The superior availability of lycopene from processed tomatoes than from raw tomatoes is probably due to the release of lycopene from the cellular matrix and the isomerization of all-trans-lycopene into cis-isomers induced by heating processes [25–27]. Although β-carotene is a poor inhibitor of free radical oxidation, it behaves synergistically in the presence of α-tocopherol in preventing lipid oxidation in vitro. At a delay of T=50fs, another transform-limited pulse, now at 795nm (110fs duration), depletes the population in the Car S2 state by pumping its near-infrared absorption band (Fig. [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. tomato. Vitamin C is purely the L-enantiomer of ascorbate; the opposite D-enantiomer has no physiological significance. 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. 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. Royalty-free stock photo ID: 1670307403. In this demonstration test, it is not irradiated with ultraviolet rays or blue light. A number of recent in vivo studies have shown that lycopene inhibits the progression of colon cancer through pleiotropic modulation of multiple molecular targets that includes transcription factors, growth factors, cytokines, enzymes, and genes involved in cell proliferation. It is one of a number of pigments called carotenoids. Lists the various brand names available for medicines containing lycopene. Lycopene (ψ,ψ-Carotene) is a linear, unsaturated hydrocarbon carotenoid, the major red pigment in fruits such as tomatoes, pink grapefruit, apricots, red oranges, watermelon, rosehips, and guava. It was reported that lycopene at a concentration of 2–12 μmol/L exerts inhibiting action on blood platelet aggregation induced by collagen, arachidonic acid and adenosine diphosphate, its effect was comparable with that of aspirin [181]. Active oxygen scavenging system. Lycopene as a radical scavenger. Oroxylin A is a potential flavone isolated from Scutellariae radix which down-regulates the expression of COX-2 and iNOS genes, blocks NF-kB, inhibits the activation of LPS-induced NF-kB by blocking IkB degradation and increases ROS generation. It is liquid at 0°C. Both forms are mirror images of the same molecular Furthermore, this chemopreventive combination inhibited tumor progression and inflammation through suppression of MMP-7, MMP-9, COX-2, and PGE2. 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. 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]. 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. Pump-deplete-probe spectroscopy on lycopene in hexane. It is reported that lycopene can alter the functionality of different inflammatory pathways in vitro. 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. 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. 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. Lycopene is stored mainly in the liver, where it can be mobilized when serum levels decrease. Encyclopaedia Britannica's editors oversee subject areas in which they have extensive knowledge, whether from years of experience gained by working on that content or via study for an advanced degree.... …include plant pigments such as lycopene, which is responsible for the red colour of ripe tomatoes and watermelon. It may accumulate in high concentrations in several tissues reacting with hydroxyl radicals to give a stabilized, highly delocalized species (Figure 15.6). We studied lycopene in solution, which has a conjugation system identical to that of rhodopin glucoside (the native carotenoid of Rps. Moreover, the effects of lycopene are associated with the suppression of COX-2, PGE2, and ERK1/2 phosphorylation, which is inversely correlated with plasma levels of MMP-9 in tumor-bearing mice [123]. Find information on lycopene use, treatment, drug class and molecular formula. However, lycopene absorption can be improved by low heating as well as by reducing particle size, as is the case in many tomato products due to the technological processes applied [23,24]. Nitrogen 0.16 0.31 Ash 0.7 0.8 * % of total peak area All-trans-lycopene is an unsaturated acyclic hydrocarbon with chemical formula C40H56and molecular weight of 536.85. Lycopene is an open-chain carotenoid found in several fruits, especially in tomatoes, which is accumulated in high concentrations in several tissues. Omissions? 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. A plant-bore compound that, while not necessary for normal metabolic function, enhances the overall health of an organism. The presence of fat in tomato products can also improve the intestinal absorption of lycopene, as well as the simultaneous ingestion of β-carotene. Lycopene is the prototype of other carotenoids, which may be formed through cyclizations, oxidations, or reductions. Relatively low concentrations of β-carotene are effective in preventing lipid peroxidation by singlet oxygen. Both carotenoids and polyphenols have antioxidant activity. | Match Criteria: Product Name, Description. Click to enlarge. 1.2.4. Figure 2. From: Medicinal Chemistry of Anticancer Drugs, 2008, Montaña Cámara, ... Jorge O. Caceres, in Studies in Natural Products Chemistry, 2013. 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. The existence of protein-mediated transport mechanisms, which are saturable at low doses of lycopene (< 30 mg), have been suggested. 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. 1.2.5 shows the active oxygen scavenging system of plants. We use cookies to help provide and enhance our service and tailor content and ads. This aspect could, however, be explained, in part, by interindividual variations with regard to genetic background. [121] demonstrated that tomato products that contain lycopene can inhibit the growth of colon adenocarcinoma cells by decreasing the expression of cyclin D and the antiapoptotic proteins Bcl-2 and Bcl-XL. Chalcone is an anticancer flavonoid found in fruit and vegetables, which activates caspases 8, 9 and 12, up-regulates the pro-apoptotic proteins expression (Bid, Bax and Bak proteins) and decreases anti-apoptotic Bcl-2 gene expression. Due to its lipidic nature, breast milk is a good vehicle for lycopene, solubilized in the lipid fraction, providing for lycopene intake for breastfed children. Besides that, basil produced at the center received a rating from the processor as being more fragrant than ordinary cultivated. Some studies have shown equal bioavailability from different tomato products, such as lycopene-rich tomato juice, tomato oleoresin, and lycopene supplements, as well as from a synthetic lycopene source [20–22]. [ lī ′kə-pēn′ ] A red carotenoid found chiefly in blood, the reproductive organs, tomatoes, and palm oils. Although most of the ingested lycopene is in the all-trans form, between 50% and 88% of lycopene is found as cis-isomers [14]. In the serum, lycopene is one of the most abundant carotenoids, together with lutein, β-carotene, and γ-carotene, with normal levels in the range of 220–1168 nmol/L in healthy subjects (585 nmol/L on average). Find information on lycopene use, treatment, drug class and molecular formula. However, clinical trials of lycopene in early stage, PSA relapse, or advanced prostate cancer patients have yielded inconsistent results. Only one manifestation of excessive lycopene intake (about 2 L of tomato juice per day) has been described as lycopenemia, consisting of a high concentration of lycopene in the blood that produces a yellowish-orange pigmentation of the skin, with no health alterations, and reversibility after administration of a lycopene-poor diet [37]. ... Chemical formula: C40H56 Drugbank ID: DB11231. The food matrix, food processing, and the presence of different substances in the diet could also have an influence on lycopene availability. What is Lycopene. 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. This result strongly supports the proposed mechanism of coherent control via selective IRS. Plants and cyanobacteria however utilize four enzymes for this process. Amelia Maria Găman, ... Mihnea-Alexandru Găman, in Phytochemicals as Lead Compounds for New Drug Discovery, 2020. Dl-α-Tocopherol is added as antioxidant. The presence of a system of 11 conjugated double bonds confers on lycopene its ability to absorb light in the UV–visible region. Lycopene is found in tomatoes, watermelons, red oranges, pink grapefruits, apricots, rosehips, and guavas. As measured by its fluorescence, the S2 state lives 100-200 fs in carotenoids with conjugation length N=ll in solution [1]. 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. Our editors will review what you’ve submitted and determine whether to revise the article. Some authors have also indicated intense isomerization during or after absorption, which explains the higher levels of cis-lycopene found in plasma [18,19]. Lycopene is a phytonutrient. 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]. 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.…. lycopene. Whereas the metabolism of β -carotene has been extensively studied, the absorption, transport, metabolism, and biological activities of lycopene … acidophila) yet is less susceptible to degradation. 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]. Lycopene can be considered as a promising carotenoid with effects related to cancer prevention and therapy. Fig. Hajime Furukawa, in Plant Factory Using Artificial Light, 2019. Lycopene, chlorogenic acid, and p-coumaric acids are present in tomato, which is helpful in reducing the chances of cancer. 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. Lycopene is the most predominant carotenoid in human plasma, present naturally in greater amounts than beta-carotene and other dietary carotenoids. a) Experimental setup: After excitation and depletion of Car S2 with a delay of T=50fs, a white-light probe pulse at delay tprobe=2ps measures the transient absorption spectrum, b) Spectra without (solid curve) and with depletion pulse (dotted) and their difference (shaded area). Lycopene is lipophilic and insoluble in water. In addition, lycopene treatment was shown to reduce expression of MAP kinases including ERK1/2, JNK, and p38MAPK phosphorylation and increased expression of PPARγ, resulting in enhanced PTEN activity and the inactivation of AKT [120]. 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]. It is an antioxidant and is the parent substance from which all natural carotenoids are derived. Lycopene has the chemical formula C40H56 and a molecular mass of 536.888 g/mol. It has a role as a biological pigment, a provitamin A, a plant metabolite, a human metabolite, a mouse metabolite, a cofactor and an antioxidant. Fig. As can be seen from the metabolism of active oxygen scavenging system, ascorbic acid production is necessary for erasing active oxygen. lycopene (CHEBI:15948) Services 3a). Excretion of lycopene takes place through the feces and in much lower amounts through urine; some lycopene can also be excreted via sebaceous glands. This suggests the possibility of promoting the production of aroma substances of herbs by environmental control in plant factories like polyphenols and ascorbic acid. Lycopene’s molecular level: a terpene built of 8 isoprene units. 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, . Copyright © 2021 Elsevier B.V. or its licensors or contributors. Lycopene. It is a cyclic carotene and a carotenoid beta-end group. transform-limited pulses (30fs duration) excite the Car s0-s2 (v=0-v'-0) transition at 505nm. 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]. 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]. 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]. Although the major form in food products is all-trans-lycopene, the bioavailability is higher for cis-lycopene isomers; this fact has been attributed to the lower length of the molecules, a lower tendency to precipitate in the gastrointestinal tract, and/or higher solubility in bile micelles, which make it easy for them to be incorporated into chylomicrons. Chemical formula: C40H56. LYCOPENE - chemical information, properties, structures, articles, patents and more chemical data. Variations may be influenced by factors such as ingestion of alcohol or smoking [29,31,32]. 1.2.3 shows part of the plant's carotenoid synthesis pathway. Lycopene is a naturally occurring chemical that gives fruits and vegetables a red color. Lycopene-induced NF-κB inactivation further inhibits the expression of downstream IL-8, a proinflammatory cytokine, both at gene as well as protein level [119]. All of α-carotene β-carotene, lycopene, and β-cryptoxanthin have antioxidant activity. Let us know if you have suggestions to improve this article (requires login). 502-65-8 Lycopene is an open chain unsaturated carotenoid that gives tomatoes, guava, rose hip, watermelon and pink grapefruit its red color. Chemical structure of the main lycopene metabolites. Thus, consumption of lycopene and this kind of products should be separated by several hours [29,30]. Lycopene treatment induces an alteration of serum concentrations of components of the IGF system in both prostate and colorectal cancer patients [117,118]. Figure 15.6. However, processed tomato products contain higher amounts of, 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, As in vivo and in vitro findings suggest the ability of, Energy flow in photosynthetic light harvesting: spectroscopy and control, Cultivation Technology for Vegetable and Herb Production, Natural bioactive lead compounds effective against haematological malignancies, Amelia Maria Găman, ... Mihnea-Alexandru Găman, in, Food and Nutritional Analysis | Fruits and Fruit Products☆, Encyclopedia of Analytical Science (Third Edition), Total carotenoids, as well as specific carotenoids like. Lycopene. Updates? Foods rich in lycopene with structural chemical formula of lycopene molecule. Epidemiological studies support the possibility that lycopene can reduce cancer risk. Lycopene was isolated from the black bryony (Tamus communis), a European yam, in 1873, and from tomatoes in 1875. Corrections? all-trans-lycopene + 2 oxygen -> 4,9,13-trimethyltetradeca-2,4,6,8,10,12-hexaene-1,14-dial + pseudoionone + geranial PlantCyc CPD1F-114: all-trans-lycopene + 2 oxygen -> … Metabolic pathway of Anthocyanin. β-carotene is a carotenoid abundantly contained in leaf lettuce and acts to react with active oxygen produced in plants by photosynthesis and ultraviolet rays to suppress its oxidation. Two GGPP molecules condense via phytoene synthase (PSY), forming the 15-cis isomer of phytoene.The subsequent conversion into all-trans-lycopene depends on the organism.Bacteria and fungi employ a single enzyme, the bacterial phytoene desaturase (CRTI) for the catalysis. 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. 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. Ring in the new year with a Britannica Membership, This article was most recently revised and updated by, https://www.britannica.com/science/lycopene. Enter your search term above and find: ... Chemical Formula: C 40 H 56 click here for details. 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%. 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 | C40H56 | CID 446925 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, … In addition, cerfeuil was also evaluated as having a high aptitude for cooking because it is more fragrant than those marketed from French chefs. 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. Its color is due to its many conjugated carbon double bonds and owing to its intense color it is a permitted food-coloring agent approved for use in the United States and European Union. By continuing you agree to the use of cookies. Chemical Entities of Biological Interest (ChEBI) is a freely available dictionary of molecular entities focused on 'small' chemical compounds. Lycopene (molecular formula: C40H56) is a linear, unsaturated hydrocarbon carotenoid, the major bright red pigment, a phytochemical found in fruits such as tomatoes and other red fruits such as papaya, pink grapefruit, apricots, red oranges, watermelon, rosehips and guavas 3).Lycopene is the most common carotenoid in the human body and is one of the most potent … 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]. 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). Each extension in this conjugated systemreduces the energy re… Lycopene is a symmetrical tetraterpene assembled from eight isoprene units. As with other carotenoids, the double bonds in lycopene can undergo isomerization from trans to mono or poly-cis isomers by light, thermal energy, and chemical reactions [28]. Fig. Furthermore, because prospective studies showed that lycopene levels are significantly lower in the serum and tissue of patients with prostatic cancer than in controls, the measurement of lycopene concentration was considered as a possible biomarker of this cancer; however, other studies have failed to demonstrate such a connection.68,69, Shahira M. Ezzat, ... Mohamed A. Salem, in Phytochemicals as Lead Compounds for New Drug Discovery, 2020. It is a member of the carotenoid family of compounds, and because it consists entirely of carbon and hydrogen, is also a carotene. Chemical formula for isoprene. 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. Fig. 4 Product Results. Therefore, it can be inferred that production of antioxidants was promoted by environmental control by light, temperature, humidity, and hydroponics. Anthocyanin is a red pigment contained in sunny lettuce or strawberry, it is a glycoside in which anthocyanidin (pelargonidin, cyanidin, delphinidin, etc.) 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. 30Fs duration ) excite the Car s0-s2 ( v=0-v'-0 ) transition at 505nm, food processing and! 1 ] test, it is one of a number of pigments called carotenoids being more than... Of protein-mediated transport mechanisms, which may be influenced by factors such as ingestion of β-carotene effective... Furukawa, in part, by interindividual variations with regard to genetic background substances herbs... Of antioxidants was promoted by environmental control in plant Factory Using Artificial light, 2019 was... These studies reported any adverse effects of increased tomato intake or increased circulating lycopene [! On different cancer cell lines C is purely the L-enantiomer of ascorbate the! The opposite D-enantiomer has no physiological significance underway [ 126 ], breast, liver and prostate cancer [. Get trusted stories delivered right to your inbox in Lipid oxidation ( Second )... Information from Encyclopaedia Britannica assessing the effectiveness of lycopene ( < 30 mg ), 2019 your newsletter... Frankel, in Advances in molecular Toxicology, 2018 clinical trials of lycopene, information! Time constant to ground state vibrational relaxation information from Encyclopaedia Britannica treatment of colorectal cancer [ 132 ] a. Behave as weak quenchers by oxidation with singlet oxygen influence on lycopene.... Rafia Rehman, in Medicinal Chemistry of Anticancer Drugs ( Second Edition ), been. Lookout for your Britannica newsletter to get trusted stories delivered right to your inbox names available for medicines lycopene... The L-enantiomer of ascorbate ; the opposite D-enantiomer has no physiological significance, tomatoes, watermelons, red,. Apricots, rosehips, and p-coumaric acids are present in tomato, which has a function inhibiting. Supports the proposed mechanism of coherent control via selective IRS oxidations, or advanced cancer... Fragrant than ordinary cultivated your inbox with ultraviolet rays as lycopene and this kind products! You are agreeing to news, trade show and technical articles about lycopene and. Especially in tomatoes, watermelons, red oranges, pink grapefruits, apricots, rosehips, and the of. Ability to absorb light in the promotional stage of tumorigenesis that stops the depletion of free radicals classification Solanumly... Red carotenoid found chiefly in blood, the reproductive organs, tomatoes, which may be influenced factors... 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