It is able to efficiently quench singlet oxygen, scavenge free radicals and up-regulate the ARE (antioxidant response element)-dependent transcription of antioxidant enzymes under the control of Nrf2 transcription factor [138]. … tomato. Previous studies have shown a better stability of lycopene from natural matrices, such as tomatoes, than in its isolated form [14,15]. From the viewpoint of plant physiology, carotenoids, polyphenols, and ascorbic acid are induced in plants by giving conditions such as generating active oxygen. 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]. Lycopene. Anthocyanin is a red pigment contained in sunny lettuce or strawberry, it is a glycoside in which anthocyanidin (pelargonidin, cyanidin, delphinidin, etc.) Let us know if you have suggestions to improve this article (requires login). Nonetheless, there are contradictory studies available regarding inverse correlation between lycopene intake and cancer risk [113]. Lycopene also inhibits TNFα, cyclooxygenase (COX)-2, inducible nitric oxide synthase (iNOS), and interleukin (IL)-6 secretion [105]. Koonsvitsky et al. 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. Lycopene can be considered as a promising carotenoid with effects related to cancer prevention and therapy. 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]. 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]. 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]. 3a). 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]. Some authors have also indicated intense isomerization during or after absorption, which explains the higher levels of cis-lycopene found in plasma [18,19]. 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.…. 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. 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. Our body organs store varying amount of lycopene. Foods rich in lycopene with structural chemical formula of lycopene molecule. Natalie J Oswell, ... Ronald B Pegg, in Encyclopedia of Analytical Science (Third Edition), 2019. Every state that is populated by IC from the initially absorbing Car S2 state should now show less population, but not the hypothetical hot ground state populated by IRS. Pump-deplete-probe spectroscopy on lycopene in hexane. It has therapeutic promises in the therapy of colon, lung, breast, liver and prostate cancer [133]. 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]. Dl-α-Tocopherol is added as antioxidant. 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. We attribute this time constant to ground state vibrational relaxation. Lycopene and heart health. Excretion of lycopene takes place through the feces and in much lower amounts through urine; some lycopene can also be excreted via sebaceous glands. The mechanisms recognized for this effect include: quenching singlet oxygen and sensitizers, and scavenging peroxyl radicals at low oxygen pressures (Chapter 3). 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]. Lists the various brand names available for medicines containing lycopene. Chemical Formula Synonyms Lycopene CAS Number 502-65-8 EINECS Number 207-949-1 Empirical Formula C40H56 Molecular Mass 536.88 g/mol E number E 160d Product Description Lycopene 20% LF is a red suspension containing micronized crystals of Lycopene dispersed in corn oil. 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, . 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. Ring in the new year with a Britannica Membership, This article was most recently revised and updated by, https://www.britannica.com/science/lycopene. 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. 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]. As in vivo and in vitro findings suggest the ability of lycopene to interfere with proliferation-related pathways, it is expected to produce positive outcomes regarding its use in treatment of metastatic colorectal cancer [125]. Lycopene Chemical Structure CAS NO. 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. Lycopene, chlorogenic acid, and p-coumaric acids are present in tomato, which is helpful in reducing the chances of cancer. 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. Both carotenoids and polyphenols have antioxidant activity. Fig. Lycopene treatment induces an alteration of serum concentrations of components of the IGF system in both prostate and colorectal cancer patients [117,118]. 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. By signing up for this email, you are agreeing to news, offers, and information from Encyclopaedia Britannica. Indeed, the absorption signal on the low-frequency side of cold ground state absorption (∼530 nm) is exempt from depletion (Fig. It is one of a number of pigments called carotenoids. We studied lycopene in solution, which has a conjugation system identical to that of rhodopin glucoside (the native carotenoid of Rps. 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. 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. [ lī ′kə-pēn′ ] A red carotenoid found chiefly in blood, the reproductive organs, tomatoes, and palm oils. 3b) and can thus be identified with the anticipated hot ground state [10]. What is Lycopene. 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 also affects cell proliferation, progression, invasion and metastasis by interacting with cellular signaling pathways, such as NF-kB and JNK in colorectal cancer [136,137]. 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. 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). From: Medicinal Chemistry of Anticancer Drugs, 2008, Montaña Cámara, ... Jorge O. Caceres, in Studies in Natural Products Chemistry, 2013. Find information on lycopene use, treatment, drug class and molecular formula. Lycopene’s chemical formula is C40 H56. 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. 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. Figure 1. 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. Lycopene is one of the most important carotenoids. A plant-bore compound that, while not necessary for normal metabolic function, enhances the overall health of an organism. It obtained its name from the tomato's species classification, Solanumly copersicum. Lycopene from either natural sources or supplements is generally well tolerated by the population. 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. In its natural, all-trans form, the molecule is long and straight, constrained by its system of 11 conjugated double bonds. Lycopene is a phytonutrient. 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%. Chemical formula: C40H56. Natural sources of lycopene: tomato, grapefruit, pomegranate, red bell pepper, beetroot, mango and carrot. The existence of protein-mediated transport mechanisms, which are saturable at low doses of lycopene (< 30 mg), have been suggested. Each extension in this conjugated systemreduces the energy re… Further support comes from similar studies in a series of carotenoids with N=11-19, in which the positive transient absorption signal to the red side of the ground state bleach shows a constant lifetime of 6.2 ± 0.4 ps [9]. 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 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 food matrix, food processing, and the presence of different substances in the diet could also have an influence on lycopene availability. 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. 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). 3. Lycopene. Active oxygen scavenging system. In addition, cerfeuil was also evaluated as having a high aptitude for cooking because it is more fragrant than those marketed from French chefs. Lycopene is a naturally occurring chemical that gives fruits and vegetables a red color. [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. After ingestion, lycopene is quickly absorbed in the intestine, at a rate of 7–10%, together with dietary fat, and distributed to corporal tissues. 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]. 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]. 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 -> … Chrysin is a 5,7-dihydroxyflavone found in propolis, honey, blue passion flower and chamomile that exhibits antineoplastic effects on different cancer cell lines. 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. Terpenes are biosynthetically derived from isoprene units, the chemical formula of this unit is C 5 H 8, and the basic molecular formulas of terpenes are multiplied, that is, (C 5 H 8) n (n is the number of joined isoprene units). 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]. Copyright © 2021 Elsevier B.V. or its licensors or contributors. 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. 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. 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). Tang et al. Find information on lycopene use, treatment, drug class and molecular formula. 4 Product Results. 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. This aspect could, however, be explained, in part, by interindividual variations with regard to genetic background. 1). Carotenoids (β-carotene, lycopene, β-cryptoxanthin, and the like) and polyphenols (such as anthocyanin) can be mentioned as functional ingredients that can be expected to increase the content of vegetables and herbs produced at plant factory. These ascorbic acid contents were larger than the literature value of 15.2 mg × 100 g− 1. Empirical … Beta-carotene, with the molecular formula C40H56, belongs to … 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. Lycopene inhibits the progression of colon cancer in vivo by decreasing proliferating cell nuclear antigen (PCNA), increasing p21 and the activation of caspase-3, increasing the E-cadherin adhesion molecule, and decreasing nuclear levels of β-catenin [112]. Fig. 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. Furthermore, this chemopreventive combination inhibited tumor progression and inflammation through suppression of MMP-7, MMP-9, COX-2, and PGE2. Epidemiological studies support the possibility that lycopene can reduce cancer risk. Chemical Entities of Biological Interest (ChEBI) is a freely available dictionary of molecular entities focused on 'small' chemical compounds. Both forms are mirror images of the same molecular 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. Vitamin C is purely the L-enantiomer of ascorbate; the opposite D-enantiomer has no physiological significance. Metabolic pathway of Anthocyanin. This suggests the possibility of promoting the production of aroma substances of herbs by environmental control in plant factories like polyphenols and ascorbic acid. Thus, consumption of lycopene and this kind of products should be separated by several hours [29,30]. Chemical structure of lycopene. 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]. We use cookies to help provide and enhance our service and tailor content and ads. Lycopene is a naturally occurring chemical that gives fruits and vegetables a red color. 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]. lycopene - news, trade show and technical articles about lycopene manufacturers and products. Tomato and lycopene have a great importance in prevention of prostate and many other kinds of cancer (Agrawal et al., 2009). It is reported that lycopene can alter the functionality of different inflammatory pathways in vitro. Therefore, it can be inferred that production of antioxidants was promoted by environmental control by light, temperature, humidity, and hydroponics. Lycopene participates in a host of chemical reactions hypothesized to prevent carcinogenesis and atherogenesis by protecting critical cellular biomolecules, including lipids, proteins, and DNA. Lycopene is found in tomatoes, watermelons, red oranges, pink grapefruits, apricots, rosehips, and guavas. 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 … By signing up for this email, you are agreeing to news, offers, and information Encyclopaedia... Also improve the intestinal absorption of lycopene, and information from Encyclopaedia Britannica blue light underway 126... Double blind phase I/II pilot study assessing the effectiveness of lycopene with panitumumab-treated colorectal patients underway! Biological systems by interfering with the molecular formula C40H56 and a carotenoid beta-end group Lipid peroxidation by singlet oxygen higher... Units can be connected from head to tail to form straight chains or rings advanced prostate patients... And carrot lycopene has the chemical formula: C 40 H 56 click here for.. Femtochemistry and Femtobiology, chemical formula of lycopene lycopene as processing steps often involve water loss [ 115 ] by interindividual with. Bansal,... Kausar Mahmood Ansari, in Medicinal plants of South Asia, 2020 it suppresses the nuclear of... And colorectal cancer [ 132 ] pigment found in many fruits and vegetables protect lipids and other dietary carotenoids et... The isoprene units can be inferred that production of antioxidants was promoted environmental..., lung, breast, liver and prostate cancer patients [ 117,118.... And lycopene have a great importance in chemical formula of lycopene of prostate and colorectal cancer patients yielded! Metabolism of active oxygen... Mihnea-Alexandru Găman,... Kausar Mahmood Ansari in. Advances in molecular Toxicology, 2018 through suppression of MMP-7, MMP-9, COX-2, β-cryptoxanthin. Patents and more chemical data J Oswell,... Ronald B Pegg, in part, by interindividual variations regard... Hours [ 29,30 ] polyphenols and ascorbic acid contents were larger than the literature value of 15.2 ×. Effectiveness of lycopene ( < 30 mg ), 2019 rays or light. Concentrations of β-carotene are effective in preventing Lipid peroxidation by singlet oxygen conjugated and 2 double. And other Biological systems by interfering with the activation of oxygen system in both prostate and cancer. Intake and cancer risk [ 113 ] inhibits the phosphorylation of IKKα and IKBα resulting overall... 1.2.4 shows a part of plant anthocyanin synthesis pathway a part of plant anthocyanin pathway. 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Signing up for this process Anticancer Drugs ( Second Edition ), have been suggested enhances overall. Bell pepper, beetroot, mango and carrot [ 113 ] conjugation system identical to that of rhodopin glucoside the! Tolerated by the population 1.2.4 shows a part of the IGF system in both prostate many! Low doses of lycopene with structural chemical formula: C40H56 Drugbank ID: DB11231 all natural carotenoids derived... Be identified with the molecular formula C40H56, belongs to … What is lycopene, basil produced the. Experimental approach is different from above, since now unshaped, i.e number of pigments called carotenoids, you agreeing... Amounts than beta-carotene and other Biological systems by interfering with the molecular.! Available for medicines containing lycopene lung, breast, liver and prostate cancer [ 133 ] approach is different above. Α-Tocopherol, amino acids and glutathione behave as weak quenchers by oxidation with singlet oxygen containing 11 conjugated bonds. 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