Lycopene is a symmetrical tetraterpene because it consists entirely of carbon and hydrogen and is derived from eight isoprene subunits.[5] 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 somewhat flat, constrained by its system of 11 conjugated double bonds. The extended conjugation is responsible for its deep red color.[5]
Plants and photosynthetic bacteria produce all-trans lycopene.[5] When exposed to light or heat, lycopene can undergo isomerization to any of a number of cis-isomers, which have a less linear shape. Isomers distinct stabilities, with highest stability: 5-cis ≥ all-trans ≥ 9-cis ≥ 13-cis > 15-cis > 7-cis > 11-cis: lowest.[9][10] In human blood, various cis-isomers constitute more than 60% of the total lycopene concentration, but the biological effects of individual isomers have not been investigated.[11]
Lycopene is a key intermediate in the biosynthesis of many carotenoids.
Carotenoids like lycopene are found in photosynthetic pigment-protein complexes in plants, photosynthetic bacteria, fungi, and algae.[5] They are responsible for the bright orange–red colors of fruits and vegetables, perform various functions in photosynthesis, and protect photosynthetic organisms from excessive light damage. Lycopene is a key intermediate in the biosynthesis of carotenoids, such as beta-carotene, and xanthophylls.[12]
Dispersed lycopene molecules can be encapsulated into carbon nanotubes enhancing their optical properties.[13] Efficient energy transfer occurs between the encapsulated dye and nanotube—light is absorbed by the dye and without significant loss is transferred to the nanotube. Encapsulation increases chemical and thermal stability of lycopene molecules; it also allows their isolation and individual characterization.[14]
Biosynthesis
The unconditioned biosynthesis of lycopene in eukaryotic plants and in prokaryotic cyanobacteria is similar, as are the enzymes involved.[5] Synthesis begins with mevalonic acid, which is converted into dimethylallyl pyrophosphate. This is then condensed with three molecules of isopentenyl pyrophosphate (an isomer of dimethylallyl pyrophosphate), to give the 20-carbon geranylgeranyl pyrophosphate. Two molecules of this product are then condensed in a tail-to-tail configuration to give the 40-carbon phytoene, the first committed step in carotenoid biosynthesis. Through several desaturation steps, phytoene is converted into lycopene. The two terminal isoprene groups of lycopene can be cyclized to produce beta-carotene, which can then be transformed into a wide variety of xanthophylls.[5]
Staining and removal
Lycopene is the pigment in tomato sauces that turns plastic cookware orange. It is insoluble in plain water, but it can be dissolved in organic solvents and oils. Because of its non-polarity, lycopene in food preparations will stain any sufficiently porous material, including most plastics. To remove this staining, the plastics may be soaked in a solution containing a small amount of chlorine bleach.[15]
The bleach oxidizes the lycopene, thus allowing the product to dissolve.
Diet
Consumption by humans
Absorption of lycopene requires that it be combined with bile salts and fat to form micelles.[5] Intestinal absorption of lycopene is enhanced by the presence of fat and by cooking.[5] Lycopene dietary supplements (in oil) may be more efficiently absorbed than lycopene from food.[5]
Lycopene is not an essential nutrient for humans, but is commonly found in the diet mainly from dishes prepared from tomatoes.[4][5] The median and 99th percentile of dietary lycopene intake have been estimated to be 5.2 and 123 mg/d, respectively.[16]
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.[5]Ketchup is a common dietary source of lycopene.[5] Although gac (Momordica cochinchinensis Spreng) has the highest content of lycopene of any known fruit or vegetable (multiple times more than tomatoes),[19][20] tomatoes and tomato-based sauces, juices, and ketchup account for more than 85% of the dietary intake of lycopene for most people.[5] The lycopene content of tomatoes depends on variety and increases as the fruit ripens.[21]
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.[5][22] Lycopene in tomato paste is up to four times more bioavailable than in fresh tomatoes.[23] Processed tomato products such as pasteurized tomato juice, soup, sauce, and ketchup contain a higher concentration of bioavailable lycopene compared to raw tomatoes.[5][24]
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 has high lycopene content derived mainly from its seed coats.[25]Cara cara navel, and other citrus fruit, such as pink grapefruit, also contain lycopene.[4][26] Some foods that do not appear red also contain lycopene, e.g., asparagus, which contains about 30 μg of lycopene per 100-g serving[4] (0.3 μg/g) and dried parsley and basil, which contain around 3.5–7.0 μg/g of lycopene.[4]
When lycopene is used as a food additive (E160d), it is usually obtained from tomatoes.[27]
Adverse effects
Test tube containing a dichloromethane solution of lycopene
Lycopene is non-toxic and commonly found in the diet, mainly from tomato products. There are cases of intolerance or allergic reaction to dietary lycopene, which may cause diarrhea, nausea, stomach pain or cramps, gas, and loss of appetite.[28] Lycopene may increase the risk of bleeding when taken with anticoagulant drugs.[28] Because lycopene may cause low blood pressure, interactions with drugs that affect blood pressure may occur. Lycopene may affect the immune system, the nervous system, sensitivity to sunlight, or drugs used for stomach ailments.[28]
Lycopenemia is an orange discoloration of the skin that is observed with high intakes of lycopene.[16] The discoloration is expected to fade after discontinuing excessive lycopene intake.[16]
A 2015 review found that dietary lycopene was associated with reduced risk of prostate cancer,[31] whereas a 2021 meta-analysis found that dietary lycopene did not affect prostate cancer risk.[32] Other reviews concluded that research has been insufficient to establish whether lycopene consumption affects human health.[33]
Regulatory status in Europe and the United States
In a review of literature on lycopene and its potential benefit in the diet, the European Food Safety Authority concluded there was insufficient evidence for lycopene having antioxidant effects in humans, particularly in skin, heart function, or vision protection from ultraviolet light.[34]
Although lycopene from tomatoes has been tested in humans for cardiovascular diseases and prostate cancer, no effect on any disease was found.[35] The US Food and Drug Administration, in rejecting manufacturers' requests in 2005 to allow "qualified labeling" for lycopene and the reduction of various cancer risks, provided a conclusion that remains in effect as of 2017[update]:
...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.
^ abcTrumbo PR (2005). "Are there adverse effects of lycopene exposure?". The Journal of Nutrition. 135 (8): 2060S–1S. doi:10.1093/jn/135.8.2060s. PMID16046742. Lycopenemia, characterized by an orange discoloration of the skin, has been observed with high intakes of lycopene-containing foods. One case study reported the incidence of lycopenemia in a 61-y-old woman who had consumed ~2 L of tomato juice daily for several years (10). Although there was evidence of lycopene and fatty deposits in the liver, there was an absence of measurable hepatic dysfunction. After 3 wk of consuming a diet free of tomato juice, the orange discoloration faded.
^Ishida, BK; Turner, C; Chapman, MH; McKeon, TA (28 January 2004). "Fatty acid and carotenoid composition of gac (Momordica cochinchinensis Spreng) fruit". Journal of Agricultural and Food Chemistry. 52 (2): 274–9. doi:10.1021/jf030616i. PMID14733508.
^Kamiloglu, S.; Demirci, M.; Selen, S.; Toydemir, G.; Boyacioglu, D.; Capanoglu, E. (2014). "Home processing of tomatoes (Solanum lycopersicum): Effects onin vitrobioaccessibility of total lycopene, phenolics, flavonoids, and antioxidant capacity". Journal of the Science of Food and Agriculture. 94 (11): 2225–33. doi:10.1002/jsfa.6546. PMID24375495.
^Yamaguchi, Masayoshi (2010). Carotenoids : Properties, Effects and Diseases. New York: Nova Science Publishers. p. 125. ISBN9781612097138.
^Alquezar, B; Rodrigo, M. J.; Zacarías, L (2008). "Regulation of carotenoid biosynthesis during fruit maturation in the red-fleshed orange mutant Cara Cara". Phytochemistry. 69 (10): 1997–2007. doi:10.1016/j.phytochem.2008.04.020. PMID18538806.
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