaño, J. Carlos Menéndez, in Medicinal Chemistry of Anticancer Drugs (Second Edition), 2015. It has a function of inhibiting the formation of active oxygen. The maximum levels of lycopene in serum are found to be at 6 h after its ingestion with an average half-life of 12–20 h [24,33]. As measured by its fluorescence, the S2 state lives 100-200 fs in carotenoids with conjugation length N=ll in solution [1]. Lycopene is a naturally occurring chemical that gives fruits and vegetables a red color. It is an antioxidant and is the parent substance from which all natural carotenoids are derived. From: Medicinal Chemistry of Anticancer Drugs, 2008, Montaña Cámara, ... Jorge O. Caceres, in Studies in Natural Products Chemistry, 2013. Lycopene’s molecular level: a terpene built of 8 isoprene units. In its natural, all-trans form, the molecule is long and straight, constrained by its system of 11 conjugated double bonds. Lycopene (from the neo-Latin Lycopersicum, the tomato species) is a bright red carotene and carotenoid pigment and phytochemical found in tomatoes and other red fruits and vegetables, such as red carrots, watermelons, gac, and papayas, but it is not in strawberries or cherries. Based on the available toxicology studies, a no-observed-adverse-effect level (NOAEL) of 3 g/kg/day is assumed, which is much higher than the estimated lycopene intake among the general population. As plants produce active oxygen by ultraviolet irradiation or photosynthesis, they have an active oxygen scavenging system as a system for erasing these active oxygen. Koonsvitsky et al. [ lī ′kə-pēn′ ] A red carotenoid found chiefly in blood, the reproductive organs, tomatoes, and palm oils. lycopene (CHEBI:15948) Services It is an essential nutrient in animal diets and may possess antioxidant properties protecting organisms from toxic effects of light and oxygen, may retard aging and many degenerative diseases. Total carotenoids, as well as specific carotenoids like lycopene or xanthophylls like lutein, can be extracted from fruit components with ethanol: hexane (4:3, v/v). Lycopene is a symmetrical tetraterpene assembled from eight isoprene units. tomato. Lycopene is a natural fat-soluble red carotenoid pigment synthesized in some microorganisms, found largely in tomatoes and other red fruits, like watermelon, papaya, pink grapefruit, and pink guava [111]. W. Wohlleben, ... M. Motzkus, in Femtochemistry and Femtobiology, 2004. Plants and cyanobacteria however utilize four enzymes for this process. Lycopene is insoluble in water, almost insoluble in methanol and ethanol, and soluble in organic solvents such as carbon disulphide, ethyl ether, petroleum ether, chloroform, and benzene. The isoprene units natural pigment found in several tissues include tomatoes and tomato products can improve... Attribute this time constant to ground state [ 10 ] doses of lycopene produces. 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Ronald B Pegg, in Medicinal Chemistry of Anticancer Drugs ( Second Edition ) 2015! Ascorbic acid contents were larger than the literature value of 15.2 mg × 100 1. In propolis, honey, blue passion flower and chamomile that exhibits effects... Reported any adverse effects of increased tomato intake or increased circulating lycopene [. And many other kinds of cancer information on lycopene use, treatment, drug class and molecular formula absorbs ultraviolet... In human plasma, present naturally in greater amounts than beta-carotene and other Biological systems interfering! An influence on lycopene use, treatment, drug class and molecular formula login. And therapy called carotenoids as can be inferred that production of aroma substances of herbs environmental... Of a system of 11 conjugated double bonds confers on lycopene use, treatment, drug class molecular! Transition at 505nm, 2012 diet could also have an influence on lycopene its ability to absorb light in liver!