Lycopene, synthetic:IN 160d(i)

Origin: 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, although not in strawberries, red bell peppers, or cherries.[2] Although lycopene is chemically a carotene, it has no vitamin A activity.[3] Foods that are not red may also contain lycopene, such as brown beans or parsley.[2]In plants, algae, and other photosynthetic organisms, lycopene is an important intermediate in the biosynthesis of many carotenoids, including beta carotene, which is responsible for yellow, orange, or red pigmentation, photosynthesis, and photo-protection. Like all carotenoids, lycopene is a polyunsaturated hydrocarbon, i.e. an unsubstituted alkene. Structurally, lycopene is a tetraterpene and assembled from eight isoprene units that are composed entirely of carbon and hydrogen. It is insoluble in water. Lycopene’s eleven conjugated double bonds give its deep red color and its antioxidant activity. Owing to the strong color and non-toxicity, lycopene is a useful food coloring (registered as E160d) and is approved for usage in the USA,[4] Australia and New Zealand (registered as 160d)[5] and the EU.[6]

Function & characteristics: Lycopene is a symmetrical tetraterpene assembled from eight isoprene units. It is a member of the carotenoid family of compounds, and because it consists entirely of carbon and hydrogen, is also a carotene.[9] Isolation procedures for lycopene were first reported in 1910, and the structure of the molecule was determined by 1931. In its natural, all-trans form, the molecule is long and straight, constrained by its system of eleven conjugated double bonds. Each extension in this conjugated system reduces the energy required for electrons to transition to higher energy states, allowing the molecule to absorb visible light of progressively longer wavelengths. Lycopene absorbs all but the longest wavelengths of visible light, so it appears red.[10]Plants and photosynthetic bacteria naturally produce all-trans lycopene, but a total of 72 geometric isomers of the molecule are sterically possible.[11] When exposed to light or heat, lycopene can undergo isomerization to any of a number of these cis-isomers, which have a bent rather than linear shape. Different isomers were shown to have different stabilities due to their molecular energy (highest stability: 5-cis ≥ all-trans ≥ 9-cis ≥ 13-cis > 15-cis > 7-cis > 11-cis: lowest).[12] In the human bloodstream, various cis-isomers constitute more than 60% of the total lycopene concentration, but the biological effects of individual isomers have not been investigated.

Products: Fruits and vegetables that are high in lycopene include autumn olive, gac, tomatoes, watermelon, pink grapefruit, pink guava, papaya, seabuckthorn, wolfberry (goji, a berry relative of tomato), and rosehip. Although gac (Momordica cochinchinensis Spreng) has the highest content of lycopene of any known fruit or vegetable, up to 70 times more than tomatoes for example,[18] due to gac’s rarity outside its native region of southeast Asia, tomatoes and tomato-based sauces, juices, and ketchup account for more than 85% of the dietary intake of lycopene for most people.[19] The lycopene content of tomatoes depends on species and increases as the fruit ripens.[20]Unlike other fruits and vegetables, where nutritional content such as vitamin C is diminished upon cooking, processing of tomatoes increases the concentration of bioavailable lycopene.[21] Lycopene in tomato paste is up to four times more bioavailable than in fresh tomatoes.[22]While most green leafy vegetables and other sources of lycopene are low in fats and oils, lycopene is insoluble in water and is tightly bound to vegetable fiber. Processed tomato products such as pasteurized tomato juice, soup, sauce, and ketchup contain the highest concentrations of bioavailable lycopene from tomato-based sources.[citation needed]Cooking and crushing tomatoes (as in the canning process) and serving in oil-rich dishes (such as spaghetti sauce or pizza) greatly increases assimilation from the digestive tract into the bloodstream. Lycopene is fat-soluble, so the oil is said to help absorption. Gac is a notable exception, containing high concentrations of lycopene and also saturated and unsaturated fatty acids.[23]Lycopene may be obtained from vegetables and fruits such as the tomato, but another source of lycopene is the fungus Blakeslea trispora. Gac is a possible commercial source of lycopene for the purposes of extraction and purification, as its seed content of lycopene is high.[24]The cis-lycopene from some varieties of tomato is more bioavailable.[25]Note that there are some resources which make the mistaken assumption that all red fruits contain lycopene, when in fact many are pigmented by other chemicals. An example is the blood orange, which is colored by anthocyanins,[26] while other red colored oranges, such as the Cara cara navel, and other citrus fruit, such as pink grapefruit, are colored by lycopene.[2][27]In addition, some foods that do not appear red also contain lycopene, e.g., asparagus, which contains approximately 30μg of lycopene per 100 gram serving[2] (0.3μg/g) and dried parsley and basil, which contain approximately 3.5-7 μg of lycopene per gram.[2]

Daily intake:Up to 1 mg/kg body weight

Side effects:Given its potential properties in vivo, substantial research has been devoted to a possible correlation between lycopene consumption and general health. Lycopene from tomatoes has been tested in human studies for cardiovascular diseases and prostate cancer. These studies, however, did not attain sufficient scientific agreement to conclude an effect on any disease.[8] The FDA, in rejecting manufacturers requests in 2005 to allow “qualified labeling” for lycopene and the reduction of various cancer risks stated:”…no studies provided information about whether lycopene intake may reduce the risk of any of the specific forms of cancer. Based on the above, FDA concludes that there is no credible evidence supporting a relationship between lycopene consumption, either as a food ingredient, a component of food, or as a dietary supplement, and any of these cancers.”A 2011 Cochrane review found insufficient evidence to come to any conclusion about what effect lycopene might have on prostate symptoms, PSA levels or prostate cancer.[32] A 2013 review concluded that lycopene appears to be negatively associated with prostate cancer risk.[33]

Dietary restrictions: yes


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