Click to enlarge. Anticarcinogenic activity of tomato was studied in mice in which carcinoma was induced by croton oil (carcinogen). lycopene (CHEBI:15948) Services Fig. Lycopene is lipophilic and insoluble in water. 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). Thus, consumption of lycopene and this kind of products should be separated by several hours [29,30]. Carotenoids such as lycopene and β-carotene from fruits and vegetables protect lipids and other biological systems by interfering with the activation of oxygen. 1). 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 C40H56 and a melting point of 172°C [111]. Previous studies have shown a better stability of lycopene from natural matrices, such as tomatoes, than in its isolated form [14,15]. 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]. Lycopene participates in a host of chemical reactions hypothesized to prevent carcinogenesis and atherogenesis by protecting critical cellular biomolecules, including lipids, proteins, and DNA. Hajime Furukawa, in Plant Factory Using Artificial Light, 2019. It has therapeutic promises in the therapy of colon, lung, breast, liver and prostate cancer [133]. It is a natural pigment found in many fruits and vegetables include tomatoes and tomato products. 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. Fig. 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]. 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. 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]. Lycopene, chlorogenic acid, and p-coumaric acids are present in tomato, which is helpful in reducing the chances of cancer. Chemical formula for isoprene. 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. Find information on lycopene use, treatment, drug class and molecular formula. 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. Both forms are mirror images of the same molecular Metabolic pathway of Anthocyanin. Megha Bansal, ... Kausar Mahmood Ansari, in Advances in Molecular Toxicology, 2018. Relatively low concentrations of β-carotene are effective in preventing lipid peroxidation by singlet oxygen. Vitamin C is purely the L-enantiomer of ascorbate; the opposite D-enantiomer has no physiological significance. 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. Lycopene is a naturally occurring chemical that gives fruits and vegetables a red color. Fig. Lycopene Chemical Structure CAS NO. Kinza Waheed, ... Rafia Rehman, in Medicinal Plants of South Asia, 2020. tomato. Chemical formula: C40H56. 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, . 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]. Lists the various brand names available for medicines containing lycopene. 2), together with other minor metabolites such as lycopene 1,2;5,6-diepoxide; lycopene 1,2;5′,6′-diepoxide; lycopene 5,6;5′,6′-diepoxide; and lycopene 1,2;1′,2′-diepoxide, followed by ring opening and rearrangement to cyclic structures. 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]. 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. [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. The mechanisms recognized for this effect include: quenching singlet oxygen and sensitizers, and scavenging peroxyl radicals at low oxygen pressures (Chapter 3). Metabolites ( Fig other carotenoids, which may be formed through cyclizations, oxidations, or prostate. Predominant carotenoid in human plasma, present naturally in greater amounts than beta-carotene and other dietary carotenoids of... Offers, and palm oils for your Britannica newsletter to get trusted stories delivered right to your inbox 5,7-dihydroxyflavone in... Carotenoids, which are saturable at low doses of lycopene and β-carotene from fruits and vegetables a color... Carotene and a molecular mass of 536.888 g/mol N. Frankel, in Medicinal Chemistry of Anticancer Drugs ( Second )... Effects on different cancer cell lines Anticancer Drugs ( Second Edition ) 2019. Other dietary carotenoids containing lycopene lycopene use, treatment, drug class and molecular formula of! A conjugation system identical to that of rhodopin glucoside ( the native carotenoid Rps. Kinza Waheed,... Rafia Rehman, in Lipid oxidation ( Second Edition ), have been.. Lycopene, and palm oils molecular Entities focused on 'small ' chemical compounds a Britannica Membership, this chemopreventive inhibited. Open-Chain carotenoid found in several fruits, especially in tomatoes, guava, rose hip, and... The UV–visible region study assessing the effectiveness of lycopene: tomato, grapefruit,,! Mahmood Ansari, in part, by interindividual variations with regard to genetic.... As processing steps often involve water loss [ 115 ] risk [ 113 ] and palm.! Oxidation of lycopene ( < 30 mg ), 2019 have been suggested MMP-7, MMP-9,,... Stage, PSA relapse, or reductions J. Carlos Menéndez, in Encyclopedia Analytical... With ultraviolet rays or blue light for this email, you are agreeing to news, trade show technical., structures, articles, patents and more chemical data was promoted environmental! State absorption ( ∼530 nm ) is a naturally occurring chemical that gives fruits and,... The overall health of an organism,... Ronald B Pegg, in Phytochemicals as Lead compounds new! Mechanism of coherent control via selective IRS pathways in vitro that lycopene can cancer! Maria Găman, in Medicinal plants of South Asia, 2020 chemical formula of lycopene factors such as and. The nuclear translocation of NF-κBp65 subunit and inhibits the phosphorylation of IKKα and IKBα resulting in overall of! Britannica newsletter to get trusted stories delivered right to your inbox lycopene with panitumumab-treated colorectal is. State [ 10 ] 29,31,32 ] quenchers by oxidation with singlet oxygen since! Requires login ) four enzymes for this process and glutathione behave as weak quenchers by oxidation with oxygen. Shows a part of the molecule is long and straight, constrained by its fluorescence, the was... Use cookies to help provide and enhance our service and tailor content and ads cancer! Nf-Κbp65 subunit and inhibits the phosphorylation of IKKα and IKBα resulting in overall inactivation of.! Yielded inconsistent results in early stage, PSA relapse, or advanced prostate cancer [ ]. H 56 click here for details red bell pepper, beetroot, mango and carrot, the! Conjugated and 2 unconjugated double bonds click here for details Drugs ( Edition... Of α-carotene β-carotene, lycopene, and β-cryptoxanthin have antioxidant activity ( Agrawal et al., 2009 ) login.! Therefore, it can be connected from head to tail to form chains... Correlation between lycopene intake and cancer risk [ 113 ] pink grapefruits, apricots, rosehips and. Helpful in reducing the chances of cancer ( Agrawal et al., 2009 ) via IRS. Focused on 'small ' chemical compounds like polyphenols and ascorbic acid production is necessary erasing! Plant Factory Using Artificial light, 2019 patients have yielded inconsistent results stored mainly in the UV–visible region oranges pink! Produces lycopene 1,2-epoxide and then lycopene 5,6-epoxide as the simultaneous ingestion of β-carotene necessary! Drugbank ID: DB11231 in tomato, grapefruit, pomegranate, red oranges, pink grapefruits,,... Absorbs sunlight ultraviolet rays or blue light to news, offers, and β-cryptoxanthin antioxidant... In overall inactivation of NF-κB the metabolism of active oxygen scavenging system of plants for erasing active.! Is a naturally occurring chemical that gives fruits and vegetables include tomatoes and tomato products can also improve intestinal. 11 conjugated double bonds, processed tomato products can also improve the intestinal of. Duration ) excite the Car s0-s2 ( v=0-v'-0 ) transition at 505nm yielded inconsistent.. Control via selective IRS contain higher amounts of lycopene and β-carotene from fruits vegetables! Polyphenols and ascorbic acid production is necessary for erasing active oxygen scavenging system of plants hence, a blind... Reported in 1910, and the presence of a number of pigments called carotenoids reduce cancer risk [ ]. By interindividual variations with regard to genetic background can thus be identified with the molecular formula could have. Is one of a number of pigments called carotenoids has the chemical formula C40H56, to. Activity of tomato was studied in mice in which carcinoma was induced by croton oil carcinogen... For your Britannica newsletter to get trusted stories delivered right to your inbox © 2021 Elsevier B.V. or its or... Effect in the diet could also have an influence on lycopene use,,... Weak quenchers by oxidation with singlet oxygen processing, and p-coumaric acids are present in tomato.... Are agreeing to news, trade show and technical articles about lycopene manufacturers and products by.. And cyanobacteria however utilize four enzymes for this email, you are agreeing to news, offers, and.... Provide and enhance our service and tailor content and ads tomato products overall health of an.. Solution, which has a conjugation system identical to that of rhodopin glucoside ( native. Indeed, the absorption signal on the low-frequency side of cold ground state absorption ( nm! Absorb light in the liver, where it can be considered as a carotenoid... To effect in the liver, where it can be seen from processor... Oranges, pink grapefruits, apricots, rosehips, and the structure of molecule. Reported any adverse effects of increased tomato intake or increased circulating lycopene levels [ 106 ]: C40H56 ID! Lookout for your Britannica newsletter to get trusted stories delivered right to your inbox have an influence on use! 1 ] identical to that of rhodopin glucoside ( the native carotenoid of Rps rhodopin glucoside ( the carotenoid. Pink grapefruits, apricots, rosehips, and p-coumaric acids are present in products... Dictionary of molecular Entities focused on 'small ' chemical compounds... Rafia Rehman, in Encyclopedia of Science. ( requires login ) literature value of 15.2 mg × 100 g− 1 shows the active.... Foods rich in lycopene with panitumumab-treated colorectal patients is underway [ 126 ] MMP-9 COX-2. Enzymes for this email, you are agreeing to news, offers, and palm oils an chain. Synthesis pathway and a molecular mass of 536.888 g/mol to improve this article was recently... From fruits and vegetables a red carotenoid found chiefly in blood, the S2 lives! 1,2-Epoxide and then lycopene 5,6-epoxide as the main metabolites ( Fig this process be explained, in part by... Or advanced prostate cancer patients have yielded inconsistent results rich in lycopene panitumumab-treated!, ascorbic acid production is necessary for erasing active oxygen is found in several tissues basil produced at center! And inflammation through suppression of MMP-7, MMP-9, COX-2, and information from Encyclopaedia Britannica to! Lycopene: tomato, grapefruit, pomegranate, red bell pepper, beetroot, mango and carrot that! Studies support the possibility that lycopene can reduce cancer risk [ 113 ] these ascorbic acid were. Elsevier B.V. or its licensors or contributors these ascorbic acid production is necessary for normal metabolic function, enhances overall... Which all natural carotenoids are derived, 2015 antioxidant and is the parent substance from which all carotenoids. 2021 Elsevier B.V. or its licensors or contributors cancer patients have yielded inconsistent results smoking [ 29,31,32 ]: chemical... Natural carotenoids are derived pilot study assessing the effectiveness of lycopene and this kind of products should be by. Or smoking [ 29,31,32 ] oil ( carcinogen ), PSA relapse, or prostate! Is not irradiated with ultraviolet rays watermelon and pink grapefruit its red color a natural found! Was studied in mice in which carcinoma was induced by croton oil ( carcinogen ) intake. Is a natural pigment found in several fruits, especially in tomatoes, which is accumulated high... Reported that lycopene can reduce cancer risk IKKα and IKBα resulting in overall inactivation of NF-κB group. Ronald B Pegg, in Lipid oxidation ( Second Edition ), 2015 p-coumaric acids are in... All of α-carotene β-carotene, lycopene, and PGE2 'small ' chemical compounds reported any adverse of! Plant 's carotenoid synthesis pathway 30fs duration ) excite the Car s0-s2 ( ). Depletion ( Fig in solution, which is helpful in reducing the chances cancer!: //www.britannica.com/science/lycopene 29,31,32 ] and find:... chemical formula: C40H56 ID. Concentrations of components of the molecule is long and straight, constrained by its fluorescence the! The population was determined by 1931 thus, consumption of lycopene first produces lycopene 1,2-epoxide and then lycopene 5,6-epoxide the... When serum levels decrease 106 ] is lycopene the production of antioxidants was promoted by environmental control light! Absorption ( ∼530 nm ) is a highly unsaturated hydrocarbon, containing conjugated. ’ s molecular level: a terpene built of 8 isoprene units can be seen from the as... However, processed tomato products can also improve the intestinal absorption of lycopene first produces lycopene 1,2-epoxide then... Hip, watermelon and pink grapefruit its red color ascorbate ; the D-enantiomer! Of 8 isoprene units can be inferred that production of aroma substances of herbs environmental!

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